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

General Information of Drug (ID: DR0198)
Drug Name
Benzphetamine
Synonyms
Benzfetamina; Benzfetamina [DCIT]; Benzfetamine; Benzfetaminum; Benzylamphetamine; benzaphetamine; benzphetamine; d-Benzphetamine; (+)-N-benzyl-N,alpha-dimethylphenethylamine; (+)-benzphetamine; (2S)-N-benzyl-N-methyl-1-phenylpropan-2-amine; (S)-(+)-N-benzyl-N,alpha-dimethylphenethylamine; (S)-(+)-benzphetamine; (S)-benzphetamine; 0M3S43XK27; 156-08-1; CHEBI:3044; D-N-Methyl-N-benzyl-beta-phenylisopropylamine; N-methyl-1-phenyl-N-(phenylmethyl)propan-2-amine; UNII-0M3S43XK27
Indication Obesity [ICD11: 5B81] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 239.35 Topological Polar Surface Area 3.2
Heavy Atom Count 18 Rotatable Bond Count 5
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
5311017
PubChem SID
7978770 ; 11056212 ; 16755070 ; 39340748 ; 46506102 ; 48415616 ; 51016290 ; 57359323 ; 92740969 ; 114155064 ; 136075686 ; 137001240 ; 138314525 ; 175267688 ; 179116575 ; 226432951 ; 252347855
ChEBI ID
CHEBI:3044
CAS Number
156-08-1
TTD Drug ID
D0T5UL
Formula
C17H21N
Canonical SMILES
CC(CC1=CC=CC=C1)N(C)CC2=CC=CC=C2
InChI
1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1
InChIKey
YXKTVDFXDRQTKV-HNNXBMFYSA-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
2-nitroso-1-phenylpropane DM005401
124315
Unclear 1 [3]
Amphetamine DM003887
3007
Unclear 1 [6]
MethAmphetamine DM005397
10836
Unclear 1 [6]
N-benzylethyl-alpha-phenylnitrone DM005400 N. A. Unclear 1 [7]
N-hydroxynorbenzphetamine DM005399 N. A. Unclear 1 [7]
Norbenzphetamine DM005398
102554
Unclear 1 [7]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR005723 Benzphetamine Amphetamine Unclear Unclear [6]
MR005724 Benzphetamine MethAmphetamine Unclear Unclear [6]
MR005725 Benzphetamine Norbenzphetamine Unclear Unclear [7]
MR005726 Benzphetamine N-hydroxynorbenzphetamine Unclear Unclear [7]
MR005727 Benzphetamine N-benzylethyl-alpha-phenylnitrone Unclear Unclear [7]
MR005728 Benzphetamine 2-nitroso-1-phenylpropane Unclear Unclear [3]
⏷ Show the Full List of 6 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2B6 (CYP2B6) DME0020 Homo sapiens
CP2B6_HUMAN
1.14.14.1
[2]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[3]
Docosahexaenoic acid omega-hydroxylase (CYP4F11) DME0616 Homo sapiens
CP4FB_HUMAN
1.14.14.1
[4]
NADPH-cytochrome P450 reductase (CPR) DME0076 Homo sapiens
NCPR_HUMAN
1.6.2.4
[5]
References
1 Benzphetamine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Mechanistic analysis of the inactivation of cytochrome P450 2B6 by phencyclidine: effects on substrate binding, electron transfer, and uncoupling. Drug Metab Dispos. 2009 Apr;37(4):745-52.
3 Identification of the human and animal hepatic cytochromes P450 involved in clonazepam metabolism. Fundam Clin Pharmacol. 1993;7(2):69-75.
4 Expression and characterization of human cytochrome P450 4F11: putative role in the metabolism of therapeutic drugs and eicosanoids. Toxicol Appl Pharmacol. 2004 Sep 15;199(3):295-304.
5 On the mechanism of the inactivation of the major phenobarbital-inducible isozyme of rat liver cytochrome P-450 by chloramphenicol. J Biol Chem. 1985 Jul 15;260(14):8397-403.
6 DrugBank(Pharmacology-Metabolism):Benzphetamine
7 Interaction of constitutive and phenobarbital-induced cytochrome P-450 isozymes during the sequential oxidation of benzphetamine. Explanation for the difference in benzphetamine-induced hydrogen peroxide production and 455-nm complex formation in microsomes from untreated and phenobarbital-treated rats

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