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

General Information of Drug (ID: DR0250)
Drug Name
Butyrfentanyl
Synonyms
Butyr-fentanyl; Butyrfentanyl; Butyrfentanyl (Butyrylfentanyl); Butyryl fentanyl; Methyl-3-fentanyl; QQOMYEQLWQJRKK-UHFFFAOYSA-N; TRA0094848; ZINC32266443; 07V1H7R6ZN; 1169-70-6; AC1LDM56; AKOS025243418; AS-48590; Butanamide, N-phenyl-N-[1-(2-phenylethyl)-4-piperidinyl]-; CS-D0505; CTK0G0348; DB09173; DEA No. 9822; DTXSID30347410; MFCD22054430; N-(1-Phenethylpiperidin-4-yl)-N-phenylbutyramide; N-PHENYL-N-[1-(2-PHENYLETHYL)PIPERIDIN-4-YL]BUTANAMIDE; N-Phenyl-N-(1-phenethyl-4-piperidinyl)butanamide; SCHEMBL18623773; UNII-07V1H7R6ZN
Indication Anaesthesia [ICD11: 8E22] Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 350.5 Topological Polar Surface Area 23.6
Heavy Atom Count 26 Rotatable Bond Count 7
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
621174
CAS Number
1169-70-6
Formula
C23H30N2O
Canonical SMILES
CCCC(=O)N(C1CCN(CC1)CCC2=CC=CC=C2)C3=CC=CC=C3
InChI
1S/C23H30N2O/c1-2-9-23(26)25(21-12-7-4-8-13-21)22-15-18-24(19-16-22)17-14-20-10-5-3-6-11-20/h3-8,10-13,22H,2,9,14-19H2,1H3
InChIKey
QQOMYEQLWQJRKK-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
(omega-1)-hydroxy-butyrylfentanyl DM006970
11574175
Oxidation - Hydrolyzationn 1 [3]
4'-hydroxy-butyrylfentanyl DM006967 N. A. Oxidation - Hydrolyzationn 1 [3]
Beta-hydroxy-butyrylfentanyl DM006969 N. A. Oxidation - Hydrolyzationn 1 [3]
Nor-butyrylfentanyl DM006971
10658099
Unclear 1 [3]
Omega-hydroxy-butyrylfentany DM006965 N. A. Oxidation - Hydrolyzationn 1 [3] , [2]
4'-hydroxy-3'- methoxy-butyrylfentanyl DM006968 N. A. Unclear 2 [3]
Omega-carboxy-fentanyl DM006966
23635044
Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007584 Butyrfentanyl Omega-hydroxy-butyrylfentany Oxidation - Hydrolyzationn CYP2D6 [3], [2]
MR007586 Butyrfentanyl 4'-hydroxy-butyrylfentanyl Oxidation - Hydrolyzationn Unclear [3]
MR007588 Butyrfentanyl Beta-hydroxy-butyrylfentanyl Oxidation - Hydrolyzationn CYP3A4 [3]
MR007589 Butyrfentanyl (omega-1)-hydroxy-butyrylfentanyl Oxidation - Hydrolyzationn CYP3A4 [3]
MR007590 Butyrfentanyl Nor-butyrylfentanyl Unclear CYP3A4 [3]
MR007587 4'-hydroxy-butyrylfentanyl 4'-hydroxy-3'- methoxy-butyrylfentanyl Unclear Unclear [3]
MR007585 Omega-hydroxy-butyrylfentany Omega-carboxy-fentanyl Unclear Unclear [3]
⏷ 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 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
References
1 Butyrfentanyl (Butyrylfentanyl) Critical Review Report.
2 Studies on the metabolism of the fentanyl-derived designer drug butyrfentanyl in human in vitro liver preparations and authentic human samples using liquid chromatography-high resolution mass spectrometry (LC-HRMS). Drug Test Anal. 2017 Jul;9(7):1085-1092.
3 Metabolism of butyrylfentanyl in fresh human hepatocytes: chemical synthesis of authentic metabolite standards for definitive identification. Biol Pharm Bull. 2019;42(4):623-630.

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