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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
17beta-Hydroxy-2alpha-methyl-5alpha-androstan-3-oneNot AvailableNot Available
2alpha-MethyldihydrotestosteroneNot AvailableNot Available
Dihydro-2alpha-methyltestosteroneNot AvailableNot Available
DromostanoloneNot AvailableNot Available
DrostanolonaNot AvailableNot Available
DrostanoloneNot AvailableNot Available
DrostanolonumNot AvailableNot Available
MedrosteronNot AvailableNot Available
MedrotestronNot AvailableNot Available
MetholoneNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
DrolbanLilly
MasterilSyntex
MasteronRecordati
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number58-19-5
WeightAverage: 304.4669
Monoisotopic: 304.240230268
Chemical FormulaC20H32O2
InChI KeyIKXILDNPCZPPRV-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[8.7.0.0²,⁷.0¹¹,¹⁵]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
Taxonomy
DescriptionThis 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.
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-oxo-5-alpha-steroid
  • 17-hydroxysteroid
  • Oxosteroid
  • Hydroxysteroid
  • 3-oxosteroid
  • Cyclohexanone
  • Cyclic alcohol
  • Cyclic ketone
  • Secondary alcohol
  • Ketone
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Alcohol
  • Aliphatic homopolycyclic compound
Molecular FrameworkAliphatic homopolycyclic compounds
External Descriptors
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
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.984
Caco-2 permeable+0.8629
P-glycoprotein substrateSubstrate0.5627
P-glycoprotein inhibitor IInhibitor0.5153
P-glycoprotein inhibitor IINon-inhibitor0.6722
Renal organic cation transporterNon-inhibitor0.8105
CYP450 2C9 substrateNon-substrate0.7608
CYP450 2D6 substrateNon-substrate0.9117
CYP450 3A4 substrateSubstrate0.7529
CYP450 1A2 substrateNon-inhibitor0.5
CYP450 2C9 substrateNon-inhibitor0.6907
CYP450 2D6 substrateNon-inhibitor0.9731
CYP450 2C19 substrateNon-inhibitor0.8725
CYP450 3A4 substrateNon-inhibitor0.8587
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9634
Ames testNon AMES toxic0.9326
CarcinogenicityNon-carcinogens0.8955
BiodegradationNot ready biodegradable0.9827
Rat acute toxicity2.2244 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9399
hERG inhibition (predictor II)Non-inhibitor0.5786
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 Solubility0.00605 mg/mLALOGPS
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 Å2ChemAxon
Rotatable Bond Count0ChemAxon
Refractivity88.18 m3·mol-1ChemAxon
Polarizability36.79 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (2.96 KB)
SpectraMS
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.

General ReferenceNot Available
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

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

Enzymes

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

Carriers

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

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Drug created on June 13, 2005 07:24 / Updated on April 15, 2014 17:06