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

General Information of Drug (ID: DR0690)
Drug Name
Fentanyl citrate
Synonyms
Fentanest; Fentanil; Fentanil [DCIT]; Fentanila; Fentanila [INN-Spanish]; Fentanyl-100; Fentanyl-12; Fentanyl-25; Fentanyl-50; Fentanyl-75; Fentanylum; Fentanylum [INN-Latin]; Fentora; IONSYS; Matrifen; Phentanyl; Sentonil; Duragesic; Duragesic-100; Duragesic-12; Duragesic-25; Duragesic-50; Duragesic-75; Durogesic; Sublimase; Sublimaze; fentanyl; 1-Phenethyl-4-N-propionylanilinopiperidine; 437-38-7; N-(1-Phenethyl-4-piperidyl)propionanilide; N-(1-Phenethylpiperidin-4-yl)-N-phenylpropionamide; N-Phenethyl-4-(N-propionylanilino)piperidine; FENTANYL CITRATE; Fentanyl citrate salt; Fentanyl dihydrogen citrate; Fentaz; MUN5LYG46H; McN-JR 4263; McN-JR-4263-49; Oralet; Phentanyl citrate; R 5240; SUBLIMAZE PRESERVATIVE FREE; 990-73-8; CHEBI:31602; EINECS 213-588-0; FENTANYL CITRATE PRESERVATIVE FREE; N-(1-Phenethyl-4-piperidinyl)propionanilide dihydrogen citrate; N-(1-Phenethyl-4-piperidyl)propionanilide citrate; N-(1-Phenethyl-4-piperidyl)propionanilide citrate (1:1); N-(1-Phenethyl-4-piperidyl)propionanilide dihydrogen citrate; UNII-MUN5LYG46H
Indication Anaesthesia [ICD11: 8E22] Approved [1]
Structure
3D MOL is unavailable 2D MOL
Pharmaceutical Properties Molecular Weight 528.6 Topological Polar Surface Area 156
Heavy Atom Count 38 Rotatable Bond Count 11
Hydrogen Bond Donor Count 4 Hydrogen Bond Acceptor Count 9
Cross-matching ID
PubChem CID
13810
ChEBI ID
CHEBI:31602
CAS Number
990-73-8
TTD Drug ID
D0E1WI
Formula
C28H36N2O8
Canonical SMILES
CCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3.C(C(=O)O)C(CC(=O)O)(C(=O)O)O
InChI
1S/C22H28N2O.C6H8O7/c1-2-22(25)24(20-11-7-4-8-12-20)21-14-17-23(18-15-21)16-13-19-9-5-3-6-10-19;7-3(8)1-6(13,5(11)12)2-4(9)10/h3-12,21H,2,13-18H2,1H3;13H,1-2H2,(H,7,8)(H,9,10)(H,11,12)
InChIKey
IVLVTNPOHDFFCJ-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
Despropionylfentanyl DM000170
88890
Hydrolysis - Amide Hydrolysis 1 [3] , [5]
Hydroxyfentanyl DM000167
62278
Oxidation - Methyl Hydroxylation 1 [3]
Norfentanyl DM000169
259381
Oxidation - N-Dealkylation 1 [3] , [6] , [7] , [8]
Unclear DM009999 N. A. Unclear 1 [9]
Hydroxynorfentanyl DM000168
71749220
Oxidation - Dealkylation 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001022 Fentanyl citrate Hydroxyfentanyl Oxidation - Methyl Hydroxylation Unclear [3]
MR001023 Fentanyl citrate Norfentanyl Oxidation - N-Dealkylation CYP3A4 ... [3], [6], [7], [8]
MR001024 Fentanyl citrate Despropionylfentanyl Hydrolysis - Amide Hydrolysis Unclear [3], [5]
MR001025 Fentanyl citrate . Unclear CYP3A7 [9]
MR001021 Hydroxyfentanyl Hydroxynorfentanyl Oxidation - Dealkylation Unclear [3]
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 Fentanyl Citrate was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Three-dimensional-quantitative structure activity relationship analysis of cytochrome P-450 3A4 substrates. J Pharmacol Exp Ther. 1999 Oct;291(1):424-33.
3 Pharmacogenomics as molecular autopsy for forensic toxicology: genotyping cytochrome P450 3A4*1B and 3A5*3 for 25 fentanyl cases. J Anal Toxicol. 2005 Oct;29(7):590-8.
4 Drug Interactions Flockhart Table
5 Detecting Fentanyl Analogs in Urine Using Precursor Ion Scan Mode. J Anal Toxicol. 2021 Jan 8:bkab002. doi: 10.1093/jat/bkab002.
6 Fentanyl Absorption, Distribution, Metabolism, and Excretion: Narrative Review and Clinical Significance Related to Illicitly Manufactured Fentanyl. J Addict Med. 2023 May 17. doi: 10.1097/ADM.0000000000001185.
7 Predictors of the Rate of Illicit Fentanyl Metabolism in a Cohort of Pregnant Individuals. J Addict Med. 2023 Jan-Feb 01;17(1):85-88. doi: 10.1097/ADM.0000000000001043.
8 Bupivacaine Metabolite Can Interfere with Norfentanyl Measurement by LC-MS/MS. J Appl Lab Med. 2022 Jun 30;7(4):854-862. doi: 10.1093/jalm/jfac009.
9 Drug Interactions Flockhart Table:Docetaxel

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