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 1 Sources: http://drugcentral.org/drugcard/3927	Palliative		Approved 4033	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 882 inhibitor 753 activator 39	inhibitor 825	inhibitor 894	inhibitor 775 inducer 15

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 725 CYP2A6 334 CYP2C19 700 CYP2E1 424	17-beta-HSD2 1 3-alpha-HSD3 1 17-beta-HSD7 1 UGT2B17 97 UGT1A1 198 UGT1A3 195 UGT1A4 171 UGT1A6 148 UGT1A7 114 UGT1A8 137 UGT1A9 180 UGT1A10 136 UGT2A1 14 UGT2B4 120 UGT2B7 182 UGT2B15 96 P-gp 724 CYP19A1 10 OATP1B1 155 OATP1B3 130 MRP2 83 MRP3 22 MRP4 45 BCRP 237	MRP4 17

Drug as perpetrator

Target	Modality	Activity
CYP3A4 920	inhibitor 1612 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D	inconclusive [Activation 15.8489 uM]
CYP3A4 920	activator 106 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D	no [Activation >15.8489 uM]
CYP1A2 805	inhibitor 1612 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2A6 356	inhibitor 1612 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2C19 738	inhibitor 1612 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2C9 851	inhibitor 1612 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2D6 908	inhibitor 1612 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D	no [IC50 >10 uM]
CYP2E1 467	inhibitor 1612 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
MRP1 87	supressor 73 Sources: https://pubmed.ncbi.nlm.nih.gov/17003774/	yes
MRP4 124	inducer 772 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000521186, https://pubmed.ncbi.nlm.nih.gov/17003774/	yes
MRP5 26	supressor 73 Sources: https://pubmed.ncbi.nlm.nih.gov/17003774/	yes

Drug as victim

Target	Modality	Activity	Metabolite
MRP4 45	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	likely	Dihydrotestosterone glucuronide 1
MRP3 22	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	major [Km 5.7 uM]	Dihydrotestosterone glucuronide 1
UGT2B17 97	substrate 1689 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 137	substrate 1689 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 83	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	minor [Km 78.9 uM]	Dihydrotestosterone glucuronide 1
UGT2B15 96	substrate 1689 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 198	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/, https://www.annualreviews.org/doi/suppl/10.1146/annurev.pharmtox.40.1.581	no
UGT1A10 136	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A3 195	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A6 148	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A7 114	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A9 180	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT2B4 120	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
BCRP 237	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	weak [Km 676.4 uM]	Dihydrotestosterone glucuronide 1
UGT1A4 171	substrate 1689 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 1	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/19772289/	yes [Km 2.6 uM]
17-beta-HSD2 1	substrate 1689 Sources: https://clincancerres.aacrjournals.org/content/17/18/5913.full-text.pdf	yes
3-alpha-HSD3 1	substrate 1689 Sources: https://clincancerres.aacrjournals.org/content/17/18/5913.full-text.pdf	yes
CYP19A1 10	substrate 1689 Sources: https://www.jbc.org/article/S0021-9258(20)63219-7/fulltext	yes
CYP3A4 882	substrate 1689 Sources: https://www.jbc.org/article/S0021-9258(20)63219-7/fulltext	yes
OATP1B1 155	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/32587096/	yes	Dihydrotestosterone glucuronide 1
OATP1B3 130	substrate 1689 Sources: https://pubmed.ncbi.nlm.nih.gov/32587096/	yes	Dihydrotestosterone glucuronide 1
P-gp 724	substrate 1689 Sources: https://go.drugbank.com/drugs/DB02901, https://pubmed.ncbi.nlm.nih.gov/14991868/	yes
UGT2A1 14	substrate 1689 Sources: https://www.annualreviews.org/doi/suppl/10.1146/annurev.pharmtox.40.1.581	yes
UGT2B7 182	substrate 1689 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 796	inducer 18 Sources: https://pubmed.ncbi.nlm.nih.gov/18599551/
hERG 796	inhibitor 786 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
Differential estrogen receptor binding of estrogenic substances: a species comparison.	2000 Nov 15	11162928
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
Antitumor effect of an HER2-specific antibody-toxin fusion protein on human prostate cancer cells.	2001 Apr	11304726
Regional variations of insulin-like growth factor I (IGF-I), IGF-II, and receptor type I in benign prostatic hyperplasia tissue and their correlation with intraprostatic androgens.	2001 Apr	11297606
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
Gonadal dysgenesis and bone metabolism.	2001 Feb	11235777
Role of androgens in the growth of endometrial carcinoma: an in vivo animal model.	2001 Feb	11228478
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
Testosterone inhibits osteoclast formation stimulated by parathyroid hormone through androgen receptor.	2001 Feb 23	11226426
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
[7alpha-18F]fluoro-17alpha-methyl-5alpha-dihydrotestosterone: a ligand for androgen receptor-mediated imaging of prostate cancer.	2001 Jan	11182568
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
Inhibitors of type II 17beta-hydroxysteroid dehydrogenase.	2001 Jan 22	11165020
Compounded percutaneous testosterone gel: use and effects in hypogonadal men.	2001 Jan-Feb	11206690
Suppression of spermatogenesis with desogestrel and testosterone pellets is not enhanced by addition of finasteride.	2001 Jan-Feb	11191092
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
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
Phenotypic variation in a family with partial androgen insensitivity syndrome explained by differences in 5alpha dihydrotestosterone availability.	2001 Mar	11238515
Interrelationships among lipoprotein levels, sex hormones, anthropometric parameters, and age in hypogonadal men treated for 1 year with a permeation-enhanced testosterone transdermal system.	2001 Mar	11238481
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
Negative feedback regulation of the secretion and actions of gonadotropin-releasing hormone in males.	2001 Mar	11207186
Androgen receptors in thymic epithelium modulate thymus size and thymocyte development.	2001 Mar	11181545
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
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
Tissue effects of saw palmetto and finasteride: use of biopsy cores for in situ quantification of prostatic androgens.	2001 May	11337315
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
Effects of cyclic adenosine-monophosphate on growth and PSA secretion of human prostate cancer cell line.	2001 May	11295058
Impact of sex and gonadal steroids on prolongation of ventricular repolarization and arrhythmias induced by I(K)-blocking drugs.	2001 May 1	11331264
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

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