(1R,8S,13S,14R)-14-(2-chloroacetyl)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate

• ChemBase ID: 478
• Molecular Formular: C25H31ClF2O5
• Molecular Mass: 484.9604464
• Monoisotopic Mass: 484.18280821
• SMILES: ClCC(=O)[C@]1(OC(=O)CC)C2(C(C3[C@](F)(C(O)C2)C2(C(=CC(=O)C=C2)[C@@H](F)C3)C)C[C@@H]1C)C
• Canonical SMILES: CCC(=O)O[C@@]1([C@@H](C)CC2C1(C)CC(O)[C@]1(C2C[C@@H](C2=CC(=O)C=CC12C)F)F)C(=O)CCl
• InChI: InChI=1S/C25H31ClF2O5/c1-5-21(32)33-25(20(31)12-26)13(2)8-15-16-10-18(27)17-9-14(29)6-7-22(17,3)24(16,28)19(30)11-23(15,25)4/h6-7,9,13,15-16,18-19,30H,5,8,10-12H2,1-4H3/t13-,15?,16?,18-,19?,22?,23?,24-,25-/m0/s1
• InChIKey: BDSYKGHYMJNPAB-YKQIDFLYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,8S,13S,14R)-14-(2-chloroacetyl)-1,8-difluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl propanoate
• IUPAC Traditional name: halobetasol propionate
• Brand Name: Halobetasol; Ulobetasol Propionate; Ultravate
• Synonyms: Halobetasol Propionate

Database IDs

• CAS Number: 66852-54-8
• PubChem SID: 160963941; 46506187
• PubChem CID: 48175

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.545719
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 3.8381035
• LogD (pH = 7.4): 3.8381033
• Log P: 3.8381035
• Molar Refractivity: 119.1457 cm^3
• Polarizability: 46.300114 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 3.81
• LOG S: -4.81
• Solubility (Water): 7.57e-03 g/l

PROPERTIES

Physical Property

• Solubility: Mostly insoluble
• Hydrophobicity(logP): 2.9

DETAILS

DrugBank - DB00596

• Drug Groups: approved
• Description: Halobetasol propionate is thought to act by the induction of phospholipase A2 inhibitory proteins, collectively called lipocortins. It is postulated that these proteins control the biosynthesis of potent mediators of inflammation such as prostaglandins and leukotrienes by inhibiting the release of their common precursor arachidonic acid. Arachidonic acid is released from membrane phospholipids by phospholipase A2. It is used for the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
• Indication: For the relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses.
• Affected Organisms: Humans and other mammals
• Absorption: The extent of percutaneous absorption of topical corticosteroids is determined by many factors including the vehicle and the integrity of the epidermal barrier. Inflammation and/or other disease processes in the skin may increase percutaneous absorption.
• External Links: RxList; PDRhealth; Drugs.com