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

General Information of Drug (ID: DR1916)
Drug Name
BRN-2217626
Synonyms
Androkinine; Androstanon-3-alpha-ol-17-one; Androtine; Atromide ICI; androsterone; cis-Androsterone; 3-Epihydroxyetioallocholan-17-one; 3-alpha-Hydroxy-17-androstanone; 3-alpha-Hydroxy-5-alpha-androstan-17-one; 3-alpha-Hydroxyetioallocholan-17-one; 3alpha-Hydroxy-17-androstanone; 3alpha-Hydroxy-5alpha-androstan-17-one; 3alpha-Hydroxyetioallocholan-17-one; 5-alpha-Androstan-3-alpha-ol-17-one; 53-41-8; 5alpha-Androstane-3alpha-ol-17-one; 5alpha-Androsterone; Androstan-17-one, 3-hydroxy-, (3alpha,5alpha)-; Caswell No. 051G
Indication Female infertility [ICD11: GA31] Phase 3 [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
5879
ChEBI ID
CHEBI:16032
CAS Number
53-41-8
TTD Drug ID
D0H5HO
Formula
C19H30O2
Canonical SMILES
CC12CCC(CC1CCC3C2CCC4(C3CCC4=O)C)O
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/h12-16,20H,3-11H2,1-2H3/t12-,13+,14-,15-,16-,18-,19-/m0/s1
InChIKey
QGXBDMJGAMFCBF-HLUDHZFRSA-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
Androstanedione DM002517
222865
Unclear 1 [2]
Epiandrosterone DM002518
441302
Unclear 1 [2]
5alpha-dihydrotestosterone DM002519
10635
Unclear 2 [2]
Epiandrosterone DM002518
441302
Unclear 2 [2]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR003307 BRN-2217626 Androstanedione Unclear HSD17B6 [2]
MR003308 BRN-2217626 Epiandrosterone Unclear HSD17B1 [2]
MR003305 Androstanedione Epiandrosterone Unclear HSD17B1 [2]
MR003306 Androstanedione 5alpha-dihydrotestosterone Unclear HSD17B1 [2]
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
17-beta-hydroxysteroid dehydrogenase type 6 (HSD17B6) DMEN054 Homo sapiens
H17B6_HUMAN
Not Available [2]
Alcohol dehydrogenase class-II (ADH4) DME0130 Homo sapiens
ADH4_HUMAN
1.1.1.105
[3]
Aldo-keto reductase 1C3 (AKR1C3) DME0118 Homo sapiens
AK1C3_HUMAN
1.1.1.357
[4]
Estradiol 17-beta-dehydrogenase 1 (HSD17B1) DME0420 Homo sapiens
DHB1_HUMAN
1.1.1.62
[2]
Farnesol dehydrogenase (AKR1B15) DME0399 Homo sapiens
AK1BF_HUMAN
1.1.1.54
[5]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME0072 Homo sapiens
UD16_HUMAN
2.4.1.17
[6]
⏷ Show the Full List of 6  DME(s)
Experimental Enzyme Kinetic Data of This Drug
DME Name DME Info Kinetic Data Uniprot ID REF
Farnesol dehydrogenase (AKR1B15) DME0399 Km = 0.0028 microM
AK1BF_HUMAN
[5]
Aldo-keto reductase 1C3 (AKR1C3) DME0118 Km = 0.0035 microM
AK1C3_HUMAN
[4]
UDP-glucuronosyltransferase 1A6 (UGT1A6) DME0072 Km = 0.0066 microM
UD16_HUMAN
[6]
References
1 ClinicalTrials.gov (NCT02151006) Does Dehydro Epiandrosterone (DHEA) Improve Pregnancy Rate in Women Undergoing IVF/ICSI With Expected Poor Ovarian Response?.
2 Inactivation of androgens by UDP-glucuronosyltransferase enzymes in humans Trends Endocrinol Metab. 2003 Dec;14(10):473-9. doi: 10.1016/j.tem.2003.10.005.
3 13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands? Biochem Biophys Res Commun. 2003 Mar 28;303(1):273-8.
4 Expression and characterization of four recombinant human dihydrodiol dehydrogenase isoforms: oxidation of trans-7, 8-dihydroxy-7,8-dihydrobenzo[a]pyrene to the activated o-quinone metabolite benzo[a]pyrene-7,8-dione. Biochemistry. 1998 May 12;37(19):6781-90.
5 Aldo-keto Reductase 1B15 (AKR1B15): a mitochondrial human aldo-keto reductase with activity toward steroids and 3-keto-acyl-CoA conjugates. J Biol Chem. 2015 Mar 6;290(10):6531-45.
6 Structural and functional studies of UDP-glucuronosyltransferases. Drug Metab Rev. 1999 Nov;31(4):817-99.

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