(1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-2,16-dimethyl-6-oxopentacyclo[9.7.0.02,8.03,5.012,16]octadeca-7,9-dien-15-yl (1,2-13C2,2H3)acetate

• ChemBase ID: 165315
• Molecular Formular: C24H29ClO4
• Molecular Mass: 418.92296968
• Monoisotopic Mass: 418.18214676
• SMILES: [C@H]12[C@H](C(=O)C=C3[C@]1([C@@H]1[C@@H](C=C3Cl)[C@H]3[C@](CC1)([C@](CC3)(C(=O)C)O[13C](=O)[13CH3])C)C)C2
• Canonical SMILES: [13CH3][13C](=O)O[C@@]1(CC[C@@H]2[C@]1(C)CC[C@H]1[C@H]2C=C(C2=CC(=O)[C@H]3[C@@H]([C@]12C)C3)Cl)C(=O)C
• InChI: InChI=1S/C24H29ClO4/c1-12(26)24(29-13(2)27)8-6-16-14-10-20(25)19-11-21(28)15-9-18(15)23(19,4)17(14)5-7-22(16,24)3/h10-11,14-18H,5-9H2,1-4H3/t14-,15+,16-,17-,18-,22-,23-,24-/m0/s1/i2+1,13+1
• InChIKey: UWFYSQMTEOIJJG-GDYUVENASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-2,16-dimethyl-6-oxopentacyclo[9.7.0.0^2,^8.0^3,^5.0^1^2,^1^6]octadeca-7,9-dien-15-yl (1,2-^1^3C₂,^2H₃)acetate
• IUPAC Traditional name: (1S,2S,3S,5R,11R,12S,15R,16S)-15-acetyl-9-chloro-2,16-dimethyl-6-oxopentacyclo[9.7.0.0^2,^8.0^3,^5.0^1^2,^1^6]octadeca-7,9-dien-15-yl (1,2-^1^3C₂,^2H₃)acetate
• Synonyms: (1β,2β)-17-(Acetyloxy-13C2,d3)-6-chloro-1,2-dihydro-3'H-cyclopropa[1,2]pregna-1,4,6-triene-3,20-dione; Androcur-13C2,d3; CPA; Cyprostat-13C2,d3; Cyproterone 17-O-Acetate-13C2,d3; Cyproterone 17α-Acetate-13C2,d3; Cyproviron-13C2,d3; NSC 81430-13C2,d3; SH 714-13C2,d3; Cyproterone Acetate-13C2,d3

Database IDs

• PubChem SID: 162259448
• PubChem CID: 71315142

CALCULATED PROPERTIES

• Acid pKa: 17.829681
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.638857
• LogD (pH = 7.4): 3.638857
• Log P: 3.638857
• Molar Refractivity: 111.8095 cm^3
• Polarizability: 43.571102 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - C989102

Labelled Cyproterone Acetate. The free alcohol is an anti-androgen; the acetate is both an anti-androgen and a progestogen. Combined with estrogen it is used in the treatment of acne.

REFERENCES

• Moltz, L., et al.: Contraception, 21, 393 (1980)
• Hammerstein, J., et al.: J. Steroid Biochem., 29, 591 (1983)