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

General Information of Drug (ID: DR5131)
Drug Name
Testosterone
Synonyms
AndroGel; Androderm; Androlin; Andronaq; Andropatch; Androsorb; Andrusol; Depotest; Halotensin; Homosteron; Homosterone; Intrinsa; LibiGel; Malerone; Mertestate; Neotestis; Oreton; Orquisteron; Perandren; Primotest; Primoteston; Relibra; Striant; Sustanon; Sustanone; Teslen; Testandrone; Testaqua; Testiculosterone; Testim; Testobase; Testoderm; Testogel; Testolin; Testopropon; Testosteroid; Testosteron; Testosterona; Testosteronum; Testostosterone; Testoviron; Testrone; Testryl; Virormone; Virosterone; Beta testosterone; Cristerona T; Cristerone T; Malogen in Oil; Oreton F; Percutacrine androgenique; Synandrol F; Testoderm Tts; Testopel Pellets; Testosterone and its esters; Testosterone hydrate; Testosterone solution; Testoviron Schering; Testoviron T; Testro AQ; Virilon IM; AA 2500; Andro 100; Andronate 100; Andronate 200; Andropository 200; Andryl 200; CDB 111C; CMC_13449; COL 1621; CP 601B; Everone 200; Sustason 250; Testamone 100; Testred Cypionate 200; Androderm (TN); Androgel (TN); Geno-cristaux gremy; Malestrone (amps); Malogen, aquaspension injection; Neo-Hombreol F; Neo-testis; Oreton-F; Scheinpharm Testone-Cyp; Striant (TN); T-Cypionate; Testim (TN); Testoject-50; Testosterona [INN-Spanish]; Testosterone [Androgenic steroids, anabolic]; Testosterone [INN:BAN]; Testosteronum [INN-Latin]; Trans-Testosterone; Testosterone (JAN/USP); Testrin-P.A; Delta4-Androsten-17beta-ol-3-one; Delta4-androsten-17b-ol-3-one; Androst-4-en-17beta-ol-3-one; Delta(sup 4)-Androsten-17(beta)-ol-3-one; (17beta)-17-Hydroxyandrost-4-en-3-one; (8R,9S,10R,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthren-3-one; 17-Hydroxy-(17-beta)-androst-4-en-3-one; 17-Hydroxy-(17beta)-androst-4-en-3-one; 17-Hydroxy-4-androsten-3-one; 17-beta-Hydroxy-delta(sup 4)-androsten-3-one; 17-beta-Hydroxyandrost-4-en-3-one; 17b-hydroxy-4-androsten-3-one; 17beta-Hydroxy-3-oxo-4-androstene; 17beta-Hydroxy-4-androsten-3-one; 17beta-Hydroxy-delta(sup4)-androsten-3-one; 17beta-Hydroxyandrost-4-en-3-one; 17beta-Hydroxyandrost-4-ene-3-one; 4-Androsten-17-ol-3-one; 4-Androsten-17beta-ol-3-one; 4-androstene-17beta-ol-3-one; 7-beta-Hydroxyandrost-4-en-3-one
Indication Osteoporosis [ICD11: FB83] Approved [1]
Hormone deficiency [ICD11: ICD11: 5A60-5A61] Phase 2 [2]
Testosterone deficiency [ICD11: ICD11: 5A81] Investigative [3]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 288.4 Topological Polar Surface Area 37.3
Heavy Atom Count 21 Rotatable Bond Count 0
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
6013
ChEBI ID
CHEBI:17347
CAS Number
58-22-0
TTD Drug ID
D06XMU
Formula
C19H28O2
Canonical SMILES
C[C@]12CC[C@H]3[C@H]([C@@H]1CC[C@@H]2O)CCC4=CC(=O)CC[C@]34C
InChI
InChI=1S/C19H28O2/c1-18-9-7-13(20)11-12(18)3-4-14-15-5-6-17(21)19(15,2)10-8-16(14)18/h11,14-17,21H,3-10H2,1-2H3/t14-,15-,16-,17-,18-,19-/m0/s1
InChIKey
MUMGGOZAMZWBJJ-DYKIIFRCSA-N
The Predicted Metabolic Roadmap of This Drug
The Full List of Predicted Drug Metabolites (PDM) of This Drug
PDM Name PDM ID PubChem ID Reaction PDM Level Biosystem
11beta-hydroxyandrostenedione DM003808
94141
Oxidation - Oxygenation 1 Human
Androst-4-ene-3,17-dione (4ADN) DM001962
6128
Oxidation - Dehydrogenation from CyProduct 1 Human
Testosterone M10 PDM014405
7339
Conjugation - Glycosylation 1 Human
Testosterone M11 PDM014419
439236
Conjugation - Phosphorylation 1 Human
Testosterone M12 PDM014420
440101
Other reaction - Intramolecular transfer of functional group 1 Human
Testosterone M13 PDM014418
439184
Other reaction - Isomerization 1 Human
Testosterone M14 PDM014437
18439579
Other reaction - Transfer of ketol group 1 Human
Testosterone M2 PDM014406
10634
Oxidation - Dehydrogenation from CyProduct 1 Human
Testosterone M3 PDM014412
108192
Conjugation - Glycosylation 1 Human
Testosterone M7 PDM014415
223997
Oxidation - Dehydrogenation from CyProduct 1 Human
Testosterone M8 PDM014404
6029
Hydrolysis - Hydrolysis of nucleotide 1 Human
UDP DM002412
6031
Conjugation - Glycosylation 1 Human
UMP DM002411
6030
Hydrolysis - Hydrolysis of nucleotide 1 Human
Uracil DM002419
1174
Conjugation - Glycosylation 1 Human
Xylulose-5-P DM003850
439190
Other reaction - Epimerization 1 Human
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
[4]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[5]
Cytochrome P450 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[5]
Mephenytoin 4-hydroxylase (CYP2C19) DME0021 Homo sapiens
CP2CJ_HUMAN
1.14.14.1
[5]
UDP-glucuronosyltransferase 2B17 (UGT2B17) DME0066 Homo sapiens
UDB17_HUMAN
2.4.1.17
[6]
References
1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 2858).
2 ARDANA ANNOUNCES PHASE I RESULTS FOR TESTOSTERONE CREAM. FDAnews report.
3 Molecular mechanism of androgen action. Trends Endocrinol Metab. 1998 Oct 1;9(8):317-24.
4 Further characterization of the expression in liver and catalytic activity of CYP2B6. J Pharmacol Exp Ther. 1998 Sep;286(3):1253-9.
5 Characterization of testosterone 11 beta-hydroxylation catalyzed by human liver microsomal cytochromes P450
6 UDP-glucuronosyltransferases (UGTs) 2B7 and UGT2B17 display converse specificity in testosterone and epitestosterone glucuronidation, whereas UGT2A1 conjugates both androgens similarly

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