(1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-14,17-dihydroxy-14-[2-hydroxy(2H2)acetyl]-2,13,15-trimethyl(6,8,8-2H3)tetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 161165
• Molecular Formular: C22H29ClO5
• Molecular Mass: 408.91566
• Monoisotopic Mass: 408.17035171
• 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)CO)O)C)C)O)Cl)C
• Canonical SMILES: 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)Cl
• InChI: InChI=1S/C22H29ClO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1
• InChIKey: NBMKJKDGKREAPL-DVTGEIKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-14,17-dihydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,13,15-trimethyl(6,8,8-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: (1R,2S,10S,11S,13S,14R,15S,17S)-1-chloro-14,17-dihydroxy-14-[2-hydroxy(^2H₂)acetyl]-2,13,15-trimethyl(6,8,8-^2H₃)tetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• Synonyms: (11β,16β)-9-Chloro-11,17,21-trihydroxy-16-methylpregna-1,4-diene-3,20-dione-d5; 9α-Chloro-16β-methylprednisolone-d5; Beclometasone-d5; Becolvent-d5; Beclomethasone-d5

Database IDs

• PubChem SID: 162255300
• PubChem CID: 71313644

CALCULATED PROPERTIES

• Acid pKa: 12.43441
• H Acceptors: 5
• H Donor: 3
• LogD (pH = 5.5): 2.1450696
• LogD (pH = 7.4): 2.1450658
• Log P: 2.1450698
• Molar Refractivity: 107.236 cm^3
• Polarizability: 41.7352 Å^3
• Polar Surface Area: 94.83 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dioxane; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 236-238°C

Safety Information

• Storage Condition: -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - B131002

Glucocorticoid. Used in chronic asthma and allergic rhinitis. Antiallergic, antiasthmatic (inhalant). Anti-inflammatory (topical).

REFERENCES

• Malfitan, V.A., et al.: Clin. Ther., 4, 472 (1982)
• Rao, M., et al.: J. Asthma, 19, 21 (1982)
• Small, P., et al.: Ann. Allergy, 49, 127 (1982)
• Brogden, R.N., et al.: Drugs, 28, 99 (1982)