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

General Information of Drug (ID: DR0061)
Drug Name
Alfentanil
Synonyms
Alfenta; Alfentanil [INN:BAN]; Alfentanilum; Alfentanilum [INN-Latin]; Alfentanyl; IDBPHNDTYPBSNI-UHFFFAOYSA-N; R-39209; 1N74HM2BS7; 71195-58-9; BRN 1188293; CHEBI:2569; DEA No. 9737; HSDB 6789; N-(1-(2-(4-Ethyl-4,5-dihydro-5-oxotetrazolyl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilid; N-(1-(2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl)-4-(methoxymethyl)-4-piperidyl)propionanilide; N-[1-[2-(4-Ethyl-5-oxo-2-tetrazolin-1-yl)ethyl]-4-(methoxymethyl)-4-piperidyl]propionanilide; UNII-1N74HM2BS7; ALFENTANIL
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 416.5 Topological Polar Surface Area 81
Heavy Atom Count 30 Rotatable Bond Count 9
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 6
Cross-matching ID
PubChem CID
51263
PubChem SID
10205 ; 6822617 ; 7978661 ; 8181985 ; 14904607 ; 34715715 ; 46505618 ; 48415530 ; 50020238 ; 50612502 ; 51091461 ; 53788617 ; 57313372 ; 85209901 ; 87246411 ; 103188878 ; 103922046 ; 104296815 ; 117591885 ; 124953714 ; 124953715 ; 126419214 ; 127331480 ; 127331481 ; 127331482 ; 127331483 ; 127331484 ; 128150604 ; 134338379 ; 135010258 ; 137003164 ; 139212444 ; 160964144 ; 175268599 ; 175443466 ; 178103685 ; 179116971 ; 198993182 ; 223886469 ; 226414154 ; 250113133 ; 251961664 ; 252658644
ChEBI ID
CHEBI:2569
CAS Number
71195-58-9
TTD Drug ID
D0G5QB
Formula
C21H32N6O3
Canonical SMILES
CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCN3C(=O)N(N=N3)CC)COC
InChI
1S/C21H32N6O3/c1-4-19(28)27(18-9-7-6-8-10-18)21(17-30-3)11-13-24(14-12-21)15-16-26-20(29)25(5-2)22-23-26/h6-10H,4-5,11-17H2,1-3H3
InChIKey
IDBPHNDTYPBSNI-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-(4-ethyl-5-oxo-1,2,3,4-tetrazol-1-yl)acetaldehyde DM000036
154699939
Oxidation - N-Dealkylation 1 [5]
Alfentanil metabolite AM14 DM000037 N. A. Oxidation - O-Demethylation 1 [5]
Alfentanil metabolite AM5 DM000033
74325
Oxidation - Oxidation 1 [5]
N-phenylpropionamide DM000035
12107
Oxidation - O-Demethylation 1 [6]
Noralfentanil DM000031
162172
Oxidation - N-Dealkylation 1 [6]
Alfentanil metabolite AM3 DM000034
1983
Hydrolysis - Amid Hydrolysis; Acetylation 2 [5]
Alfentanil metabolite AM5 DM000033
74325
Oxidation - Oxidation 2 [5]
Alfentanil metabolite AM6 DM000032 N. A. Oxidation - O-Demethylation 2 [5]
Alfentanil metabolite AM3 DM000034
1983
Hydrolysis - Amid Hydrolysis; Acetylation 3 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000122 Alfentanil Noralfentanil Oxidation - N-Dealkylation CYP3A4 ... [6]
MR000123 Alfentanil Alfentanil metabolite AM5 Oxidation - Oxidation CYP [5]
MR000124 Alfentanil N-phenylpropionamide Oxidation - O-Demethylation Unclear [6]
MR000125 Alfentanil 2-(4-ethyl-5-oxo-1,2,3,4-tetrazol-1-yl)acetaldehyde Oxidation - N-Dealkylation CYP3A4 [5]
MR000126 Alfentanil Alfentanil metabolite AM14 Oxidation - O-Demethylation CYP [5]
MR000119 Noralfentanil Alfentanil metabolite AM6 Oxidation - O-Demethylation CYP [5]
MR000120 Noralfentanil Alfentanil metabolite AM5 Oxidation - Oxidation CYP [5]
MR000121 Alfentanil metabolite AM5 Alfentanil metabolite AM3 Hydrolysis - Amid Hydrolysis; Acetylation CYP [5]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Cytochrome P450 3A5 (CYP3A5) DME0012 Homo sapiens
CP3A5_HUMAN
1.14.14.1
[3]
Cytochrome P450 3A7 (CYP3A7) DME0015 Homo sapiens
CP3A7_HUMAN
1.14.14.1
[4]
References
1 Alfentanil was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Pharmacogenetic determinants of human liver microsomal alfentanil metabolism and the role of cytochrome P450 3A5. Anesthesiology. 2005 Mar;102(3):550-6.
3 Influence of CYP3A5 genotype on the pharmacokinetics and pharmacodynamics of the cytochrome P4503A probes alfentanil and midazolam. Clin Pharmacol Ther. 2007 Oct;82(4):410-26.
4 Drug Interactions Flockhart Table
5 Alfentanil pharmacokinetics and metabolism in humans Anesthesiology. 1988 Oct;69(4):527-34. doi: 10.1097/00000542-198810000-00012.
6 Metabolism of alfentanil by cytochrome p4503a (cyp3a) enzymes. Drug Metab Dispos. 2005 Mar;33(3):303-11.

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