(1R,2S,13R,14R,15S,17S)-1-chloro-14-(2-chloroacetyl)-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl furan-2-carboxylate

• ChemBase ID: 119891
• Molecular Formular: C27H30Cl2O6
• Molecular Mass: 521.4295
• Monoisotopic Mass: 520.14194404
• SMILES: [C@]12([C@](OC(=O)c3occc3)([C@@H](CC1C1[C@@]([C@@]3(C(=CC(=O)C=C3)CC1)C)([C@H](C2)O)Cl)C)C(=O)CCl)C
• Canonical SMILES: ClCC(=O)[C@@]1(OC(=O)c2ccco2)[C@H](C)CC2[C@]1(C)C[C@H](O)[C@]1(C2CCC2=CC(=O)C=C[C@]12C)Cl
• InChI: InChI=1S/C27H30Cl2O6/c1-15-11-19-18-7-6-16-12-17(30)8-9-24(16,2)26(18,29)21(31)13-25(19,3)27(15,22(32)14-28)35-23(33)20-5-4-10-34-20/h4-5,8-10,12,15,18-19,21,31H,6-7,11,13-14H2,1-3H3/t15-,18?,19?,21+,24+,25+,26+,27+/m1/s1
• InChIKey: WOFMFGQZHJDGCX-NKEDMXMMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,13R,14R,15S,17S)-1-chloro-14-(2-chloroacetyl)-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl furan-2-carboxylate
• IUPAC Traditional name: (1R,2S,13R,14R,15S,17S)-1-chloro-14-(2-chloroacetyl)-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl furan-2-carboxylate
• Synonyms: (9R,10S,11S,13S,16R,17R)-9-chloro-17-(2-chloroacetyl)-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl furan-2-carboxylate; Elocon; Elocom; Mometasone Furoate

Database IDs

• CAS Number: 83919-23-7
• PubChem SID: 162108196
• PubChem CID: 9871375

CALCULATED PROPERTIES

• Acid pKa: 13.836226
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 5.055208
• LogD (pH = 7.4): 5.0552077
• Log P: 5.055208
• Molar Refractivity: 132.4999 cm^3
• Polarizability: 51.422264 Å^3
• Polar Surface Area: 93.81 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: false

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Glucocorticoid steroid

Product Information

• Application(s): Antiallergic agent; Antiinflammatory

REFERENCES

• Shapiro, E.L. et al., J. Med. Chem., 1987, 30, 1581, (synth, pharmacol, deriv)
• Popper, T.L. et al., J. Steroid Biochem., 1987, 27, 837, (pharmacol)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 737
• Prakash, A. et al., Drugs, 1998, 55, 145-163, (pharmacol, rev)
• Onrust, S.V. et al., Drugs, 1998, 56, 725-745, (mometasone furoate, rev)
• Draper, R.W. et al., Tetrahedron, 1999, 55, 3355-3364, (furoate, synth)
• Sharpe, M. et al., Drugs, 2001, 61, 1325-1350, (rev)