DrugBank: Drostanolone (DB00858)

targets (1) enzymes (1) carriers (1)

Identification

Name

Drostanolone

Accession Number

DB00858 (APRD00938)

Type

small molecule

Groups

illicit, approved

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

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Drolban
Dromostanolone

Salts

Not Available

Brand names

Name	Company
Emdisterone
Masterid
Masteril
Masteron
Masterone
Metholone
Permastril

Brand mixtures

Not Available

Categories

Anabolic Agents
Antineoplastic Agents, Hormonal

CAS number

58-19-5

Weight

Average: 304.4669
Monoisotopic: 304.240230268

Chemical Formula

C₂₀H₃₂O₂

InChI Key

InChIKey=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

Plain Text

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

Plain Text

Mass Spec

show (2.96 KB)

Taxonomy

Kingdom

Not Available

Classes

Not Available

Substructures

Not Available

Pharmacology

Indication

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.

Pharmacodynamics

Dromostanolone 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 action

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.

Absorption

Well absorbed following parenteral administration.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

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

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Eli lilly and co

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
melting point	151 °C	PhysProp
logP	3.99	HANSCH,C ET AL. (1995)

Predicted Properties

Property	Value	Source
water solubility	6.05e-03 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	ChemAxon
rotatable bond count	0	ChemAxon
refractivity	88.18	ChemAxon
polarizability	36.79	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Compound	C14605
ChEBI	34838
ChEMBL	34838
Therapeutic Targets Database	DAP000840
PharmGKB	PA164760855
Wikipedia	http://en.wikipedia.org/wiki/Drostanolone

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Not Available

Food Interactions

Not Available

Targets
1. Androgen receptor Pharmacological action: yes Actions: agonist The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Activated, but not phosphorylated, by HIPK3 Organism class: human UniProt ID: P10275 Gene: AR Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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 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 Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

Targets

1. Androgen receptor

Pharmacological action: yes
Actions: agonist

The steroid hormones and their receptors are involved in the regulation of eukaryotic gene expression and affect cellular proliferation and differentiation in target tissues. Activated, but not phosphorylated, by HIPK3

Organism class: human
UniProt ID: P10275 Link_out

Gene: AR

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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
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
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 Actions: inhibitor Catalyzes the formation of aromatic C18 estrogens from C19 androgens UniProt ID: P11511 Gene: CYP19A1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: 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

Enzymes

1. Cytochrome P450 19A1

Actions: inhibitor

Catalyzes the formation of aromatic C18 estrogens from C19 androgens

UniProt ID: P11511 Link_out

Gene: CYP19A1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

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 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 UniProt ID: P04278 Gene: SHBG Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed 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

Carriers

1. Sex hormone-binding globulin

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

UniProt ID: P04278 Link_out

Gene: SHBG Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
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 February 08, 2013 16:19