2-[(1R,2S,8S,10S,11S,13R,14S,15S,17S)-1-chloro-8-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl 2,2-dimethylpropanoate

• ChemBase ID: 717
• Molecular Formular: C27H36ClFO5
• Molecular Mass: 495.0231432
• Monoisotopic Mass: 494.22353015
• SMILES: Cl[C@@]12[C@H]([C@H]3[C@@]([C@H]([C@@H](C3)C)C(=O)COC(=O)C(C)(C)C)(C[C@@H]1O)C)C[C@H](F)C1=CC(=O)C=C[C@]21C
• Canonical SMILES: O=C1C=C[C@]2(C(=C1)[C@@H](F)C[C@@H]1[C@]2(Cl)[C@@H](O)C[C@]2([C@H]1C[C@H]([C@@H]2C(=O)COC(=O)C(C)(C)C)C)C)C
• InChI: InChI=1S/C27H36ClFO5/c1-14-9-16-17-11-19(29)18-10-15(30)7-8-26(18,6)27(17,28)21(32)12-25(16,5)22(14)20(31)13-34-23(33)24(2,3)4/h7-8,10,14,16-17,19,21-22,32H,9,11-13H2,1-6H3/t14-,16+,17+,19+,21+,22-,25+,26+,27+/m1/s1
• InChIKey: SXYZQZLHAIHKKY-GSTUPEFVSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(1R,2S,8S,10S,11S,13R,14S,15S,17S)-1-chloro-8-fluoro-17-hydroxy-2,13,15-trimethyl-5-oxotetracyclo[8.7.0.0^{2,7}.0^{11,15}]heptadeca-3,6-dien-14-yl]-2-oxoethyl 2,2-dimethylpropanoate; 2-[(1R,2S,8S,10S,11S,13R,14S,15S,17S)-1-chloro-8-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 2,2-dimethylpropanoate
• IUPAC Traditional name: cloderm; clocortolone
• Brand Name: Cloderm
• Synonyms: Clocortolone; Clocortolone pivalate; (6α,11β,16α)-9-Chloro-21-(2,2-dimethyl-1-oxopropoxy)-6-fluoro-11-hydroxy-16-methypregna-1,4-diene-3,20-dione; 9-Chloro-6α-fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione 21-Pivalate; CL 68; Clocortolone trimethylacetate; Cloderm; Purantix; SH 863; Clocortolone Pivalate

Database IDs

• CAS Number: 34097-16-0
• PubChem SID: 160964180
• PubChem CID: 5282493

CALCULATED PROPERTIES

JChem

• Acid pKa: 13.806746
• H Acceptors: 4
• H Donor: 1
• LogD (pH = 5.5): 4.7154837
• LogD (pH = 7.4): 4.7154837
• Log P: 4.7154837
• Molar Refractivity: 128.5903 cm^3
• Polarizability: 50.176743 Å^3
• Polar Surface Area: 80.67 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 4.17
• LOG S: -5.68
• Solubility (Water): 1.03e-03 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 3.8

DETAILS

DrugBank - DB00838

• Drug Groups: approved
• Description: Clocortolone is a medium potency corticosteroid that is often used as a topical cream for the relief of inflammatory oand pruritic (itching) arising from steroid-responsive dermatoses of the scalp.
• Indication: For short-term topical treatment of the inflammatory and pruritic manifestations of moderate to severe corticosteroid-responsive dermatoses of the scalp.
• Pharmacology: Like other topical corticosteroids, clocortolone has anti-inflammatory, antipruritic, and vasoconstrictive properties. Once absorbed through the skin, topical corticosteroids are handled through pharmacokinetic pathways similar to systemically administered corticosteroids. Clocortolone is a moderate potency topical corticosteroid that should not be used with occlusive dressings. It is recommended that treatment should be limited to 2 consecutive weeks and therapy should be discontinued when adequate results have been achieved.
• Toxicity: Topically applied clocortolone can be absorbed in sufficient amounts to produce systemic effects. Symptoms of overdose include thinning of skin and suppression of adrenal cortex (decreased ability to respond to stress).
• Affected Organisms: Humans and other mammals
• Biotransformation: Metabolized, primarily in the liver, and then excreted by the kidneys.
• Absorption: Topical corticosteroids can be absorbed from intact healthy skin. The extent of percutaneous absorption of topical corticosteroids is determined by many factors, including the vehicle and the integrity of the epidermal barrier. Occlusion, inflammation and/or other disease processes in the skin may also increase percutaneous absorption.
• External Links: Wikipedia; RxList; Drugs.com

Toronto Research Chemicals - C583810

A corticosteroid used in the treatment of atopic dermatitis.

REFERENCES

• Torok, H.M. et al.: Cutis, 72, 161 (2003)
• Svensson, A. et al.: Curr. Med. Res. Opin., 27, 1395 (2011):