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

General Information of Drug (ID: DR0246)
Drug Name
Buprenorphine hydrochloride
Synonyms
Belbuca; Buprenex (TN); Buprenorphine; Buprenorphine Depot; Buprex; CHEBI:652822; CL 112,302; CL 112302; CL-112302; EINECS 258-396-8; Finibron; MR 56; NIH 8805; NIH-8805; Norspan; RX 6029-M; RX 6029-M HCl; RX-6029-M; Transtec; UM 952; UM-952; UNII-56W8MW3EN1; Buprenex; Buprenophine; Buprenorfina; Buprenorfina [INN-Spanish]; Buprenorphinum; Buprenorphinum [INN-Latin]; CAM2038; CHEBI:3216; EINECS 257-950-6; Probuphenine; Probuphine; RX 6029M; Temgesic (TN); UNII-40D3SCR4GZ; (-)-buprenorphine; 21-cyclopropyl-7alpha-[(S)-1-hydroxy-1,2,2-trimethylpropyl]-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine; 40D3SCR4GZ; 6029-M; Buprel; 21-Cyclopropyl-7alpha-((S)-1-hydroxy-1,2,2-trimethylpropyl)-6,14-endo-ethano-6,7,8,14-tetrahydrooripavine hydrochloride; 53152-21-9; 56W8MW3EN1; BEMA LA; BEMA-buprenorphine; BUPRENORPHINE HYDROCHLORIDE
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 504.1 Topological Polar Surface Area 62.2
Heavy Atom Count 35 Rotatable Bond Count 5
Hydrogen Bond Donor Count 3 Hydrogen Bond Acceptor Count 5
Cross-matching ID
PubChem CID
3033050
ChEBI ID
CHEBI:652822
CAS Number
53152-21-9
TTD Drug ID
D06AWE
Formula
C29H42ClNO4
Canonical SMILES
CC(C)(C)C(C)(C1CC23CCC1(C4C25CCN(C3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)O.Cl
InChI
1S/C29H41NO4.ClH/c1-25(2,3)26(4,32)20-15-27-10-11-29(20,33-5)24-28(27)12-13-30(16-17-6-7-17)21(27)14-18-8-9-19(31)23(34-24)22(18)28;/h8-9,17,20-21,24,31-32H,6-7,10-16H2,1-5H3;1H/t20-,21-,24-,26+,27-,28+,29-;/m1./s1
InChIKey
UAIXRPCCYXNJMQ-RZIPZOSSSA-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
Buprenorphine glucuronide DM000674
131769995
Conjugation - Glucuronidation 1 [2] , [8] , [9] , [10]
Hydroxybuprenorphine DM000673
131769916
Oxidation - Hydroxylation 1 [2]
Norbuprenorphine DM000669
114976
Oxidation - N-Dealkylation 1 [2]
Hydroxynorbuprenorphine DM000670 N. A. Oxidation - N-Dealkylation 2 [2]
Hydroxynorbuprenorphine DM000670 N. A. Oxidation - Oxidation 2 [2] , [9] , [10]
Norbuprenorphine glucuronide DM000672
91800110
Conjugation - Glucuronidation 2 [2] , [9] , [10]
Hydroxynorbuprenorphine glucuronide DM000671 N. A. Conjugation - Glucuronidation 3 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000491 Bupivacaine hydrochloride Hydroxybuprenorphine Oxidation - Hydroxylation CYP3A4 ... [2]
MR000492 Bupivacaine hydrochloride Buprenorphine glucuronide Conjugation - Glucuronidation UGT2B7 ... [2], [8], [9], [10]
MR000490 Buprenorphine hydrochloride Norbuprenorphine Oxidation - N-Dealkylation CYP2C9 ... [2]
MR000489 Hydroxybuprenorphine Hydroxynorbuprenorphine Oxidation - N-Dealkylation Unclear [2]
MR000486 Norbuprenorphine Hydroxynorbuprenorphine Oxidation - Oxidation Unclear [2], [9], [10]
MR000487 Norbuprenorphine Norbuprenorphine glucuronide Conjugation - Glucuronidation UGT1A1 ... [2], [9], [10]
MR000488 Hydroxynorbuprenorphine Hydroxynorbuprenorphine glucuronide Conjugation - Glucuronidation Unclear [2]
⏷ Show the Full List of 7 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C18 (CYP2C18) DME0017 Homo sapiens
CP2CI_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[3]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[4]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[6]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[7]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[4]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[8]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[8]
UDP-glucuronosyltransferase 1A3 (UGT1A3) DME0041 Homo sapiens
UD13_HUMAN
2.4.1.17
[8]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[8]
⏷ Show the Full List of 11  DME(s)
References
1 Buprenorphine Hydrochloride was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 In vitro metabolism study of buprenorphine: evidence for new metabolic pathways. Drug Metab Dispos. 2005 May;33(5):689-95.
3 Buprenorphine in cancer pain. Support Care Cancer. 2005 Nov;13(11):878-87.
4 Substrates, inducers, inhibitors and structure-activity relationships of human Cytochrome P450 2C9 and implications in drug development. Curr Med Chem. 2009;16(27):3480-675.
5 Effect of nonspecific binding to microsomes and metabolic elimination of buprenorphine on the inhibition of cytochrome P4502D6. Biol Pharm Bull. 2005 Feb;28(2):212-6.
6 Drug interactions of clinical importance among the opioids, methadone and buprenorphine, and other frequently prescribed medications: a review. Am J Addict. 2010 Jan-Feb;19(1):4-16.
7 Buprenorphine pharmacology review: update on transmucosal and long-acting formulations. J Addict Med. 2019 Mar/Apr;13(2):93-103.
8 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.
9 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.
10 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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