Calusterone
Identification
- Name
- Calusterone
- Accession Number
- DB01564
- Type
- Small Molecule
- Groups
- Experimental, Illicit
- Description
A 17-alkylated orally active androgenic steroid. A Schedule IV drug in Canada.
- 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
- Calusterona
- Calusterone
- Calusteronum
- CLS
- External IDs
- NSC-88536 / U-22,550 / U-22550i
- International/Other Brands
- Methosarb
- Categories
- UNII
- 0678G6Q58A
- CAS number
- 17021-26-0
- Weight
- Average: 316.4776
Monoisotopic: 316.240230268 - Chemical Formula
- C21H32O2
- 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
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.
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
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction (R)-warfarin The therapeutic efficacy of (R)-warfarin can be increased when used in combination with Calusterone. (S)-Warfarin The therapeutic efficacy of (S)-Warfarin can be increased when used in combination with Calusterone. 4-hydroxycoumarin The therapeutic efficacy of 4-hydroxycoumarin can be increased when used in combination with Calusterone. Abciximab The therapeutic efficacy of Abciximab can be increased when used in combination with Calusterone. Acenocoumarol The therapeutic efficacy of Acenocoumarol can be increased when used in combination with Calusterone. Acetylsalicylic acid The therapeutic efficacy of Acetylsalicylic acid can be increased when used in combination with Calusterone. Aldosterone The risk or severity of edema formation can be increased when Calusterone is combined with Aldosterone. Alteplase The therapeutic efficacy of Alteplase can be increased when used in combination with Calusterone. Amediplase The therapeutic efficacy of Amediplase can be increased when used in combination with Calusterone. Anagrelide The therapeutic efficacy of Anagrelide can be increased when used in combination with Calusterone. - Food Interactions
- Not Available
References
- General References
- Meli RJ, Ros PR: MR appearance of intra-abdominal metastatic melanoma. Magn Reson Imaging. 1992;10(4):705-8. [PubMed:1501542]
- External Links
- Human Metabolome Database
- HMDB0004627
- PubChem Compound
- 28204
- PubChem Substance
- 46507441
- ChemSpider
- 26239
- ChEBI
- 135356
- ChEMBL
- CHEMBL455706
- 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
Taxonomy
- 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
- Androgen-skeleton / 3-oxo-delta-4-steroid / 3-oxosteroid / Hydroxysteroid / Oxosteroid / 17-hydroxysteroid / Delta-4-steroid / Cyclohexenone / Tertiary alcohol / Cyclic alcohol
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- Not Available
Targets
- 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. [PubMed:17016423]
- Brodkin RA, Cooper MR: Calusterone. Ann Intern Med. 1978 Dec;89(6):945-8. [PubMed:152592]
- 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:17322500]
- 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:17084172]
- 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:17086931]
- McPhaul MJ, Young M: Complexities of androgen action. J Am Acad Dermatol. 2001 Sep;45(3 Suppl):S87-94. [PubMed:11511858]
Drug created on July 31, 2007 07:10 / Updated on December 20, 2018 09:20