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

General Information of Drug (ID: DR1508)
Drug Name
Sufentanil
Synonyms
Sufentanilum; Sufentanilum [INN-Latin]; Sufentanyl; Sulfentanil; Sulfentanyl; Zalviso; 56030-54-7; C22H30N2O2S; CHEBI:9316; AFE2YW0IIZ; Chronogesic; GGCSSNBKKAUURC-UHFFFAOYSA-N; R 30730; R-30730; SUFENTANIL; HSDB 6760; N-(4-(Methoxymethyl)-1-(2-(2-thienyl)ethyl)-4-piperidinyl)-N-phenylpropanamide; N-(4-(Methoxymethyl)-1-(2-(2-thienyl)ethyl)-4-piperidyl)propionanilide; N-[4-(methoxymethyl)-1-(2-thiophen-2-ylethyl)piperidin-4-yl]-N-phenylpropanamide; UNII-AFE2YW0IIZ
Indication Neuropathic pain [ICD11: 8E43] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 386.6 Topological Polar Surface Area 61
Heavy Atom Count 27 Rotatable Bond Count 8
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
41693
PubChem SID
10222 ; 6311194 ; 7980695 ; 8177237 ; 14804981 ; 34707309 ; 46504737 ; 47207596 ; 47252825 ; 47326870 ; 47624342 ; 47846995 ; 48416563 ; 50064909 ; 50787758 ; 57312595 ; 85209320 ; 103189274 ; 103924757 ; 104337672 ; 111978170 ; 117568208 ; 124953716 ; 124953717 ; 127949007 ; 134222396 ; 134337667 ; 135003073 ; 137002461 ; 139212423 ; 160964052 ; 164035747 ; 175268924 ; 175443463 ; 178100513 ; 179150640 ; 185971931 ; 198991634 ; 210274958 ; 210280596 ; 223398861 ; 224247843 ; 226414514 ; 241097876 ; 250113166 ; 251880715 ; 252481124
ChEBI ID
CHEBI:9316
CAS Number
56030-54-7
TTD Drug ID
D0D8DD
Formula
C22H30N2O2S
Canonical SMILES
CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC3=CC=CS3)COC
InChI
1S/C22H30N2O2S/c1-3-21(25)24(19-8-5-4-6-9-19)22(18-26-2)12-15-23(16-13-22)14-11-20-10-7-17-27-20/h4-10,17H,3,11-16,18H2,1-2H3
InChIKey
GGCSSNBKKAUURC-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
Desmethylsufentanil DM006373
21120849
Oxidation - Oxidationn 1 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR006844 Sufentanil Desmethylsufentanil Oxidation - Oxidationn CYP3A4 [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]
References
1 Sufentanil was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Possible involvement of multiple cytochrome P450S in fentanyl and sufentanil metabolism as opposed to alfentanil. Biochem Pharmacol. 1997 Jun 1;53(11):1613-9.
3 Identification of human liver cytochrome P-450 3A4 as the enzyme responsible for fentanyl and sufentanil N-dealkylation. Anesth Analg. 1996 Jan;82(1):167-72.

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