ANDROSTANOLONE

First approved in 1953

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H30O2
Molecular Weight	290.4403
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@H](O)[C@@]1(C)CC[C@@]3([H])[C@@]2([H])CC[C@@]4([H])CC(=O)CC[C@]34C

InChI

InChIKey=NVKAWKQGWWIWPM-ABEVXSGRSA-N

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

HIDE SMILES / InChI

Description
Sources: http://www.hmdb.ca/metabolites/HMDB0002961 | https://www.ncbi.nlm.nih.gov/mesh/68013196 | http://www.inchem.org/documents/pims/pharm/pim917.htm

STANOLONE, also known as dihydrotestosterone, is a potent androgenic metabolite of testosterone and anabolic agent for systemic use. It may be used as a replacement of male sex steroids in men who have androgen deficiency, for example as a result of the loss of both testes, and also the treatment of certain rare forms of aplastic anemia which are or may be responsive to anabolic androgens.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Anemia of chronic renal failure 4 Sources: http://drugcentral.org/drugcard/3927	Palliative		Approved 8429	Neodrol Approved Use Anemia of chronic renal failure

C_max

Value	Dose	Co-administered	Analyte	Population
7.8 nM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9709942/	16 mg single, topical dose: 16 mg route of administration: Topical experiment type: SINGLE co-administered:		STANOLONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
44.8 nM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9709942/	16 mg single, topical dose: 16 mg route of administration: Topical experiment type: SINGLE co-administered:		STANOLONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
12 day EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9709942/	16 mg single, topical dose: 16 mg route of administration: Topical experiment type: SINGLE co-administered:		STANOLONE serum	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
2% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1778174/	unknown, unknown		STANOLONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
250 mg 1 times / day multiple, transdermal Highest studied dose Dose: 250 mg, 1 times / day Route: transdermal Route: multiple Dose: 250 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/11932266 https://pubmed.ncbi.nlm.nih.gov/3935902	healthy, 58 years (range: 50-70 years) n = 60 Health Status: healthy Age Group: 58 years (range: 50-70 years) Sex: M Population Size: 60 Sources: https://pubmed.ncbi.nlm.nih.gov/11932266 https://pubmed.ncbi.nlm.nih.gov/3935902	Sources: https://pubmed.ncbi.nlm.nih.gov/11932266 https://pubmed.ncbi.nlm.nih.gov/3935902

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737 inhibitor 1587 activator 80	inhibitor 1767	inhibitor 1852	inhibitor 1612 inducer 23

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1524 CYP2A6 707 CYP2C19 1478 CYP2E1 882	17-beta-HSD2 10 3-alpha-HSD3 10 17-beta-HSD7 4 UGT2B17 213 UGT1A1 418 UGT1A3 422 UGT1A4 347 UGT1A6 307 UGT1A7 236 UGT1A8 283 UGT1A9 380 UGT1A10 291 UGT2A1 32 UGT2B4 249 UGT2B7 389 UGT2B15 203 P-gp 1537 CYP19A1 23 OATP1B1 406 OATP1B3 350 MRP2 205 MRP3 50 MRP4 77 BCRP 561	MRP4 32

Drug as perpetrator

Target	Modality	Activity
CYP3A4 1925	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D	inconclusive [Activation 15.8489 uM]
CYP3A4 1925	activator 214 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D	no [Activation >15.8489 uM]
CYP1A2 1692	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2A6 739	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2C19 1553	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2C9 1819	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2D6 1891	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D	no [IC50 >10 uM]
CYP2E1 970	inhibitor 3277 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
MRP1 172	supressor 155 Sources: https://pubmed.ncbi.nlm.nih.gov/17003774/	yes
MRP4 238	inducer 1573 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000521186, https://pubmed.ncbi.nlm.nih.gov/17003774/	yes
MRP5 48	supressor 155 Sources: https://pubmed.ncbi.nlm.nih.gov/17003774/	yes

Drug as victim

Target	Modality	Activity	Metabolite
MRP4 77	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	likely	Dihydrotestosterone glucuronide 4
MRP3 50	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	major [Km 5.7 uM]	Dihydrotestosterone glucuronide 4
UGT2B17 213	substrate 3367 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000521186, https://pubmed.ncbi.nlm.nih.gov/16595710/, https://pubmed.ncbi.nlm.nih.gov/11159850/, https://www.annualreviews.org/doi/abs/10.1146/annurev.pharmtox.40.1.581	major
UGT1A8 283	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/, https://www.annualreviews.org/doi/abs/10.1146/annurev.pharmtox.40.1.581	minor [Km 382.3 uM]
MRP2 205	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	minor [Km 78.9 uM]	Dihydrotestosterone glucuronide 4
UGT2B15 203	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/, https://pubmed.ncbi.nlm.nih.gov/11159850/, https://www.annualreviews.org/doi/abs/10.1146/annurev.pharmtox.40.1.581	minor
UGT1A1 418	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/, https://www.annualreviews.org/doi/suppl/10.1146/annurev.pharmtox.40.1.581	no
UGT1A10 291	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A3 422	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A6 307	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A7 236	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A9 380	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT2B4 249	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
BCRP 561	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	weak [Km 676.4 uM]	Dihydrotestosterone glucuronide 4
UGT1A4 347	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/, https://www.annualreviews.org/doi/suppl/10.1146/annurev.pharmtox.40.1.581	weak
17-beta-HSD7 4	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/19772289/	yes [Km 2.6 uM]
17-beta-HSD2 10	substrate 3367 Sources: https://clincancerres.aacrjournals.org/content/17/18/5913.full-text.pdf	yes
3-alpha-HSD3 10	substrate 3367 Sources: https://clincancerres.aacrjournals.org/content/17/18/5913.full-text.pdf	yes
CYP19A1 23	substrate 3367 Sources: https://www.jbc.org/article/S0021-9258(20)63219-7/fulltext	yes
CYP3A4 1737	substrate 3367 Sources: https://www.jbc.org/article/S0021-9258(20)63219-7/fulltext	yes
OATP1B1 406	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/32587096/	yes	Dihydrotestosterone glucuronide 4
OATP1B3 350	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/32587096/	yes	Dihydrotestosterone glucuronide 4
P-gp 1537	substrate 3367 Sources: https://go.drugbank.com/drugs/DB02901, https://pubmed.ncbi.nlm.nih.gov/14991868/	yes
UGT2A1 32	substrate 3367 Sources: https://www.annualreviews.org/doi/suppl/10.1146/annurev.pharmtox.40.1.581	yes
UGT2B7 389	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/, https://pubmed.ncbi.nlm.nih.gov/11159850/, https://www.annualreviews.org/doi/suppl/10.1146/annurev.pharmtox.40.1.581	yes

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1647	inducer 27 Sources: https://pubmed.ncbi.nlm.nih.gov/18599551/
hERG 1647	inhibitor 1626 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D

Sourcing

Vendor/Aggregator	ID	URL
AHH Chemical co.,ltd	MT-00381	http://www.ahhchemical.com/product/MT-00381.html
AbMole Bioscience	M6033	http://www.abmole.com/products/dihydrotestosterone.html
Acadechem	ACDS-064001	http://www.acadechemical.com/product/138700
Achemtek	0104-019358	http://www.achemtek.com/521-18-6
Acorn PharmaTech	ACN-032031	http://www.acornpharmatech.com/
Aurora Fine Chemicals LLC	A13.139.278	http://online.aurorafinechemicals.com/info?ID=A13.139.278
Aurum Pharmatech LLC	Z-2983	http://www.Aurumpharmatech.com/Product/ProductDetails/Z_2983-STANOLONE-
BenchChem	B526130	https://www.benchchem.com/product/b526130
BioCrick	BCC9153	http://www.biocrick.com/Stanolone-BCC9153.html
Chem Scene	CS-5096	http://www.chemscene.com/Dihydrotestosterone.html
ChemMol	30105144	http://www.chemmol.com/chemmol/30105144.html
ChemMol	44003826	http://www.chemmol.com/chemmol/44003826.html
Clearsynth	CS-O-02388	https://www.clearsynth.com/en/CSO02388.html
LGC Standards	DRE-C10255010	https://www.lgcstandards.com/US/en/p/DRE-C10255010
LGC Standards	LGCAMP0565.00-11	https://www.lgcstandards.com/US/en/p/LGCAMP0565.00-11
LGC Standards	LGCFOR0565.00	https://www.lgcstandards.com/US/en/p/LGCFOR0565.00
LGC Standards	MM0565.00	https://www.lgcstandards.com/US/en/p/MM0565.00
Lab Network	LN00838892	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00838892
MedChem Express	HY-A0120	http://www.medchemexpress.com/Dihydrotestosterone.html
OChem	5204	http://www.ocheminc.com/index.php?act=psearch&pid=521S186
Parchem	61560	https://www.parchem.com/chemical-supplier-distributor/5-(4-Methoxyphenyl)pyrimidin-2-ylamine-061560.aspx
Selleck Chemicals	S4757	http://www.selleckchem.com/products/dihydrotestosterone.html
Sigma-Aldrich	D-073_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/d073?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	31573_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/31573?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	10300_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/10300?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	A8380_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/a8380?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S048344	http://www.sinfoobiotech.com/product/1051742
Smolecule	S518893	http://www.smolecule.com/products/s518893
Smolecule	S526130	http://www.smolecule.com/products/s526130
THE BioTek	bt-259932	https://www.thebiotek.com/product/inhibitors/bt-259932
THE BioTek	bt-264857	https://www.thebiotek.com/product/inhibitors/bt-264857
abcr GmbH	AB141682	http://www.abcr.de/shop/en/AB141682
mcule	MCULE-5987413622	https://mcule.com/MCULE-5987413622/

PubMed

Title	Date	PubMed
Steroid feedback on gonadotropin release and pituitary gonadotropin subunit mRNA in mice lacking a functional estrogen receptor alpha.	1999 Oct	10709760
Cellular and molecular mechanisms of action of linuron: an antiandrogenic herbicide that produces reproductive malformations in male rats.	2000 Aug	10910998
1alpha,25-dihydroxyvitamin D3 inhibits prostate cancer cell growth by androgen-dependent and androgen-independent mechanisms.	2000 Jul	10875257
Differential estrogen receptor binding of estrogenic substances: a species comparison.	2000 Nov 15	11162928
Effects of in utero exposure to linuron on androgen-dependent reproductive development in the male Crl:CD(SD)BR rat.	2000 Sep 1	10964759
Testosterone, corticosterone, and photoperiod interact to regulate plasma levels of binding globulin and free steroid hormone in dark-eyed juncos, Junco hyemalis.	2001 Apr	11352555
Antitumor effect of an HER2-specific antibody-toxin fusion protein on human prostate cancer cells.	2001 Apr	11304726
Evaluation of the male pubertal onset assay to detect testosterone and steroid biosynthesis inhibitors in CD rats.	2001 Apr	11248141
Androgen receptor stabilization in recurrent prostate cancer is associated with hypersensitivity to low androgen.	2001 Apr 1	11306464
Caveolin-1 interacts with androgen receptor. A positive modulator of androgen receptor mediated transactivation.	2001 Apr 20	11278309
Effects of the anti-androgen finasteride on the modulatory actions of oestradiol on androgen metabolism by human gingival fibroblasts.	2001 Feb	11163318
Relative enzymatic activity, protein stability, and tissue distribution of human steroid-metabolizing UGT2B subfamily members.	2001 Feb	11159850
Messenger ribonucleic acid levels of steroid 5 alpha-reductase 2 in human prostate predict the enzyme activity.	2001 Feb	11158057
Human types 1 and 3 3 alpha-hydroxysteroid dehydrogenases: differential lability and tissue distribution.	2001 Feb	11158055
Estrogen and androgen elicit growth hormone release via dissimilar patterns of hypothalamic neuropeptide secretion.	2001 Feb	11146085
Establishment of an androgen-responsive prostatic cell line "PEA5" from a p53-deficient mouse.	2001 Feb 15	11170150
Testosterone inhibits osteoclast formation stimulated by parathyroid hormone through androgen receptor.	2001 Feb 23	11226426
Functional interaction of human Cdc37 with the androgen receptor but not with the glucocorticoid receptor.	2001 Feb 23	11085988
Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol.	2001 Feb 28	11223173
Androstanolone treatment for congenital penile curvature.	2001 Jan	11223694
Biochemical roles of testosterone and epitestosterone to 5 alpha-reductase as indicators of male-pattern baldness.	2001 Jan	11168798
Maternal steroids and contaminants in common tern eggs: a mechanism of endocrine disruption?	2001 Jan	11166677
Social influences on androgen levels in the southern leopard frog, Rana sphenocephala.	2001 Jan	11161771
Androgens and isolation from adult tutors differentially affect the development of songbird neurons critical to vocal plasticity.	2001 Jan	11152703
The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors.	2001 Jan	11145985
Mutations at the boundary of the hinge and ligand binding domain of the androgen receptor confer increased transactivation function.	2001 Jan	11145738
Comparison of histological compositions and apoptosis in canine spontaneous benign prostatic hyperplasia treated with androgen suppressive agents chlormadinone acetate and finasteride.	2001 Jan	11125427
Manipulation of androgens causes different energetic responses to cold in 60- and 40-day-old male rats.	2001 Jan	11124160
Sex steroid hormones enhance immune function in male and female Siberian hamsters.	2001 Jan	11124153
Effects of hyperprolactinemia on rat prostate growth: evidence of androgeno-dependence.	2001 Jan	11120666
In vivo model mimicking natural history of dog prostate cancer using DPC-1, a new canine prostate carcinoma cell line.	2001 Jan 1	11170126
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase.	2001 Jan 22	11165020
In vivo regulation of syndecan-3 expression in the rat uterus by 17 beta-estradiol.	2001 Jan 5	11024013
Molecular cloning of the human kallikrein 15 gene (KLK15). Up-regulation in prostate cancer.	2001 Jan 5	11010966
Fetal androgen exposure inhibits fetal rat lung fibroblast lipid uptake and release.	2001 Jan-Feb	11202061
Androgen regulates the level and subcellular distribution of the AU-rich ribonucleic acid-binding protein HuR both in vitro and in vivo.	2001 Jun	11356683
Impact of genetic polymorphisms of 17-hydroxylase cytochrome P-450 (CYP17) and steroid 5alpha-reductase type II (SRD5A2) genes on prostate-cancer risk among the Japanese population.	2001 Jun 1	11340572
Characterization of a novel type of human microsomal 3alpha -hydroxysteroid dehydrogenase: unique tissue distribution and catalytic properties.	2001 Jun 22	11294878
Induction of primer pheromone production by dihydrotestosterone in the male goat.	2001 Mar	11307942
Effects of indomethacin, luteinizing hormone (LH), prostaglandin E2 (PGE2), trilostane, mifepristone, ethamoxytriphetol (MER-25) on secretion of prostaglandin E (PGE), prostaglandin F2alpha (PGF2alpha) and progesterone by ovine corpora lutea of pregnancy or the estrous cycle.	2001 Mar	11305696
Covariate measurement error adjustment for matched case-control studies.	2001 Mar	11252619
Differentiation-dependent expression of connective tissue growth factor and lysyl oxidase messenger ribonucleic acids in rat granulosa cells.	2001 Mar	11181522
Administration of tamoxifen but not flutamide to hormonally intact, adult male rats mimics the effects of short-term gonadectomy on the catecholamine innervation of the cerebral cortex.	2001 Mar 19	11223814
Adrenal steroids in human prostatic cancer cell lines.	2001 Mar-Apr	11297065
Structural and functional alterations in the androgen receptor in spinal bulbar muscular atrophy.	2001 May	11356158
Tissue effects of saw palmetto and finasteride: use of biopsy cores for in situ quantification of prostatic androgens.	2001 May	11337315
Effects of cyclic adenosine-monophosphate on growth and PSA secretion of human prostate cancer cell line.	2001 May	11295058
Nongenomic effect of testosterone on chloride secretion in cultured rat efferent duct epithelia.	2001 May	11287329
Impact of sex and gonadal steroids on prolongation of ventricular repolarization and arrhythmias induced by I(K)-blocking drugs.	2001 May 1	11331264
Role of canine basal cells in prostatic post natal development, induction of hyperplasia, sex hormone-stimulated growth; and the ductal origin of carcinoma.	2001 May 15	11351344

Patents

Name

Type

Language

ANDROSTANOLONE

Official Name

English

DIHYDROTESTOSTERONE

Common Name

English

17.BETA.-HYDROXY-5.ALPHA.-ANDROSTAN-3-ONE

Systematic Name

English

STANOLONE [MI]

Common Name

English

STANOLONE

Common Name

English

ANDRACTIM

Brand Name

English

ANABOLEX

Brand Name

English

androstanolone [INN]

Common Name

English

4-DIHYDROTESTOSTERONE

Common Name

English

17.BETA.-HYDROXY-5.ALPHA.-ANDROSTANE-3-ONE

Systematic Name

English

NSC-10972

Code

English

TESTOSTERONE IMPURITY F [EP IMPURITY]

Common Name

English

Androstanolone [WHO-DD]

Common Name

English

ANDROSTANOLONE [MART.]

Common Name

English

5ALPHA-DIHYDROTESTOSTERONE

Common Name

English

DIHYDROTESTOSTERONE (DHT)

Common Name

English

NEODROL

Brand Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2298