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

• ChemBase ID: 119828
• Molecular Formular: C25H32ClFO5
• Molecular Mass: 466.9699832
• Monoisotopic Mass: 466.19223002
• SMILES: [C@]12([C@]([C@H](CC1C1[C@@]([C@@]3(C(=CC(=O)C=C3)CC1)C)([C@H](C2)O)F)C)(C(=O)CCl)OC(=O)CC)C
• Canonical SMILES: CCC(=O)O[C@@]1([C@@H](C)CC2[C@]1(C)C[C@H](O)[C@]1(C2CCC2=CC(=O)C=C[C@]12C)F)C(=O)CCl
• InChI: InChI=1S/C25H32ClFO5/c1-5-21(31)32-25(20(30)13-26)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,27)19(29)12-23(18,25)4/h8-9,11,14,17-19,29H,5-7,10,12-13H2,1-4H3/t14-,17?,18?,19-,22-,23-,24-,25-/m0/s1
• InChIKey: CBGUOGMQLZIXBE-BHPVMOEKSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-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 propanoate
• IUPAC Traditional name: (1R,2S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-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 propanoate
• Synonyms: (9R,10S,11S,13S,16S,17R)-17-(2-chloroacetyl)-9-fluoro-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 propionate; Dermovate; Butavate; Clobesol; Decloban; Myalone; Temovate; Clobetasol (O-propionate)

Database IDs

• CAS Number: 25122-46-7
• PubChem SID: 162107934
• PubChem CID: 5702274

CALCULATED PROPERTIES

• Acid pKa: 13.626671
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.1778226
• LogD (pH = 7.4): 4.1778226
• Log P: 4.1778226
• Molar Refractivity: 119.3223 cm^3
• Polarizability: 46.51583 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Mechanism of Action: Corticosteroid

Product Information

• Application(s): Antiallergic agent; Antiinflammatory; Dermatological agent; Used to treat eczema and psoriasis

REFERENCES

• Ger. Pat., 1969, Glaxo, 1 902 340; CA, 72, 44021y, (synth, pharmacol)
• Tamura, J. et al., J. Toxicol. Sci., 1980, 5, 45; 177, (tox)
• Allenby, C.F. et al., Br. J. Dermatol., 1981, 104, 179
• Topical Corticosteroids, (Eds. Maibach, H.I. et al), Karger, 1992, (book)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 726
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 10195; 10400, (synonyms)
• Khalid, M. et al., Int. J. Dermatol., 1995, 34, 203, (clin trial)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, CMW300; CMW400