ContaminantDB: Drostanolone

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (4)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:51 UTC

Update Date

2026-05-14 16:50:55 UTC

Accession Number

CHEM002291

Identification

Common Name

Drostanolone

Class

Small Molecule

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.

Contaminant Sources

HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Anabolic Agent
Antineoplastic Agent, Hormonal
Drug
Ester
Ether
Metabolite
Organic Compound
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
17beta-Hydroxy-2alpha-methyl-5alpha-androstan-3-one	ChEBI
2alpha-Methyldihydrotestosterone	ChEBI
Dihydro-2alpha-methyltestosterone	ChEBI
Dromostanolone	ChEBI
Drostanolona	ChEBI
Drostanolonum	ChEBI
Medrosteron	ChEBI
Medrotestron	ChEBI
17b-Hydroxy-2a-methyl-5a-androstan-3-one	Generator
17Β-hydroxy-2α-methyl-5α-androstan-3-one	Generator
2a-Methyldihydrotestosterone	Generator
2Α-methyldihydrotestosterone	Generator
Dihydro-2a-methyltestosterone	Generator
Dihydro-2α-methyltestosterone	Generator
Drolban	HMDB
Metholone	HMDB
Dromostanolone, (5alpha,17beta)-isomer	HMDB
Prometholone	HMDB
Drostanolon	HMDB
17 beta-Hydroxy-2 alpha-methyl-5 alpha-androstan-3-one	HMDB
Methalone	HMDB
Drostanolone	ChEBI

Chemical Formula

C₂₀H₃₂O₂

Average Molecular Mass

304.467 g/mol

Monoisotopic Mass

304.240 g/mol

CAS Registry Number

58-19-5

IUPAC Name

(1S,3aS,3bR,5aS,8R,9aS,9bS,11aS)-1-hydroxy-8,9a,11a-trimethyl-hexadecahydro-1H-cyclopenta[a]phenanthren-7-one

Traditional Name

drostanolone

SMILES

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

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

InChI Key

IKXILDNPCZPPRV-RFMGOVQKSA-N

Chemical Taxonomy

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.

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

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

Molecular Framework

Aliphatic homopolycyclic compounds

External Descriptors

3-oxo steroid (CHEBI:34838 )
17beta-hydroxy steroid (CHEBI:34838 )
anabolic androgenic steroid (CHEBI:34838 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular
Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

antineoplastic agent

Biological Roles

anabolic agent

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	151°C
Boiling Point	Not Available
Solubility	6.05e-03 g/L

Predicted Properties

Property	Value	Source
Water Solubility	0.006 g/L	ALOGPS
logP	3.81	ALOGPS
logP	3.95	ChemAxon
logS	-4.7	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	88.18 m³·mol⁻¹	ChemAxon
Polarizability	36.79 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

Spectra

Spectrum Type	Description	Splash Key	View
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-01u9-0290000000-692c470ca66bdb33f8cd	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positive	splash10-08fs-3249000000-faaa19221c2eb1b1a219	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-052r-0195000000-d6ce78753754982edcde	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-052r-0291000000-dce1079644608ccf2d76	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0gbm-2790000000-bb7896733d6ff696a1fa	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0029000000-601877ac3c6aed55c1c2	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0059000000-70257557fd2f0d3d532c	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0079-3090000000-cca24aebaf0ba5f4c845	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-000i-0092000000-5f392111cd6198b67db7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a6r-1951000000-454d26a526f739add98a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0a6r-1900000000-0194bfdeaee7cb6f33e8	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0009000000-f9d10b76ade80bd401ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-0009000000-f9d10b76ade80bd401ad	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0udi-0098000000-eb87ce2a04744f9a7151	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0f6w-8931000000-0d33c997ec04e3071c8c	Spectrum

Toxicity Profile

Route of Exposure

Well absorbed following parenteral administration.

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.

Metabolism

Not Available

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

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.

Minimum Risk Level

Not Available

Health Effects

Not Available

Symptoms

Side effects include virilization (masculine traits in women), acne, fluid retention, and hypercalcemia.

Treatment

Not Available

Concentrations

Not Available

External Links

DrugBank ID

DB00858

HMDB ID

HMDB0014996

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chemspider ID

ChEBI ID

PubChem Compound ID

Kegg Compound ID

YMDB ID

Not Available

ECMDB ID

Not Available

References

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.

MSDS

Not Available

General References

1. Simons K, Toomre D: Lipid rafts and signal transduction. Nat Rev Mol Cell Biol. 2000 Oct;1(1):31-9.

2. Watson AD: Thematic review series: systems biology approaches to metabolic and cardiovascular disorders. Lipidomics: a global approach to lipid analysis in biological systems. J Lipid Res. 2006 Oct;47(10):2101-11. Epub 2006 Aug 10.

3. Sethi JK, Vidal-Puig AJ: Thematic review series: adipocyte biology. Adipose tissue function and plasticity orchestrate nutritional adaptation. J Lipid Res. 2007 Jun;48(6):1253-62. Epub 2007 Mar 20.

4. Lingwood D, Simons K: Lipid rafts as a membrane-organizing principle. Science. 2010 Jan 1;327(5961):46-50. doi: 10.1126/science.1174621.

5. The lipid handbook with CD-ROM

Drostanolone (CHEM002291)

Structure for CHEM002291: Drostanolone