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

General Information of Drug (ID: DR0466)
Drug Name
Dexfenfluramine
Synonyms
Dexfenfluramina; Dexfenfluramine; Dexfenfluramine (INN); Dexfenfluramine [INN:BAN]; Dexfenfluraminum; Dextrofenfluramine; ZINC294; Adifax; d-Fenfluramine; (+)-Fenfluramine; (2S)-N-ethyl-1-[3-(trifluoromethyl)phenyl]propan-2-amine; (S)-Fenfluramine; 3239-44-9; AC1L24ZO; AC1Q4JS0; BDBM85596; CHEBI:439329; CHEMBL248702; E35R3G56OV; HSDB 7356; NCGC00247710-01; NSC_65801; Phenethylamine, N-ethyl-alpha-methyl-m-(trifluoromethyl)-, (S)-; Redux; SCHEMBL16706; UNII-E35R3G56OV; d-N-Ethyl-alpha-methyl-m-trifluoromethylphenethylamine; ip001
Indication Obesity [ICD11: 5B81] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 231.26 Topological Polar Surface Area 12
Heavy Atom Count 16 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 4
Cross-matching ID
PubChem CID
66265
PubChem SID
11646562 ; 14822931 ; 15220690 ; 43122969 ; 46508388 ; 47285835 ; 47954450 ; 48253936 ; 48329036 ; 77105781 ; 85629918 ; 96024502 ; 103558716 ; 104335985 ; 117504738 ; 124954078 ; 127709650 ; 134982470 ; 136351696 ; 137100755 ; 179150317 ; 198941478 ; 198941479 ; 198956174 ; 223518912 ; 226406858
ChEBI ID
CHEBI:439329
CAS Number
3239-44-9
TTD Drug ID
D0F9SG
Formula
C12H16F3N
Canonical SMILES
CCNC(C)CC1=CC(=CC=C1)C(F)(F)F
InChI
1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3/t9-/m0/s1
InChIKey
DBGIVFWFUFKIQN-VIFPVBQESA-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
Nordexfenfluramine DM006586
9815618
Oxidation - N-dealkylation 1 [3]
1-(3-CF3 -phenyl)-propan-2-one DM006587
89101
Unclear 2 [3]
N-hydroxynordexfenfluramine DM006592
82684697
Unclear 2 [3]
1-(3-CF3 -phenyl)-propan-1,2-diol DM006591
85910
Unclear 3 [3]
1-(3-CF3 -phenyl)-propan-2-ol DM006590
150791
Unclear 3 [3]
M-trifluoromethyl-benzoic acid DM006588
9963
Unclear 3 [3]
M-trifluoromethylhippuric acid DM006589
2777432
Unclear 4 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR007102 Dexfenfluramine Nordexfenfluramine Oxidation - N-dealkylation CYP2D6 ... [3]
MR007103 Nordexfenfluramine 1-(3-CF3 -phenyl)-propan-2-one Unclear Unclear [3]
MR007108 Nordexfenfluramine N-hydroxynordexfenfluramine Unclear Unclear [3]
MR007104 1-(3-CF3 -phenyl)-propan-2-one M-trifluoromethyl-benzoic acid Unclear Unclear [3]
MR007106 1-(3-CF3 -phenyl)-propan-2-one 1-(3-CF3 -phenyl)-propan-2-ol Unclear Unclear [3]
MR007107 1-(3-CF3 -phenyl)-propan-2-one 1-(3-CF3 -phenyl)-propan-1,2-diol Unclear Unclear [3]
MR007105 M-trifluoromethyl-benzoic acid M-trifluoromethylhippuric acid 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 1A2 (CYP1A2) DME0003 Homo sapiens
CP1A2_HUMAN
1.14.14.1
[2]
Cytochrome P450 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[3]
References
1 Obesity: pathophysiology and clinical management. Curr Med Chem. 2009;16(4):506-21.
2 Appetite suppressant drugs as inhibitors of human cytochromes P450: in vitro inhibition of P450-2D6 by D- and L-fenfluramine, but not phentermine. J Clin Psychopharmacol. 1998 Aug;18(4):338-41.
3 Metabolism of dexfenfluramine in human liver microsomes and by recombinant enzymes: role of CYP2D6 and 1A2. Pharmacogenetics. 1998 Oct;8(5):423-32.

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