(2R,10R,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-6,8-dien-14-yl acetate

• ChemBase ID: 119829
• Molecular Formular: C24H32O4
• Molecular Mass: 384.50848
• Monoisotopic Mass: 384.2300595
• SMILES: C12=CC(=O)CC[C@@]1(C1[C@@H](C=C2C)C2[C@@]([C@@](CC2)(OC(=O)C)C(=O)C)(CC1)C)C
• Canonical SMILES: O=C1CC[C@]2(C(=C1)C(=C[C@@H]1C2CC[C@]2(C1CC[C@]2(OC(=O)C)C(=O)C)C)C)C
• InChI: InChI=1S/C24H32O4/c1-14-12-18-19(22(4)9-6-17(27)13-21(14)22)7-10-23(5)20(18)8-11-24(23,15(2)25)28-16(3)26/h12-13,18-20H,6-11H2,1-5H3/t18-,19?,20?,22-,23+,24+/m1/s1
• InChIKey: RQZAXGRLVPAYTJ-UFZHOBIOSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,10R,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• IUPAC Traditional name: (2R,10R,14R,15S)-14-acetyl-2,8,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-6,8-dien-14-yl acetate
• Synonyms: (8R,10R,13S,17R)-17-acetyl-6,10,13-trimethyl-3-oxo-2,3,8,9,10,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl acetate; Megestrol Acetate

Database IDs

• CAS Number: 595-33-5
• PubChem SID: 162107935
• PubChem CID: 17571578

CALCULATED PROPERTIES

• Acid pKa: 17.826162
• H Acceptors: 3
• H Donor: 0
• LogD (pH = 5.5): 3.7237444
• LogD (pH = 7.4): 3.7237444
• Log P: 3.7237444
• Molar Refractivity: 108.6554 cm^3
• Polarizability: 42.444622 Å^3
• Polar Surface Area: 60.44 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Also has direct cytotoxic effects on breast cancer cells in tissue culture and suppresses luteinising hormone release from the pituitary; The biochemical mechanism of progestin antitumour activity is not well but may involve interaction with progesterone and glucocorticoid receptors, androgenic properties; The precise mechanism by which megestrol acetate produces effects in anorexia and cachexia is unknown at the present time

Product Information

• Application(s): against carcinoma of the breast and endometrium; Antineoplastic agent; Oral contraceptive

REFERENCES

• Ringold, M.J. et al., J.A.C.S., 1959, 81, 3712, (synth)
• Ellis, B. et al., J.C.S., 1960, 2828, (synth)
• Elce, J.S. et al., Biochem. J., 1967, 104, 58P
• Cooper, J.M. et al., Steroids, 1968, 11, 133
• Annen, K. et al., Annalen, 1983, 712, (deriv)
• Ni, Y. et al., CA, 1984, 101, 23805, (deriv)
• Guo, Z. et al., CA, 1985, 103, 54356, (deriv)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 7162, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 1187
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, VTF000