Details of the Metabolic Reaction (MR)

General Information of This Metabolic Reaction (MR) (ID: MR000491)
Formula
CYP3A4 ...
SVG example
Hydroxylation
Reactant Bupivacaine hydrochloride Product Hydroxybuprenorphine
Reactant Info Product Info
Metabolic Enzyme Cytochrome P450 3A4 (CYP3A4) DME Info
Cytochrome P450 3A5 (CYP3A5) DME Info
Cytochrome P450 3A7 (CYP3A7) DME Info
Metabolic Type Oxidation - Hydroxylation
Other MR(s) Related to The Reactant of This MR
Other MR(s) That Metabolize The Reactant of This MR
MR ID Reactant Product MR Type Related Drug REF
MR000480 Bupivacaine hydrochloride 3'-OH-bupivacaine Oxidation - Hydroxylation Bupivacaine hydrochloride [1]
MR000478 Bupivacaine hydrochloride 4'-OH-bupivacaine Oxidation - Hydroxylation Bupivacaine hydrochloride [2]
MR000482 Bupivacaine hydrochloride Bupivacaine hydrochloride metabolite B1 Oxidation - Hydroxylation Bupivacaine hydrochloride [1]
MR000483 Bupivacaine hydrochloride Bupivacaine hydrochloride metabolite B4 Oxidation - Oxidation Bupivacaine hydrochloride [1]
MR000484 Bupivacaine hydrochloride Bupivacaine hydrochloride metabolite B5 Oxidation - Hydroxylation Bupivacaine hydrochloride [1]
MR000492 Bupivacaine hydrochloride Buprenorphine glucuronide Conjugation - Glucuronidation Buprenorphine hydrochloride [3], [4], [5], [6]
MR000479 Bupivacaine hydrochloride Dihydroxybupivacaine Oxidation - Hydroxylation Bupivacaine hydrochloride [1]
MR000481 Bupivacaine hydrochloride N-desbutylbupivacaine Unclear Bupivacaine hydrochloride [1]
MR000485 Bupivacaine hydrochloride Sulfated hydroxy bupivacaine Conjugation - Sulfation Bupivacaine hydrochloride [1]
Other MR(s) Related to The Product of This MR
Other MR(s) That Metabolize The Produtc of This MR
MR ID Reactant Product MR Type Related Drug REF
MR000489 Hydroxybuprenorphine Hydroxynorbuprenorphine Oxidation - N-Dealkylation Buprenorphine hydrochloride [3]
References
1 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.
2 Oxidative metabolism of bupivacaine into pipecolylxylidine in humans is mainly catalyzed by CYP3A. Drug Metab Dispos. 2000 Apr;28(4):383-5.
3 In vitro metabolism study of buprenorphine: evidence for new metabolic pathways. Drug Metab Dispos. 2005 May;33(5):689-95.
4 Contribution of the different UDP-glucuronosyltransferase (UGT) isoforms to buprenorphine and norbuprenorphine metabolism and relationship with the main UGT polymorphisms in a bank of human liver microsomes. Drug Metab Dispos. 2010 Jan;38(1):40-5.
5 Interaction between buprenorphine and norbuprenorphine in neonatal opioid withdrawal syndrome. Drug Alcohol Depend. 2023 Jun 21;249:110832. doi: 10.1016/j.drugalcdep.2023.110832.
6 Determination of buprenorphine, norbuprenorphine, naloxone, and their glucuronides in urine by liquid chromatography-tandem mass spectrometry. Drug Test Anal. 2021 Sep;13(9):1658-1667. doi: 10.1002/dta.3104.

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