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Record Information

Version

5.0

Status

Expected but not Quantified

Creation Date

2012-09-06 15:16:49 UTC

Update Date

2022-03-07 02:51:37 UTC

HMDB ID

HMDB0014442

Secondary Accession Numbers

HMDB14442

Metabolite Identification

Common Name

Bupivacaine

Description

Bupivacaine is only found in individuals that have used or taken this drug. It is a widely used local anesthetic agent. [PubChem]Bupivacaine blocks the generation and the conduction of nerve impulses, presumably by increasing the threshold for electrical excitation in the nerve, by slowing the propagation of the nerve impulse, and by reducing the rate of rise of the action potential. Bupivacaine binds to the intracellular portion of sodium channels and blocks sodium influx into nerve cells, which prevents depolarization. In general, the progression of anesthesia is related to the diameter, myelination and conduction velocity of affected nerve fibers. Clinically, the order of loss of nerve function is as follows: (1) pain, (2) temperature, (3) touch, (4) proprioception, and (5) skeletal muscle tone. The analgesic effects of Bupivicaine are thought to potentially be due to its binding to the prostaglandin E2 receptors, subtype EP1 (PGE2EP1), which inhibits the production of prostaglandins, thereby reducing fever, inflammation, and hyperalgesia.

Structure

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

HMDB0243533
     RDKit          3D
Dextrobupivacaine
 49 50  0  0  0  0  0  0  0  0999 V2000
   -3.3053    2.7983   -0.7779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3094    1.7176   -0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6371    0.3630   -0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4780    0.2878    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8241   -0.9551    0.4668 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4965   -2.0848    0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764   -3.2334    1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8592   -3.5741   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0555   -2.4093   -0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429   -1.0637   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -0.1817    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2642    0.5521    1.1635 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6715   -0.1927   -0.4943 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7847    0.6244   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8441    1.8724   -0.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8360    2.3567   -1.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8844    2.6910   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8467    2.2613    0.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7545    1.0068    1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6972    0.1651    0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6002   -1.1817    1.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8222    3.7475   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7720    2.4608   -1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455    2.9132    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7755    1.9180    0.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0848    1.7393   -1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3867   -0.4298   -0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998    0.2095   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8980    0.5779    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7596    1.0779    0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0743   -1.8312    1.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987   -2.4427    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8082   -2.8894    1.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266   -4.1298    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1820   -4.4270    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5575   -3.9027   -0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1722   -2.5765   -1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9717   -2.5002   -0.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9036   -0.6566   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437   -0.8040   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326    1.5280   -2.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3621    3.0323   -2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0033    2.8938   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0135    3.6826   -0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6631    2.9248    0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164    0.6896    1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874   -1.9027    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6381   -1.5429    1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0495   -1.1798    2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 10  5  1  0
 20 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 13 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
M  END

297
  Mrv0541 02231214352D          

 21 22  0  0  1  0            999 V2000
    5.9370   -0.2063    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    1.4438    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -0.2063    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370    2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224    0.2063    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.3645    1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6500    1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -1.4438    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.2224   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.7935   -2.2688    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.9370   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.0791   -1.0313    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.5080   -2.6813    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1 10  2  0  0  0  0
  2  4  1  0  0  0  0
  2  6  1  0  0  0  0
  2  9  1  0  0  0  0
  3 10  1  0  0  0  0
  3 13  1  0  0  0  0
  4  5  1  0  0  0  0
  4 10  1  0  0  0  0
  5  7  1  0  0  0  0
  6  8  1  0  0  0  0
  7  8  1  0  0  0  0
  9 11  1  0  0  0  0
 11 12  1  0  0  0  0
 12 14  1  0  0  0  0
 13 15  2  0  0  0  0
 13 16  1  0  0  0  0
 15 17  1  0  0  0  0
 15 19  1  0  0  0  0
 16 18  2  0  0  0  0
 16 20  1  0  0  0  0
 17 21  2  0  0  0  0
 18 21  1  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0014442

> <DATABASE_NAME>
hmdb

> <SMILES>
CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C

> <INCHI_IDENTIFIER>
InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)

> <INCHI_KEY>
LEBVLXFERQHONN-UHFFFAOYSA-N

> <FORMULA>
C18H28N2O

> <MOLECULAR_WEIGHT>
288.4277

> <EXACT_MASS>
288.220163528

> <JCHEM_ACCEPTOR_COUNT>
2

> <JCHEM_AVERAGE_POLARIZABILITY>
34.194430336787995

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

> <ALOGPS_LOGP>
3.31

> <JCHEM_LOGP>
4.515518884333334

> <ALOGPS_LOGS>
-3.47

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
2

> <JCHEM_PHYSIOLOGICAL_CHARGE>
1

> <JCHEM_PKA_STRONGEST_ACIDIC>
13.623539229353206

> <JCHEM_PKA_STRONGEST_BASIC>
8.003403055870814

> <JCHEM_POLAR_SURFACE_AREA>
32.34

> <JCHEM_REFRACTIVITY>
90.19330000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
5

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
9.77e-02 g/l

> <JCHEM_TRADITIONAL_IUPAC>
bupivacaine

> <JCHEM_VEBER_RULE>
1

$$$$

HMDB0243533
     RDKit          3D
Dextrobupivacaine
 49 50  0  0  0  0  0  0  0  0999 V2000
   -3.3053    2.7983   -0.7779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3094    1.7176   -0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6371    0.3630   -0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4780    0.2878    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8241   -0.9551    0.4668 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4965   -2.0848    0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764   -3.2334    1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8592   -3.5741   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0555   -2.4093   -0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429   -1.0637   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -0.1817    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2642    0.5521    1.1635 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6715   -0.1927   -0.4943 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7847    0.6244   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8441    1.8724   -0.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8360    2.3567   -1.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8844    2.6910   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8467    2.2613    0.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7545    1.0068    1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6972    0.1651    0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6002   -1.1817    1.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8222    3.7475   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7720    2.4608   -1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455    2.9132    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7755    1.9180    0.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0848    1.7393   -1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3867   -0.4298   -0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998    0.2095   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8980    0.5779    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7596    1.0779    0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0743   -1.8312    1.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987   -2.4427    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8082   -2.8894    1.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266   -4.1298    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1820   -4.4270    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5575   -3.9027   -0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1722   -2.5765   -1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9717   -2.5002   -0.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9036   -0.6566   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437   -0.8040   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326    1.5280   -2.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3621    3.0323   -2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0033    2.8938   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0135    3.6826   -0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6631    2.9248    0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164    0.6896    1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874   -1.9027    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6381   -1.5429    1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0495   -1.1798    2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 10  5  1  0
 20 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 13 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
M  END

HEADER    PROTEIN                                 23-FEB-12   NONE
TITLE     NULL                                                        
COMPND    MOLECULE: 297                                               
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   23-FEB-12         0                                  
HETATM    1  O   UNK     0      11.082  -0.385   0.000  0.00  0.00           O+0
HETATM    2  N   UNK     0       8.415   2.695   0.000  0.00  0.00           N+0
HETATM    3  N   UNK     0       8.415  -0.385   0.000  0.00  0.00           N+0
HETATM    4  C   UNK     0       9.748   1.925   0.000  0.00  0.00           C+0
HETATM    5  C   UNK     0      11.082   2.695   0.000  0.00  0.00           C+0
HETATM    6  C   UNK     0       8.415   4.235   0.000  0.00  0.00           C+0
HETATM    7  C   UNK     0      11.082   4.235   0.000  0.00  0.00           C+0
HETATM    8  C   UNK     0       9.748   5.005   0.000  0.00  0.00           C+0
HETATM    9  C   UNK     0       7.081   1.925   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0       9.748   0.385   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0       5.748   2.695   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0       4.414   1.925   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0       8.415  -1.925   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0       3.080   2.695   0.000  0.00  0.00           C+0
HETATM   15  C   UNK     0       9.748  -2.695   0.000  0.00  0.00           C+0
HETATM   16  C   UNK     0       7.081  -2.695   0.000  0.00  0.00           C+0
HETATM   17  C   UNK     0       9.748  -4.235   0.000  0.00  0.00           C+0
HETATM   18  C   UNK     0       7.081  -4.235   0.000  0.00  0.00           C+0
HETATM   19  C   UNK     0      11.082  -1.925   0.000  0.00  0.00           C+0
HETATM   20  C   UNK     0       5.748  -1.925   0.000  0.00  0.00           C+0
HETATM   21  C   UNK     0       8.415  -5.005   0.000  0.00  0.00           C+0
CONECT    1   10                                                            
CONECT    2    4    6    9                                                  
CONECT    3   10   13                                                       
CONECT    4    2    5   10                                                  
CONECT    5    4    7                                                       
CONECT    6    2    8                                                       
CONECT    7    5    8                                                       
CONECT    8    6    7                                                       
CONECT    9    2   11                                                       
CONECT   10    1    3    4                                                  
CONECT   11    9   12                                                       
CONECT   12   11   14                                                       
CONECT   13    3   15   16                                                  
CONECT   14   12                                                            
CONECT   15   13   17   19                                                  
CONECT   16   13   18   20                                                  
CONECT   17   15   21                                                       
CONECT   18   16   21                                                       
CONECT   19   15                                                            
CONECT   20   16                                                            
CONECT   21   17   18                                                       
MASTER        0    0    0    0    0    0    0    0   21    0   44    0
END

COMPND    HMDB0014442
HETATM    1  C1  UNL     1       3.586   2.919  -0.028  1.00  0.00           C  
HETATM    2  C2  UNL     1       4.511   1.750   0.187  1.00  0.00           C  
HETATM    3  C3  UNL     1       3.742   0.598   0.795  1.00  0.00           C  
HETATM    4  C4  UNL     1       2.645   0.215  -0.152  1.00  0.00           C  
HETATM    5  N1  UNL     1       1.831  -0.878   0.312  1.00  0.00           N  
HETATM    6  C5  UNL     1       2.580  -2.120   0.338  1.00  0.00           C  
HETATM    7  C6  UNL     1       1.747  -3.262   0.848  1.00  0.00           C  
HETATM    8  C7  UNL     1       0.291  -3.130   0.478  1.00  0.00           C  
HETATM    9  C8  UNL     1       0.240  -2.359  -0.824  1.00  0.00           C  
HETATM   10  C9  UNL     1       0.653  -0.932  -0.502  1.00  0.00           C  
HETATM   11  C10 UNL     1      -0.487  -0.181   0.100  1.00  0.00           C  
HETATM   12  O1  UNL     1      -0.424   0.411   1.195  1.00  0.00           O  
HETATM   13  N2  UNL     1      -1.711  -0.134  -0.607  1.00  0.00           N  
HETATM   14  C11 UNL     1      -2.860   0.553  -0.125  1.00  0.00           C  
HETATM   15  C12 UNL     1      -3.083   1.881  -0.423  1.00  0.00           C  
HETATM   16  C13 UNL     1      -2.110   2.616  -1.262  1.00  0.00           C  
HETATM   17  C14 UNL     1      -4.210   2.536   0.057  1.00  0.00           C  
HETATM   18  C15 UNL     1      -5.129   1.861   0.846  1.00  0.00           C  
HETATM   19  C16 UNL     1      -4.918   0.531   1.151  1.00  0.00           C  
HETATM   20  C17 UNL     1      -3.793  -0.089   0.661  1.00  0.00           C  
HETATM   21  C18 UNL     1      -3.571  -1.503   0.985  1.00  0.00           C  
HETATM   22  H1  UNL     1       3.028   3.076   0.934  1.00  0.00           H  
HETATM   23  H2  UNL     1       2.938   2.793  -0.894  1.00  0.00           H  
HETATM   24  H3  UNL     1       4.239   3.818  -0.191  1.00  0.00           H  
HETATM   25  H4  UNL     1       4.866   1.407  -0.818  1.00  0.00           H  
HETATM   26  H5  UNL     1       5.392   2.031   0.797  1.00  0.00           H  
HETATM   27  H6  UNL     1       4.467  -0.226   0.949  1.00  0.00           H  
HETATM   28  H7  UNL     1       3.398   0.916   1.783  1.00  0.00           H  
HETATM   29  H8  UNL     1       3.110  -0.035  -1.128  1.00  0.00           H  
HETATM   30  H9  UNL     1       1.986   1.088  -0.314  1.00  0.00           H  
HETATM   31  H10 UNL     1       3.013  -2.322  -0.645  1.00  0.00           H  
HETATM   32  H11 UNL     1       3.400  -1.969   1.082  1.00  0.00           H  
HETATM   33  H12 UNL     1       1.880  -3.440   1.925  1.00  0.00           H  
HETATM   34  H13 UNL     1       2.128  -4.195   0.341  1.00  0.00           H  
HETATM   35  H14 UNL     1      -0.258  -2.621   1.287  1.00  0.00           H  
HETATM   36  H15 UNL     1      -0.203  -4.104   0.303  1.00  0.00           H  
HETATM   37  H16 UNL     1      -0.758  -2.342  -1.259  1.00  0.00           H  
HETATM   38  H17 UNL     1       1.027  -2.771  -1.476  1.00  0.00           H  
HETATM   39  H18 UNL     1       0.827  -0.444  -1.506  1.00  0.00           H  
HETATM   40  H19 UNL     1      -1.829  -0.613  -1.538  1.00  0.00           H  
HETATM   41  H20 UNL     1      -2.407   3.659  -1.385  1.00  0.00           H  
HETATM   42  H21 UNL     1      -1.118   2.585  -0.772  1.00  0.00           H  
HETATM   43  H22 UNL     1      -2.015   2.062  -2.215  1.00  0.00           H  
HETATM   44  H23 UNL     1      -4.386   3.573  -0.174  1.00  0.00           H  
HETATM   45  H24 UNL     1      -6.006   2.383   1.214  1.00  0.00           H  
HETATM   46  H25 UNL     1      -5.656   0.034   1.769  1.00  0.00           H  
HETATM   47  H26 UNL     1      -4.118  -2.117   0.219  1.00  0.00           H  
HETATM   48  H27 UNL     1      -2.513  -1.810   0.933  1.00  0.00           H  
HETATM   49  H28 UNL     1      -3.962  -1.696   2.001  1.00  0.00           H  
CONECT    1    2   22   23   24
CONECT    2    3   25   26
CONECT    3    4   27   28
CONECT    4    5   29   30
CONECT    5    6   10
CONECT    6    7   31   32
CONECT    7    8   33   34
CONECT    8    9   35   36
CONECT    9   10   37   38
CONECT   10   11   39
CONECT   11   12   12   13
CONECT   13   14   40
CONECT   14   15   15   20
CONECT   15   16   17
CONECT   16   41   42   43
CONECT   17   18   18   44
CONECT   18   19   45
CONECT   19   20   20   46
CONECT   20   21
CONECT   21   47   48   49
END

HMDB0243533
     RDKit          3D
Dextrobupivacaine
 49 50  0  0  0  0  0  0  0  0999 V2000
   -3.3053    2.7983   -0.7779 C   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3094    1.7176   -0.4377 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.6371    0.3630   -0.5019 C   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4780    0.2878    0.4931 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.8241   -0.9551    0.4668 N   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4965   -2.0848    0.9182 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5764   -3.2334    1.2444 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8592   -3.5741   -0.0496 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.0555   -2.4093   -0.4981 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.6429   -1.0637   -0.2957 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4421   -0.1817    0.1823 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.2642    0.5521    1.1635 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.6715   -0.1927   -0.4943 N   0  0  0  0  0  0  0  0  0  0  0  0
    2.7847    0.6244   -0.1101 C   0  0  0  0  0  0  0  0  0  0  0  0
    2.8441    1.8724   -0.7055 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.8360    2.3567   -1.6814 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.8844    2.6910   -0.3740 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.8467    2.2613    0.5405 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.7545    1.0068    1.1155 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6972    0.1651    0.7830 C   0  0  0  0  0  0  0  0  0  0  0  0
    3.6002   -1.1817    1.3997 C   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8222    3.7475   -1.0027 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7720    2.4608   -1.7084 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.6455    2.9132    0.0831 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.7755    1.9180    0.5458 H   0  0  0  0  0  0  0  0  0  0  0  0
   -5.0848    1.7393   -1.2256 H   0  0  0  0  0  0  0  0  0  0  0  0
   -4.3867   -0.4298   -0.2919 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.2998    0.2095   -1.5465 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8980    0.5779    1.4755 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7596    1.0779    0.1347 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.0743   -1.8312    1.8524 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.1987   -2.4427    0.1074 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8082   -2.8894    1.9598 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.1266   -4.1298    1.5659 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1820   -4.4270    0.1595 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.5575   -3.9027   -0.8415 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.1722   -2.5765   -1.5934 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9717   -2.5002   -0.0296 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9036   -0.6566   -1.3259 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.8437   -0.8040   -1.3243 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4326    1.5280   -2.3182 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3621    3.0323   -2.3880 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.0033    2.8938   -1.1812 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0135    3.6826   -0.7878 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.6631    2.9248    0.7890 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.5164    0.6896    1.8286 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.1874   -1.9027    0.6636 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.6381   -1.5429    1.6554 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.0495   -1.1798    2.3635 H   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  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
 10 11  1  0
 11 12  2  0
 11 13  1  0
 13 14  1  0
 14 15  2  0
 15 16  1  0
 15 17  1  0
 17 18  2  0
 18 19  1  0
 19 20  2  0
 20 21  1  0
 10  5  1  0
 20 14  1  0
  1 22  1  0
  1 23  1  0
  1 24  1  0
  2 25  1  0
  2 26  1  0
  3 27  1  0
  3 28  1  0
  4 29  1  0
  4 30  1  0
  6 31  1  0
  6 32  1  0
  7 33  1  0
  7 34  1  0
  8 35  1  0
  8 36  1  0
  9 37  1  0
  9 38  1  0
 10 39  1  0
 13 40  1  0
 16 41  1  0
 16 42  1  0
 16 43  1  0
 17 44  1  0
 18 45  1  0
 19 46  1  0
 21 47  1  0
 21 48  1  0
 21 49  1  0
M  END

View in JSmol View Stereo Labels

Synonyms

Value	Source
Bupivacaina	ChEBI
Bupivacainum	ChEBI
DL-Bupivacaine	ChEBI
Marcaine	ChEBI
Bucaine	Kegg
Exparel	Kegg
(+-)-Bupivacaine	HMDB
Bloqueina	HMDB
Bupivacaine HCL	HMDB
Bupivacaine HCL kit	HMDB
CBupivacaine	HMDB
DUR-843	HMDB
LAC-43	HMDB
Braun, bupivacaina	MeSH, HMDB
Bupivacaine carbonate	MeSH, HMDB
Bupivacaine monohydrochloride, monohydrate	MeSH, HMDB
Strathmann brand OF bupivacaine hydrochloride	MeSH, HMDB
Abbott brand OF bupivacaine hydrochloride	MeSH, HMDB
Astra brand OF bupivacaine hydrochloride	MeSH, HMDB
Carbostesin	MeSH, HMDB
Dolanaest	MeSH, HMDB
Inibsa brand OF bupivacaine hydrochloride	MeSH, HMDB
Janapharm, bupivacain	MeSH, HMDB
1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide	MeSH, HMDB
Anhydrous, bupivacaine	MeSH, HMDB
Bupivacain janapharm	MeSH, HMDB
Bupivacain-RPR	MeSH, HMDB
Bupivacaina braun	MeSH, HMDB
Bupivacaine anhydrous	MeSH, HMDB
Bupivacaine hydrochloride	MeSH, HMDB
Carbonate, bupivacaine	MeSH, HMDB
Jenapharm brand OF bupivacaine hydrochloride	MeSH, HMDB
Sensorcaine	MeSH, HMDB
AstraZeneca brand OF bupivacaine hydrochloride	MeSH, HMDB
Aventis brand OF bupivacaine hydrochloride	MeSH, HMDB
Braun brand OF bupivacaine hydrochloride	MeSH, HMDB
Bupivacain RPR	MeSH, HMDB
Buvacaina	MeSH, HMDB
Hydrochloride, bupivacaine	MeSH, HMDB
Marcain	MeSH, HMDB
Pisa brand OF bupivacaine hydrochloride	MeSH, HMDB
Svedocain sin vasoconstr	MeSH, HMDB

Chemical Formula

C₁₈H₂₈N₂O

Average Molecular Weight

288.4277

Monoisotopic Molecular Weight

288.220163528

IUPAC Name

1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide

Traditional Name

bupivacaine

CAS Registry Number

2180-92-9

SMILES

CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C

InChI Identifier

InChI=1S/C18H28N2O/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21)

InChI Key

LEBVLXFERQHONN-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as alpha amino acid amides. These are amide derivatives of alpha amino acids.

Kingdom

Organic compounds

Super Class

Organic acids and derivatives

Class

Carboxylic acids and derivatives

Sub Class

Amino acids, peptides, and analogues

Direct Parent

Alpha amino acid amides

Alternative Parents

Substituents

Alpha-amino acid amide
2-piperidinecarboxamide
Piperidinecarboxamide
Anilide
M-xylene
Xylene
N-arylamide
Monocyclic benzene moiety
Benzenoid
Piperidine
Carboxamide group
Tertiary aliphatic amine
Tertiary amine
Secondary carboxylic acid amide
Azacycle
Organoheterocyclic compound
Organic nitrogen compound
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Organonitrogen compound
Organopnictogen compound
Carbonyl group
Organic oxygen compound
Amine
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

piperidinecarboxamide (CHEBI:77431 )
tertiary amino compound (CHEBI:77431 )
aromatic amide (CHEBI:77431 )

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	107 - 108 °C	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	0.098 g/L	Not Available
LogP	3.6	Not Available

Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct Type	Data Source	CCS Value (Å²)	Reference
[M+H]+	CBM	173.1	30932474
[M+H]+	Not Available	171.619	http://allccs.zhulab.cn/database/detail?ID=AllCCS00001291

Predicted Molecular Properties

Property	Value	Source
Water Solubility	0.098 g/L	ALOGPS
logP	3.31	ALOGPS
logP	4.52	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	13.62	ChemAxon
pKa (Strongest Basic)	8	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	32.34 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	90.19 m³·mol⁻¹	ChemAxon
Polarizability	34.19 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	168.446	31661259
DarkChem	[M-H]-	166.749	31661259
DeepCCS	[M+H]+	174.285	30932474
DeepCCS	[M-H]-	171.927	30932474
DeepCCS	[M-2H]-	204.813	30932474
DeepCCS	[M+Na]+	180.378	30932474
AllCCS	[M+H]+	172.8	32859911
AllCCS	[M+H-H2O]+	169.5	32859911
AllCCS	[M+NH4]+	175.8	32859911
AllCCS	[M+Na]+	176.7	32859911
AllCCS	[M-H]-	174.7	32859911
AllCCS	[M+Na-2H]-	175.2	32859911
AllCCS	[M+HCOO]-	175.9	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Bupivacaine	CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C	2726.9	Standard polar	33892256
Bupivacaine	CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C	2317.2	Standard non polar	33892256
Bupivacaine	CCCCN1CCCCC1C(=O)NC1=C(C)C=CC=C1C	2280.9	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Bupivacaine,1TMS,isomer #1	CCCCN1CCCCC1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C	2163.0	Semi standard non polar	33892256
Bupivacaine,1TMS,isomer #1	CCCCN1CCCCC1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C	2224.1	Standard non polar	33892256
Bupivacaine,1TMS,isomer #1	CCCCN1CCCCC1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C	2862.7	Standard polar	33892256
Bupivacaine,1TBDMS,isomer #1	CCCCN1CCCCC1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C	2383.9	Semi standard non polar	33892256
Bupivacaine,1TBDMS,isomer #1	CCCCN1CCCCC1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C	2453.3	Standard non polar	33892256
Bupivacaine,1TBDMS,isomer #1	CCCCN1CCCCC1C(=O)N(C1=C(C)C=CC=C1C)[Si](C)(C)C(C)(C)C	2963.4	Standard polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Bupivacaine GC-MS (Non-derivatized) - 70eV, Positive	splash10-006t-6920000000-20e4e8d5c09a52a31c75	2017-09-01	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bupivacaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Bupivacaine GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupivacaine LC-ESI-QFT , positive-QTOF	splash10-000i-0290000000-c1dbebb634be5e7e1140	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupivacaine LC-ESI-QFT , positive-QTOF	splash10-0006-0910000000-ae34de204bcb9a9deb23	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupivacaine LC-ESI-QFT , positive-QTOF	splash10-0006-0900000000-7ea7001506aae0c271a0	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupivacaine LC-ESI-QFT , positive-QTOF	splash10-0006-2900000000-ef819c5e235d6d524d8c	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupivacaine LC-ESI-QFT , positive-QTOF	splash10-0006-7900000000-22d7491053c05d773e93	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupivacaine LC-ESI-QFT , positive-QTOF	splash10-001l-9400000000-71357b8186126c5933ce	2017-09-14	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupivacaine 90V, Positive-QTOF	splash10-001l-9400000000-f152216f702642a2a96b	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupivacaine 15V, Positive-QTOF	splash10-000i-0290000000-473772a88887df5462f7	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupivacaine 45V, Positive-QTOF	splash10-0006-0900000000-73c58abee6a70ae243ed	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupivacaine 30V, Positive-QTOF	splash10-0006-0910000000-2d35aaa0fbbc69b60c7d	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupivacaine 60V, Positive-QTOF	splash10-0006-2900000000-c1144b59f68c25239771	2021-09-20	HMDB team, MONA	View Spectrum
Experimental LC-MS/MS	LC-MS/MS Spectrum - Bupivacaine 75V, Positive-QTOF	splash10-0006-7900000000-a4b8408dc9df27267589	2021-09-20	HMDB team, MONA	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupivacaine 10V, Positive-QTOF	splash10-0079-0970000000-e665f05dc8da9fafd8f0	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupivacaine 20V, Positive-QTOF	splash10-00dl-2900000000-6396ddc6fc9d5e9b6c64	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupivacaine 40V, Positive-QTOF	splash10-0ac0-9200000000-befeaee90e72918d68b3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupivacaine 10V, Negative-QTOF	splash10-000i-0290000000-e01610a30f93d9c5ec2a	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupivacaine 20V, Negative-QTOF	splash10-00ri-0970000000-e26949f880557c6da815	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupivacaine 40V, Negative-QTOF	splash10-00xr-3900000000-56dfe5d9cd7f629f17e3	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupivacaine 10V, Negative-QTOF	splash10-000i-0090000000-e83ab5b70775090159b7	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupivacaine 20V, Negative-QTOF	splash10-000i-0690000000-6ff0193988455d286726	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupivacaine 40V, Negative-QTOF	splash10-00xr-1920000000-87f1897c4a60793791d5	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupivacaine 10V, Positive-QTOF	splash10-000i-0190000000-23ffc562239624515183	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupivacaine 20V, Positive-QTOF	splash10-000g-3920000000-6aaf7d8f5f0149cec33e	2021-09-25	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Bupivacaine 40V, Positive-QTOF	splash10-0007-8900000000-e62af4b8065c6c1caf01	2021-09-25	Wishart Lab	View Spectrum

Biological Properties

Cellular Locations

Extracellular
Membrane

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Name	SMPDB/PathBank	KEGG
Bupivacaine 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 DB00297	21059682	details
Urine	Expected but not Quantified	Not Quantified	Not Available	Not Available	Taking drug identified by DrugBank entry DB00297	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

DB00297

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

2380

KEGG Compound ID

C07529

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Bupivacaine

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

77431

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

Picard J, Meek T: Lipid emulsion to treat overdose of local anaesthetic: the gift of the glob. Anaesthesia. 2006 Feb;61(2):107-9. [PubMed:16430560 ]
Rosenblatt MA, Abel M, Fischer GW, Itzkovich CJ, Eisenkraft JB: Successful use of a 20% lipid emulsion to resuscitate a patient after a presumed bupivacaine-related cardiac arrest. Anesthesiology. 2006 Jul;105(1):217-8. [PubMed:16810015 ]
eMedicine [Link]

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

Gantenbein M, Attolini L, Bruguerolle B, Villard PH, Puyoou F, Durand A, Lacarelle B, Hardwigsen J, Le-Treut YP: Oxidative metabolism of bupivacaine into pipecolylxylidine in humans is mainly catalyzed by CYP3A. Drug Metab Dispos. 2000 Apr;28(4):383-5. [PubMed:10725304 ]
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 2C19

General function:: Involved in monooxygenase activity
Specific function:: Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:: CYP2C19
Uniprot ID:: P33261
Molecular weight:: 55944.565

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. 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

4. 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

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. Prostaglandin E2 receptor EP1 subtype

General function:: Involved in G-protein coupled receptor protein signaling pathway
Specific function:: Receptor for prostaglandin E2 (PGE2). The activity of this receptor is mediated by G(q) proteins which activate a phosphatidylinositol-calcium second messenger system. May play a role as an important modulator of renal function. Implicated the smooth muscle contractile response to PGE2 in various tissues
Gene Name:: PTGER1
Uniprot ID:: P34995
Molecular weight:: 41800.7

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Beloeil H, Gentili M, Benhamou D, Mazoit JX: The effect of a peripheral block on inflammation-induced prostaglandin E2 and cyclooxygenase expression in rats. Anesth Analg. 2009 Sep;109(3):943-50. doi: 10.1213/ane.0b013e3181aff25e. [PubMed:19690271 ]

Enzyme Details

6. Sodium channel protein type 10 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 sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms
Gene Name:: SCN10A
Uniprot ID:: Q9Y5Y9
Molecular weight:: 220623.6

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
Sheets MF, Fozzard HA, Lipkind GM, Hanck DA: Sodium channel molecular conformations and antiarrhythmic drug affinity. Trends Cardiovasc Med. 2010 Jan;20(1):16-21. doi: 10.1016/j.tcm.2010.03.002. [PubMed:20685573 ]

Showing metabocard for Bupivacaine (HMDB0014442)

MOL for HMDB0014442 (Bupivacaine)

3D MOL for HMDB0014442 (Bupivacaine)

3D SDF for HMDB0014442 (Bupivacaine)

3D-SDF for HMDB0014442 (Bupivacaine)

PDB for HMDB0014442 (Bupivacaine)

3D PDB for HMDB0014442 (Bupivacaine)

SMILES for HMDB0014442 (Bupivacaine)

INCHI for HMDB0014442 (Bupivacaine)

Structure for HMDB0014442 (Bupivacaine)

3D Structure for HMDB0014442 (Bupivacaine)

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

References

References