ANDROSTANOLONE VALERATE

First approved in 1953

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C24H38O3
Molecular Weight	374.5567
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=AGXPLMCKHGTYNP-KXBDTHCRSA-N

InChI=1S/C24H38O3/c1-4-5-6-22(26)27-21-10-9-19-18-8-7-16-15-17(25)11-13-23(16,2)20(18)12-14-24(19,21)3/h16,18-21H,4-15H2,1-3H3/t16-,18-,19-,20-,21-,23-,24-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C24H38O3
Molecular Weight	374.5567
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	7 / 7
E/Z Centers	0
Optical Activity	UNSPECIFIED

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 8583	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) Health Status: healthy Age Group: 58 years (range: 50-70 years) Sex: M 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 1946 inhibitor 2252 activator 150	inhibitor 2438	inhibitor 2507	inhibitor 2217 inducer 24

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 2153 CYP2A6 879 CYP2C19 2057 CYP2E1 1060	17-beta-HSD2 11 3-alpha-HSD3 11 17-beta-HSD7 4 UGT2B17 237 UGT1A1 479 UGT1A3 470 UGT1A4 399 UGT1A6 343 UGT1A7 249 UGT1A8 323 UGT1A9 423 UGT1A10 331 UGT2A1 39 UGT2B4 278 UGT2B7 456 UGT2B15 236 P-gp 2052 CYP19A1 26 OATP1B1 503 OATP1B3 435 MRP2 252 MRP3 58 MRP4 91 BCRP 697	MRP4 53

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D	inconclusive [Activation 15.8489 uM]
CYP3A4 2633	activator 342 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D	no [Activation >15.8489 uM]
CYP1A2 2333	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzU2IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2A6 911	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzNjIyIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwzMzk3IiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyODkiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D	no [IC50 >10 uM]
CYP2E1 1146	inhibitor 4027 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkw1MjgxIiwidXNlX2N1c3RvbV9xdWVyeSI6dHJ1ZSwic2VhcmNoX3Rlcm0iOiIiLCJ0ZXh0X2ZpbHRlciI6IkNIRU1CTDI3NzY5In19	no [IC50 >10 uM]
MRP1 232	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/17003774/	yes
MRP4 345	inducer 1966 Sources: https://bioinformatics.charite.de/transformer/index.php?site=fullinfo&cname=000521186, https://pubmed.ncbi.nlm.nih.gov/17003774/	yes
MRP5 80	supressor 160 Sources: https://pubmed.ncbi.nlm.nih.gov/17003774/	yes

Drug as victim

Target	Modality	Activity	Metabolite
MRP4 91	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	likely	Dihydrotestosterone glucuronide 4
MRP3 58	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	major [Km 5.7 uM]	Dihydrotestosterone glucuronide 4
UGT2B17 237	substrate 4014 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 323	substrate 4014 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 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	minor [Km 78.9 uM]	Dihydrotestosterone glucuronide 4
UGT2B15 236	substrate 4014 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 479	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/, https://www.annualreviews.org/doi/suppl/10.1146/annurev.pharmtox.40.1.581	no
UGT1A10 331	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A3 470	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A6 343	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A7 249	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT1A9 423	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
UGT2B4 278	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/16595710/	no
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/30959153/	weak [Km 676.4 uM]	Dihydrotestosterone glucuronide 4
UGT1A4 399	substrate 4014 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 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/19772289/	yes [Km 2.6 uM]
17-beta-HSD2 11	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/17/18/5913.full-text.pdf	yes
3-alpha-HSD3 11	substrate 4014 Sources: https://clincancerres.aacrjournals.org/content/17/18/5913.full-text.pdf	yes
CYP19A1 26	substrate 4014 Sources: https://www.jbc.org/article/S0021-9258(20)63219-7/fulltext	yes
CYP3A4 1946	substrate 4014 Sources: https://www.jbc.org/article/S0021-9258(20)63219-7/fulltext	yes
OATP1B1 503	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32587096/	yes	Dihydrotestosterone glucuronide 4
OATP1B3 435	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/32587096/	yes	Dihydrotestosterone glucuronide 4
P-gp 2052	substrate 4014 Sources: https://go.drugbank.com/drugs/DB02901, https://pubmed.ncbi.nlm.nih.gov/14991868/	yes
UGT2A1 39	substrate 4014 Sources: https://www.annualreviews.org/doi/suppl/10.1146/annurev.pharmtox.40.1.581	yes
UGT2B7 456	substrate 4014 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 2263	inducer 28 Sources: https://pubmed.ncbi.nlm.nih.gov/18599551/
hERG 2263	inhibitor 2237 Sources: https://www.ebi.ac.uk/chembl/g/#browse/activities/full_state/eyJsaXN0Ijp7InNldHRpbmdzX3BhdGgiOiJFU19JTkRFWEVTX05PX01BSU5fU0VBUkNILkFDVElWSVRZIiwiY3VzdG9tX3F1ZXJ5IjoidGFyZ2V0X2NoZW1ibF9pZDpDSEVNQkwyNDAiLCJ1c2VfY3VzdG9tX3F1ZXJ5Ijp0cnVlLCJzZWFyY2hfdGVybSI6IiIsInRleHRfZmlsdGVyIjoiQ0hFTUJMMjc3NjkifX0%3D

Sourcing

Vendor/Aggregator	ID	URL
abcr GmbH	AB141682	http://www.abcr.de/shop/en/AB141682
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/
AHH Chemical co.,ltd	MT-00381	http://www.ahhchemical.com/product/MT-00381.html
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
Lab Network	LN00838892	https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN00838892
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
mcule	MCULE-5987413622	https://mcule.com/MCULE-5987413622/
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	10300_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/10300?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	A8380_SIGMA	https://www.sigmaaldrich.com/catalog/product/sigma/a8380?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	D-073_CERILLIAN	https://www.sigmaaldrich.com/catalog/product/cerillian/d073?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

PubMed

Title	Date	PubMed
Characterization of a novel type of human microsomal 3alpha -hydroxysteroid dehydrogenase: unique tissue distribution and catalytic properties.	2001-06-22	11294878
Brain aromatase is neuroprotective.	2001-06-15	11351342
N-cadherin is regulated by gonadal steroids in adult sexually dimorphic spinal motoneurons.	2001-06-15	11351337
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.	2001-06-01	11340572
Dihydrotestosterone enhances transforming growth factor-beta-induced apoptosis in hormone-sensitive prostate cancer cells.	2001-06	11356690
Androgen regulates the level and subcellular distribution of the AU-rich ribonucleic acid-binding protein HuR both in vitro and in vivo.	2001-06	11356683
A missense substitution A49T in the steroid 5-alpha-reductase gene (SRD5A2) is not associated with prostate cancer in Finland.	2001-05-18	11355945
Role of canine basal cells in prostatic post natal development, induction of hyperplasia, sex hormone-stimulated growth; and the ductal origin of carcinoma.	2001-05-15	11351344
Hypogonadism following prostate-bed radiation therapy for prostate carcinoma.	2001-05-15	11346871
Human oestrogenic 17beta-hydroxysteroid dehydrogenase specificity: enzyme regulation through an NADPH-dependent substrate inhibition towards the highly specific oestrone reduction.	2001-05-15	11336660
Initial induction and subsequent reduction of alpha(2u)-globulin in urine and serum of mature male rats after repeated intraperitoneal injections of (anti)estrogen.	2001-05-11	11337107
Impact of sex and gonadal steroids on prolongation of ventricular repolarization and arrhythmias induced by I(K)-blocking drugs.	2001-05-01	11331264
Structural and functional alterations in the androgen receptor in spinal bulbar muscular atrophy.	2001-05	11356158
5alpha-reductases in human breast carcinoma: possible modulator of in situ androgenic actions.	2001-05	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.	2001-05	11342922
The hormonal milieu in early stages of bone cell differentiation modifies the subsequent sex-specific responsiveness of the developing bone to gonadal steroids.	2001-05	11341327
Tissue effects of saw palmetto and finasteride: use of biopsy cores for in situ quantification of prostatic androgens.	2001-05	11337315
Are serum hormones associated with the risk of prostate cancer? Prospective results from the Massachusetts Male Aging Study.	2001-05	11337297
Androgens alter corticotropin releasing hormone and arginine vasopressin mRNA within forebrain sites known to regulate activity in the hypothalamic-pituitary-adrenal axis.	2001-05	11328455
Behavioral and hormonal effects of exogenous vasotocin and corticosterone in the green treefrog.	2001-05	11316424
Effects of cyclic adenosine-monophosphate on growth and PSA secretion of human prostate cancer cell line.	2001-05	11295058
Nongenomic effect of testosterone on chloride secretion in cultured rat efferent duct epithelia.	2001-05	11287329
Cross-talk between signal transducer and activator of transcription 3 and androgen receptor signaling in prostate carcinoma cells.	2001-04-27	11322786
Caveolin-1 interacts with androgen receptor. A positive modulator of androgen receptor mediated transactivation.	2001-04-20	11278309
Effects of finasteride on size of the prostate gland and semen quality in dogs with benign prostatic hypertrophy.	2001-04-15	11330612
Adrenal steroids in human prostatic cancer cell lines.	2001-04-12	11297065
Androgen receptor stabilization in recurrent prostate cancer is associated with hypersensitivity to low androgen.	2001-04-01	11306464
Testosterone, corticosterone, and photoperiod interact to regulate plasma levels of binding globulin and free steroid hormone in dark-eyed juncos, Junco hyemalis.	2001-04	11352555
Androgen metabolism in the brain of the green anole lizard (Anolis carolinensis): effects of sex and season.	2001-04	11352552
Aromatase inhibition reduces specifically one display of the ring dove courtship behavior.	2001-04	11352550
Antitumor effect of an HER2-specific antibody-toxin fusion protein on human prostate cancer cells.	2001-04	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.	2001-04	11297606
Evaluation of the male pubertal onset assay to detect testosterone and steroid biosynthesis inhibitors in CD rats.	2001-04	11248141
Finasteride cream in hirsutism.	2001-03-16	11250761
Sex-dependent regulation by dexamethasone of murine hydroxysteroid sulfotransferase gene expression.	2001-03-08	11246177
Long-term exposure of tumor necrosis factor alpha causes hypersensitivity to androgen and anti-androgen withdrawal phenomenon in LNCaP prostate cancer cells.	2001-03-01	11241555
3alpha-Hydroxysteroid dehydrogenase in animal and human tissues.	2001-03	11333148
Age and gender specific stimulation of creatine kinase specific activity by gonadal steroids in human bone-derived cells in culture.	2001-03	11314745
Induction of primer pheromone production by dihydrotestosterone in the male goat.	2001-03	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.	2001-03	11305696
Covariate measurement error adjustment for matched case-control studies.	2001-03	11252619
Proliferation and differentiation of prostatic stromal cells.	2001-03	11251536
Phenotypic variation in a family with partial androgen insensitivity syndrome explained by differences in 5alpha dihydrotestosterone availability.	2001-03	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.	2001-03	11238481
Paracrine regulation of apoptosis by steroid hormones in the male and female reproductive system.	2001-02	11313721
Oral contraceptives in the treatment of acne.	2001-02	11242137
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

Patents

Substance Class	Chemical Created by `admin` on `Wed Apr 02 08:45:33 GMT 2025` Edited by `admin` on `Wed Apr 02 08:45:33 GMT 2025`
Record UNII	B43U3P3X26
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

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

Preferred Name

English

ANDROSTANOLONE VALERATE

Common Name

English

ANDROSTAN-3-ONE, 17-((1-OXOPENTYL)OXY)-, (5.ALPHA.,17.BETA.)-

Systematic Name

English

Code System Code Type Description

CAS

26271-72-7