STANOLONE BENZOATE

First approved in 1953

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C26H34O3
Molecular Weight	394.5464
Optical Activity	UNSPECIFIED
Defined Stereocenters	7 / 7
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12CC[C@H](OC(=O)C3=CC=CC=C3)[C@@]1(C)CC[C@@]4([H])[C@@]2([H])CC[C@@]5([H])CC(=O)CC[C@]45C

InChI

InChIKey=ZGDZDAPCWHIIKB-LVYWIKMTSA-N

InChI=1S/C26H34O3/c1-25-14-12-19(27)16-18(25)8-9-20-21-10-11-23(26(21,2)15-13-22(20)25)29-24(28)17-6-4-3-5-7-17/h3-7,18,20-23H,8-16H2,1-2H3/t18-,20-,21-,22-,23-,25-,26-/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
The fungicide procymidone alters sexual differentiation in the male rat by acting as an androgen-receptor antagonist in vivo and in vitro.	1999 Jan-Mar	10188193
Examination of selected food additives and organochlorine food contaminants for androgenic activity in vitro.	2000 Feb	10696776
The pregnane X receptor: a promiscuous xenobiotic receptor that has diverged during evolution.	2000 Jan	10628745
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
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
Oral contraceptives in the treatment of acne.	2001 Feb	11242137
Effects of the anti-androgen finasteride on the modulatory actions of oestradiol on androgen metabolism by human gingival fibroblasts.	2001 Feb	11163318
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
The octadecaneuropeptide ODN stimulates neurosteroid biosynthesis through activation of central-type benzodiazepine receptors.	2001 Jan	11145985
Comparison of histological compositions and apoptosis in canine spontaneous benign prostatic hyperplasia treated with androgen suppressive agents chlormadinone acetate and finasteride.	2001 Jan	11125427
Sex steroid hormones enhance immune function in male and female Siberian hamsters.	2001 Jan	11124153
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
Negative feedback regulation of the secretion and actions of gonadotropin-releasing hormone in males.	2001 Mar	11207186
Sex-dependent regulation by dexamethasone of murine hydroxysteroid sulfotransferase gene expression.	2001 Mar 8	11246177
Nongenomic effect of testosterone on chloride secretion in cultured rat efferent duct epithelia.	2001 May	11287329
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

STANOLONE BENZOATE

Common Name

English

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

Common Name

English

NSC-69549

Code

English

VETRANAL

Brand Name

English

ANDROSTANOLONE BENZOATE

Common Name

English

DIHYDROTESTOSTERONE BENZOATE

Common Name

English

Classification Tree Code System Code

DEA NO.

4000