A potent androgenic metabolite of testosterone. Dihydrotestosterone (DHT) is generated by a 5-alpha reduction of testosterone. Unlike testosterone, DHT cannot be aromatized to estradiol therefore DHT is considered a pure androgenic steroid.

Structure

Similar Structures

Synonyms

17beta-Hydroxy-5alpha-androstan-3-one
17beta-Hydroxy-5alpha-androstane-3-one
17beta-Hydroxyandrostan-3-one
17β-hydroxy-3-oxo-5α-androstanone
17β-hydroxy-5α-androstan-3-one
4-Dihydrotestosterone
5alpha-Dihydrotestosterone
5α-DHT
Androstanolona
Androstanolone
Androstanolonum
DHT
Dihydrotestosteron
Dihydrotestostérone
Dihydrotestosterone

International/Other Brands

Anaboleen / Anabolex / Anaprotin / Andractim / Androlone / Cristerona MB / Neodrol / Proteina / Protona / Stanaprol

Categories

UNII

08J2K08A3Y

CAS number

521-18-6

Weight

Average: 290.4403
Monoisotopic: 290.224580204

Chemical Formula

C₁₉H₃₀O₂

InChI Key

NVKAWKQGWWIWPM-ABEVXSGRSA-N

InChI

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

IUPAC Name

(1S,2S,7S,10R,11S,14S,15S)-14-hydroxy-2,15-dimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one

SMILES

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

Pharmacology

Indication

Not Available

Pharmacodynamics

Not Available

Mechanism of action

Target	Actions	Organism
UEstradiol 17-beta-dehydrogenase 1	Not Available	Humans
UAndrogen receptor	Not Available	Humans
UEstrogen receptor alpha	Not Available	Humans
UMineralocorticoid receptor	Not Available	Humans

Absorption

Bioavailability is very low (0-2%) following oral administration.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Oral LD₅₀ in rat is 7060 mg/kg. Oral LD₅₀ in mouse is 3450 mg/kg.

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction
(R)-warfarin	Stanolone may increase the anticoagulant activities of (R)-warfarin.
(S)-Warfarin	Stanolone may increase the anticoagulant activities of (S)-Warfarin.
2,4-thiazolidinedione	Stanolone may increase the hypoglycemic activities of 2,4-thiazolidinedione.
4-hydroxycoumarin	Stanolone may increase the anticoagulant activities of 4-hydroxycoumarin.
Abciximab	The therapeutic efficacy of Abciximab can be increased when used in combination with Stanolone.
Abemaciclib	The serum concentration of Stanolone can be increased when it is combined with Abemaciclib.
Acarbose	Stanolone may increase the hypoglycemic activities of Acarbose.
Acebutolol	The serum concentration of Stanolone can be increased when it is combined with Acebutolol.
Acenocoumarol	Stanolone may increase the anticoagulant activities of Acenocoumarol.
Acetaminophen	The serum concentration of Stanolone can be increased when it is combined with Acetaminophen.

Food Interactions

Not Available

References

Synthesis Reference

A. Glenn Braswell, Aftab J. Ahmed, "Composition for inhibiting production of dihydrotestosterone to treat benign prostate hyperplasia." U.S. Patent US6264996, issued October, 1996.

US6264996

General References

Not Available

External Links

Human Metabolome Database: HMDB0002961
KEGG Drug: D07456
KEGG Compound: C03917
PubChem Compound: 10635
PubChem Substance: 46506828
ChemSpider: 10189
BindingDB: 18161
ChEBI: 16330
ChEMBL: CHEMBL27769
HET: DHT
Wikipedia: Dihydrotestosterone

ATC Codes

A14AA01 — Androstanolone

G03BB02 — Androstanolone

PDB Entries

1d2s / 1dht / 1f5f / 1i37 / 1i38 / 1kdk / 1kdm / 1t5z / 1t63 / 1t65 …

show 34 more

MSDS

Download (111 KB)

Clinical Trials

Clinical Trials: Not Available

Pharmacoeconomics

Manufacturers: Not Available
Packagers: Not Available
Dosage forms: Not Available
Prices: Not Available
Patents: Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	181 °C	PhysProp
water solubility	525 mg/mL (at 25 °C)	YALKOWSKY,SH & DANNENFELSER,RM (1992)
logP	3.55	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
Water Solubility	0.00998 mg/mL	ALOGPS
logP	3.37	ALOGPS
logP	3.41	ChemAxon
logS	-4.5	ALOGPS
pKa (Strongest Acidic)	19.38	ChemAxon
pKa (Strongest Basic)	-0.88	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	37.3 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	83.6 m³·mol^-1	ChemAxon
Polarizability	34.69 Å³	ChemAxon
Number of Rings	4	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9818
Caco-2 permeable	+	0.8846
P-glycoprotein substrate	Substrate	0.57
P-glycoprotein inhibitor I	Non-inhibitor	0.5631
P-glycoprotein inhibitor II	Non-inhibitor	0.846
Renal organic cation transporter	Non-inhibitor	0.7884
CYP450 2C9 substrate	Non-substrate	0.7715
CYP450 2D6 substrate	Non-substrate	0.93
CYP450 3A4 substrate	Substrate	0.7314
CYP450 1A2 substrate	Non-inhibitor	0.6853
CYP450 2C9 inhibitor	Non-inhibitor	0.9071
CYP450 2D6 inhibitor	Non-inhibitor	0.971
CYP450 2C19 inhibitor	Non-inhibitor	0.9025
CYP450 3A4 inhibitor	Non-inhibitor	0.8546
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.9647
Ames test	Non AMES toxic	0.9414
Carcinogenicity	Non-carcinogens	0.9182
Biodegradation	Not ready biodegradable	0.9686
Rat acute toxicity	1.9757 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9444
hERG inhibition (predictor II)	Non-inhibitor	0.576

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Download (11.2 KB)

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
GC-MS Spectrum - EI-B	GC-MS	splash10-015c-8970000000-ef0c6a4fd9c52be30284
GC-MS Spectrum - EI-B	GC-MS	splash10-001l-1790000000-60cff73adc796876d469
Mass Spectrum (Electron Ionization)	MS	splash10-000x-9870000000-f6d80b2a53942c9af50b
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
13C NMR Spectrum	1D NMR	Not Applicable

Taxonomy

Description: This compound belongs to the class of organic compounds known as androgens and derivatives. These are 3-hydroxylated C19 steroid hormones. They are known to favor the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Kingdom: Organic compounds
Super Class: Lipids and lipid-like molecules
Class: Steroids and steroid derivatives
Sub Class: Androstane steroids
Direct Parent: Androgens and derivatives
Alternative Parents: 3-oxo-5-alpha-steroids / 17-hydroxysteroids / Secondary alcohols / Cyclic ketones / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents: Androgen-skeleton / 3-oxosteroid / 3-oxo-5-alpha-steroid / 17-hydroxysteroid / Oxosteroid / Hydroxysteroid / Cyclic alcohol / Cyclic ketone / Secondary alcohol / Ketone
Molecular Framework: Aliphatic homopolycyclic compounds
External Descriptors: 3-oxo steroid, 17beta-hydroxy steroid, 17beta-hydroxyandrostan-3-one (CHEBI:16330) / C19 steroids (androgens) and derivatives, Androstane and derivatives, Androgens (C03917) / C19 steroids (androgens) and derivatives (LMST02020042)

Targets

Details1. Estradiol 17-beta-dehydrogenase 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Testosterone dehydrogenase (nad+) activity
Specific Function: Favors the reduction of estrogens and androgens. Also has 20-alpha-HSD activity. Uses preferentially NADH.
Gene Name: HSD17B1
Uniprot ID: P14061
Uniprot Name: Estradiol 17-beta-dehydrogenase 1
Molecular Weight: 34949.715 Da

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	0.05	N/A	N/A
EC 50 (nM)	2	N/A	N/A	19606870
EC 50 (nM)	2.8	7.4	22	17181141
EC 50 (nM)	20	N/A	N/A	19863083
EC 50 (nM)	5	N/A	N/A	9925725
EC 50 (nM)	5.1	N/A	N/A	18442912
EC 50 (nM)	5.1	7.4	37	17034117 / 17257838 / 17887661
EC 50 (nM)	5.7	N/A	N/A	17703938 / 18400499
EC 50 (nM)	5.7	7.4	37	17439112
EC 50 (nM)	6	N/A	N/A	9871534 / 10230628 / 10230629 / 10340624
EC 50 (nM)	6.2	N/A	N/A	22094279 / 23199477
IC 50 (nM)	>10	N/A	N/A	10230628
IC 50 (nM)	>10000	N/A	N/A	10230629 / 10340624 / 17703938 / 18442912 / 22094279 / 23199477
IC 50 (nM)	0	N/A	N/A	9925725
IC 50 (nM)	0.05	N/A	N/A	18442912
IC 50 (nM)	1	N/A	N/A	19606870
IC 50 (nM)	1.82	N/A	N/A	17149866
IC 50 (nM)	10	N/A	N/A	21036041
IC 50 (nM)	2.1	N/A	N/A	22094279 / 23199477
IC 50 (nM)	4	N/A	N/A	10230628
Ki (nM)	0.2	N/A	N/A	18442912
Ki (nM)	0.2	7.4	37	17034117 / 17257838 / 17887661
Ki (nM)	0.3	7.4	22	17181141
Ki (nM)	0.3	7.4	37	17439112
Ki (nM)	0.9	N/A	N/A	18400499
Ki (nM)	10	N/A	N/A
Ki (nM)	2	N/A	N/A	9871534 / 10230629 / 10340624
Ki (nM)	3	N/A	N/A	9925725
Ki (nM)	4.7	N/A	N/A	20510622

Details2. Androgen receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Zinc ion binding
Specific Function: Steroid hormone receptors are ligand-activated transcription factors that regulate eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Transcription ...
Gene Name: AR
Uniprot ID: P10275
Uniprot Name: Androgen receptor
Molecular Weight: 98987.9 Da

References

Askew EB, Gampe RT Jr, Stanley TB, Faggart JL, Wilson EM: Modulation of androgen receptor activation function 2 by testosterone and dihydrotestosterone. J Biol Chem. 2007 Aug 31;282(35):25801-16. Epub 2007 Jun 25. [PubMed:17591767]
Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Details3. Estrogen receptor alpha

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Zinc ion binding
Specific Function: Nuclear hormone receptor. The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissu...
Gene Name: ESR1
Uniprot ID: P03372
Uniprot Name: Estrogen receptor
Molecular Weight: 66215.45 Da

References

Kojima H, Iida M, Katsura E, Kanetoshi A, Hori Y, Kobayashi K: Effects of a diphenyl ether-type herbicide, chlornitrofen, and its amino derivative on androgen and estrogen receptor activities. Environ Health Perspect. 2003 Apr;111(4):497-502. [PubMed:12676605]

Details4. Mineralocorticoid receptor

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Zinc ion binding
Specific Function: Receptor for both mineralocorticoids (MC) such as aldosterone and glucocorticoids (GC) such as corticosterone or cortisol. Binds to mineralocorticoid response elements (MRE) and transactivates targ...
Gene Name: NR3C2
Uniprot ID: P08235
Uniprot Name: Mineralocorticoid receptor
Molecular Weight: 107066.575 Da

References

Takeda AN, Pinon GM, Bens M, Fagart J, Rafestin-Oblin ME, Vandewalle A: The synthetic androgen methyltrienolone (r1881) acts as a potent antagonist of the mineralocorticoid receptor. Mol Pharmacol. 2007 Feb;71(2):473-82. Epub 2006 Nov 14. [PubMed:17105867]

Enzymes

Details1. Cholesterol side-chain cleavage enzyme, mitochondrial

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function: Catalyzes the side-chain cleavage reaction of cholesterol to pregnenolone.
Gene Name: CYP11A1
Uniprot ID: P05108
Uniprot Name: Cholesterol side-chain cleavage enzyme, mitochondrial
Molecular Weight: 60101.87 Da

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Details2. Steroid 17-alpha-hydroxylase/17,20 lyase

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Steroid 17-alpha-monooxygenase activity
Specific Function: Conversion of pregnenolone and progesterone to their 17-alpha-hydroxylated products and subsequently to dehydroepiandrosterone (DHEA) and androstenedione. Catalyzes both the 17-alpha-hydroxylation ...
Gene Name: CYP17A1
Uniprot ID: P05093
Uniprot Name: Steroid 17-alpha-hydroxylase/17,20 lyase
Molecular Weight: 57369.995 Da

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Property	Measurement	pH	Temperature (°C)	References
Ki (nM)	1550	N/A	N/A	2918514
Ki (nM)	220	N/A	N/A	2918514

Details3. Cytochrome P450 19A1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Oxygen binding
Specific Function: Catalyzes the formation of aromatic C18 estrogens from C19 androgens.
Gene Name: CYP19A1
Uniprot ID: P11511
Uniprot Name: Aromatase
Molecular Weight: 57882.48 Da

References

Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256]

Carriers

Property	Measurement	pH	Temperature (°C)	References
IC 50 (nM)	3.8	N/A	N/A	2296011
Kd (nM)	0.182	N/A	N/A	18330978

Details1. Sex hormone-binding globulin

Kind: Protein
Organism: Humans
Pharmacological action: Unknown

General Function: Androgen binding
Specific Function: Functions as an androgen transport protein, but may also be involved in receptor mediated processes. Each dimer binds one molecule of steroid. Specific for 5-alpha-dihydrotestosterone, testosterone...
Gene Name: SHBG
Uniprot ID: P04278
Uniprot Name: Sex hormone-binding globulin
Molecular Weight: 43778.755 Da

References

Metzger J, Schnitzbauer A, Meyer M, Soder M, Cuilleron CY, Hauptmann H, Huber E, Luppa PB: Binding analysis of 1alpha- and 17alpha-dihydrotestosterone derivatives to homodimeric sex hormone-binding globulin. Biochemistry. 2003 Nov 25;42(46):13735-45. [PubMed:14622020]
Hauptmann H, Metzger J, Schnitzbauer A, Cuilleron CY, Mappus E, Luppa PB: Syntheses and ligand-binding studies of 1 alpha- and 17 alpha-aminoalkyl dihydrotestosterone derivatives to human sex hormone-binding globulin. Steroids. 2003 Sep;68(7-8):629-39. [PubMed:12957668]

Transporters

Details1. Multidrug resistance protein 1

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate

General Function: Xenobiotic-transporting atpase activity
Specific Function: Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name: ABCB1
Uniprot ID: P08183
Uniprot Name: Multidrug resistance protein 1
Molecular Weight: 141477.255 Da

References

Fedoruk MN, Gimenez-Bonafe P, Guns ES, Mayer LD, Nelson CC: P-glycoprotein increases the efflux of the androgen dihydrotestosterone and reduces androgen responsive gene activity in prostate tumor cells. Prostate. 2004 Apr 1;59(1):77-90. [PubMed:14991868]

Drug created on June 13, 2005 07:24 / Updated on December 14, 2018 05:38

Stanolone

Identification

Structure for Stanolone (DB02901)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References

References

Enzymes

References

References

References

Carriers

References

Transporters

References