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
Structure for Calusterone (DB01564)
- 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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Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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.
Target Actions Organism AAndrogen receptor Not Available Humans - 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbciximab Calusterone may increase the anticoagulant activities of Abciximab. Acenocoumarol Calusterone may increase the anticoagulant activities of Acenocoumarol. Alteplase Calusterone may increase the anticoagulant activities of Alteplase. Ancrod Calusterone may increase the anticoagulant activities of Ancrod. Anistreplase Calusterone may increase the anticoagulant activities of Anistreplase. Antithrombin Alfa Calusterone may increase the anticoagulant activities of Antithrombin Alfa. Antithrombin III human Calusterone may increase the anticoagulant activities of Antithrombin III human. Apixaban Calusterone may increase the anticoagulant activities of Apixaban. Ardeparin Calusterone may increase the anticoagulant activities of Ardeparin. Argatroban Calusterone may increase the anticoagulant activities of Argatroban. 
Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - Food Interactions
- Not Available
Products
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- 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,2R,9S,10R,11S,14S,15S)-14-hydroxy-2,9,14,15-tetramethyltetracyclo[8.7.0.0²,⁷.0¹¹,¹⁵]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
References
- General References
- Meli RJ, Ros PR: MR appearance of intra-abdominal metastatic melanoma. Magn Reson Imaging. 1992;10(4):705-8. [Article]
- External Links
- Human Metabolome Database
- HMDB0004627
- PubChem Compound
- 28204
- PubChem Substance
- 46507441
- ChemSpider
- 26239
- ChEBI
- 135356
- ChEMBL
- CHEMBL455706
- ZINC
- ZINC000004215173
- Wikipedia
- Calusterone
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 128 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.0112 mg/mL ALOGPS logP 3.55 ALOGPS logP 3.93 ChemAxon logS -4.4 ALOGPS pKa (Strongest Acidic) 19.56 ChemAxon pKa (Strongest Basic) -0.53 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 37.3 Å2 ChemAxon Rotatable Bond Count 0 ChemAxon Refractivity 93.62 m3·mol-1 ChemAxon Polarizability 37.77 Å3 ChemAxon Number of Rings 4 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 1.0 Blood Brain Barrier + 0.9774 Caco-2 permeable + 0.8737 P-glycoprotein substrate Substrate 0.6431 P-glycoprotein inhibitor I Inhibitor 0.5981 P-glycoprotein inhibitor II Non-inhibitor 0.732 Renal organic cation transporter Non-inhibitor 0.757 CYP450 2C9 substrate Non-substrate 0.8075 CYP450 2D6 substrate Non-substrate 0.8604 CYP450 3A4 substrate Substrate 0.7916 CYP450 1A2 substrate Non-inhibitor 0.8619 CYP450 2C9 inhibitor Non-inhibitor 0.8844 CYP450 2D6 inhibitor Non-inhibitor 0.951 CYP450 2C19 inhibitor Non-inhibitor 0.6629 CYP450 3A4 inhibitor Non-inhibitor 0.8713 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8711 Ames test Non AMES toxic 0.9429 Carcinogenicity Non-carcinogens 0.9361 Biodegradation Not ready biodegradable 0.9494 Rat acute toxicity 2.0516 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.886 hERG inhibition (predictor II) Non-inhibitor 0.7219
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- 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
- 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]
- Brodkin RA, Cooper MR: Calusterone. Ann Intern Med. 1978 Dec;89(6):945-8. [Article]
- 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]
- 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]
- 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]
- McPhaul MJ, Young M: Complexities of androgen action. J Am Acad Dermatol. 2001 Sep;45(3 Suppl):S87-94. [Article]
Drug created on July 31, 2007 13:10 / Updated on February 21, 2021 18:51