Stanolone
Identification
- Generic Name
- Stanolone
- DrugBank Accession Number
- DB02901
- Background
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.
- Type
- Small Molecule
- Groups
- Illicit, Investigational
- Structure
- Weight
- Average: 290.4403
Monoisotopic: 290.224580204 - Chemical Formula
- C19H30O2
- 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
- Dihydrotestosterone
- Dihydrotestostérone
- External IDs
- LG 152
Pharmacology
- Indication
Not Available
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- Pharmacodynamics
Not Available
- Mechanism of action
Target Actions Organism UEstrogen receptor alpha Not Available Humans UMineralocorticoid receptor Not Available Humans UAndrogen receptor Not Available Humans UEstradiol 17-beta-dehydrogenase 1 Not Available Humans - Absorption
Bioavailability is very low (0-2%) following oral administration.
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
- Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.
- Toxicity
Oral LD50 in rat is 7060 mg/kg. Oral LD50 in mouse is 3450 mg/kg.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab Stanolone may increase the anticoagulant activities of Abciximab. Acarbose Stanolone may increase the hypoglycemic activities of Acarbose. Acenocoumarol Stanolone may increase the anticoagulant activities of Acenocoumarol. Acetohexamide Stanolone may increase the hypoglycemic activities of Acetohexamide. Albiglutide Stanolone may increase the hypoglycemic activities of Albiglutide. - Food Interactions
- Not Available
Products
- Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.
- International/Other Brands
- Anaboleen / Anabolex / Andractim / Androlone / Cristerona MB / Neodrol / Proteina / Protona / Stanaprol
Categories
- ATC Codes
- A14AA01 — Androstanolone
- A14AA — Androstan derivatives
- A14A — ANABOLIC STEROIDS
- A14 — ANABOLIC AGENTS FOR SYSTEMIC USE
- A — ALIMENTARY TRACT AND METABOLISM
- Drug Categories
- 5-Androstanon (3) Derivatives
- Alimentary Tract and Metabolism
- Anabolic Agents for Systemic Use
- Anabolic Steroids
- Androgens
- Androstan Derivatives
- Androstanes
- Androstanols
- Fused-Ring Compounds
- Genito Urinary System and Sex Hormones
- Gonadal Hormones
- Gonadal Steroid Hormones
- Hormones
- Hormones, Hormone Substitutes, and Hormone Antagonists
- P-glycoprotein substrates
- Sex Hormones and Modulators of the Genital System
- Steroids
- Testosterone and derivatives
- Testosterone Congeners
- Thyroxine-binding globulin inhibitors
- Chemical TaxonomyProvided by Classyfire
- 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
- 17-hydroxysteroid / 3-oxo-5-alpha-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Carbonyl group / Cyclic alcohol / Cyclic ketone / Hydrocarbon derivative
- 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)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 08J2K08A3Y
- CAS number
- 521-18-6
- 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,3aS,3bR,5aS,9aS,9bS,11aS)-1-hydroxy-9a,11a-dimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-7-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
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
- 50366473
- ChEBI
- 16330
- ChEMBL
- CHEMBL27769
- ZINC
- ZINC000003814360
- PDBe Ligand
- DHT
- Wikipedia
- Dihydrotestosterone
- PDB Entries
- 1d2s / 1dht / 1f5f / 1i37 / 1i38 / 1kdk / 1kdm / 1t5z / 1t63 / 1t65 … show 45 more
- MSDS
- Download (111 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 2 Completed Treatment Hypogonadism / Late Onset Hypogonadism / Testosterone Deficiency 1 1, 2 Completed Treatment Healthy Subjects (HS) 1 0 Terminated Diagnostic Prostate Cancer 1
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 34.54 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
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 177.2360681 predictedDarkChem Lite v0.1.0 [M-H]- 177.0600681 predictedDarkChem Lite v0.1.0 [M-H]- 176.7554681 predictedDarkChem Lite v0.1.0 [M-H]- 176.4532 predictedDeepCCS 1.0 (2019) [M-H]- 177.2360681 predictedDarkChem Lite v0.1.0 [M-H]- 177.0600681 predictedDarkChem Lite v0.1.0 [M-H]- 176.7554681 predictedDarkChem Lite v0.1.0 [M-H]- 176.4532 predictedDeepCCS 1.0 (2019) [M+H]+ 177.6143681 predictedDarkChem Lite v0.1.0 [M+H]+ 177.2701681 predictedDarkChem Lite v0.1.0 [M+H]+ 177.5086681 predictedDarkChem Lite v0.1.0 [M+H]+ 178.34862 predictedDeepCCS 1.0 (2019) [M+H]+ 177.6143681 predictedDarkChem Lite v0.1.0 [M+H]+ 177.2701681 predictedDarkChem Lite v0.1.0 [M+H]+ 177.5086681 predictedDarkChem Lite v0.1.0 [M+H]+ 178.34862 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.5800681 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.1565681 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.35066 predictedDeepCCS 1.0 (2019) [M+Na]+ 177.5800681 predictedDarkChem Lite v0.1.0 [M+Na]+ 177.1565681 predictedDarkChem Lite v0.1.0 [M+Na]+ 184.35066 predictedDeepCCS 1.0 (2019)
Targets
![](https://go.drugbank.com/assets/locked/DrugTargets2-682eb846d210ae4bf33ca03febccfb57bb1c61318e699b729e5df4dfab2c5b67.png)
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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. [Article]
- 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
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
- Douglas JA, Zuhlke KA, Beebe-Dimmer J, Levin AM, Gruber SB, Wood DP, Cooney KA: Identifying susceptibility genes for prostate cancer--a family-based association study of polymorphisms in CYP17, CYP19, CYP11A1, and LH-beta. Cancer Epidemiol Biomarkers Prev. 2005 Aug;14(8):2035-9. doi: 10.1158/1055-9965.EPI-05-0170. [Article]
- 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
- Tang W, Norlin M: Regulation of steroid hydroxylase CYP7B1 by androgens and estrogens in prostate cancer LNCaP cells. Biochem Biophys Res Commun. 2006 Jun 2;344(2):540-6. Epub 2006 Apr 4. [Article]
- 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
- Douglas JA, Zuhlke KA, Beebe-Dimmer J, Levin AM, Gruber SB, Wood DP, Cooney KA: Identifying susceptibility genes for prostate cancer--a family-based association study of polymorphisms in CYP17, CYP19, CYP11A1, and LH-beta. Cancer Epidemiol Biomarkers Prev. 2005 Aug;14(8):2035-9. doi: 10.1158/1055-9965.EPI-05-0170. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Product of
- General Function
- Trans-1,2-dihydrobenzene-1,2-diol dehydrogenase activity
- Specific Function
- Catalyzes the conversion of aldehydes and ketones to alcohols. Catalyzes the reduction of prostaglandin (PG) D2, PGH2 and phenanthrenequinone (PQ) and the oxidation of 9-alpha,11-beta-PGF2 to PGD2....
- Gene Name
- AKR1C3
- Uniprot ID
- P42330
- Uniprot Name
- Aldo-keto reductase family 1 member C3
- Molecular Weight
- 36852.89 Da
References
- Adeniji A, Uddin MJ, Zang T, Tamae D, Wangtrakuldee P, Marnett LJ, Penning TM: Discovery of (R)-2-(6-Methoxynaphthalen-2-yl)butanoic Acid as a Potent and Selective Aldo-keto Reductase 1C3 Inhibitor. J Med Chem. 2016 Aug 25;59(16):7431-44. doi: 10.1021/acs.jmedchem.6b00160. Epub 2016 Aug 12. [Article]
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. [Article]
- 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. [Article]
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. [Article]
Drug created at June 13, 2005 13:24 / Updated at February 21, 2024 02:33