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

General Information of Drug (ID: DR0114)
Drug Name
Androstanolone
Synonyms
Anaboleen; Anabolex; Andractim; Androlone; Androstanolona; Androstanolone; Androstanolonum; Cristerona MB; Dihydrotestosteron; LG 152; Neodrol; Proteina; Protona; STANOLONE; Stanaprol; Stanolon; Stanorone; Testosterone, dihydro-; dihydrotestosterone; 17beta-Hydroxy-3-androstanone; 17beta-Hydroxy-5alpha-androstan-3-one; 17beta-Hydroxyandrostan-3-one; 4,5alpha-Dihydrotestosterone; 4-Dihydrotestosterone; 5-alpha-Dihydrotestosterone; 521-18-6; 5alpha-Androstan-17beta-ol-3-one; 5alpha-DHT; 5alpha-Dihydrotestosterone; DHT
Indication Hypogonadism [ICD11: 5A61] Phase 4 [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 290.4 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
10635
PubChem SID
6646 ; 76024 ; 583926 ; 583927 ; 583928 ; 583929 ; 583930 ; 583932 ; 583933 ; 583934 ; 585358 ; 585359 ; 585360 ; 585692 ; 824234 ; 836816 ; 838818 ; 841438 ; 7887032 ; 7979089 ; 8145454 ; 8157682 ; 11532131 ; 12146093 ; 14751321 ; 14751322 ; 17389515 ; 24702282 ; 24891337 ; 25621350 ; 26707661 ; 26737076 ; 26737079 ; 26737083 ; 26737086 ; 26737089 ; 26737091 ; 26737094 ; 26737096 ; 26737098 ; 26737108 ; 26737500 ; 29229109 ; 38671806 ; 46392350 ; 46393206 ; 46393207 ; 46393212 ; 46518267 ; 48421870
ChEBI ID
CHEBI:16330
CAS Number
521-18-6
TTD Drug ID
D04DJN
Formula
C19H30O2
Canonical SMILES
CC12CCC(=O)CC1CCC3C2CCC4(C3CCC4O)C
InChI
1S/C19H30O2/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/h12,14-17,21H,3-11H2,1-2H3/t12-,14-,15-,16-,17-,18-,19-/m0/s1
InChIKey
NVKAWKQGWWIWPM-ABEVXSGRSA-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
11-beta-hydroxyandrosterone-3-glucuronide DM001574
53480452
Unclear 1 [5]
11-Oxo-androsterone glucuronide DM001572
270604
Unclear 1 [5]
3alpha-Androstanediol glucuronide DM001573
53480451
Unclear 1 [5]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR000241 Androstanolone 11-Oxo-androsterone glucuronide Unclear Unclear [5]
MR000242 Androstanolone 3alpha-Androstanediol glucuronide Unclear Unclear [5]
MR000243 Androstanolone 11-beta-hydroxyandrosterone-3-glucuronide Unclear Unclear [5]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Aldo-keto reductase 1C1 (AKR1C1) DME0197 Homo sapiens
AK1C1_HUMAN
1.1.1.149
[2]
Aromatase (CYP19A1) DME0002 Homo sapiens
CP19A_HUMAN
1.14.14.14
[3]
Steroid 17-alpha-monooxygenase (CYP17A1) DME0024 Homo sapiens
CP17A_HUMAN
1.14.99.9
[3]
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME0004 Homo sapiens
UD11_HUMAN
2.4.1.17
[4]
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Aldo-keto reductase 1C1 (AKR1C1) DME0197 Km = 0.00218 microM
AK1C1_HUMAN
[2]
References
1 ClinicalTrials.gov (NCT00062790) Effect Of Dutasteride On Intraprostatic Dihydrotestosterone (DHT) Levels.
2 Human 3-alpha hydroxysteroid dehydrogenase type 3 (3alpha-HSD3): the V54L mutation restricting the steroid alternative binding and enhancing the 20alpha-HSD activity. J Steroid Biochem Mol Biol. 2014 May;141:135-43.
3 Identifying susceptibility genes for prostate cancer--a family-based association study of polymorphisms in CYP17, CYP19, CYP11A1, and LH-beta. Cancer Epidemiol Biomarkers Prev. 2005 Aug;14(8):2035-9.
4 UDP-glucuronosyltransferase 2B15 (UGT2B15) and UGT2B17 enzymes are major determinants of the androgen response in prostate cancer LNCaP cells. J Biol Chem. 2007 Nov 16;282(46):33466-74.
5 DrugBank(Pharmacology-Metabolism)Androstanolone

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