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

• ChemBase ID: 104131
• Molecular Formular: C28H37ClO7
• Molecular Mass: 521.04218
• Monoisotopic Mass: 520.2227812
• SMILES: O=C(OCC(=O)[C@]1(OC(=O)CC)[C@]2(C[C@H](O)[C@]3(Cl)[C@@]4(C(=CC(=O)C=C4)CC[C@H]3[C@@H]2C[C@@H]1C)C)C)CC
• 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)Cl)C(=O)COC(=O)CC
• InChI: InChI=1S/C28H37ClO7/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: KUVIULQEHSCUHY-XYWKZLDCSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-17-hydroxy-2,13,15-trimethyl-5-oxo-14-(propanoyloxy)tetracyclo[8.7.0.0?,?.0??,??]heptadeca-3,6-dien-14-yl]-2-oxoethyl propanoate; 2-[(1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-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: beconase
• Synonyms: 9α-Chloro-16β-methylprednisolone 17,21-dipropionate; Aerobec; Aldecin; Beclometasone Dipropionate; Beclotide; Clenil A; Entyderma; QVAR; Sanasthmax; Viarox; Ventolair; 9-Chloro-11β, 17,21-trihydroxy-16 β-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate; BECLOMETHASONE DIPROPIONATE; Beclomethasone dipropionate; 9-氯-11β,17,21-三羟基-16β-甲基孕甾-1,4-二烯-3,20-二酮-17,21-二丙酸酯; 倍氯米松丙酸酯

Database IDs

• CAS Number: 5534-09-8
• EC Number: 226-886-0
• MDL Number: MFCD00135613
• PubChem SID: 162092732
• PubChem CID: 21700

CALCULATED PROPERTIES

• Acid pKa: 13.850513
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 4.4283924
• LogD (pH = 7.4): 4.428392
• Log P: 4.4283924
• Molar Refractivity: 134.7928 cm^3
• Polarizability: 53.09888 Å^3
• Polar Surface Area: 106.97 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate; Methanol
• Apperance: White Solid
• Melting Point: 208-210°C; 212°C

Safety Information

• Storage Condition: -20°C Freezer; 2-8°C, Protect from light
• RTECS: TU3805000
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 60-61
• Safety Statements: 53-36/37/39-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• 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
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥99%
• Grade: analytical standard, for drug analysis

DETAILS

MP Biomedicals - 02154814

(9-Chloro-11β, 17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione 17,21-dipropionate)

Toronto Research Chemicals - B131030

Antiallergic, antiasthmatic (inhalate). Anti-inflammatory (topical).

REFERENCES

• Laube, B., et al.: J. Allergy Clin. Immunol., 101, 475 (1998)
• Harrison, L., et al.: Eur. J. Clin. Pharmacol., 58, 191 (1998)
• Maneechotesuwan, K., et al.: J. Allergy Clin. Immunol., 121, 43 (2008).