Clocortolone Pivalate

• CAT Number: R054368
• CAS Number: 34097-16-0
• Molecular Formula: C27H36ClFO5
• Molecular Weight: 495.028
• Purity: ≥95%
• Synonyms: (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; Purant
• Target: Drug Metabolite
• Storage: Store at RT
• IUPAC Name: [2-[(6S,8S,9R,10S,11S,13S,14S,16R,17S)-9-chloro-6-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-7,8,11,12,14,15,16,17-octahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] 2,2-dimethylpropanoate
• 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
• SMILES: CC1CC2C3CC(C4=CC(=O)C=CC4(C3(C(CC2(C1C(=O)COC(=O)C(C)(C)C)C)O)Cl)C)F

Clocortolone is a Corticosteroid Hormone Receptor Agonist. It is used in the form of an ester, clocortolone pivalate, and applied as a cream. It is used for the treatment of dermatitis and is considered a medium-strength corticosteroid. It is unusual among steroids in that it contains a chlorine atom and a fluorine atom. Clocortolone is an upper-mid potency topical corticosteroid formulation. It is rated at a class 4 potency on a scale of 1 (highest potency) to 7 (lowest potency). Most patients are treated with mid-potency topical corticosteroids, for they are an effective medium between safety and efficacy for short and long-term conditions.

Reference

1:Transitioning from brand to generic with topical products and the importance of maintaining the formulation and therapeutic profiles of the original product: focus on clocortolone pivalate 0.1% cream. Del Rosso JQ, Kircik LH.J Drugs Dermatol. 2014 Jul;13(7):s77-83. PMID: 25007376 2:The role of a midpotency topical corticosteroid and the clinical relevance of formulation characteristics in the management of commonly encountered eczematous and inflammatory dermatoses in adults and children: focus on the pharmacologic properties of clocortolone pivalate 0.1% cream. Del Rosso JQ, Kircik LH.J Drugs Dermatol. 2013 Feb;12(2):s5-s10. PMID: 23377405 3:Clocortolone pivalate: a topical corticosteroid with a unique structure. Kircik LH.J Drugs Dermatol. 2013 Feb;12(2):s3-4. PMID: 23377404 4:The treatment of inflammatory facial dermatoses with topical corticosteroids: focus on clocortolone pivalate 0.1% cream. Kircik LH, Del Rosso JQ.J Drugs Dermatol. 2012 Oct;11(10):1194-8. PMID: 23134984 5:A Comprehensive Review of Clocortolone Pivalate 0.1% Cream: Structural Development, Formulation Characteristics, and Studies Supporting Treatment of Corticosteroid-responsive Dermatoses. Del Rosso JQ, Kircik L.J Clin Aesthet Dermatol. 2012 Jul;5(7):20-4. PMID: 22798972 Free PMC Article6:Clinical utility of clocortolone pivalate for the treatment of corticosteroid-responsive skin disorders: a systematic review. Singh S, Mann BK.Clin Cosmet Investig Dermatol. 2012;5:61-8. doi: 10.2147/CCID.S23227. Epub 2012 Jun 22. PMID: 22791998 Free PMC Article7:Identification and characterization of three impurities in clocortolone pivalate. Xu W, Jia X, Liu W, Zhang X, Chen Y, Zhou L, You S.J Pharm Biomed Anal. 2012 Mar 25;62:167-71. doi: 10.1016/j.jpba.2011.11.021. Epub 2011 Dec 8. PMID: 22264563 8:Adherence to clocortolone pivalate cream 0.1% in a pediatric population with atopic dermatitis. Conde JF, Kaur M, Fleischer AB Jr, Tusa MG, Camacho F, Feldman SR.Cutis. 2008 May;81(5):435-41. PMID: 18543596 9:Clocortolone pivalate cream 0.1% used concomitantly with tacrolimus ointment 0.1% in atopic dermatitis. Torok HM, Maas-Irslinger R, Slayton RM.Cutis. 2003 Aug;72(2):161-6. PMID: 12953943 10:Safety and efficacy of clocortolone pivalate 0.1 percent cream in the treatment of atopic dermatitis, contact dermatitis, and seborrheic dermatitis. Nierman MM.Cutis. 1981 Jun;27(6):670-1. Review. No abstract available. PMID: 6453703