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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:51 UTC

Update Date

2022-03-07 02:51:56 UTC

HMDB ID

HMDB0015326

Secondary Accession Numbers

HMDB15326

Metabolite Identification

Common Name

Flecainide

Description

Flecainide, also known as (+-)-flecainide or ccris 313, belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring. In humans, flecainide is involved in the flecainide action pathway. Flecainide is a primary metabolite. Primary metabolites are metabolically or physiologically essential metabolites. They are directly involved in an organism’s growth, development or reproduction. Based on a literature review a significant number of articles have been published on Flecainide.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI

1195
  Mrv0541 02231215192D          

 28 29  0  0  1  0            999 V2000
    1.9520   -0.7697    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.3572    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.6592    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -3.3553    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.9534   -3.6573    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.7784   -2.2284    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.1823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.0553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.7053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.2448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.1823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    3.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -2.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2 27  1  0  0  0  0
  3 27  1  0  0  0  0
  4 28  1  0  0  0  0
  5 28  1  0  0  0  0
  6 28  1  0  0  0  0
  7 18  2  0  0  0  0
  8 20  1  0  0  0  0
  8 25  1  0  0  0  0
  9 22  1  0  0  0  0
  9 26  1  0  0  0  0
 10 12  1  0  0  0  0
 10 16  1  0  0  0  0
 11 17  1  0  0  0  0
 11 18  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 23  1  0  0  0  0
 21 22  2  0  0  0  0
 22 24  1  0  0  0  0
 23 24  2  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END

HMDB0015326
     RDKit          3D
Flecainide
 48 49  0  0  0  0  0  0  0  0999 V2000
    0.4239    0.8660    1.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1162   -0.2029    1.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6474   -1.3768    1.1006 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9995   -1.4191    1.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8653   -0.4997    0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881   -0.9587   -0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4529    0.2234   -1.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8573    0.4518   -0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9476    0.5292    0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2534   -0.5280    1.3090 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4373   -0.0459    0.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388    1.2167    0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2997    1.4460    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    2.7141    0.1710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563    3.7699    0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0042    5.0339    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2952    5.3333   -0.6022 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1397    4.8940    1.4564 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2736    6.0787    1.2690 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0246    0.4251   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4467   -0.8211   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1604   -1.0749   -0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328   -2.2819   -0.1185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9034   -3.5108   -0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9509   -3.6656   -2.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8827   -2.8972   -2.6689 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2325   -4.9906   -2.4256 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739   -3.3483   -2.5816 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086   -2.2716    0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3748   -2.4510    1.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9415   -1.1494    2.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508    0.5428    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595   -1.8310   -0.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968   -1.2592   -0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522    1.1046   -1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783    0.0307   -2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1879    1.4377   -1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5193   -0.3029   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5072    1.4909    0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0341    0.5072    0.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6816   -1.4666    1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    2.0788    1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310    3.8915    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8736    3.5506    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0176    0.5486   -0.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175   -1.6304   -0.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8660   -3.9552   -0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -4.2269   -0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 13 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 10  5  1  0
 22 11  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 12 42  1  0
 15 43  1  0
 15 44  1  0
 20 45  1  0
 21 46  1  0
 24 47  1  0
 24 48  1  0
M  END

1195
  Mrv0541 02231215192D          

 28 29  0  0  1  0            999 V2000
    1.9520   -0.7697    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    0.3572    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    2.7770    0.6592    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804   -3.3553    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    6.9534   -3.6573    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    7.7784   -2.2284    0.0000 F   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.1823    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -0.0553    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -1.7053    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    3.2448    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.1823    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515    2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    2.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    2.4198    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0804    3.2448    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659    3.6573    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.0073    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.7697    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.2928    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.7053    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.4678    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6515   -2.5303    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -0.0553    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.3659   -2.9428    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 27  1  0  0  0  0
  2 27  1  0  0  0  0
  3 27  1  0  0  0  0
  4 28  1  0  0  0  0
  5 28  1  0  0  0  0
  6 28  1  0  0  0  0
  7 18  2  0  0  0  0
  8 20  1  0  0  0  0
  8 25  1  0  0  0  0
  9 22  1  0  0  0  0
  9 26  1  0  0  0  0
 10 12  1  0  0  0  0
 10 16  1  0  0  0  0
 11 17  1  0  0  0  0
 11 18  1  0  0  0  0
 12 13  1  0  0  0  0
 12 17  1  0  0  0  0
 13 14  1  0  0  0  0
 14 15  1  0  0  0  0
 15 16  1  0  0  0  0
 18 19  1  0  0  0  0
 19 20  2  0  0  0  0
 19 21  1  0  0  0  0
 20 23  1  0  0  0  0
 21 22  2  0  0  0  0
 22 24  1  0  0  0  0
 23 24  2  0  0  0  0
 25 27  1  0  0  0  0
 26 28  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0015326

> <DATABASE_NAME>
hmdb

> <SMILES>
FC(F)(F)COC1=CC(C(=O)NCC2CCCCN2)=C(OCC(F)(F)F)C=C1

> <INCHI_IDENTIFIER>
InChI=1S/C17H20F6N2O3/c18-16(19,20)9-27-12-4-5-14(28-10-17(21,22)23)13(7-12)15(26)25-8-11-3-1-2-6-24-11/h4-5,7,11,24H,1-3,6,8-10H2,(H,25,26)

> <INCHI_KEY>
DJBNUMBKLMJRSA-UHFFFAOYSA-N

> <FORMULA>
C17H20F6N2O3

> <MOLECULAR_WEIGHT>
414.3427

> <EXACT_MASS>
414.137811746

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_AVERAGE_POLARIZABILITY>
35.91568083566059

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
2

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
N-(piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide

> <ALOGPS_LOGP>
2.98

> <JCHEM_LOGP>
3.1881419053333335

> <ALOGPS_LOGS>
-4.11

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA>
19.557778400329568

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.681351736903963

> <JCHEM_PKA_STRONGEST_BASIC>
9.616620255251357

> <JCHEM_POLAR_SURFACE_AREA>
59.59

> <JCHEM_REFRACTIVITY>
88.39630000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
9

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
3.24e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
flecainide

> <JCHEM_VEBER_RULE>
0

$$$$

HMDB0015326
     RDKit          3D
Flecainide
 48 49  0  0  0  0  0  0  0  0999 V2000
    0.4239    0.8660    1.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1162   -0.2029    1.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6474   -1.3768    1.1006 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9995   -1.4191    1.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8653   -0.4997    0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881   -0.9587   -0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4529    0.2234   -1.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8573    0.4518   -0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9476    0.5292    0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2534   -0.5280    1.3090 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4373   -0.0459    0.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388    1.2167    0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2997    1.4460    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    2.7141    0.1710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563    3.7699    0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0042    5.0339    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2952    5.3333   -0.6022 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1397    4.8940    1.4564 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2736    6.0787    1.2690 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0246    0.4251   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4467   -0.8211   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1604   -1.0749   -0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328   -2.2819   -0.1185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9034   -3.5108   -0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9509   -3.6656   -2.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8827   -2.8972   -2.6689 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2325   -4.9906   -2.4256 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739   -3.3483   -2.5816 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086   -2.2716    0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3748   -2.4510    1.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9415   -1.1494    2.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508    0.5428    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595   -1.8310   -0.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968   -1.2592   -0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522    1.1046   -1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783    0.0307   -2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1879    1.4377   -1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5193   -0.3029   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5072    1.4909    0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0341    0.5072    0.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6816   -1.4666    1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    2.0788    1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310    3.8915    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8736    3.5506    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0176    0.5486   -0.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175   -1.6304   -0.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8660   -3.9552   -0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -4.2269   -0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 13 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 10  5  1  0
 22 11  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 12 42  1  0
 15 43  1  0
 15 44  1  0
 20 45  1  0
 21 46  1  0
 24 47  1  0
 24 48  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 1195                                              
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  F   UNK     0       3.644  -1.437   0.000  0.00  0.00           F+0
HETATM    2  F   UNK     0       3.080   0.667   0.000  0.00  0.00           F+0
HETATM    3  F   UNK     0       5.184   1.231   0.000  0.00  0.00           F+0
HETATM    4  F   UNK     0      15.083  -6.263   0.000  0.00  0.00           F+0
HETATM    5  F   UNK     0      12.980  -6.827   0.000  0.00  0.00           F+0
HETATM    6  F   UNK     0      14.520  -4.160   0.000  0.00  0.00           F+0
HETATM    7  O   UNK     0       8.415   2.207   0.000  0.00  0.00           O+0
HETATM    8  O   UNK     0       7.081  -0.103   0.000  0.00  0.00           O+0
HETATM    9  O   UNK     0      12.416  -3.183   0.000  0.00  0.00           O+0
HETATM   10  N   UNK     0      12.416   6.057   0.000  0.00  0.00           N+0
HETATM   11  N   UNK     0      11.082   2.207   0.000  0.00  0.00           N+0
HETATM   12  C   UNK     0      12.416   4.517   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      13.750   3.747   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      15.083   4.517   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0      15.083   6.057   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0      13.750   6.827   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0      11.082   3.747   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       9.748   1.437   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0       9.748  -0.103   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       8.415  -0.873   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0      11.082  -0.873   0.000  0.00  0.00           C+0
HETATM   22  C   UNK     0      11.082  -2.413   0.000  0.00  0.00           C+0
HETATM   23  C   UNK     0       8.415  -2.413   0.000  0.00  0.00           C+0
HETATM   24  C   UNK     0       9.748  -3.183   0.000  0.00  0.00           C+0
HETATM   25  C   UNK     0       5.748  -0.873   0.000  0.00  0.00           C+0
HETATM   26  C   UNK     0      12.416  -4.723   0.000  0.00  0.00           C+0
HETATM   27  C   UNK     0       4.414  -0.103   0.000  0.00  0.00           C+0
HETATM   28  C   UNK     0      13.750  -5.493   0.000  0.00  0.00           C+0
CONECT    1   27                                                            
CONECT    2   27                                                            
CONECT    3   27                                                            
CONECT    4   28                                                            
CONECT    5   28                                                            
CONECT    6   28                                                            
CONECT    7   18                                                            
CONECT    8   20   25                                                       
CONECT    9   22   26                                                       
CONECT   10   12   16                                                       
CONECT   11   17   18                                                       
CONECT   12   10   13   17                                                  
CONECT   13   12   14                                                       
CONECT   14   13   15                                                       
CONECT   15   14   16                                                       
CONECT   16   10   15                                                       
CONECT   17   11   12                                                       
CONECT   18    7   11   19                                                  
CONECT   19   18   20   21                                                  
CONECT   20    8   19   23                                                  
CONECT   21   19   22                                                       
CONECT   22    9   21   24                                                  
CONECT   23   20   24                                                       
CONECT   24   22   23                                                       
CONECT   25    8   27                                                       
CONECT   26    9   28                                                       
CONECT   27    1    2    3   25                                             
CONECT   28    4    5    6   26                                             
MASTER        0    0    0    0    0    0    0    0   28    0   58    0
END

COMPND    HMDB0015326
HETATM    1  O1  UNL     1       0.424   0.866   1.577  1.00  0.00           O  
HETATM    2  C1  UNL     1      -0.116  -0.203   1.068  1.00  0.00           C  
HETATM    3  N1  UNL     1       0.647  -1.377   1.101  1.00  0.00           N  
HETATM    4  C2  UNL     1       2.000  -1.419   1.670  1.00  0.00           C  
HETATM    5  C3  UNL     1       2.865  -0.500   0.884  1.00  0.00           C  
HETATM    6  C4  UNL     1       2.888  -0.959  -0.582  1.00  0.00           C  
HETATM    7  C5  UNL     1       3.453   0.223  -1.362  1.00  0.00           C  
HETATM    8  C6  UNL     1       4.857   0.452  -0.867  1.00  0.00           C  
HETATM    9  C7  UNL     1       4.948   0.529   0.627  1.00  0.00           C  
HETATM   10  N2  UNL     1       4.253  -0.528   1.309  1.00  0.00           N  
HETATM   11  C8  UNL     1      -1.437  -0.046   0.533  1.00  0.00           C  
HETATM   12  C9  UNL     1      -2.039   1.217   0.595  1.00  0.00           C  
HETATM   13  C10 UNL     1      -3.300   1.446   0.105  1.00  0.00           C  
HETATM   14  O2  UNL     1      -3.891   2.714   0.171  1.00  0.00           O  
HETATM   15  C11 UNL     1      -3.156   3.770   0.760  1.00  0.00           C  
HETATM   16  C12 UNL     1      -4.004   5.034   0.713  1.00  0.00           C  
HETATM   17  F1  UNL     1      -4.295   5.333  -0.602  1.00  0.00           F  
HETATM   18  F2  UNL     1      -5.140   4.894   1.456  1.00  0.00           F  
HETATM   19  F3  UNL     1      -3.274   6.079   1.269  1.00  0.00           F  
HETATM   20  C13 UNL     1      -4.025   0.425  -0.471  1.00  0.00           C  
HETATM   21  C14 UNL     1      -3.447  -0.821  -0.538  1.00  0.00           C  
HETATM   22  C15 UNL     1      -2.160  -1.075  -0.045  1.00  0.00           C  
HETATM   23  O3  UNL     1      -1.633  -2.282  -0.119  1.00  0.00           O  
HETATM   24  C16 UNL     1      -1.903  -3.511  -0.588  1.00  0.00           C  
HETATM   25  C17 UNL     1      -1.951  -3.666  -2.070  1.00  0.00           C  
HETATM   26  F4  UNL     1      -2.883  -2.897  -2.669  1.00  0.00           F  
HETATM   27  F5  UNL     1      -2.233  -4.991  -2.426  1.00  0.00           F  
HETATM   28  F6  UNL     1      -0.674  -3.348  -2.582  1.00  0.00           F  
HETATM   29  H1  UNL     1       0.309  -2.272   0.730  1.00  0.00           H  
HETATM   30  H2  UNL     1       2.375  -2.451   1.556  1.00  0.00           H  
HETATM   31  H3  UNL     1       1.942  -1.149   2.750  1.00  0.00           H  
HETATM   32  H4  UNL     1       2.551   0.543   0.882  1.00  0.00           H  
HETATM   33  H5  UNL     1       3.559  -1.831  -0.702  1.00  0.00           H  
HETATM   34  H6  UNL     1       1.897  -1.259  -0.921  1.00  0.00           H  
HETATM   35  H7  UNL     1       2.852   1.105  -1.070  1.00  0.00           H  
HETATM   36  H8  UNL     1       3.478   0.031  -2.438  1.00  0.00           H  
HETATM   37  H9  UNL     1       5.188   1.438  -1.271  1.00  0.00           H  
HETATM   38  H10 UNL     1       5.519  -0.303  -1.319  1.00  0.00           H  
HETATM   39  H11 UNL     1       4.507   1.491   0.964  1.00  0.00           H  
HETATM   40  H12 UNL     1       6.034   0.507   0.891  1.00  0.00           H  
HETATM   41  H13 UNL     1       4.682  -1.467   1.146  1.00  0.00           H  
HETATM   42  H14 UNL     1      -1.539   2.079   1.033  1.00  0.00           H  
HETATM   43  H15 UNL     1      -2.231   3.891   0.176  1.00  0.00           H  
HETATM   44  H16 UNL     1      -2.874   3.551   1.800  1.00  0.00           H  
HETATM   45  H17 UNL     1      -5.018   0.549  -0.872  1.00  0.00           H  
HETATM   46  H18 UNL     1      -4.017  -1.630  -0.946  1.00  0.00           H  
HETATM   47  H19 UNL     1      -2.866  -3.955  -0.168  1.00  0.00           H  
HETATM   48  H20 UNL     1      -1.123  -4.227  -0.147  1.00  0.00           H  
CONECT    1    2    2
CONECT    2    3   11
CONECT    3    4   29
CONECT    4    5   30   31
CONECT    5    6   10   32
CONECT    6    7   33   34
CONECT    7    8   35   36
CONECT    8    9   37   38
CONECT    9   10   39   40
CONECT   10   41
CONECT   11   12   12   22
CONECT   12   13   42
CONECT   13   14   20   20
CONECT   14   15
CONECT   15   16   43   44
CONECT   16   17   18   19
CONECT   20   21   45
CONECT   21   22   22   46
CONECT   22   23
CONECT   23   24
CONECT   24   25   47   48
CONECT   25   26   27   28
END

HMDB0015326
     RDKit          3D
Flecainide
 48 49  0  0  0  0  0  0  0  0999 V2000
    0.4239    0.8660    1.5765 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1162   -0.2029    1.0682 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.6474   -1.3768    1.1006 N   0  0  0  0  0  0  0  0  0  0  0  0
    1.9995   -1.4191    1.6704 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8653   -0.4997    0.8842 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8881   -0.9587   -0.5820 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.4529    0.2234   -1.3618 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8573    0.4518   -0.8666 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9476    0.5292    0.6271 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.2534   -0.5280    1.3090 N   0  0  0  0  0  0  0  0  0  0  0  0
   -1.4373   -0.0459    0.5333 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.0388    1.2167    0.5946 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2997    1.4460    0.1046 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8905    2.7141    0.1710 O   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1563    3.7699    0.7597 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0042    5.0339    0.7133 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.2952    5.3333   -0.6022 F   0  0  0  0  0  0  0  0  0  0  0  0
   -5.1397    4.8940    1.4564 F   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2736    6.0787    1.2690 F   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0246    0.4251   -0.4712 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4467   -0.8211   -0.5376 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1604   -1.0749   -0.0449 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6328   -2.2819   -0.1185 O   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9034   -3.5108   -0.5880 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9509   -3.6656   -2.0705 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8827   -2.8972   -2.6689 F   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2325   -4.9906   -2.4256 F   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6739   -3.3483   -2.5816 F   0  0  0  0  0  0  0  0  0  0  0  0
    0.3086   -2.2716    0.7304 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3748   -2.4510    1.5559 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.9415   -1.1494    2.7495 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.5508    0.5428    0.8824 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5595   -1.8310   -0.7023 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8968   -1.2592   -0.9207 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8522    1.1046   -1.0702 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4783    0.0307   -2.4378 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.1879    1.4377   -1.2712 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5193   -0.3029   -1.3194 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.5072    1.4909    0.9637 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.0341    0.5072    0.8911 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6816   -1.4666    1.1465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5394    2.0788    1.0327 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.2310    3.8915    0.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8736    3.5506    1.8004 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0176    0.5486   -0.8717 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.0175   -1.6304   -0.9460 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8660   -3.9552   -0.1676 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1234   -4.2269   -0.1472 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0
  2  3  1  0
  3  4  1  0
  4  5  1  0
  5  6  1  0
  6  7  1  0
  7  8  1  0
  8  9  1  0
  9 10  1  0
  2 11  1  0
 11 12  2  0
 12 13  1  0
 13 14  1  0
 14 15  1  0
 15 16  1  0
 16 17  1  0
 16 18  1  0
 16 19  1  0
 13 20  2  0
 20 21  1  0
 21 22  2  0
 22 23  1  0
 23 24  1  0
 24 25  1  0
 25 26  1  0
 25 27  1  0
 25 28  1  0
 10  5  1  0
 22 11  1  0
  3 29  1  0
  4 30  1  0
  4 31  1  0
  5 32  1  0
  6 33  1  0
  6 34  1  0
  7 35  1  0
  7 36  1  0
  8 37  1  0
  8 38  1  0
  9 39  1  0
  9 40  1  0
 10 41  1  0
 12 42  1  0
 15 43  1  0
 15 44  1  0
 20 45  1  0
 21 46  1  0
 24 47  1  0
 24 48  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
(+-)-Flecainide	ChEBI
CCRIS 313	ChEBI
Flecaine	ChEBI
Flecainida	ChEBI
Flecainidum	ChEBI
N-(2-Piperidinylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide	ChEBI
Apocard	MeSH, HMDB
Flecainide monoacetate, (S)-isomer	MeSH, HMDB
Flecainide, 5-HO-N-(6-oxo)-derivative	MeSH, HMDB
Merck dura brand OF flecainide acetate	MeSH, HMDB
Alpharma brand OF flecainide acetate	MeSH, HMDB
Flecainide, 5-HO-N-(6-oxo)-derivative, (+-)-isomer	MeSH, HMDB
Flecatab	MeSH, HMDB
Tambocor	MeSH, HMDB
3m Brand OF flecainide acetate	MeSH, HMDB
Alphapharm brand OF flecainide acetate	MeSH, HMDB
Flecadura	MeSH, HMDB
Flecainid-isis	MeSH, HMDB
Flecainide acetate	MeSH, HMDB
Flecainide monoacetate, (R)-isomer	MeSH, HMDB
Flecainide, (R)-isomer	MeSH, HMDB
Flecainide, (S)-isomer	MeSH, HMDB
Riker brand OF flecainide acetate	MeSH, HMDB
Acetate, flecainide	MeSH, HMDB
Flecainid isis	MeSH, HMDB
Flecainide monoacetate	MeSH, HMDB
Flecainide monoacetate, (+-)-isomer	MeSH, HMDB
United drug brand OF flecainide acetate	MeSH, HMDB

Chemical Formula

C₁₇H₂₀F₆N₂O₃

Average Molecular Weight

414.3427

Monoisotopic Molecular Weight

414.137811746

IUPAC Name

N-(piperidin-2-ylmethyl)-2,5-bis(2,2,2-trifluoroethoxy)benzamide

Traditional Name

flecainide

CAS Registry Number

54143-55-4

SMILES

FC(F)(F)COC1=CC(C(=O)NCC2CCCCN2)=C(OCC(F)(F)F)C=C1

InChI Identifier

InChI=1S/C17H20F6N2O3/c18-16(19,20)9-27-12-4-5-14(28-10-17(21,22)23)13(7-12)15(26)25-8-11-3-1-2-6-24-11/h4-5,7,11,24H,1-3,6,8-10H2,(H,25,26)

InChI Key

DJBNUMBKLMJRSA-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as benzamides. These are organic compounds containing a carboxamido substituent attached to a benzene ring.

Kingdom

Organic compounds

Super Class

Benzenoids

Class

Benzene and substituted derivatives

Sub Class

Benzoic acids and derivatives

Direct Parent

Benzamides

Alternative Parents

Substituents

Benzamide
Phenoxy compound
Benzoyl
Phenol ether
Alkyl aryl ether
Piperidine
Amino acid or derivatives
Carboxamide group
Secondary carboxylic acid amide
Carboxylic acid derivative
Secondary aliphatic amine
Ether
Azacycle
Organoheterocyclic compound
Secondary amine
Organohalogen compound
Alkyl halide
Alkyl fluoride
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organopnictogen compound
Organofluoride
Organonitrogen compound
Organooxygen compound
Amine
Organic oxygen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidines (CHEBI:75984 )
organofluorine compound (CHEBI:75984 )
aromatic ether (CHEBI:75984 )
monocarboxylic acid amide (CHEBI:75984 )

Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 31557052)

Source

Exogenous

Exogenous (PMID: 31557052)

Process

Not Available

Role

Not Available

Physical Properties

State

Solid

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.032 g/L	Not Available
LogP	4.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	192.2	30932474

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.032 g/L	ALOGPS
logP	2.98	ALOGPS
logP	3.19	ChemAxon
logS	-4.1	ALOGPS
pKa (Strongest Acidic)	13.68	ChemAxon
pKa (Strongest Basic)	9.62	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	59.59 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	88.4 m³·mol⁻¹	ChemAxon
Polarizability	35.92 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DeepCCS	[M+H]+	188.928	30932474
DeepCCS	[M-H]-	186.57	30932474
DeepCCS	[M-2H]-	220.724	30932474
DeepCCS	[M+Na]+	196.076	30932474
AllCCS	[M+H]+	188.2	32859911
AllCCS	[M+H-H2O]+	185.7	32859911
AllCCS	[M+NH4]+	190.4	32859911
AllCCS	[M+Na]+	191.1	32859911
AllCCS	[M-H]-	186.1	32859911
AllCCS	[M+Na-2H]-	186.3	32859911
AllCCS	[M+HCOO]-	186.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Flecainide	FC(F)(F)COC1=CC(C(=O)NCC2CCCCN2)=C(OCC(F)(F)F)C=C1	2284.3	Standard polar	33892256
Flecainide	FC(F)(F)COC1=CC(C(=O)NCC2CCCCN2)=C(OCC(F)(F)F)C=C1	2306.8	Standard non polar	33892256
Flecainide	FC(F)(F)COC1=CC(C(=O)NCC2CCCCN2)=C(OCC(F)(F)F)C=C1	2322.7	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Flecainide,1TMS,isomer #1	C[Si](C)(C)N(CC1CCCCN1)C(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2206.6	Semi standard non polar	33892256
Flecainide,1TMS,isomer #1	C[Si](C)(C)N(CC1CCCCN1)C(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2328.9	Standard non polar	33892256
Flecainide,1TMS,isomer #1	C[Si](C)(C)N(CC1CCCCN1)C(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2439.0	Standard polar	33892256
Flecainide,1TMS,isomer #2	C[Si](C)(C)N1CCCCC1CNC(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2337.9	Semi standard non polar	33892256
Flecainide,1TMS,isomer #2	C[Si](C)(C)N1CCCCC1CNC(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2298.8	Standard non polar	33892256
Flecainide,1TMS,isomer #2	C[Si](C)(C)N1CCCCC1CNC(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2621.5	Standard polar	33892256
Flecainide,2TMS,isomer #1	C[Si](C)(C)N(CC1CCCCN1[Si](C)(C)C)C(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2316.7	Semi standard non polar	33892256
Flecainide,2TMS,isomer #1	C[Si](C)(C)N(CC1CCCCN1[Si](C)(C)C)C(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2424.8	Standard non polar	33892256
Flecainide,2TMS,isomer #1	C[Si](C)(C)N(CC1CCCCN1[Si](C)(C)C)C(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2483.5	Standard polar	33892256
Flecainide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1CCCCN1)C(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2378.4	Semi standard non polar	33892256
Flecainide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1CCCCN1)C(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2561.6	Standard non polar	33892256
Flecainide,1TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1CCCCN1)C(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2526.8	Standard polar	33892256
Flecainide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCCCC1CNC(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2520.1	Semi standard non polar	33892256
Flecainide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCCCC1CNC(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2504.2	Standard non polar	33892256
Flecainide,1TBDMS,isomer #2	CC(C)(C)[Si](C)(C)N1CCCCC1CNC(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2687.1	Standard polar	33892256
Flecainide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1CCCCN1[Si](C)(C)C(C)(C)C)C(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2692.2	Semi standard non polar	33892256
Flecainide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1CCCCN1[Si](C)(C)C(C)(C)C)C(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2805.9	Standard non polar	33892256
Flecainide,2TBDMS,isomer #1	CC(C)(C)[Si](C)(C)N(CC1CCCCN1[Si](C)(C)C(C)(C)C)C(=O)C1=CC(OCC(F)(F)F)=CC=C1OCC(F)(F)F	2671.7	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Flecainide GC-MS (Non-derivatized) - 70eV, Positive	splash10-0f89-5009000000-7b1564870deda7f2d21e	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flecainide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flecainide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flecainide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Flecainide GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-001i-9000000000-b732167df77d39193144	2014-09-20	Not Available	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide LC-ESI-QFT , negative-QTOF	splash10-00dl-0095000000-644485d209c90776a32d	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide LC-ESI-QFT , negative-QTOF	splash10-00di-0190000000-201f2152d161a1ff83e5	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide LC-ESI-QFT , negative-QTOF	splash10-00di-0790000000-928874c4b348381ad1b8	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide LC-ESI-QFT , negative-QTOF	splash10-0596-0940000000-ee7a94ba0d7bcfa2fe93	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide LC-ESI-QFT , negative-QTOF	splash10-052g-1910000000-a32ac2f605f11fbbc5e0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide LC-ESI-QFT , negative-QTOF	splash10-0297-1900000000-f1c49d25a6b161ff44d9	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide 30V, Negative-QTOF	splash10-00di-0090000000-8d4a6a9978cccc816b47	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide 15V, Negative-QTOF	splash10-00dl-0095000000-43e08367bbe8d04a6a08	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide 60V, Negative-QTOF	splash10-0596-0940000000-8c3aff3bc24541d8739d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide 20V, Negative-QTOF	splash10-00dl-0090000000-7b5a76e5b473705a0de5	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide 10V, Negative-QTOF	splash10-03k9-0007900000-c01a08b2f11aa54d8718	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide 45V, Negative-QTOF	splash10-00di-0790000000-d9ff0b268b85eaeda91c	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide 40V, Negative-QTOF	splash10-00di-0090000000-b1e686e3fcae67c0c6a0	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide 30V, Negative-QTOF	splash10-00di-0190000000-8de6d230a8cd23c50272	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide LC-ESI-QFT , positive-QTOF	splash10-014i-0000900000-9820e909cb01d45fa815	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide LC-ESI-QFT , positive-QTOF	splash10-00kb-2009500000-68b872fada8afdd4e580	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide LC-ESI-QFT , positive-QTOF	splash10-0f6t-5019000000-8fa5e4257c88beda0ea1	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide LC-ESI-QFT , positive-QTOF	splash10-0uea-8069000000-149a79cf429446ec77c2	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide LC-ESI-QFT , positive-QTOF	splash10-0uei-6292000000-103ccdef98c4b6c9e408	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide LC-ESI-QFT , positive-QTOF	splash10-0pdi-8970000000-9258d139b203d6c98df0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide 15V, Positive-QTOF	splash10-014i-0000900000-3df851e0ff354ab1be59	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide 30V, Positive-QTOF	splash10-00kb-2009500000-c58556b6a88ebc0729bc	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide 20V, Positive-QTOF	splash10-014i-0001900000-9830e722af2fab717f28	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide 10V, Positive-QTOF	splash10-014i-0000900000-c80ce9de474de184ff13	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Flecainide 45V, Positive-QTOF	splash10-0f6t-5019000000-00737a572b9aa2cd61a3	2021-09-20	HMDB team, MONA	View Spectrum

Biological Properties

Cellular Locations

Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Flecainide Action Pathway		Not Available

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01195	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB01195	21059682	details

Abnormal Concentrations

Not Available

Predicted Concentrations

Biospecimen	Value	Original age	Original sex	Original condition	Comments
Blood	0.000 uM	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities
Blood	0.000 umol/mmol creatinine	Adult (>18 years old)	Both	Normal	Predicted based on drug qualities

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

DB01195

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3239

KEGG Compound ID

C07001

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Flecainide

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

75984

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

Not Available

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

Gill JS, Mehta D, Ward DE, Camm AJ: Efficacy of flecainide, sotalol, and verapamil in the treatment of right ventricular tachycardia in patients without overt cardiac abnormality. Br Heart J. 1992 Oct;68(4):392-7. [PubMed:1449923 ]
Echt DS, Liebson PR, Mitchell LB, Peters RW, Obias-Manno D, Barker AH, Arensberg D, Baker A, Friedman L, Greene HL, et al.: Mortality and morbidity in patients receiving encainide, flecainide, or placebo. The Cardiac Arrhythmia Suppression Trial. N Engl J Med. 1991 Mar 21;324(12):781-8. [PubMed:1900101 ]
Sakurada H, Hiyoshi Y, Tejima T, Yanase O, Tokuyasu Y, Watanabe K, Motomiya T, Sugiura M, Hiraoka M: [Effects of oral flecainide treatment of refractory tachyarrhythmias]. Kokyu To Junkan. 1990 May;38(5):471-6. [PubMed:2115193 ]
Greenberg HM, Dwyer EM Jr, Hochman JS, Steinberg JS, Echt DS, Peters RW: Interaction of ischaemia and encainide/flecainide treatment: a proposed mechanism for the increased mortality in CAST I. Br Heart J. 1995 Dec;74(6):631-5. [PubMed:8541168 ]
Gasparini M, Priori SG, Mantica M, Napolitano C, Galimberti P, Ceriotti C, Simonini S: Flecainide test in Brugada syndrome: a reproducible but risky tool. Pacing Clin Electrophysiol. 2003 Jan;26(1 Pt 2):338-41. [PubMed:12687841 ]

Enzymes

Enzyme Details

1. Cytochrome P450 2C9

General function:: Involved in monooxygenase activity
Specific function:: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:: CYP2C9
Uniprot ID:: P11712
Molecular weight:: 55627.365

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

2. Cytochrome P450 2D6

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic antidepressants.
Gene Name:: CYP2D6
Uniprot ID:: P10635
Molecular weight:: 55768.94

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]

Enzyme Details

3. Sodium channel protein type 4 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. This sodium channel may be present in both denervated and innervated skeletal muscle
Gene Name:: SCN4A
Uniprot ID:: P35499
Molecular weight:: 208059.2

References

Desaphy JF, De Luca A, Didonna MP, George AL Jr, Camerino Conte D: Different flecainide sensitivity of hNav1.4 channels and myotonic mutants explained by state-dependent block. J Physiol. 2004 Jan 15;554(Pt 2):321-34. Epub 2003 Nov 7. [PubMed:14608015 ]

Enzyme Details

4. Sodium channel protein type 5 subunit alpha

General function:: Involved in ion channel activity
Specific function:: This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:: SCN5A
Uniprot ID:: Q14524
Molecular weight:: 226937.5

References

Nagatomo T, January CT, Makielski JC: Preferential block of late sodium current in the LQT3 DeltaKPQ mutant by the class I(C) antiarrhythmic flecainide. Mol Pharmacol. 2000 Jan;57(1):101-7. [PubMed:10617684 ]
Benhorin J, Taub R, Goldmit M, Kerem B, Kass RS, Windman I, Medina A: Effects of flecainide in patients with new SCN5A mutation: mutation-specific therapy for long-QT syndrome? Circulation. 2000 Apr 11;101(14):1698-706. [PubMed:10758053 ]
Priori SG, Napolitano C, Schwartz PJ, Bloise R, Crotti L, Ronchetti E: The elusive link between LQT3 and Brugada syndrome: the role of flecainide challenge. Circulation. 2000 Aug 29;102(9):945-7. [PubMed:10961955 ]
Cerrone M, Crotti L, Faggiano G, De Michelis V, Napolitano C, Schwartz PJ, Priori SG: [Long QT syndrome and Brugada syndrome: 2 aspects of the same disease?]. Ital Heart J Suppl. 2001 Mar;2(3):253-7. [PubMed:11307783 ]
Viswanathan PC, Bezzina CR, George AL Jr, Roden DM, Wilde AA, Balser JR: Gating-dependent mechanisms for flecainide action in SCN5A-linked arrhythmia syndromes. Circulation. 2001 Sep 4;104(10):1200-5. [PubMed:11535580 ]
Ramos E, O'leary ME: State-dependent trapping of flecainide in the cardiac sodium channel. J Physiol. 2004 Oct 1;560(Pt 1):37-49. Epub 2004 Jul 22. [PubMed:15272045 ]
Shimizu W, Antzelevitch C, Suyama K, Kurita T, Taguchi A, Aihara N, Takaki H, Sunagawa K, Kamakura S: Effect of sodium channel blockers on ST segment, QRS duration, and corrected QT interval in patients with Brugada syndrome. J Cardiovasc Electrophysiol. 2000 Dec;11(12):1320-9. [PubMed:11196553 ]
Liu H, Atkins J, Kass RS: Common molecular determinants of flecainide and lidocaine block of heart Na+ channels: evidence from experiments with neutral and quaternary flecainide analogues. J Gen Physiol. 2003 Mar;121(3):199-214. [PubMed:12601084 ]
Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]

Showing metabocard for Flecainide (HMDB0015326)

MOL for HMDB0015326 (Flecainide)

3D MOL for HMDB0015326 (Flecainide)

3D SDF for HMDB0015326 (Flecainide)

3D-SDF for HMDB0015326 (Flecainide)

PDB for HMDB0015326 (Flecainide)

3D PDB for HMDB0015326 (Flecainide)

SMILES for HMDB0015326 (Flecainide)

INCHI for HMDB0015326 (Flecainide)

Structure for HMDB0015326 (Flecainide)

3D Structure for HMDB0015326 (Flecainide)

Experimental Collision Cross Sections

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

Enzymes

References

References

References

References