NAV

Calusterone

Identification

Generic Name
Calusterone
DrugBank Accession Number
DB01564
Background

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

Type
Small Molecule
Groups
Experimental, Illicit
Structure
3D
Similar Structures
Weight
Average: 316.4776
Monoisotopic: 316.240230268
Chemical Formula
C21H32O2
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
  • Calusterona
  • Calusterone
  • Calusteronum
  • CLS
External IDs
  • NSC-88536
  • U-22,550
  • U-22550i

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.

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Contraindications & Blackbox Warnings
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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.

TargetActionsOrganism
AAndrogen receptorNot AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AbciximabCalusterone may increase the anticoagulant activities of Abciximab.
AcenocoumarolCalusterone may increase the anticoagulant activities of Acenocoumarol.
AlteplaseCalusterone may increase the anticoagulant activities of Alteplase.
AncrodCalusterone may increase the anticoagulant activities of Ancrod.
AnistreplaseCalusterone may increase the anticoagulant activities of Anistreplase.
Antithrombin AlfaCalusterone may increase the anticoagulant activities of Antithrombin Alfa.
Antithrombin III humanCalusterone may increase the anticoagulant activities of Antithrombin III human.
ApixabanCalusterone may increase the anticoagulant activities of Apixaban.
ArdeparinCalusterone may increase the anticoagulant activities of Ardeparin.
ArgatrobanCalusterone may increase the anticoagulant activities of Argatroban.
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Food Interactions
Not Available

Products

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International/Other Brands
Methosarb / Riedemil

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This 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.
Kingdom
Organic compounds
Super Class
Lipids and lipid-like molecules
Class
Steroids and steroid derivatives
Sub Class
Androstane steroids
Direct Parent
Androgens and derivatives
Alternative Parents
3-oxo delta-4-steroids / 17-hydroxysteroids / Delta-4-steroids / Cyclohexenones / Tertiary alcohols / Cyclic alcohols and derivatives / Organic oxides / Hydrocarbon derivatives
Substituents
17-hydroxysteroid / 3-oxo-delta-4-steroid / 3-oxosteroid / Alcohol / Aliphatic homopolycyclic compound / Androgen-skeleton / Carbonyl group / Cyclic alcohol / Cyclic ketone / Cyclohexenone
Molecular Framework
Aliphatic homopolycyclic compounds
External Descriptors
Not Available
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
0678G6Q58A
CAS number
17021-26-0
InChI Key
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
IUPAC Name
(1S,3aS,3bR,4S,9aR,9bS,11aS)-1-hydroxy-1,4,9a,11a-tetramethyl-1H,2H,3H,3aH,3bH,4H,5H,7H,8H,9H,9aH,9bH,10H,11H,11aH-cyclopenta[a]phenanthren-7-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

References

General References
  1. Meli RJ, Ros PR: MR appearance of intra-abdominal metastatic melanoma. Magn Reson Imaging. 1992;10(4):705-8. [Article]
Human Metabolome Database
HMDB0004627
PubChem Compound
28204
PubChem Substance
46507441
ChemSpider
26239
ChEBI
135356
ChEMBL
CHEMBL455706
ZINC
ZINC000004215173
Wikipedia
Calusterone

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)128 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.0112 mg/mLALOGPS
logP3.55ALOGPS
logP3.93Chemaxon
logS-4.4ALOGPS
pKa (Strongest Acidic)18.8Chemaxon
pKa (Strongest Basic)-0.53Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count2Chemaxon
Hydrogen Donor Count1Chemaxon
Polar Surface Area37.3 Å2Chemaxon
Rotatable Bond Count0Chemaxon
Refractivity93.62 m3·mol-1Chemaxon
Polarizability37.77 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9774
Caco-2 permeable+0.8737
P-glycoprotein substrateSubstrate0.6431
P-glycoprotein inhibitor IInhibitor0.5981
P-glycoprotein inhibitor IINon-inhibitor0.732
Renal organic cation transporterNon-inhibitor0.757
CYP450 2C9 substrateNon-substrate0.8075
CYP450 2D6 substrateNon-substrate0.8604
CYP450 3A4 substrateSubstrate0.7916
CYP450 1A2 substrateNon-inhibitor0.8619
CYP450 2C9 inhibitorNon-inhibitor0.8844
CYP450 2D6 inhibitorNon-inhibitor0.951
CYP450 2C19 inhibitorNon-inhibitor0.6629
CYP450 3A4 inhibitorNon-inhibitor0.8713
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8711
Ames testNon AMES toxic0.9429
CarcinogenicityNon-carcinogens0.9361
BiodegradationNot ready biodegradable0.9494
Rat acute toxicity2.0516 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.886
hERG inhibition (predictor II)Non-inhibitor0.7219
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

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Details1. Androgen receptor
Kind
Protein
Organism
Humans
Pharmacological action
Yes
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 ...
Gene Name
AR
Uniprot ID
P10275
Uniprot Name
Androgen receptor
Molecular Weight
98987.9 Da
References
  1. 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. [Article]
  2. Brodkin RA, Cooper MR: Calusterone. Ann Intern Med. 1978 Dec;89(6):945-8. [Article]
  3. 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. [Article]
  4. Small EJ, Ryan CJ: The case for secondary hormonal therapies in the chemotherapy age. J Urol. 2006 Dec;176(6 Pt 2):S66-71. [Article]
  5. Omwancha J, Brown TR: Selective androgen receptor modulators: in pursuit of tissue-selective androgens. Curr Opin Investig Drugs. 2006 Oct;7(10):873-81. [Article]
  6. McPhaul MJ, Young M: Complexities of androgen action. J Am Acad Dermatol. 2001 Sep;45(3 Suppl):S87-94. [Article]

Drug created at July 31, 2007 13:10 / Updated at February 21, 2021 18:51