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Identification
NameDrostanolone
Accession NumberDB00858  (APRD00938)
Typesmall molecule
Groupsapproved, illicit
Description

Drostanolone (also known as dromostanolone) 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.

Structure
Thumb
Synonyms
SynonymLanguageCode
DromostanoloneNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
DrolbanNot Available
MasterilNot Available
MasteronNot Available
Brand mixturesNot Available
CategoriesNot Available
CAS number58-19-5
WeightAverage: 304.4669
Monoisotopic: 304.240230268
Chemical FormulaC20H32O2
InChI KeyInChIKey=IKXILDNPCZPPRV-RFMGOVQKSA-N
InChI
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
IUPAC Name
(1S,2S,4R,7S,10R,11S,14S,15S)-14-hydroxy-2,4,15-trimethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]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)[C@H](C)C[C@]12C
Mass Specshow(2.96 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassLipids
ClassSteroids and Steroid Derivatives
SubclassAndrogens and Derivatives
Direct parentAndrogens and Derivatives
Alternative parentsKetosteroids; Hydroxysteroids; Cyclohexanones; Secondary Alcohols; Cyclic Alcohols and Derivatives; Polyamines
Substituentscyclohexanone; cyclic alcohol; secondary alcohol; ketone; polyamine; alcohol; carbonyl group
Classification descriptionThis compound belongs to the androgens and derivatives. These are hydroxylated C19 steroid hormones. They are known to favour the development of masculine characteristics. They also show profound effects on scalp and body hair in humans.
Pharmacology
IndicationFor use in females, for palliation of androgenresponsive recurrent mammary cancer in women who are more than one year but less than five years postmenopausal.
PharmacodynamicsDromostanolone is a synthetic androgen, or male hormone, similar to testosterone. Dromostanolone works by attaching itself to androgen receptors; this causes it to interact with the parts of the cell involved in the making of proteins. It may cause an increase in the synthesis of some proteins or a decrease in the synthesis of others. These proteins have a variety of effects, including blocking the growth of some types of breast cancer cells, stimulating cells that cause male sexual characteristics, and stimulating the production of red blood cells.
Mechanism of actionDromostanolone 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.
AbsorptionWell absorbed following parenteral administration.
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicitySide effects include virilization (masculine traits in women), acne, fluid retention, and hypercalcemia.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.984
Caco-2 permeable + 0.8629
P-glycoprotein substrate Substrate 0.5627
P-glycoprotein inhibitor I Inhibitor 0.5153
P-glycoprotein inhibitor II Non-inhibitor 0.6722
Renal organic cation transporter Non-inhibitor 0.8105
CYP450 2C9 substrate Non-substrate 0.7608
CYP450 2D6 substrate Non-substrate 0.9117
CYP450 3A4 substrate Substrate 0.7529
CYP450 1A2 substrate Non-inhibitor 0.5
CYP450 2C9 substrate Non-inhibitor 0.6907
CYP450 2D6 substrate Non-inhibitor 0.9731
CYP450 2C19 substrate Non-inhibitor 0.8725
CYP450 3A4 substrate Non-inhibitor 0.8587
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9634
Ames test Non AMES toxic 0.9326
Carcinogenicity Non-carcinogens 0.8955
Biodegradation Not ready biodegradable 0.9827
Rat acute toxicity 2.2244 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9399
hERG inhibition (predictor II) Non-inhibitor 0.5786
Pharmacoeconomics
Manufacturers
  • Eli lilly and co
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point151 °CPhysProp
logP3.99HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility6.05e-03 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 area37.3ChemAxon
rotatable bond count0ChemAxon
refractivity88.18ChemAxon
polarizability36.79ChemAxon
number of rings4ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleYesChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC14605
ChEBI34838
ChEMBLCHEMBL1582
Therapeutic Targets DatabaseDAP000840
PharmGKBPA164760855
WikipediaDrostanolone
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

1. Androgen receptor

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Androgen receptor P10275 Details

References:

  1. Zakar T, Kaufmann G, Toth M: Assignment of anabolic-androgenic and antiandrogenic properties to some chlorine-substituted steroids on the basis of their binding characteristics to the androgen receptor of the rat seminal vesicle. Exp Clin Endocrinol. 1986 Jul;87(2):133-41. Pubmed
  2. Takahashi M, Tatsugi Y, Kohno T: Endocrinological and pathological effects of anabolic-androgenic steroid in male rats. Endocr J. 2004 Aug;51(4):425-34. Pubmed
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

1. Cytochrome P450 19A1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Cytochrome P450 19A1 P11511 Details

References:

  1. Navarro-Martin L, Blazquez M, Piferrer F: Masculinization of the European sea bass (Dicentrarchus labrax) by treatment with an androgen or aromatase inhibitor involves different gene expression and has distinct lasting effects on maturation. Gen Comp Endocrinol. 2009 Jan 1;160(1):3-11. Epub 2008 Oct 18. Pubmed

1. Sex hormone-binding globulin

Kind: protein

Organism: Human

Pharmacological action: unknown

Components

Name UniProt ID Details
Sex hormone-binding globulin P04278 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed

Comments
Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:12