Clocortolone

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 317550

CAS#: 4828-27-7 (free base)

Description: 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.


Chemical Structure

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Clocortolone
CAS# 4828-27-7 (free base)

Theoretical Analysis

MedKoo Cat#: 317550
Name: Clocortolone
CAS#: 4828-27-7 (free base)
Chemical Formula: C22H28ClFO4
Exact Mass: 410.16602
Molecular Weight: 410.91
Elemental Analysis: C, 64.31; H, 6.87; Cl, 8.63; F, 4.62; O, 15.57

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Related CAS #: 4258-85-9 (acetate)   34097-16-0 (pivalate)   4891-71-8 (caproate)   4828-27-7 (free base)  

Synonym: Clocortolona; Clocortolonum; Clocortolone; Cloderm

IUPAC/Chemical Name: (6S,8S,9R,10S,11S,13S,14S,16R,17S)-9-chloro-6-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one

InChi Key: YMTMADLUXIRMGX-RFPWEZLHSA-N

InChi Code: InChI=1S/C22H28ClFO4/c1-11-6-13-14-8-16(24)15-7-12(26)4-5-21(15,3)22(14,23)18(28)9-20(13,2)19(11)17(27)10-25/h4-5,7,11,13-14,16,18-19,25,28H,6,8-10H2,1-3H3/t11-,13+,14+,16+,18+,19-,20+,21+,22+/m1/s1

SMILES Code: C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@H]1C(=O)CO)C)O)Cl)C)F

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 410.91 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Del Rosso JQ, Kircik LH. 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. J Drugs Dermatol. 2014 Jul;13(7):s77-83. PubMed PMID: 25007376.

2: Kircik LH. A study to assess the occlusivity and moisturization potential of three topical corticosteroid products using the skin trauma after razor shaving (STARS) bioassay. J Drugs Dermatol. 2014 May;13(5):582-5. PubMed PMID: 24809882.

3: Del Rosso JQ, Kircik LH. 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. J Drugs Dermatol. 2013 Feb;12(2):s5-s10. PubMed PMID: 23377405.

4: Kircik LH. Clocortolone pivalate: a topical corticosteroid with a unique structure. J Drugs Dermatol. 2013 Feb;12(2):s3-4. PubMed PMID: 23377404.

5: Kircik LH, Del Rosso JQ. The treatment of inflammatory facial dermatoses with topical corticosteroids: focus on clocortolone pivalate 0.1% cream. J Drugs Dermatol. 2012 Oct;11(10):1194-8. PubMed PMID: 23134984.

6: Del Rosso JQ, Kircik L. A Comprehensive Review of Clocortolone Pivalate 0.1% Cream: Structural Development, Formulation Characteristics, and Studies Supporting Treatment of Corticosteroid-responsive Dermatoses. J Clin Aesthet Dermatol. 2012 Jul;5(7):20-4. PubMed PMID: 22798972; PubMed Central PMCID: PMC3396454.

7: Singh S, Mann BK. Clinical utility of clocortolone pivalate for the treatment of corticosteroid-responsive skin disorders: a systematic review. Clin Cosmet Investig Dermatol. 2012;5:61-8. doi: 10.2147/CCID.S23227. Epub 2012 Jun 22. PubMed PMID: 22791998; PubMed Central PMCID: PMC3393117.

8: Xu W, Jia X, Liu W, Zhang X, Chen Y, Zhou L, You S. Identification and characterization of three impurities in clocortolone pivalate. J Pharm Biomed Anal. 2012 Mar 25;62:167-71. doi: 10.1016/j.jpba.2011.11.021. Epub 2011 Dec 8. PubMed PMID: 22264563.

9: Conde JF, Kaur M, Fleischer AB Jr, Tusa MG, Camacho F, Feldman SR. Adherence to clocortolone pivalate cream 0.1% in a pediatric population with atopic dermatitis. Cutis. 2008 May;81(5):435-41. PubMed PMID: 18543596.

10: Torok HM, Maas-Irslinger R, Slayton RM. Clocortolone pivalate cream 0.1% used concomitantly with tacrolimus ointment 0.1% in atopic dermatitis. Cutis. 2003 Aug;72(2):161-6. PubMed PMID: 12953943.

Clocortolone

5.0mg / Not available