ANDROSTANOLONE

First approved in 1953

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C19H30O2
Molecular Weight	290.441
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

C[C@@]12CCC(=O)C[C@]2([H])CC[C@@]3([H])[C@]4([H])CC[C@@]([H])([C@@]4(C)CC[C@@]31[H])O

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 3 Sources: http://drugcentral.org/drugcard/3927	Palliative		Approved 8043	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 1601 inhibitor 1467 activator 74	inhibitor 1604	inhibitor 1702	inhibitor 1475 inducer 22

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1383 CYP2A6 627 CYP2C19 1325 CYP2E1 790	17-beta-HSD2 9 3-alpha-HSD3 9 17-beta-HSD7 3 UGT2B17 203 UGT1A1 393 UGT1A3 397 UGT1A4 330 UGT1A6 289 UGT1A7 221 UGT1A8 266 UGT1A9 357 UGT1A10 273 UGT2A1 31 UGT2B4 233 UGT2B7 362 UGT2B15 191 P-gp 1400 CYP19A1 21 OATP1B1 370 OATP1B3 319 MRP2 182 MRP3 46 MRP4 73 BCRP 515	MRP4 30

Drug as perpetrator

Target	Modality	Activity
CYP3A4 1772	inhibitor 3045 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D	inconclusive [Activation 15.8489 uM]
CYP3A4 1772	activator 202 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D	no [Activation >15.8489 uM]
CYP1A2 1532	inhibitor 3045 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2A6 659	inhibitor 3045 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2C19 1392	inhibitor 3045 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2C9 1648	inhibitor 3045 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2D6 1738	inhibitor 3045 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D	no [IC50 >10 uM]
CYP2E1 871	inhibitor 3045 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
MRP1 166	supressor 140 Sources: https://pubmed.ncbi.nlm.nih.gov/17003774/	yes
MRP4 226	inducer 1440 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000521186, https://pubmed.ncbi.nlm.nih.gov/17003774/	yes
MRP5 45	supressor 140 Sources: https://pubmed.ncbi.nlm.nih.gov/17003774/	yes

Drug as victim

Target	Modality	Activity	Metabolite
MRP4 73	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	likely	Dihydrotestosterone glucuronide 3
MRP3 46	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	major [Km 5.7 uM]	Dihydrotestosterone glucuronide 3
UGT2B17 203	substrate 3113 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 266	substrate 3113 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 182	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	minor [Km 78.9 uM]	Dihydrotestosterone glucuronide 3
UGT2B15 191	substrate 3113 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 393	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/, https://www.annualreviews.org/doi/suppl/10.1146/annurev.pharmtox.40.1.581	no
UGT1A10 273	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A3 397	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A6 289	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A7 221	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A9 357	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT2B4 233	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
BCRP 515	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	weak [Km 676.4 uM]	Dihydrotestosterone glucuronide 3
UGT1A4 330	substrate 3113 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 3	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/19772289/	yes [Km 2.6 uM]
17-beta-HSD2 9	substrate 3113 Sources: https://clincancerres.aacrjournals.org/content/17/18/5913.full-text.pdf	yes
3-alpha-HSD3 9	substrate 3113 Sources: https://clincancerres.aacrjournals.org/content/17/18/5913.full-text.pdf	yes
CYP19A1 21	substrate 3113 Sources: https://www.jbc.org/article/S0021-9258(20)63219-7/fulltext	yes
CYP3A4 1601	substrate 3113 Sources: https://www.jbc.org/article/S0021-9258(20)63219-7/fulltext	yes
OATP1B1 370	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/32587096/	yes	Dihydrotestosterone glucuronide 3
OATP1B3 319	substrate 3113 Sources: https://pubmed.ncbi.nlm.nih.gov/32587096/	yes	Dihydrotestosterone glucuronide 3
P-gp 1400	substrate 3113 Sources: https://go.drugbank.com/drugs/DB02901, https://pubmed.ncbi.nlm.nih.gov/14991868/	yes
UGT2A1 31	substrate 3113 Sources: https://www.annualreviews.org/doi/suppl/10.1146/annurev.pharmtox.40.1.581	yes
UGT2B7 362	substrate 3113 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 1507	inducer 25 Sources: https://pubmed.ncbi.nlm.nih.gov/18599551/
hERG 1507	inhibitor 1489 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
Morphometric analysis of cortical bone upon the exposure to sustained delivery of anabolic promoting agents using adult male rats as a model.	2001	11347405
Biocompatibility of steroid-HA delivery system using adult castrated rams as a model.	2001	11347402
Morphometric analysis of the adrenal compartments exposed to sustained delivery of androgens.	2001	11347380
Ultrastructural and quantitative immunohistochemical changes induced by nonsteroid antiandrogens on pituitary gonadotroph population of prepubertal male rats.	2001	11340263
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
Androgen metabolism in the brain of the green anole lizard (Anolis carolinensis): effects of sex and season.	2001 Apr	11352552
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.	2001 Apr	11352550
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
Effects of finasteride on size of the prostate gland and semen quality in dogs with benign prostatic hypertrophy.	2001 Apr 15	11330612
Caveolin-1 interacts with androgen receptor. A positive modulator of androgen receptor mediated transactivation.	2001 Apr 20	11278309
Cross-talk between signal transducer and activator of transcription 3 and androgen receptor signaling in prostate carcinoma cells.	2001 Apr 27	11322786
Paracrine regulation of apoptosis by steroid hormones in the male and female reproductive system.	2001 Feb	11313721
Oral contraceptives in the treatment of acne.	2001 Feb	11242137
Role of androgens in the growth of endometrial carcinoma: an in vivo animal model.	2001 Feb	11228478
Dehydroepiandrosterone stimulates proliferation and gene expression in MCF-7 cells after conversion to estradiol.	2001 Feb 28	11223173
Finasteride cream in hirsutism.	2001 Jan-Feb	11250761
Dihydrotestosterone enhances transforming growth factor-beta-induced apoptosis in hormone-sensitive prostate cancer cells.	2001 Jun	11356690
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
Brain aromatase is neuroprotective.	2001 Jun 15	11351342
N-cadherin is regulated by gonadal steroids in adult sexually dimorphic spinal motoneurons.	2001 Jun 15	11351337
Characterization of a novel type of human microsomal 3alpha -hydroxysteroid dehydrogenase: unique tissue distribution and catalytic properties.	2001 Jun 22	11294878
3alpha-Hydroxysteroid dehydrogenase in animal and human tissues.	2001 Mar	11333148
Age and gender specific stimulation of creatine kinase specific activity by gonadal steroids in human bone-derived cells in culture.	2001 Mar	11314745
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
Proliferation and differentiation of prostatic stromal cells.	2001 Mar	11251536
Polymorphism of the androgen receptor gene is associated with male pattern baldness.	2001 Mar	11231320
Androgen receptor antagonism by the organophosphate insecticide fenitrothion.	2001 Mar	11222873
Long-term exposure of tumor necrosis factor alpha causes hypersensitivity to androgen and anti-androgen withdrawal phenomenon in LNCaP prostate cancer cells.	2001 Mar 1	11241555
Sex-dependent regulation by dexamethasone of murine hydroxysteroid sulfotransferase gene expression.	2001 Mar 8	11246177
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
5alpha-reductases in human breast carcinoma: possible modulator of in situ androgenic actions.	2001 May	11344235
The gonadotropin-releasing hormone antagonist abarelix depot versus luteinizing hormone releasing hormone agonists leuprolide or goserelin: initial results of endocrinological and biochemical efficacies in patients with prostate cancer.	2001 May	11342922
The hormonal milieu in early stages of bone cell differentiation modifies the subsequent sex-specific responsiveness of the developing bone to gonadal steroids.	2001 May	11341327
Tissue effects of saw palmetto and finasteride: use of biopsy cores for in situ quantification of prostatic androgens.	2001 May	11337315
Are serum hormones associated with the risk of prostate cancer? Prospective results from the Massachusetts Male Aging Study.	2001 May	11337297
Androgens alter corticotropin releasing hormone and arginine vasopressin mRNA within forebrain sites known to regulate activity in the hypothalamic-pituitary-adrenal axis.	2001 May	11328455
Behavioral and hormonal effects of exogenous vasotocin and corticosterone in the green treefrog.	2001 May	11316424
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
Initial induction and subsequent reduction of alpha(2u)-globulin in urine and serum of mature male rats after repeated intraperitoneal injections of (anti)estrogen.	2001 May 11	11337107
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
Hypogonadism following prostate-bed radiation therapy for prostate carcinoma.	2001 May 15	11346871
Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction.	2001 May 15	11336660
A missense substitution A49T in the steroid 5-alpha-reductase gene (SRD5A2) is not associated with prostate cancer in Finland.	2001 May 18	11355945

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

ANDROSTANOLONE [WHO-DD]

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

TESTOSTERONE IMPURITY F [EP]

Common Name

English

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

Systematic Name

English

NSC-10972

Code

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