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Showing metabocard for Mexiletine (HMDB0014523)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraBiological propertiesConcentrationsLinksReferencesenzymes (7) Show 7 proteinsXML
enzymes (7) Show 7 proteins
Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2023-02-21 17:18:12 UTC
HMDB IDHMDB0014523
Secondary Accession Numbers
  • HMDB14523
Metabolite Identification
Common NameMexiletine
DescriptionMexiletine is only found in individuals that have used or taken this drug. It is an antiarrhythmic agent pharmacologically similar to lidocaine. It may have some anticonvulsant properties. [PubChem]Mexiletine, like lidocaine, inhibits the inward sodium current required for the initiation and conduction of impulses, thus reducing the rate of rise of the action potential, Phase 0. It achieves this reduced sodium current by inhibiting sodium channels. Mexiletine decreases the effective refractory period (ERP) in Purkinje fibers in the heart. The decrease in ERP is of lesser magnitude than the decrease in action potential duration (APD), which results in an increase in the ERP/APD ratio. It does not significantly affect resting membrane potential or sinus node automaticity, left ventricular function, systolic arterial blood pressure, atrioventricular (AV) conduction velocity, or QRS or QT intervals
Structure
Data?1676999892
MOL3D MOLSDF3D SDFPDB3D PDBSMILESInChI

MOL for HMDB0014523 (Mexiletine)

379
  Mrv0541 02231214382D          

 13 13  0  0  1  0            999 V2000
    3.0791    0.1568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.8068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  6 12  1  0  0  0  0
  7 10  2  0  0  0  0
  7 13  1  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
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3D MOL for HMDB0014523 (Mexiletine)

HMDB0242552
     RDKit          3D
(2R)-1-(2,6-Dimethylphenoxy)propan-2-amine
 30 30  0  0  0  0  0  0  0  0999 V2000
   -0.6878   -2.2086   -1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138   -1.1419   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8982   -1.2559   -0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6211   -0.2392    0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0429    0.8595    0.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6515    0.9129    0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072    2.0722    1.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8795   -0.0741    0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771   -0.0032    0.1709 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2866    0.5966   -0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7286    0.4362   -0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445   -1.0487   -0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9706    1.0608    0.8825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430   -2.1379   -2.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -3.1796   -0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3737   -2.0971   -0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3912   -2.1090   -0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7015   -0.3185    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6356    1.6433    1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0322    1.8803    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755    2.3792    2.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0087    2.9318    0.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544    1.6710   -0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1272    0.1130   -1.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4090    0.8777   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6077   -1.4968    0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6976   -1.6218   -1.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1640   -1.1586   -0.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9664    2.0802    0.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6290    0.5761    1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  8  2  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
M  END
Download

3D SDF for HMDB0014523 (Mexiletine)

379
  Mrv0541 02231214382D          

 13 13  0  0  1  0            999 V2000
    3.0791    0.1568    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.8068    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.3943    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    0.5693    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.0808    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.8068    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645   -1.9058    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -2.3183    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500   -0.6683    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  4  1  0  0  0  0
  1  5  1  0  0  0  0
  2  3  1  0  0  0  0
  3  4  1  0  0  0  0
  3  8  1  0  0  0  0
  5  6  2  0  0  0  0
  5  7  1  0  0  0  0
  6  9  1  0  0  0  0
  6 12  1  0  0  0  0
  7 10  2  0  0  0  0
  7 13  1  0  0  0  0
  9 11  2  0  0  0  0
 10 11  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014523

> <DATABASE_NAME>
hmdb

> <SMILES>
CC(N)COC1=C(C)C=CC=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C11H17NO/c1-8-5-4-6-9(2)11(8)13-7-10(3)12/h4-6,10H,7,12H2,1-3H3

> <INCHI_KEY>
VLPIATFUUWWMKC-UHFFFAOYSA-N

> <FORMULA>
C11H17NO

> <MOLECULAR_WEIGHT>
179.2588

> <EXACT_MASS>
179.131014171

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
21.171052729090107

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-(2,6-dimethylphenoxy)propan-2-amine

> <ALOGPS_LOGP>
2.17

> <JCHEM_LOGP>
2.4620085449999998

> <ALOGPS_LOGS>
-2.52

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_BASIC>
9.5181501174897

> <JCHEM_POLAR_SURFACE_AREA>
35.25

> <JCHEM_REFRACTIVITY>
54.9722

> <JCHEM_ROTATABLE_BOND_COUNT>
3

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
5.38e-01 g/l

> <JCHEM_TRADITIONAL_IUPAC>
1-(2,6-dimethylphenoxy)propan-2-amine

> <JCHEM_VEBER_RULE>
1

$$$$
Download

3D-SDF for HMDB0014523 (Mexiletine)

HMDB0242552
     RDKit          3D
(2R)-1-(2,6-Dimethylphenoxy)propan-2-amine
 30 30  0  0  0  0  0  0  0  0999 V2000
   -0.6878   -2.2086   -1.0430 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5138   -1.1419   -0.4348 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8982   -1.2559   -0.4774 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6211   -0.2392    0.1014 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0429    0.8595    0.7062 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.6515    0.9129    0.7149 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0072    2.0722    1.3525 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8795   -0.0741    0.1519 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4771   -0.0032    0.1709 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.2866    0.5966   -0.8146 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.7286    0.4362   -0.3729 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0445   -1.0487   -0.2594 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.9706    1.0608    0.8825 N   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8430   -2.1379   -2.1575 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1110   -3.1796   -0.7124 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.3737   -2.0971   -0.7664 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.3912   -2.1090   -0.9463 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7015   -0.3185    0.0735 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6356    1.6433    1.1529 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0322    1.8803    1.6748 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5755    2.3792    2.2395 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0087    2.9318    0.6484 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0544    1.6710   -0.9349 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1272    0.1130   -1.7896 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.4090    0.8777   -1.1286 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6077   -1.4968    0.6541 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6976   -1.6218   -1.1313 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1640   -1.1586   -0.1596 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9664    2.0802    0.8944 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6290    0.5761    1.7108 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0
  2  3  2  0
  3  4  1  0
  4  5  2  0
  5  6  1  0
  6  7  1  0
  6  8  2  0
  8  9  1  0
  9 10  1  0
 10 11  1  0
 11 12  1  0
 11 13  1  0
  8  2  1  0
  1 14  1  0
  1 15  1  0
  1 16  1  0
  3 17  1  0
  4 18  1  0
  5 19  1  0
  7 20  1  0
  7 21  1  0
  7 22  1  0
 10 23  1  0
 10 24  1  0
 11 25  1  0
 12 26  1  0
 12 27  1  0
 12 28  1  0
 13 29  1  0
 13 30  1  0
M  END
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PDB for HMDB0014523 (Mexiletine)

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 379                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0       5.748   0.293   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       8.415   3.373   0.000  0.00  0.00           N+0
HETATM    3  C   UNK     0       7.081   2.603   0.000  0.00  0.00           C+0
HETATM    4  C   UNK     0       7.081   1.063   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0       5.748  -1.247   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       7.081  -2.017   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0       4.414  -2.017   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       5.748   3.373   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081  -3.557   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       4.414  -3.557   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748  -4.327   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       8.415  -1.247   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       3.080  -1.247   0.000  0.00  0.00           C+0
CONECT    1    4    5                                                       
CONECT    2    3                                                            
CONECT    3    2    4    8                                                  
CONECT    4    1    3                                                       
CONECT    5    1    6    7                                                  
CONECT    6    5    9   12                                                  
CONECT    7    5   10   13                                                  
CONECT    8    3                                                            
CONECT    9    6   11                                                       
CONECT   10    7   11                                                       
CONECT   11    9   10                                                       
CONECT   12    6                                                            
CONECT   13    7                                                            
MASTER        0    0    0    0    0    0    0    0   13    0   26    0
END
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3D PDB for HMDB0014523 (Mexiletine)

COMPND    HMDB0014523
HETATM    1  C1  UNL     1      -1.401   1.769  -1.638  1.00  0.00           C  
HETATM    2  C2  UNL     1      -1.924   0.855  -0.588  1.00  0.00           C  
HETATM    3  C3  UNL     1      -3.174   0.974  -0.030  1.00  0.00           C  
HETATM    4  C4  UNL     1      -3.666   0.133   0.941  1.00  0.00           C  
HETATM    5  C5  UNL     1      -2.842  -0.888   1.371  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.562  -1.062   0.843  1.00  0.00           C  
HETATM    7  C7  UNL     1      -0.673  -2.159   1.302  1.00  0.00           C  
HETATM    8  C8  UNL     1      -1.127  -0.184  -0.129  1.00  0.00           C  
HETATM    9  O1  UNL     1       0.132  -0.325  -0.674  1.00  0.00           O  
HETATM   10  C9  UNL     1       1.205   0.356  -0.053  1.00  0.00           C  
HETATM   11  C10 UNL     1       2.514   0.097  -0.771  1.00  0.00           C  
HETATM   12  C11 UNL     1       3.627   0.813  -0.035  1.00  0.00           C  
HETATM   13  N1  UNL     1       2.828  -1.321  -0.772  1.00  0.00           N  
HETATM   14  H1  UNL     1      -1.029   2.720  -1.221  1.00  0.00           H  
HETATM   15  H2  UNL     1      -2.209   1.976  -2.384  1.00  0.00           H  
HETATM   16  H3  UNL     1      -0.589   1.281  -2.202  1.00  0.00           H  
HETATM   17  H4  UNL     1      -3.808   1.773  -0.372  1.00  0.00           H  
HETATM   18  H5  UNL     1      -4.654   0.236   1.375  1.00  0.00           H  
HETATM   19  H6  UNL     1      -3.193  -1.578   2.140  1.00  0.00           H  
HETATM   20  H7  UNL     1      -0.337  -2.744   0.397  1.00  0.00           H  
HETATM   21  H8  UNL     1       0.180  -1.828   1.889  1.00  0.00           H  
HETATM   22  H9  UNL     1      -1.330  -2.884   1.864  1.00  0.00           H  
HETATM   23  H10 UNL     1       1.295   0.113   1.026  1.00  0.00           H  
HETATM   24  H11 UNL     1       1.021   1.455  -0.101  1.00  0.00           H  
HETATM   25  H12 UNL     1       2.471   0.509  -1.786  1.00  0.00           H  
HETATM   26  H13 UNL     1       3.566   0.466   1.036  1.00  0.00           H  
HETATM   27  H14 UNL     1       3.460   1.913  -0.016  1.00  0.00           H  
HETATM   28  H15 UNL     1       4.606   0.607  -0.475  1.00  0.00           H  
HETATM   29  H16 UNL     1       2.804  -1.662   0.211  1.00  0.00           H  
HETATM   30  H17 UNL     1       3.809  -1.410  -1.146  1.00  0.00           H  
CONECT    1    2   14   15   16
CONECT    2    3    3    8
CONECT    3    4   17
CONECT    4    5    5   18
CONECT    5    6   19
CONECT    6    7    8    8
CONECT    7   20   21   22
CONECT    8    9
CONECT    9   10
CONECT   10   11   23   24
CONECT   11   12   13   25
CONECT   12   26   27   28
CONECT   13   29   30
END
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SMILES for HMDB0014523 (Mexiletine)

CC(N)COC1=C(C)C=CC=C1C
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INCHI for HMDB0014523 (Mexiletine)

InChI=1S/C11H17NO/c1-8-5-4-6-9(2)11(8)13-7-10(3)12/h4-6,10H,7,12H2,1-3H3
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Synonyms
ValueSource
(+-)-1-(2,6-Dimethylphenoxy)propan-2-amineChEBI
(2Rs)-1-(2,6-Dimethylphenoxy)-2-aminopropaneChEBI
1-(2',6'-Dimethylphenoxy)-2-aminopropaneChEBI
1-(2,6-Dimethylphenoxy)-2-propanamineChEBI
1-Methyl-2-(2,6-xylyloxy)ethanamineChEBI
MexiletinaChEBI
MexiletinumChEBI
MexilitineHMDB
MexileteneHMDB
Mexitil PLHMDB
Novo mexiletineHMDB
Novo-mexiletineHMDB
MexitilHMDB
MexitylHMDB
Boehringer ingelheim brand OF mexiletine hydrochlorideHMDB
Mexiletine hydrochlorideHMDB
Novopharm brand OF mexiletine hydrochlorideHMDB
Chemical FormulaC11H17NO
Average Molecular Weight179.2588
Monoisotopic Molecular Weight179.131014171
IUPAC Name1-(2,6-dimethylphenoxy)propan-2-amine
Traditional Name1-(2,6-dimethylphenoxy)propan-2-amine
CAS Registry Number31828-71-4
SMILES
CC(N)COC1=C(C)C=CC=C1C
InChI Identifier
InChI=1S/C11H17NO/c1-8-5-4-6-9(2)11(8)13-7-10(3)12/h4-6,10H,7,12H2,1-3H3
InChI KeyVLPIATFUUWWMKC-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenol ethers. These are aromatic compounds containing an ether group substituted with a benzene ring.
KingdomOrganic compounds
Super ClassBenzenoids
ClassPhenol ethers
Sub ClassNot Available
Direct ParentPhenol ethers
Alternative Parents
Substituents
  • Phenol ether
  • Xylene
  • M-xylene
  • Phenoxy compound
  • Alkyl aryl ether
  • Monocyclic benzene moiety
  • Ether
  • Amine
  • Hydrocarbon derivative
  • Primary amine
  • Organooxygen compound
  • Organonitrogen compound
  • Primary aliphatic amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Biological location
Process
Naturally occurring process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point203 - 205 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.54 g/LNot Available
LogP2.1Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.54 g/LALOGPS
logP2.17ALOGPS
logP2.46ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)9.52ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area35.25 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity54.97 m³·mol⁻¹ChemAxon
Polarizability21.17 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+140.90431661259
DarkChem[M-H]-137.09731661259
DeepCCS[M+H]+141.89230932474
DeepCCS[M-H]-139.24830932474
DeepCCS[M-2H]-175.10130932474
DeepCCS[M+Na]+150.57630932474
AllCCS[M+H]+140.432859911
AllCCS[M+H-H2O]+136.232859911
AllCCS[M+NH4]+144.232859911
AllCCS[M+Na]+145.432859911
AllCCS[M-H]-143.232859911
AllCCS[M+Na-2H]-144.332859911
AllCCS[M+HCOO]-145.632859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MexiletineCC(N)COC1=C(C)C=CC=C1C1849.7Standard polar33892256
MexiletineCC(N)COC1=C(C)C=CC=C1C1442.9Standard non polar33892256
MexiletineCC(N)COC1=C(C)C=CC=C1C1417.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Mexiletine,1TMS,isomer #1CC1=CC=CC(C)=C1OCC(C)N[Si](C)(C)C1599.1Semi standard non polar33892256
Mexiletine,1TMS,isomer #1CC1=CC=CC(C)=C1OCC(C)N[Si](C)(C)C1575.2Standard non polar33892256
Mexiletine,1TMS,isomer #1CC1=CC=CC(C)=C1OCC(C)N[Si](C)(C)C1880.7Standard polar33892256
Mexiletine,2TMS,isomer #1CC1=CC=CC(C)=C1OCC(C)N([Si](C)(C)C)[Si](C)(C)C1818.8Semi standard non polar33892256
Mexiletine,2TMS,isomer #1CC1=CC=CC(C)=C1OCC(C)N([Si](C)(C)C)[Si](C)(C)C1769.6Standard non polar33892256
Mexiletine,2TMS,isomer #1CC1=CC=CC(C)=C1OCC(C)N([Si](C)(C)C)[Si](C)(C)C1932.4Standard polar33892256
Mexiletine,1TBDMS,isomer #1CC1=CC=CC(C)=C1OCC(C)N[Si](C)(C)C(C)(C)C1813.6Semi standard non polar33892256
Mexiletine,1TBDMS,isomer #1CC1=CC=CC(C)=C1OCC(C)N[Si](C)(C)C(C)(C)C1803.8Standard non polar33892256
Mexiletine,1TBDMS,isomer #1CC1=CC=CC(C)=C1OCC(C)N[Si](C)(C)C(C)(C)C2028.6Standard polar33892256
Mexiletine,2TBDMS,isomer #1CC1=CC=CC(C)=C1OCC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2260.2Semi standard non polar33892256
Mexiletine,2TBDMS,isomer #1CC1=CC=CC(C)=C1OCC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2200.4Standard non polar33892256
Mexiletine,2TBDMS,isomer #1CC1=CC=CC(C)=C1OCC(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C2141.5Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Mexiletine EI-B (Non-derivatized)splash10-0a4i-9100000000-6d40293ed4e486f9cf9e2017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mexiletine CI-B (Non-derivatized)splash10-0a4i-9300000000-147905f020f0139cfe202017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mexiletine EI-B (Non-derivatized)splash10-0a4i-9100000000-6d40293ed4e486f9cf9e2018-05-18HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Mexiletine CI-B (Non-derivatized)splash10-0a4i-9300000000-147905f020f0139cfe202018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mexiletine GC-MS (Non-derivatized) - 70eV, Positivesplash10-006x-9400000000-e9948c49f03b5a215db02017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mexiletine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Mexiletine GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine LC-ESI-qTof , Positive-QTOFsplash10-01q9-0900000000-083bab651324c62f4cd52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine LC-ESI-qTof , Positive-QTOFsplash10-01q9-0900000000-feace6e16ed93a4bd13e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine LC-ESI-QFT , positive-QTOFsplash10-0a4i-9400000000-d9f9d0eeea2a47e427712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine LC-ESI-QFT , positive-QTOFsplash10-0a4i-9300000000-76838bfcf2fd2b0e2b172017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine LC-ESI-QFT , positive-QTOFsplash10-0a4i-9400000000-c5920fd67439f418b86f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine LC-ESI-QFT , positive-QTOFsplash10-0a4i-9500000000-b5f13a7a078d1c1926912017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine LC-ESI-QFT , positive-QTOFsplash10-0a4i-9500000000-24a61cef86793ffcf7602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine LC-ESI-QFT , positive-QTOFsplash10-0a4i-9400000000-d740cc5fc7a9b2b380a62017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine , positive-QTOFsplash10-01q9-0900000000-083bab651324c62f4cd52017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine , positive-QTOFsplash10-01q9-0900000000-feace6e16ed93a4bd13e2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine LC-ESI-QFT , positive-QTOFsplash10-0a4i-9400000000-94985b5db6692d6159712017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine LC-ESI-QFT , positive-QTOFsplash10-0a4i-9300000000-c1e103780c7df279dc6c2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine LC-ESI-QFT , positive-QTOFsplash10-0a4i-9400000000-d077857c1d4a1d567c032017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine LC-ESI-QFT , positive-QTOFsplash10-0a4i-9500000000-9ef54de393ed768d242f2017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine LC-ESI-QFT , positive-QTOFsplash10-0a4i-9500000000-9a364fda721f96e6e3682017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine 45V, Positive-QTOFsplash10-0a4i-9400000000-6b280de493776a9dc2422021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine 60V, Positive-QTOFsplash10-0a4i-9500000000-be0a7f708a3a6a0bccd02021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine 30V, Positive-QTOFsplash10-0a4i-9300000000-bacd798fb571787177122021-09-20HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Mexiletine 15V, Positive-QTOFsplash10-0a4i-9300000000-320ad3be57ff9aced9a92021-09-20HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mexiletine 10V, Positive-QTOFsplash10-001i-1900000000-939b7c3be7e71365188c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mexiletine 20V, Positive-QTOFsplash10-0a4i-9400000000-16d73c9c92a1487bbc7c2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mexiletine 40V, Positive-QTOFsplash10-052f-9200000000-9a25be6ae97cd157924e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mexiletine 10V, Negative-QTOFsplash10-004i-0900000000-3aee50267bd861738c2e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mexiletine 20V, Negative-QTOFsplash10-00di-0900000000-d552a69206ce56dd07b02016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Mexiletine 40V, Negative-QTOFsplash10-00di-3900000000-c2586c04dbdd926fce0c2016-08-03Wishart LabView Spectrum

IR Spectra

Spectrum TypeDescriptionDeposition DateSourceView
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)2023-02-03FELIX labView Spectrum
Predicted IR SpectrumIR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)2023-02-03FELIX labView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00379 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00379 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00379
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4034
KEGG Compound IDC07220
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMexiletine
METLIN IDNot Available
PubChem Compound4178
PDB IDNot Available
ChEBI ID6916
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

Enzyme Details
1. Cytochrome P450 3A4
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 performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. Acts as a 1,8-cineole 2-exo-monooxygenase. The enzyme also hydroxylates etoposide.
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular weight:
57255.585
References
  1. 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 2E1
General function:
Involved in monooxygenase activity
Specific function:
Metabolizes several precarcinogens, drugs, and solvents to reactive metabolites. Inactivates a number of drugs and xenobiotics and also bioactivates many xenobiotic substrates to their hepatotoxic or carcinogenic forms.
Gene Name:
CYP2E1
Uniprot ID:
P05181
Molecular weight:
56848.42
References
  1. 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. 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
  1. 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 ]
  2. Nakajima M, Kobayashi K, Shimada N, Tokudome S, Yamamoto T, Kuroiwa Y: Involvement of CYP1A2 in mexiletine metabolism. Br J Clin Pharmacol. 1998 Jul;46(1):55-62. [PubMed:9690950 ]
Enzyme Details
4. Cytochrome P450 2B6
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. Acts as a 1,4-cineole 2-exo-monooxygenase.
Gene Name:
CYP2B6
Uniprot ID:
P20813
Molecular weight:
56277.81
References
  1. 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
5. Cytochrome P450 1A2
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. Most active in catalyzing 2-hydroxylation. Caffeine is metabolized primarily by cytochrome CYP1A2 in the liver through an initial N3-demethylation. Also acts in the metabolism of aflatoxin B1 and acetaminophen. Participates in the bioactivation of carcinogenic aromatic and heterocyclic amines. Catalizes the N-hydroxylation of heterocyclic amines and the O-deethylation of phenacetin.
Gene Name:
CYP1A2
Uniprot ID:
P05177
Molecular weight:
58406.915
References
  1. 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 ]
  2. Nakajima M, Kobayashi K, Shimada N, Tokudome S, Yamamoto T, Kuroiwa Y: Involvement of CYP1A2 in mexiletine metabolism. Br J Clin Pharmacol. 1998 Jul;46(1):55-62. [PubMed:9690950 ]
Enzyme Details
6. Aryl hydrocarbon receptor
General function:
Involved in transcription regulator activity
Specific function:
Ligand-activated transcriptional activator. Binds to the XRE promoter region of genes it activates. Activates the expression of multiple phase I and II xenobiotic chemical metabolizing enzyme genes (such as the CYP1A1 gene). Mediates biochemical and toxic effects of halogenated aromatic hydrocarbons. Involved in cell-cycle regulation. Likely to play an important role in the development and maturation of many tissues
Gene Name:
AHR
Uniprot ID:
P35869
Molecular weight:
96146.7
References
  1. Hu W, Sorrentino C, Denison MS, Kolaja K, Fielden MR: Induction of cyp1a1 is a nonspecific biomarker of aryl hydrocarbon receptor activation: results of large scale screening of pharmaceuticals and toxicants in vivo and in vitro. Mol Pharmacol. 2007 Jun;71(6):1475-86. Epub 2007 Feb 27. [PubMed:17327465 ]
Enzyme Details
7. 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
  1. Valdivia CR, Ackerman MJ, Tester DJ, Wada T, McCormack J, Ye B, Makielski JC: A novel SCN5A arrhythmia mutation, M1766L, with expression defect rescued by mexiletine. Cardiovasc Res. 2002 Aug 1;55(2):279-89. [PubMed:12123767 ]
  2. Chinushi M, Tagawa M, Sugiura H, Komura S, Hosaka Y, Washizuka T, Aizawa Y: Ventricular tachyarrhythmias in a canine model of LQT3: arrhythmogenic effects of sympathetic activity and therapeutic effects of mexiletine. Circ J. 2003 Mar;67(3):263-8. [PubMed:12604879 ]
  3. Fabritz L, Kirchhof P, Franz MR, Nuyens D, Rossenbacker T, Ottenhof A, Haverkamp W, Breithardt G, Carmeliet E, Carmeliet P: Effect of pacing and mexiletine on dispersion of repolarisation and arrhythmias in DeltaKPQ SCN5A (long QT3) mice. Cardiovasc Res. 2003 Mar 15;57(4):1085-93. [PubMed:12650887 ]
  4. Wang HW, Zheng YQ, Yang ZF, Li CZ, Liu YM: Effect of mexiletine on long QT syndrome model. Acta Pharmacol Sin. 2003 Apr;24(4):316-20. [PubMed:12676070 ]
  5. Napolitano C, Bloise R, Priori SG: Gene-specific therapy for inherited arrhythmogenic diseases. Pharmacol Ther. 2006 Apr;110(1):1-13. Epub 2005 Sep 15. [PubMed:16168489 ]
  6. 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 ]
  7. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]