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Record Information
Version2.0
Creation Date2009-07-21 20:27:51 UTC
Update Date2014-12-24 20:25:53 UTC
Accession NumberT3D2917
Identification
Common NameDrostanolone
ClassSmall Molecule
DescriptionDrostanolone (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.
Compound Type
  • Anabolic Agent
  • Antineoplastic Agent, Hormonal
  • Drug
  • Ester
  • Ether
  • Metabolite
  • Organic Compound
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
17beta-Hydroxy-2alpha-methyl-5alpha-androstan-3-one
2alpha-Methyldihydrotestosterone
Dihydro-2alpha-methyltestosterone
Drolban
Dromostanolone
Drostanolona
Drostanolonum
Masteril
Masteron
Medrosteron
Medrotestron
Metholone
Chemical FormulaC20H32O2
Average Molecular Mass304.467 g/mol
Monoisotopic Mass304.240 g/mol
CAS Registry Number58-19-5
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
Traditional Namedrostanolone
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
InChI IdentifierInChI=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 KeyInChIKey=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.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassSteroids and steroid derivatives
Sub ClassAndrostane steroids
Direct ParentAndrogens 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 FrameworkAliphatic homopolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Cytoplasm
  • Extracellular
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological Roles
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point151°C
Boiling PointNot Available
Solubility6.05e-03 g/L
LogP3.99
Predicted Properties
PropertyValueSource
Water Solubility0.006 g/LALOGPS
logP3.81ALOGPS
logP3.95ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)19.38ChemAxon
pKa (Strongest Basic)-0.88ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 ŲChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.18 m³·mol⁻¹ChemAxon
Polarizability36.79 ųChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-01u9-0290000000-692c470ca66bdb33f8cdJSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-08fs-3249000000-faaa19221c2eb1b1a219JSpectraViewer
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0029000000-601877ac3c6aed55c1c2JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0059000000-70257557fd2f0d3d532cJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0079-3090000000-cca24aebaf0ba5f4c845JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-f9d10b76ade80bd401adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0009000000-f9d10b76ade80bd401adJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0udi-0098000000-eb87ce2a04744f9a7151JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-052r-0195000000-d6ce78753754982edcdeJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-052r-0291000000-dce1079644608ccf2d76JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0gbm-2790000000-bb7896733d6ff696a1faJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-000i-0092000000-5f392111cd6198b67db7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a6r-1951000000-454d26a526f739add98aJSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a6r-1900000000-0194bfdeaee7cb6f33e8JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0f6w-8931000000-0d33c997ec04e3071c8cJSpectraViewer | MoNA
Toxicity Profile
Route of ExposureWell absorbed following parenteral administration.
Mechanism of ToxicityDromostanolone 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.
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesFor 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 LevelNot Available
Health EffectsNot Available
SymptomsSide effects include virilization (masculine traits in women), acne, fluid retention, and hypercalcemia.
TreatmentNot Available
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00858
HMDB IDHMDB14996
PubChem Compound ID6011
ChEMBL IDCHEMBL1582
ChemSpider ID5789
KEGG IDC14605
UniProt IDNot Available
OMIM ID
ChEBI ID34838
BioCyc IDNot Available
CTD IDNot Available
Stitch IDDromostanolone
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkDrostanolone
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.

MSDSNot Available
General References
  1. 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 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

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 factor activity is modulated by bound coactivator and corepressor proteins. Transcription activation is down-regulated by NR0B2. Activated, but not phosphorylated, by HIPK3 and ZIPK/DAPK3.
Gene Name:
AR
Uniprot ID:
P10275
Molecular Weight:
98987.9 Da
References
  1. 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 ]
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 tissues. Ligand-dependent nuclear transactivation involves either direct homodimer binding to a palindromic estrogen response element (ERE) sequence or association with other DNA-binding transcription factors, such as AP-1/c-Jun, c-Fos, ATF-2, Sp1 and Sp3, to mediate ERE-independent signaling. Ligand binding induces a conformational change allowing subsequent or combinatorial association with multiprotein coactivator complexes through LXXLL motifs of their respective components. Mutual transrepression occurs between the estrogen receptor (ER) and NF-kappa-B in a cell-type specific manner. Decreases NF-kappa-B DNA-binding activity and inhibits NF-kappa-B-mediated transcription from the IL6 promoter and displace RELA/p65 and associated coregulators from the promoter. Recruited to the NF-kappa-B response element of the CCL2 and IL8 promoters and can displace CREBBP. Present with NF-kappa-B components RELA/p65 and NFKB1/p50 on ERE sequences. Can also act synergistically with NF-kappa-B to activate transcription involving respective recruitment adjacent response elements; the function involves CREBBP. Can activate the transcriptional activity of TFF1. Also mediates membrane-initiated estrogen signaling involving various kinase cascades. Isoform 3 is involved in activation of NOS3 and endothelial nitric oxide production. Isoforms lacking one or several functional domains are thought to modulate transcriptional activity by competitive ligand or DNA binding and/or heterodimerization with the full length receptor. Essential for MTA1-mediated transcriptional regulation of BRCA1 and BCAS3. Isoform 3 can bind to ERE and inhibit isoform 1.
Gene Name:
ESR1
Uniprot ID:
P03372
Molecular Weight:
66215.45 Da
References
  1. 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 ]
General Function:
Protein homodimerization activity
Specific Function:
This is a receptor for the anterior pituitary hormone prolactin (PRL). Acts as a prosurvival factor for spermatozoa by inhibiting sperm capacitation through suppression of SRC kinase activation and stimulation of AKT. Isoform 4 is unable to transduce prolactin signaling. Isoform 6 is unable to transduce prolactin signaling.
Gene Name:
PRLR
Uniprot ID:
P16471
Molecular Weight:
69505.045 Da
References
  1. 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 ]
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, and 17-beta-estradiol. Regulates the plasma metabolic clearance rate of steroid hormones by controlling their plasma concentration.
Gene Name:
SHBG
Uniprot ID:
P04278
Molecular Weight:
43778.755 Da
References
  1. 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 ]