(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

• ChemBase ID: 1348
• Molecular Formular: C21H32O2
• Molecular Mass: 316.47758
• Monoisotopic Mass: 316.24023026
• SMILES: O[C@@]1([C@@]2([C@H]([C@H]3[C@@H]([C@@]4(C(=CC(=O)CC4)C[C@@H]3C)C)CC2)CC1)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C[C@@H]([C@@H]1[C@@H]2CC[C@]2([C@H]1CC[C@]2(C)O)C)C)C
• 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
• InChIKey: IVFYLRMMHVYGJH-PVPPCFLZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,9S,10R,11S,14S,15S)-14-hydroxy-2,9,14,15-tetramethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadec-6-en-5-one; (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
• IUPAC Traditional name: calusterone
• Brand Name: Methosarb
• Synonyms: (7β,17β)-17-Hydroxy-7,17-dimethylandrost-4-en-3-one; 7β,17-Dimethyltestosterone; 17β-Hydroxy-7β,17-dimethylandrost-4-en-3-one; NSC 88536; U 22550; Methosarb; 7β,17α-Dimethyltestosterone; CLS; Calusteron; Calusterona [inn-spanish]; Calusteronum [inn-latin]; 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-Dimethyltestosterone; 7-beta,17-alpha-Dimethyl testosterone; 7beta,17-Dimethyltestosterone; 7beta,17alpha-Dimethyltestosterone; Calusterone

Database IDs

• CAS Number: 17021-26-0
• PubChem SID: 46507441; 160964808
• PubChem CID: 28204
• Chemspider ID: 26239
• Wikipedia Title: Calusterone

CALCULATED PROPERTIES

JChem

• Acid pKa: 19.564041
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.933019
• LogD (pH = 7.4): 3.9330192
• Log P: 3.9330192
• Molar Refractivity: 93.6166 cm^3
• Polarizability: 36.94731 Å^3
• Polar Surface Area: 37.3 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.55
• LOG S: -4.45
• Solubility (Water): 1.12e-02 g/l

DETAILS

DrugBank - DB01564

• Drug Groups: illicit; experimental
• Description: A 17-alkylated orally active androgenic steroid. A Schedule IV drug in Canada.
• 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.
• Pharmacology: 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.
• Affected Organisms: Humans and other mammals
• References: Meli RJ, Ros PR: MR appearance of intra-abdominal metastatic melanoma. Magn Reson Imaging. 1992;10(4):705-8. [Pubmed]

Toronto Research Chemicals - C148900

Synthetic androgen epimeric with Bolasterone (B674970). Has been used in treatment of breast cancer. Controlled substance (anabolic steroid).

REFERENCES

• Meli RJ, Ros PR: MR appearance of intra-abdominal metastatic melanoma. Magn Reson Imaging. 1992;10(4):705-8. Pubmed
• Horn, H., et al.: Br. J. Cancer, 33, 336 (1976)
• Zumoff, B., et al.: J. Clin. Endocrinol. Metab., 44(1976), 1203 (1976)