Details of the Drug

General Information of Drug (ID: DM3S8XC)

Drug Name
Dihydrotestosterone
Synonyms
Androstanolone; STANOLONE; dihydrotestosterone; 521-18-6; Andractim; Androlone; Proteina; Anaboleen; Stanaprol; Anabolex; Protona; Neodrol; Cristerona MB; 4-Dihydrotestosterone; 17beta-Hydroxy-5alpha-androstan-3-one; 5alpha-Dihydrotestosterone; Androstanolonum; Androstanolona; DHT; 5-alpha-Dihydrotestosterone; Dihydrotestosteron; Testosterone, dihydro-; 4,5alpha-Dihydrotestosterone; 5alpha-Androstan-17beta-ol-3-one; Stanorone; Stanolon; 17beta-Hydroxyandrostan-3-one; 5alpha-DHT; LG 152; 17beta-Hydroxy-3-androstanone; [3H]dihydrotestosterone
Indication
Disease Entry ICD 11 Status REF
Prostate hyperplasia GA90 Phase 4 [1]
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 290.4
Logarithm of the Partition Coefficient (xlogp) 3.7
Rotatable Bond Count (rotbonds) 0
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 2
ADMET Property
Bioavailability
The bioavailability of drug is 0-2% []
Chemical Identifiers
Formula
C19H30O2
IUPAC Name
(5S,8R,9S,10S,13S,14S,17S)-17-hydroxy-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-3-one
Canonical SMILES
C[C@]12CCC(=O)C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4O)C
InChI
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
Cross-matching ID
PubChem CID
10635
ChEBI ID
CHEBI:16330
CAS Number
521-18-6
DrugBank ID
DB02901
TTD ID
D04DJN
VARIDT ID
DR00733
INTEDE ID
DR0114

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Androgen receptor (AR) TTS64P2 ANDR_HUMAN Modulator [2]
Androgen receptor messenger RNA (AR mRNA) TTKPW01 ANDR_HUMAN Agonist [3]

Drug Transporter (DTP)
DTP Name DTP ID UniProt ID MOA REF
P-glycoprotein 1 (ABCB1) DTUGYRD MDR1_HUMAN Substrate [4]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
UDP-glucuronosyltransferase 1A1 (UGT1A1) DEYGVN4 UD11_HUMAN Substrate [5]
Aromatase (CYP19A1) DEQX145 CP19A_HUMAN Substrate [6]
Aldo-keto reductase 1C1 (AKR1C1) DE7P2FB AK1C1_HUMAN Substrate [7]
Steroid 17-alpha-monooxygenase (CYP17A1) DEX2KIA CP17A_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
17-beta-hydroxysteroid dehydrogenase type 3 (HSD17B3) OT45D396 DHB3_HUMAN Gene/Protein Processing [8]
25-hydroxyvitamin D-1 alpha hydroxylase, mitochondrial (CYP27B1) OTTK98BH CP27B_HUMAN Gene/Protein Processing [9]
3 beta-hydroxysteroid dehydrogenase/Delta 5-->4-isomerase type 2 (HSD3B2) OT02MSKN 3BHS2_HUMAN Gene/Protein Processing [8]
3-hydroxy-3-methylglutaryl-coenzyme A reductase (HMGCR) OTRT3F3U HMDH_HUMAN Gene/Protein Processing [10]
3-oxo-5-alpha-steroid 4-dehydrogenase 1 (SRD5A1) OTQRET2B S5A1_HUMAN Gene/Protein Processing [11]
5'-AMP-activated protein kinase subunit beta-2 (PRKAB2) OTLVN68B AAKB2_HUMAN Gene/Protein Processing [10]
5'-nucleotidase domain-containing protein 3 (NT5DC3) OTRHBVM5 NT5D3_HUMAN Gene/Protein Processing [10]
6-phosphofructo-2-kinase/fructose-2,6-bisphosphatase 2 (PFKFB2) OTG7NW98 F262_HUMAN Gene/Protein Processing [10]
6-pyruvoyl tetrahydrobiopterin synthase (PTS) OTTYWQXR PTPS_HUMAN Gene/Protein Processing [12]
A disintegrin and metalloproteinase with thrombospondin motifs 1 (ADAMTS1) OTTLJH8W ATS1_HUMAN Gene/Protein Processing [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease Prostate hyperplasia
ICD Disease Classification GA90
Molecule Name Molecule Type Gene Name p-value Fold-Change Z-score
Androgen receptor (AR) DTT AR 2.13E-01 -0.07 -0.11
P-glycoprotein 1 (ABCB1) DTP P-GP 2.80E-02 -1.36E-01 -1.05E+00
UDP-glucuronosyltransferase 1A1 (UGT1A1) DME UGT1A1 6.96E-03 -1.95E-01 -8.72E-01
Steroid 17-alpha-monooxygenase (CYP17A1) DME CYP17A1 2.51E-05 -2.92E-01 -2.29E+00
Aromatase (CYP19A1) DME CYP19A1 1.92E-04 -1.80E-01 -1.31E+00
Aldo-keto reductase 1C1 (AKR1C1) DME AKR1C1 2.85E-02 -3.00E-01 -7.48E-01
Molecular Expression Atlas (MEA) Jump to Detail Molecular Expression Atlas of This Drug

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: 2856).
2 Inhibition of the dihydrotestosterone-activated androgen receptor by nuclear receptor corepressor. Mol Endocrinol. 2002 Jul;16(7):1492-501.
3 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. (Target id: 628).
4 P-glycoprotein increases the efflux of the androgen dihydrotestosterone and reduces androgen responsive gene activity in prostate tumor cells. Prostate. 2004 Apr 1;59(1):77-90.
5 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.
6 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.
7 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.
8 Androgen receptor modulation following combination exposure to brominated flame-retardants. Sci Rep. 2018 Mar 19;8(1):4843. doi: 10.1038/s41598-018-23181-0.
9 25 hydroxy-vitamin D(3)-1alpha hydroxylase expression and activity in cultured human osteoblasts and their modulation by parathyroid hormone, estrogenic compounds and dihydrotestosterone. J Steroid Biochem Mol Biol. 2007 Nov-Dec;107(3-5):238-44. doi: 10.1016/j.jsbmb.2007.03.048. Epub 2007 Jun 27.
10 LSD1 activates a lethal prostate cancer gene network independently of its demethylase function. Proc Natl Acad Sci U S A. 2018 May 1;115(18):E4179-E4188.
11 Antiandrogenic mechanisms of pesticides in human LNCaP prostate and H295R adrenocortical carcinoma cells. Toxicol Sci. 2015 Jan;143(1):126-35.
12 Differentially expressed genes in the prostate cancer cell line LNCaP after exposure to androgen and anti-androgen. Cancer Genet Cytogenet. 2006 Apr 15;166(2):130-8. doi: 10.1016/j.cancergencyto.2005.09.012.
13 Regulation of A Disintegrin And Metalloproteinase with ThromboSpondin repeats-1 expression in human endometrial stromal cells by gonadal steroids involves progestins, androgens, and estrogens. J Clin Endocrinol Metab. 2006 Dec;91(12):4825-35. doi: 10.1210/jc.2006-1567. Epub 2006 Oct 3.