Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0243)
Drug Name
Bupivacaine hydrochloride
Synonyms
Bupivacaine (hydrochloride); Bupivacaine HCL; Bupivacaine hydrochloride; Bupivacaine hydrochloride [JAN]; CHEBI:31322; EINECS 241-917-8; Marcain; Marcaine Spinal; Vivacaine; Anekain; Bupivacaine; Bloqueina; Bupivacaina; Bupivacaina [INN-Spanish]; Bupivacaine HCL KIT; Bupivacainum; Bupivacainum [INN-Latin]; Carbostesin; DL-Bupivacaine; Marcaine; Win 11318; bupivacaine; bupivacaine base; cBupivacaine; dl-1-Butyl-2',6'-pipecoloxylidide; (+-)-Bupivacaine; (+/-)-Bupivacaine; 1-Butyl-2',6'-pipecoloxylidide; 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide; 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide; 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-; 2180-92-9; 38396-39-3; (+-)-Bupivacaine hydrochloride; 1-Butyl-N-(2,6-dimethylphenyl)-2-piperidinecarboxamide monohydrochloride; 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride; 14252-80-3; 18010-40-7; 2',6'-Pipecoloxylidide, 1-butyl-, hydrochloride; 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride; AH-2250
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 324.9 Topological Polar Surface Area 32.299
Heavy Atom Count 22 Rotatable Bond Count 5
Hydrogen Bond Donor Count 2 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
64737
ChEBI ID
CHEBI:31322
CAS Number
18010-40-7
TTD Drug ID
D0A0FL
Formula
C18H29ClN2O
Canonical SMILES
CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl
InChI
1S/C18H28N2O.ClH/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);1H
InChIKey
SIEYLFHKZGLBNX-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
2',6'-pipecoloxylidide DM000664
115282
Unclear 1 [3]
3'-OH-bupivacaine DM000662
10380335
Oxidation - Hydroxylation 1 [3]
4'-OH-bupivacaine DM000658
162660
Oxidation - Hydroxylation 1 [2]
Bupivacaine hydrochloride metabolite B1 DM000665 N. A. Oxidation - Hydroxylation 1 [3]
Bupivacaine hydrochloride metabolite B4 DM000666
71314303
Oxidation - Oxidation 1 [3]
Bupivacaine hydrochloride metabolite B5 DM000667
66709536
Oxidation - Hydroxylation 1 [3]
Dihydroxybupivacaine DM000660 N. A. Oxidation - Hydroxylation 1 [3]
Sulfated hydroxy bupivacaine DM000668 N. A. Conjugation - Sulfation 1 [3]
3'-OH-bupivacaine glucuronide DM000663 N. A. Conjugation - Glucuronidation 2 [3]
4'-OH-bupivacaine glucuronide DM000659 N. A. Conjugation - Glucuronidation 2 [3]
Dihydroxy glucuronide DM000661 N. A. Conjugation - Glucuronidation 2 [3]
⏷ Show the Full List of 11  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000478 Bupivacaine hydrochloride 4'-OH-bupivacaine Oxidation - Hydroxylation Unclear [2]
MR000479 Bupivacaine hydrochloride Dihydroxybupivacaine Oxidation - Hydroxylation Unclear [3]
MR000480 Bupivacaine hydrochloride 3'-OH-bupivacaine Oxidation - Hydroxylation Unclear [3]
MR000481 Bupivacaine hydrochloride N-desbutylbupivacaine Unclear CYP2D6 ... [3]
MR000482 Bupivacaine hydrochloride Bupivacaine hydrochloride metabolite B1 Oxidation - Hydroxylation Unclear [3]
MR000483 Bupivacaine hydrochloride Bupivacaine hydrochloride metabolite B4 Oxidation - Oxidation Unclear [3]
MR000484 Bupivacaine hydrochloride Bupivacaine hydrochloride metabolite B5 Oxidation - Hydroxylation Unclear [3]
MR000485 Bupivacaine hydrochloride Sulfated hydroxy bupivacaine Conjugation - Sulfation Unclear [3]
MR000477 3'-OH-bupivacaine 3'-OH-bupivacaine glucuronide Conjugation - Glucuronidation Unclear [3]
MR000475 4'-OH-bupivacaine 4'-OH-bupivacaine glucuronide Conjugation - Glucuronidation Unclear [3]
MR000476 Dihydroxybupivacaine Dihydroxy glucuronide Conjugation - Glucuronidation Unclear [3]
⏷ Show the Full List of 11 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[2]
References
1 Bupivacaine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Oxidative metabolism of bupivacaine into pipecolylxylidine in humans is mainly catalyzed by CYP3A. Drug Metab Dispos. 2000 Apr;28(4):383-5.
3 Structural elucidation of phase I and II metabolites of bupivacaine in horse urine and fungi of the Cunninghamella species using liquid chromatography/multi-stage mass spectrometry Rapid Commun Mass Spectrom. 2012 Jun 15;26(11):1338-46. doi: 10.1002/rcm.6225.

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