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

General Information of Drug (ID: DR0106)
Drug Name
Amphetamine
Synonyms
Actedron; Adipan; Allodene; Amfetamine; Anorexide; Anorexine; Benzebar; Benzedrine; Benzolone; Desoxynorephedrine; Elastonon; Fenopromin; Isoamyne; Isomyn; Mecodrin; Mydrial; Norephedrane; Novydrine; Oktedrin; Ortedrine; AMPHETAMINE; Percomon; Phenamine; Phenedrine; Profamina; Protioamphetamine; Simpatina; alpha-Methylbenzeneethaneamine; alpha-Methylphenethylamine; beta-Aminopropylbenzene; dl-Amphetamine; 1-Methyl-2-phenylethylamine; 1-Phenyl-2-aminopropane; 1-Phenyl-2-propylamine; 1-phenylpropan-2-amine; 300-62-9; Adderall; Finam
Indication Attention deficit hyperactivity disorder [ICD11: 6A05] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 135.21 Topological Polar Surface Area 26
Heavy Atom Count 10 Rotatable Bond Count 2
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 1
Cross-matching ID
PubChem CID
3007
PubChem SID
9717 ; 87765 ; 115861 ; 608004 ; 3249024 ; 5340423 ; 7978700 ; 8150111 ; 8151914 ; 10517686 ; 10524938 ; 10529136 ; 11336166 ; 11361405 ; 11462377 ; 11533323 ; 15297279 ; 24882028 ; 26746621 ; 31073245 ; 35804947 ; 36519861 ; 36651428 ; 39909068 ; 46506414 ; 47216854 ; 48110531 ; 48415560 ; 49855301 ; 49855567 ; 51091776 ; 53789505 ; 57321551 ; 57651795 ; 77830611 ; 85209571 ; 85756449 ; 99302079 ; 103164180 ; 103810791 ; 103918755 ; 104302255 ; 117525983 ; 125680154 ; 126677500 ; 127272449 ; 127272450 ; 127272451 ; 127272452 ; 127272453
ChEBI ID
CHEBI:2679
CAS Number
300-62-9
TTD Drug ID
D05BMG
Formula
C9H13N
Canonical SMILES
CC(CC1=CC=CC=C1)N
InChI
1S/C9H13N/c1-8(10)7-9-5-3-2-4-6-9/h2-6,8H,7,10H2,1H3
InChIKey
KWTSXDURSIMDCE-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
Fenethylline Metabolite M-5( p-hydroxy-AP) DM000822
3651
Oxidation - Hydroxylation 1 [4]
Metamfetamine Metabolite M5 DM001359
7678
Oxidation - Oxidative Deamination 1 [4]
Norephedrine DM001363
26934
Oxidation - Hydroxylation 1 [4]
4-hydroxynorephedrine DM001362
6931150
Oxidation - Hydroxylation 2 [5]
Midostaurin Metabolite P6 DM001360
243
Oxidation - Oxidation 2 [5]
Midostaurin Metabolite P6B DM001361
464
Conjugation - Glycine Conjugation 3 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000220 Amphetamine 4-hydroxyamphetamine Oxidation - Hydroxylation CYP2D6 [4]
MR000221 Amphetamine Phenylacetone Oxidation - Oxidative Deamination Unclear [4]
MR000222 Amphetamine Norephedrine Oxidation - Hydroxylation Unclear [4]
MR000217 4-hydroxyamphetamine 4-hydroxynorephedrine Oxidation - Hydroxylation Unclear [5]
MR000218 Phenylacetone Benzoic acid Oxidation - Oxidation Unclear [5]
MR000219 Benzoic acid Hippuric acid Conjugation - Glycine Conjugation Unclear [5]
⏷ 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 2D6 (CYP2D6) DME0009 Homo sapiens
CP2D6_HUMAN
1.14.14.1
[2]
Tyramine oxidase (tynA) DME1022 Escherichia coli
AMO_ECOLI
1.4.3.21
[3]
References
1 Amphetamine was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Involvement of CYP2D6 in the in vitro metabolism of amphetamine, two N-alkylamphetamines and their 4-methoxylated derivatives. Xenobiotica. 1999 Jul;29(7):719-32.
3 Mechanistic elucidation of amphetamine metabolism by tyramine oxidase from human gut microbiota using molecular dynamics simulations. J Cell Biochem. 2019 Jan 30.
4 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.
5 DrugBank(Pharmacology-Metabolism)Amphetamine

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