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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Stanolone
- Accession Number
- DB02901 (EXPT01199)
- Type
- Small Molecule
- Groups
- Illicit, Investigational
- Description
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
- 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
- 5-Androstanon (3) Derivatives
- Alimentary Tract and Metabolism
- Anabolic Agents for Systemic Use
- Anabolic Steroids
- Androgens
- Androstan Derivatives
- Androstanes
- Androstanols
- Genito Urinary System and Sex Hormones
- Gonadal Hormones
- Gonadal Steroid Hormones
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- P-glycoprotein/ABCB1 Substrates
- Sex Hormones and Modulators of the Genital System
- Steroids
- Testosterone Congeners
- 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
- A14AA — Androstan derivatives
- A14A — ANABOLIC STEROIDS
- A14 — ANABOLIC AGENTS FOR SYSTEMIC USE
- A — ALIMENTARY TRACT AND METABOLISM
- PDB Entries
- 1d2s / 1dht / 1f5f / 1i37 / 1i38 / 1kdk / 1kdm / 1t5z / 1t63 / 1t65 … show 34 more
- MSDS
- Download (111 KB)
Clinical Trials
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
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
- 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
- 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]
- 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]
- 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
- 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]
- 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]
- 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
- 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
- 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