2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate

• ChemBase ID: 72783
• Molecular Formular: C28H37FO7
• Molecular Mass: 504.5875832
• Monoisotopic Mass: 504.25233174
• 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)COC(=O)CC)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)COC(=O)CC
• InChI: InChI=1S/C28H37FO7/c1-6-23(33)35-15-22(32)28(36-24(34)7-2)16(3)12-20-19-9-8-17-13-18(30)10-11-25(17,4)27(19,29)21(31)14-26(20,28)5/h10-11,13,16,19-21,31H,6-9,12,14-15H2,1-5H3/t16-,19-,20-,21-,25-,26-,27-,28-/m0/s1
• InChIKey: CIWBQSYVNNPZIQ-XYWKZLDCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate; 2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate
• IUPAC Traditional name: betamethasone dipropionate; 2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate
• Synonyms: Diprospan; Diprolene; Diprosone; Diprolene AF; Betamethasone dipropionat; Betamethasone dipropionate

Database IDs

• CAS Number: 5593-20-4
• PubChem SID: 162037704
• PubChem CID: 21800

CALCULATED PROPERTIES

• Acid pKa: 13.635488
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.9648921
• LogD (pH = 7.4): 3.964892
• Log P: 3.9648921
• Molar Refractivity: 130.0497 cm^3
• Polarizability: 50.98258 Å^3
• Polar Surface Area: 106.97 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Safety Information

• Storage Condition: -20°C

Pharmacology Properties

• Mechanism of Action: ACTH secretion inhibitor; Calcium mobilizer; Corticosteroid; Gluconeogenesis promoter; Glycogen deposition inhibitor

Product Information

• Salt Data: Free Base
• Application(s): Antiinflammatory; Immunosuppressive

DETAILS

Selleck Chemicals - S1688

Research Area: Immunology,Inflammation
Biological Activity:
Betamethasone Dipropionate(Diprolene) is a glucocorticoid steroid with anti-inflammatory and immunosuppressive abilities. It mimics the action of cortisol (hydrocortisone), the naturally-occurring steroid produced in the body by the adrenal glands. Corticosteroids have potent anti-inflammatory actions and also suppress the immune response. Corticosteroids have many effects on the body, but they are often used for their potent anti-inflammatory effects, particularly in those conditions in which the immune system plays an important role. [1]

REFERENCES

• Oliveto, E.P. et al., J.A.C.S., 1958, 80, 6687, (synth)
• Taub, D. et al., J.A.C.S., 1960, 82, 4012, (synth)
• Carrington, T.R. et al., J.C.S., 1961, 4560, (synth)
• Rausser, R. et al., J.O.C., 1966, 31, 26, (synth)
• Scapagnini, U. et al., Curr. Ther. Res., Clin. Exp., 1968, 10, 464, (pharmacol)
• Merrill, E.J. et al., J. Labelled Compd., 1971, 7, 509, (synth)
• Ferrante, M.G. et al., Anal. Profiles Drug Subst., 1977, 6, 43, (rev, dipropionate)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 6th edn., Akademie-Verlag, 1987, 6645; 6676; 7580, (synonyms)
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 724
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, BFV765; BFV770; VCA000