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

General Information of Drug (ID: DR0116)
Drug Name
Androstenedione
Synonyms
Androstendione; Androstenedione [JAN]; Androtex; Fecundin; SKF 2170; androstenedione; d4-androstenedione; delta(sup 4)-Androstene-3,17-dione; delta-(sup4)-Androsten-3,17-dione; delta-4-Androsten-3,17-dione; delta-4-Androstene-3,17-dione; delta-4-Androstenedione; 17-Ketotestosterone; 3,17-Dioxoandrost-4-ene; 4-ANDROSTENE-3-17-DIONE; 4-Androsten-3,17-dione; 4-Androstene-3,17-dione; 4-Androstenedione; Androst-4-ene-3,17-dione; CHEBI:16422; EINECS 200-554-5; HSDB 7335; MLS000028510; NSC 9563; UNII-409J2J96VR
Indication Discovery agent Investigative [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 286.4 Topological Polar Surface Area 34.1
Heavy Atom Count 21 Rotatable Bond Count 0
Hydrogen Bond Donor Count 0 Hydrogen Bond Acceptor Count 2
Cross-matching ID
PubChem CID
6128
PubChem SID
3575 ; 75016 ; 598429 ; 831360 ; 841441 ; 855972 ; 3162127 ; 7847119 ; 7885977 ; 8145630 ; 8153839 ; 14775551 ; 15962866 ; 17389251 ; 17389252 ; 17404677 ; 22400337 ; 24278247 ; 24702267 ; 24869681 ; 25621509 ; 26751578 ; 29215020 ; 29225131 ; 46508011 ; 47736685 ; 48035332 ; 48422859 ; 48424700 ; 48424701 ; 49856256 ; 50104208 ; 50362263 ; 53777220 ; 53790644 ; 56354941 ; 56354943 ; 56435876 ; 56436206 ; 56436633 ; 57323206 ; 57391483 ; 57650669 ; 71850513 ; 85148334 ; 85267761 ; 85279313 ; 92297726 ; 92303593 ; 92710448
ChEBI ID
CHEBI:16422
CAS Number
63-05-8
TTD Drug ID
D0M8RO
Formula
C19H26O2
Canonical SMILES
CC12CCC(=O)C=C1CCC3C2CCC4(C3CCC4=O)C
InChI
1S/C19H26O2/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/h11,14-16H,3-10H2,1-2H3/t14-,15-,16-,18-,19-/m0/s1
InChIKey
AEMFNILZOJDQLW-QAGGRKNESA-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
11beta-hydroxyandrostenedione DM003808
94141
Unclear 1 [3]
5alpha-dihydroandrostenedione DM003812 N. A. Unclear 1 [5]
5alpha-dihydrotestosterone DM002519
10635
Unclear 1 [5]
6beta-hydroxy-androstenedione DM003810
65544
Oxidation - Aliphatic hydroxylation 1 [2]
Testosterone DM001963
6013
Unclear 1 [5]
11beta-hydroxy-5alpha-androstanedione DM003809 N. A. Unclear 2 [3]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR012847 Androstenedione 11beta-hydroxyandrostenedione Unclear Unclear [3]
MR012849 Androstenedione 6beta-hydroxy-androstenedione Oxidation - Aliphatic hydroxylation CYP3A4 [2]
MR012850 Androstenedione 5alpha-dihydrotestosterone Unclear Unclear [5]
MR012851 Androstenedione Testosterone Unclear Unclear [5]
MR012852 Androstenedione 5alpha-dihydroandrostenedione Unclear Unclear [5]
MR012848 11beta-hydroxyandrostenedione 11beta-hydroxy-5alpha-androstanedione Unclear SRD5A1 [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 3A4 (CYP3A4) DME0001 Homo sapiens
CP3A4_HUMAN
1.14.14.55
[2]
Steroid 5-alpha-reductase 1 (SRD5A1) DME0204 Homo sapiens
S5A1_HUMAN
1.3.1.22
[3]
Testicular 17-beta-hydroxysteroid dehydrogenase (HSD17B3) DME0423 Homo sapiens
DHB3_HUMAN
1.1.1.64
[4]
References
1 How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
2 Cytochromes P450: a structure-based summary of biotransformations using representative substrates Drug Metab Rev. 2008;40(1):1-100. doi: 10.1080/03602530802309742.
3 11-hydroxyandrostenedione, the product of androstenedione metabolism in the adrenal, is metabolized in LNCaP cells by 5-reductase yielding 11-hydroxy-5-androstanedione
4 17beta-hydroxysteroid dehydrogenase-3 deficiency: a rare endocrine cause of male-to-female sex reversal. Gynecol Endocrinol. 2006 Sep;22(9):488-94.
5 Androstenedione (a Natural Steroid and a Drug Supplement): A Comprehensive Review of Its Consumption, Metabolism, Health Effects, and Toxicity with Sex Differences

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