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

General Information of Drug (ID: DR1865)
Drug Name
BRN-0456976
Synonyms
Carfentanil [INN]; Carfentanila; Carfentanil; Carfentanila [INN-Spanish]; Carfentanila [Spanish]; Carfentanilum; Carfentanilum [INN-Latin]; Carfentanyl; Wildnil; CARFENTANIL; 4-((1-Oxopropyl)phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylic acid methyl ester; 59708-52-0; CHEBI:61084; Methyl 1-phenylethyl-4-(N-phenylpropionamido)isonipecotate; Methyl 4-(N-(1-oxopropyl)-N-phenylamino)-1-(2-phenylethyl)-4-piperidinecarboxylate; Methyl 4-(N-propionyl-N-phenylamino)-1-(2-phenylethyl)-4-piperidine-carboxylate; UNII-LA9DTA2L8F
Indication Anaesthesia [ICD11: 8E22] Phase 2 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 394.5 Topological Polar Surface Area 49.8
Heavy Atom Count 29 Rotatable Bond Count 8
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
62156
PubChem SID
8187910 ; 16847866 ; 22395327 ; 43119324 ; 46505501 ; 50015735 ; 57314612 ; 80840190 ; 96024451 ; 103224159 ; 103924756 ; 104222357 ; 104325105 ; 109614507 ; 117553158 ; 129780983 ; 134222605 ; 135020271 ; 137129263 ; 141935616 ; 160964782 ; 162630311 ; 164837838 ; 175443459 ; 180100818 ; 198942200 ; 226488467 ; 241102489 ; 250116464
ChEBI ID
CHEBI:61084
CAS Number
59708-52-0
TTD Drug ID
D03PJU
Formula
C24H30N2O3
Canonical SMILES
CCC(=O)N(C1=CC=CC=C1)C2(CCN(CC2)CCC3=CC=CC=C3)C(=O)OC
InChI
1S/C24H30N2O3/c1-3-22(27)26(21-12-8-5-9-13-21)24(23(28)29-2)15-18-25(19-16-24)17-14-20-10-6-4-7-11-20/h4-13H,3,14-19H2,1-2H3
InChIKey
YDSDEBIZUNNPOB-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
BRN-0456976 M11 DM006792 N. A. Oxidation - Oxidationn 1 [2]
BRN-0456976 M12 DM006789 N. A. Oxidation - Oxidationn 1 [2]
BRN-0456976 M2 DM006782 N. A. Oxidation - N-dealkylation 1 [2]
BRN-0456976 M5 DM006788 N. A. Oxidation - Monohydroxylation 1 [2]
BRN-0456976 M7 DM006785 N. A. Oxidation - Monohydroxylation 1 [2]
BRN-0456976 M8 DM006790 N. A. Oxidation - Monohydroxylation 1 [2]
BRN-0456976 M9 DM006793 N. A. Unclear 1 [2]
BRN-0456976 M1 DM006783 N. A. Oxidation - N-dealkylation 2 [2]
BRN-0456976 M10 DM006786 N. A. Oxidation - Hydrolyzationn 2 [2]
BRN-0456976 M3 DM006784 N. A. Oxidation - Monohydroxylation 2 [2]
BRN-0456976 M4 DM006791 N. A. Hydrolysis - Hydrolysis 2 [2]
BRN-0456976 M6 DM006787 N. A. Oxidation - Hydrolyzationn 2 [2]
BRN-0456976 M3 DM006784 N. A. Oxidation - Monohydroxylation 3 [2]
⏷ Show the Full List of 13  DM(s)
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007348 BRN-0456976 BRN-0456976 M2 Oxidation - N-dealkylation Unclear [2]
MR007351 BRN-0456976 BRN-0456976 M7 Oxidation - Monohydroxylation Unclear [2]
MR007354 BRN-0456976 BRN-0456976 M5 Oxidation - Monohydroxylation Unclear [2]
MR007356 BRN-0456976 BRN-0456976 M12 Oxidation - Oxidationn Unclear [2]
MR007358 BRN-0456976 BRN-0456976 M8 Oxidation - Monohydroxylation Unclear [2]
MR007360 BRN-0456976 BRN-0456976 M11 Oxidation - Oxidationn Unclear [2]
MR007361 BRN-0456976 BRN-0456976 M9 Unclear Unclear [2]
MR007357 BRN-0456976 M12 BRN-0456976 M10 Oxidation - Hydrolyzationn Unclear [2]
MR007349 BRN-0456976 M2 BRN-0456976 M1 Oxidation - N-dealkylation CYP3A5 [2]
MR007355 BRN-0456976 M5 BRN-0456976 M3 Oxidation - Monohydroxylation Unclear [2]
MR007352 BRN-0456976 M7 BRN-0456976 M10 Oxidation - Hydrolyzationn Unclear [2]
MR007353 BRN-0456976 M7 BRN-0456976 M6 Oxidation - Hydrolyzationn Unclear [2]
MR007359 BRN-0456976 M8 BRN-0456976 M4 Hydrolysis - Hydrolysis Unclear [2]
MR007350 BRN-0456976 M1 BRN-0456976 M3 Oxidation - Monohydroxylation Unclear [2]
⏷ Show the Full List of 14 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Acid cholesteryl ester hydrolase (LIPA) DME0447 Homo sapiens
LICH_HUMAN
3.1.1.13
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
References
1 ClinicalTrials.gov (NCT01899170) Towards Individualized Deep Brain Stimulation Treatment of Chronic Neuropathic Pain.
2 Metabolism of carfentanil, an ultra-potent opioid, in human liver microsomes and human hepatocytes by high-resolution mass spectrometry. AAPS J. 2016 Nov;18(6):1489-1499.

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