Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-21 20:27:51 UTC |
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Update Date | 2014-12-24 20:25:53 UTC |
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Accession Number | T3D2917 |
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Identification |
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Common Name | Drostanolone |
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Class | Small Molecule |
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Description | Drostanolone (also known as dromostanolone) is only found in individuals that have used or taken this drug. It is a potent synthetic androgenic anabolic steroid similar to testosterone. Drostanolone is indicated in postmenopausal women with recurrent breast cancer, in a combined hormone therapy.Dromostanolone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, dromostanolone binds to the androgen receptor. This causes downstream genetic transcriptional changes. This ultimately causes retention of nitrogen, potassium, and phosphorus; increases protein anabolism; and decreases amino acid catabolism. The antitumour activity of dromostanolone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production. |
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Compound Type | - Anabolic Agent
- Antineoplastic Agent, Hormonal
- Drug
- Ester
- Ether
- Metabolite
- Organic Compound
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 17beta-Hydroxy-2alpha-methyl-5alpha-androstan-3-one | 2alpha-Methyldihydrotestosterone | Dihydro-2alpha-methyltestosterone | Drolban | Dromostanolone | Drostanolona | Drostanolonum | Masteril | Masteron | Medrosteron | Medrotestron | Metholone |
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Chemical Formula | C20H32O2 |
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Average Molecular Mass | 304.467 g/mol |
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Monoisotopic Mass | 304.240 g/mol |
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CAS Registry Number | 58-19-5 |
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IUPAC Name | (1S,2S,4R,7S,10R,11S,14S,15S)-14-hydroxy-2,4,15-trimethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]heptadecan-5-one |
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Traditional Name | drostanolone |
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SMILES | [H][C@]1(O)CC[C@@]2([H])[C@]3([H])CC[C@@]4([H])CC(=O)[C@]([H])(C)C[C@]4(C)[C@@]3([H])CC[C@]12C |
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InChI Identifier | InChI=1S/C20H32O2/c1-12-11-20(3)13(10-17(12)21)4-5-14-15-6-7-18(22)19(15,2)9-8-16(14)20/h12-16,18,22H,4-11H2,1-3H3/t12-,13+,14+,15+,16+,18+,19+,20+/m1/s1 |
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InChI Key | InChIKey=IKXILDNPCZPPRV-RFMGOVQKSA-N |
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Chemical Taxonomy |
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Description | 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. |
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Kingdom | Organic compounds |
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Super Class | Lipids and lipid-like molecules |
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Class | Steroids and steroid derivatives |
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Sub Class | Androstane steroids |
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Direct Parent | Androgens and derivatives |
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Alternative Parents | |
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Substituents | - Androgen-skeleton
- 3-oxosteroid
- 3-oxo-5-alpha-steroid
- 17-hydroxysteroid
- Oxosteroid
- Hydroxysteroid
- Cyclic alcohol
- Cyclic ketone
- Secondary alcohol
- Ketone
- Organic oxygen compound
- Organooxygen compound
- Hydrocarbon derivative
- Carbonyl group
- Organic oxide
- Alcohol
- Aliphatic homopolycyclic compound
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Molecular Framework | Aliphatic homopolycyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | - Cytoplasm
- Extracellular
- Membrane
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 151°C | Boiling Point | Not Available | Solubility | 6.05e-03 g/L | LogP | 3.99 |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-01u9-0290000000-692c470ca66bdb33f8cd | 2017-09-01 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive | splash10-08fs-3249000000-faaa19221c2eb1b1a219 | 2017-10-06 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-052r-0195000000-d6ce78753754982edcde | 2016-08-02 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-052r-0291000000-dce1079644608ccf2d76 | 2016-08-02 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gbm-2790000000-bb7896733d6ff696a1fa | 2016-08-02 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0029000000-601877ac3c6aed55c1c2 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0059000000-70257557fd2f0d3d532c | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0079-3090000000-cca24aebaf0ba5f4c845 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-000i-0092000000-5f392111cd6198b67db7 | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-0a6r-1951000000-454d26a526f739add98a | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0a6r-1900000000-0194bfdeaee7cb6f33e8 | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-0udi-0009000000-f9d10b76ade80bd401ad | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-0udi-0009000000-f9d10b76ade80bd401ad | 2021-10-11 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-0udi-0098000000-eb87ce2a04744f9a7151 | 2021-10-11 | View Spectrum | MS | Mass Spectrum (Electron Ionization) | splash10-0f6w-8931000000-0d33c997ec04e3071c8c | 2014-09-20 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Well absorbed following parenteral administration. |
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Mechanism of Toxicity | Dromostanolone is a synthetic androgenic anabolic steroid and is approximately 5 times as potent as natural methyltestosterone. Like testosterone and other androgenic hormones, dromostanolone binds to the androgen receptor. This causes downstream genetic transcriptional changes. This ultimately causes retention of nitrogen, potassium, and phosphorus; increases protein anabolism; and decreases amino acid catabolism. The antitumour activity of dromostanolone appears related to reduction or competitive inhibition of prolactin receptors or estrogen receptors or production. |
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Metabolism | Not Available |
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Toxicity Values | Not Available |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | For use in females, for palliation of androgenresponsive recurrent mammary cancer in women who are more than one year but less than five years postmenopausal. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Side effects include virilization (masculine traits in women), acne, fluid retention, and hypercalcemia. |
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Treatment | Not Available |
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Normal Concentrations |
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| Not Available |
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Abnormal Concentrations |
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| Not Available |
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External Links |
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DrugBank ID | DB00858 |
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HMDB ID | HMDB14996 |
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PubChem Compound ID | 6011 |
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ChEMBL ID | CHEMBL1582 |
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ChemSpider ID | 5789 |
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KEGG ID | C14605 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 34838 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | Dromostanolone |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | Drostanolone |
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References |
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Synthesis Reference | Ringold, H.J. and Rosenkranz, G.; U.S. Patent 2,908,693; October 13, 1959; assigned to
Syntex SA, Mexico.
Ringold, H.J.and Rosenkranz, G.; U.S.Patent 3,118,915; January 21, 1964; assigned to
Syntex Corporation, Panama. |
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MSDS | Not Available |
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General References | - Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
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Gene Regulation |
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Up-Regulated Genes | Not Available |
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Down-Regulated Genes | Not Available |
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