(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-17-hydroxy-14-[2-(methanesulfonyloxy)acetyl]-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl propanoate

• ChemBase ID: 162019
• Molecular Formular: C26H35FO8S
• Molecular Mass: 526.6147032
• Monoisotopic Mass: 526.2036673
• SMILES: C1=C[C@]2(C(=CC1=O)CC[C@@H]1[C@@]2([C@H](C[C@]2([C@H]1C[C@@H]([C@@]2(C(=O)COS(=O)(=O)C)OC(=O)CC)C)C)O)F)C
• Canonical SMILES: CCC(=O)O[C@@]1([C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)[C@]1([C@H]2CCC2=CC(=O)C=C[C@]12C)F)C(=O)COS(=O)(=O)C
• InChI: InChI=1S/C26H35FO8S/c1-6-22(31)35-26(21(30)14-34-36(5,32)33)15(2)11-19-18-8-7-16-12-17(28)9-10-23(16,3)25(18,27)20(29)13-24(19,26)4/h9-10,12,15,18-20,29H,6-8,11,13-14H2,1-5H3/t15-,18-,19-,20-,23-,24-,25-,26-/m0/s1
• InChIKey: LJIXIWVFIFXMTE-SOMXGXJRSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-17-hydroxy-14-[2-(methanesulfonyloxy)acetyl]-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,10S,11S,13S,14R,15S,17S)-1-fluoro-17-hydroxy-14-[2-(methanesulfonyloxy)acetyl]-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: Betamethasone 17-Propionate 21-Mesylate; (11β,16β)-9-Fluoro-11-hydroxy-16-methyl-21-[(methylsulfonyl)oxy]-17-(1-oxopropoxy)pregna-1,4-diene-3,20-dione; 9-Fluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione 21-Methanesulfonate 17-Propionate

Database IDs

• CAS Number: 15423-80-0
• PubChem SID: 162256154
• PubChem CID: 12960907

CALCULATED PROPERTIES

• Acid pKa: 13.624823
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): 2.7593951
• LogD (pH = 7.4): 2.759395
• Log P: 2.7593951
• Molar Refractivity: 129.0238 cm^3
• Polarizability: 51.477955 Å^3
• Polar Surface Area: 124.04 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: false

DETAILS

Toronto Research Chemicals - B327070

Betamethasone 17-Propionate 21-Mesylate is the 21-mesylate analogue of Betamethasone 17-Acetate (B327015) with antiinflammatory activity.

REFERENCES

• Mitsukuchi, M. et al.: Chem. Pharm. Bull., 37, 3286 (1989)