(1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-[(2H4)pyridin-3-yl]tetracyclo[8.7.0.02,7.011,15]heptadeca-7,13-dien-5-ol

• ChemBase ID: 158812
• Molecular Formular: C24H31NO
• Molecular Mass: 349.50904
• Monoisotopic Mass: 349.24056462
• SMILES: C1[C@@H](CC2=CC[C@@H]3[C@@H]([C@]2(C1)C)CC[C@]1([C@H]3CC=C1c1cccnc1)C)O
• Canonical SMILES: O[C@H]1CC[C@]2(C(=CC[C@@H]3[C@@H]2CC[C@]2([C@H]3CC=C2c2cccnc2)C)C1)C
• InChI: InChI=1S/C24H31NO/c1-23-11-9-18(26)14-17(23)5-6-19-21-8-7-20(16-4-3-13-25-15-16)24(21,2)12-10-22(19)23/h3-5,7,13,15,18-19,21-22,26H,6,8-12,14H2,1-2H3/t18-,19-,21-,22-,23-,24+/m0/s1
• InChIKey: GZOSMCIZMLWJML-VJLLXTKPSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-[(^2H₄)pyridin-3-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,13-dien-5-ol
• IUPAC Traditional name: (1S,2R,5S,10R,11S,15S)-2,15-dimethyl-14-[(^2H₄)pyridin-3-yl]tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-7,13-dien-5-ol
• Synonyms: (3β)-17-(3-Pyridinyl)androsta-5,16-dien-3-ol-d4; CB 7598-d4; Abiraterone-d4

Database IDs

• PubChem SID: 162252947
• PubChem CID: 71312697

CALCULATED PROPERTIES

• Acid pKa: 18.20429
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 3.8936753
• LogD (pH = 7.4): 3.9642935
• Log P: 3.965293
• Molar Refractivity: 107.3024 cm^3
• Polarizability: 41.77495 Å^3
• Polar Surface Area: 33.12 Å^2
• Rotatable Bonds: 1
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Methanol
• Apperance: White to Off-White Solid
• Melting Point: 213-215°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - A108492

Labelled Abiraterone (A108490). A steroidal cytochrome P 450 17α-hydroxylase-17,20-lyase inhibitor (CYP17), is currently undergoing phase II clinical trials as a potential drug for the treatment of androgen-dependent prostate cancer.

REFERENCES

• Denis, L., et al.: Cancer, 72, 3888 (1993)
• Potter, G.A., et al.: J. Med. Chem., 38, 2463 (1993)
• Denmeade, S., et al.: Nat. Rev., 2, 389(1993)
• Scher, H., et al.: J. Clin. Oncol., 23, 8253 (1993)