(1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.02,7.011,15]heptadeca-3,6-dien-5-one

• ChemBase ID: 157619
• Molecular Formular: C22H28ClFO4
• Molecular Mass: 410.9067232
• Monoisotopic Mass: 410.16601528
• 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)CCl)O)C)O)F)C
• Canonical SMILES: ClCC(=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/C22H28ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1
• InChIKey: FCSHDIVRCWTZOX-DVTGEIKXSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2S,10S,11S,13S,14R,15S,17S)-14-(2-chloroacetyl)-1-fluoro-14,17-dihydroxy-2,13,15-trimethyltetracyclo[8.7.0.0^2,^7.0^1^1,^1^5]heptadeca-3,6-dien-5-one
• IUPAC Traditional name: clobetasol
• Synonyms: (11β,16β)-21-Chloro-9-fluoro-11,17-dihydroxy-16-methylpregna-1,4-diene-3,20-dione; Clobetasol impurity G (PhEur); Clobetasol; 21-Chloro-9-fluoro-11β,17-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione; Clobetasol

Database IDs

• CAS Number: 25122-41-2
• EC Number: 246-633-8
• MDL Number: MFCD03695616
• PubChem SID: 162251756
• PubChem CID: 5311051

CALCULATED PROPERTIES

• Acid pKa: 12.468411
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 3.0361614
• LogD (pH = 7.4): 3.0361578
• Log P: 3.0361614
• Molar Refractivity: 105.5439 cm^3
• Polarizability: 40.834015 Å^3
• Polar Surface Area: 74.6 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Ethyl Acetate; Methanol
• Apperance: White to Off-White Solid
• Melting Point: 220-222°C

Safety Information

• Storage Condition: -20°C Freezer
• European Hazard Symbols: Toxic (T)
• German water hazard class: 3
• Risk Statements: 61-48/20/21-53-62
• Safety Statements: 53-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360Df-H373-H413
• GHS Precautionary statements: P201-P308 + P313
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target Organ: Adrenal gland, Immune system

Product Information

• Purity: ≥95.0% (HPLC)
• Impurities: ≤10.0% related substances; ≤5.0% solvents; ≤5.0% water
• Shelf Life: (limited shelf life, expiry date on the label)
• Empirical Formula (Hill Notation): C22H28ClFO4

DETAILS

Toronto Research Chemicals - C583490

Topical corticosteroid. Glucocorticoid; anti-inflammatory.

REFERENCES

• Olsen, E.A., et al.: J. Am. Acad. Dermatol., 15, 246 (1986)