2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate

• ChemBase ID: 132044
• Molecular Formular: C24H31FO6
• Molecular Mass: 434.4977432
• Monoisotopic Mass: 434.21046693
• SMILES: C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)COC(=O)C)O)C)O)F)C
• Canonical SMILES: CC(=O)OCC(=O)[C@@]1(O)[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
• InChI: InChI=1S/C24H31FO6/c1-13-9-18-17-6-5-15-10-16(27)7-8-21(15,3)23(17,25)19(28)11-22(18,4)24(13,30)20(29)12-31-14(2)26/h7-8,10,13,17-19,28,30H,5-6,9,11-12H2,1-4H3/t13-,17-,18-,19-,21-,22-,23-,24-/m0/s1
• InChIKey: AKUJBENLRBOFTD-QZIXMDIESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl acetate
• IUPAC Traditional name: β-val
• Synonyms: (11β,16β)-21-(Acetyloxy)-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione; 9-Fluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione 21-acetate; Betamethasone Acetate; Betamethasone 21-Acetate; 9α-Fluoro-16β-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 21-acetate; Betamethasone 21-acetate

Database IDs

• CAS Number: 987-24-6
• EC Number: 213-578-6
• MDL Number: MFCD00867462
• PubChem SID: 24892001; 162226321
• PubChem CID: 443967

CALCULATED PROPERTIES

• Acid pKa: 12.440784
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): 2.122695
• LogD (pH = 7.4): 2.1226912
• Log P: 2.1226952
• Molar Refractivity: 111.6444 cm^3
• Polarizability: 43.471127 Å^3
• Polar Surface Area: 100.9 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 203-205°C

Safety Information

• Storage Condition: Refrigerator
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 22-36
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Personal Protective Equipment: Eyeshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges

DETAILS

Sigma Aldrich - B7527

Biochem/physiol Actions
Evaluated in combination with betamethasone 21-phosphate to induce lung maturation in fetal sheep.1

Toronto Research Chemicals - B327025

Betamethasone acetate (BA) is a glucocorticoid steroid with anti-inflammatory and immunosuppressive properties which can be used in treatment of asthma and itching.

REFERENCES

• Kerns, E., et al.: J. Pharm. Sci., 90, 1838 (2001)
• Seidler, J., et al.: J. Med. Chem., 46, 4477 (2001)
• Alsenz, J., et al.: J. Pharm. Sci., 96, 1748 (2001)