(1R,2S,8S,10S,11S,13R,14R,15S,17S)-4-chloro-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 169833
• Molecular Formular: C22H27ClF2O5
• Molecular Mass: 444.8965864
• Monoisotopic Mass: 444.15150808
• SMILES: C1(=C[C@]2(C(=CC1=O)[C@H](C[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@H]([C@]2(O)C(=O)CO)C)C)O)F)F)C)Cl
• Canonical SMILES: OCC(=O)[C@@]1(O)[C@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2C[C@@H](C2=CC(=O)C(=C[C@]12C)Cl)F)F
• InChI: InChI=1S/C22H27ClF2O5/c1-10-4-11-12-5-15(24)13-6-16(27)14(23)7-19(13,2)21(12,25)17(28)8-20(11,3)22(10,30)18(29)9-26/h6-7,10-12,15,17,26,28,30H,4-5,8-9H2,1-3H3/t10-,11+,12+,15+,17+,19+,20+,21+,22+/m1/s1
• InChIKey: GGXMRPUKBWXVHE-MIHLVHIWSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,8S,10S,11S,13R,14R,15S,17S)-4-chloro-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: sicorten
• Synonyms: (6α,11β,16α)-2-Chloro-6,9-difluoro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione; 2-Chloroflumethasone; Ba 48401; C 48401Ba; Halomethasone; Sicorten; 2-Chloro-6α,9-difluoro-11β,17,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione; Halometasone

Database IDs

• CAS Number: 50629-82-8
• PubChem SID: 162263965
• PubChem CID: 9846332

CALCULATED PROPERTIES

• Acid pKa: 12.415618
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 1.7308027
• LogD (pH = 7.4): 1.7307985
• Log P: 1.7308027
• Molar Refractivity: 107.1076 cm^3
• Polarizability: 41.32199 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - H103100

A corticosteroid used in the treatment of skin disorders such as chronic eczema.

REFERENCES

• Ma, H. et al.: Yao. Liuxin. Zaz., 20, 225 (2011)
• Asche, H. et al.: Pharmac. Acta Helv., 60, 232 (2011)