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

• ChemBase ID: 134362
• Molecular Formular: C27H34ClFO7
• Molecular Mass: 525.0060632
• Monoisotopic Mass: 524.19770933
• SMILES: CCC(=O)OCC(=O)[C@]1([C@H](C[C@@H]2[C@@]1(C[C@@H](C1([C@H]2CCC2=CC(=O)C=C[C@]12C)F)O)C)C)OC(=O)CCl
• Canonical SMILES: ClCC(=O)O[C@@]1([C@@H](C)C[C@@H]2[C@]1(C)C[C@H](O)C1([C@H]2CCC2=CC(=O)C=C[C@]12C)F)C(=O)COC(=O)CC
• InChI: InChI=1S/C27H34ClFO7/c1-5-22(33)35-14-21(32)27(36-23(34)13-28)15(2)10-19-18-7-6-16-11-17(30)8-9-24(16,3)26(18,29)20(31)12-25(19,27)4/h8-9,11,15,18-20,31H,5-7,10,12-14H2,1-4H3/t15-,18-,19-,20-,24-,25-,26?,27-/m0/s1
• InChIKey: UOCNBCVPZWLUKX-HOBFILNXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2S,10S,11S,13S,14R,15S,17S)-14-[(2-chloroacetyl)oxy]-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]-2-oxoethyl propanoate
• IUPAC Traditional name: 2-[(2S,10S,11S,13S,14R,15S,17S)-14-[(2-chloroacetyl)oxy]-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]-2-oxoethyl propanoate
• Synonyms: 9α-Fluoro-16β-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 17,21-dipropionate; Betamethasone 17,21-dipropionate; (11β,16β)-9-Fluoro-11-hydroxy-16-methyl-17,21-bis(1-oxopropoxy)-pregna-1,4-diene-3,20-dione; Betamethasone 17,21-Dipropionate; Diproderm; Diprolene; Diprophos; Diprosis; Diprosone; Diprospan; Maxivate; Psorion; Rinderon DP; S 3440; Sch 11460; β-Methasone 17,21-dipropionate; Betamethasone Dipropionate

Database IDs

• CAS Number: 5593-20-4
• EC Number: 227-005-2
• MDL Number: MFCD00133140
• PubChem SID: 162228638; 24891564
• PubChem CID: 16219003

CALCULATED PROPERTIES

• Acid pKa: 13.635525
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 3.8017
• LogD (pH = 7.4): 3.8016999
• Log P: 3.8017
• Molar Refractivity: 130.176 cm^3
• Polarizability: 51.040146 Å^3
• Polar Surface Area: 106.97 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Pale Yellow Foam
• Melting Point: 108-110°C

Safety Information

• Storage Condition: -20°C Freezer
• RTECS: TU4058000
• German water hazard class: 2
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥97.0%

DETAILS

Sigma Aldrich - B1152

Biochem/physiol Actions
Betamethasone 17,21-dipropionate is a glucocorticoid with anti-inflammatory and immunosuppressive activity.

Toronto Research Chemicals - B327005

Glucocorticoid. Used as anti-inflammatory and antibacterial ointment for dermatosis.

REFERENCES

• Dahlman-Ghozlan, K., et al.: Exp. Dermatol., 13, 65 (2004)
• Gounni Abdelilah, S., et al.: Clin. Immunol., 120, 220 (2004)
• Hertl, M., et al.: J. Clin. Invest., 116, 1159 (2004)