DrugBank: Calusterone (DB01564)

targets (1)

Identification

Name

Calusterone

Accession Number

DB01564

Type

small molecule

Groups

illicit, experimental

Description

A 17-alkylated orally active androgenic steroid. A Schedule IV drug in Canada.

Structure

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

Synonyms

17-beta-Hydroxy-7-beta,17-alpha-dimethylandrost-4-ene-3-one
17beta-Hydroxy-7beta,17-dimethylandrost-4-en-3-one
17beta-Hydroxy-7beta,17alpha-dimethylandrost-4-ene-3-one
7-beta,17-alpha-Dimethyl testosterone
7-beta,17-Dimethyltestosterone
7beta,17-Dimethyltestosterone
7beta,17alpha-Dimethyltestosterone
Calusteron
Calusterona [inn-spanish]
Calusteronum [inn-latin]
CLS

Brand names

Methosarb

Brand name mixtures

Not Available

Categories

Androgens

CAS number

17021-26-0

Weight

Average: 316.4776
Monoisotopic: 316.240230268

Chemical Formula

C₂₁H₃₂O₂

InChI Key

InChIKey=IVFYLRMMHVYGJH-PVPPCFLZSA-N

InChI

InChI=1S/C21H32O2/c1-13-11-14-12-15(22)5-8-19(14,2)16-6-9-20(3)17(18(13)16)7-10-21(20,4)23/h12-13,16-18,23H,5-11H2,1-4H3/t13-,16-,17-,18+,19-,20-,21-/m0/s1

Plain Text

IUPAC Name

(1S,2R,9S,10R,11S,14S,15S)-14-hydroxy-2,9,14,15-tetramethyltetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadec-6-en-5-one

SMILES

[H][C@@]12CC[C@](C)(O)[C@@]1(C)CC[C@@]1([H])[C@@]2([H])[C@@H](C)CC2=CC(=O)CC[C@]12C

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Steroids and Steroid Derivatives

Substructures

Steroids and Steroid Derivatives
Hydroxy Compounds
Alkanes and Alkenes
Alcohols and Polyols
Cyclohexenes and Derivatives
Ketones

Pharmacology

Indication

An anabolic steroid which can theoretically aid in restauration and buildup of certain tissues, especially muscle. It is similar to synthetic testosterone and is still in early investigation. It was also investigated for use as a treatment for metastatic breast cancer.

Pharmacodynamics

Calusterone is a 17-alkylated orally active androgenic steroid. Calusterone may alter the metabolism of estradiol and reduce estrogen production. Calusterone has been investigated for possible antitumor properties.

Mechanism of action

The effects of calusterone in humans most likely occur by way of two main mechanisms: by activation of the androgen receptor, and by conversion to estradiol and activation of certain estrogen receptors. Using testosterone as the prime example, free testosterone (T) is transported into the cytoplasm of target tissue cells, where it can bind to the androgen receptor, or can be reduced to 5α-dihydrotestosterone (DHT) by the cytoplasmic enzyme 5α-reductase. DHT binds to the same androgen receptor even more strongly than T, so that its androgenic potency is about 2.5 times that of T. The T-receptor or DHT-receptor complex undergoes a structural change that allows it to move into the cell nucleus and bind directly to specific nucleotide sequences of the chromosomal DNA. The areas of binding are called hormone response elements (HREs), and influence transcriptional activity of certain genes, producing the androgen effects.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

Not Available

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Not Available

Prices

Not Available

Patents

Not Available

Properties

State

solid

Melting point

Not Available

Experimental Properties

Not Available

Predicted Properties

Property	Value	Source
water solubility	1.12e-02 g/l	ALOGPS
logP	3.55	ALOGPS
logP	3.93	ChemAxon Molconvert
logS	-4.45	ALOGPS
pKa		ChemAxon Molconvert
hydrogen acceptor count	2	ChemAxon Molconvert
hydrogen donor count	1	ChemAxon Molconvert
polar surface area	37.30	ChemAxon Molconvert
rotatable bond count	0	ChemAxon Molconvert
refractivity	93.62	ChemAxon Molconvert
polarizability	37.77	ChemAxon Molconvert

References

Synthesis Reference

Not Available

General Reference

Meli RJ, Ros PR: MR appearance of intra-abdominal metastatic melanoma. Magn Reson Imaging. 1992;10(4):705-8. Pubmed

External Links

Resource	Link
PubChem Compound	28204
PubChem Substance	46507441
ChemSpider	26239
Drug Product Database	0

ATC Codes

Not Available

AHFS Codes

Not Available

PDB Entries

Not Available

FDA label

Not Available

MSDS

Not Available

Interactions

Drug Interactions

Drug	Interaction

Food Interactions

Not Available

Targets
1. Androgen receptor Pharmacological action: yes 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: 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 Brodkin RA, Cooper MR: Calusterone. Ann Intern Med. 1978 Dec;89(6):945-8. Pubmed Lapauw B, Goemaere S, Crabbe P, Kaufman JM, Ruige JB: Is the effect of testosterone on body composition modulated by the androgen receptor gene CAG repeat polymorphism in elderly men? Eur J Endocrinol. 2007 Mar;156(3):395-401. Pubmed Small EJ, Ryan CJ: The case for secondary hormonal therapies in the chemotherapy age. J Urol. 2006 Dec;176(6 Pt 2):S66-71. Pubmed Omwancha J, Brown TR: Selective androgen receptor modulators: in pursuit of tissue-selective androgens. Curr Opin Investig Drugs. 2006 Oct;7(10):873-81. Pubmed McPhaul MJ, Young M: Complexities of androgen action. J Am Acad Dermatol. 2001 Sep;45(3 Suppl):S87-94. Pubmed

Targets

1. Androgen receptor

Pharmacological action: yes

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:

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
Brodkin RA, Cooper MR: Calusterone. Ann Intern Med. 1978 Dec;89(6):945-8. Pubmed
Lapauw B, Goemaere S, Crabbe P, Kaufman JM, Ruige JB: Is the effect of testosterone on body composition modulated by the androgen receptor gene CAG repeat polymorphism in elderly men? Eur J Endocrinol. 2007 Mar;156(3):395-401. Pubmed
Small EJ, Ryan CJ: The case for secondary hormonal therapies in the chemotherapy age. J Urol. 2006 Dec;176(6 Pt 2):S66-71. Pubmed
Omwancha J, Brown TR: Selective androgen receptor modulators: in pursuit of tissue-selective androgens. Curr Opin Investig Drugs. 2006 Oct;7(10):873-81. Pubmed
McPhaul MJ, Young M: Complexities of androgen action. J Am Acad Dermatol. 2001 Sep;45(3 Suppl):S87-94. Pubmed

Comments

Drug created on July 31, 2007 07:10 / Updated on November 10, 2010 13:49

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.