Clobetasol propionate

Clobetasol Propionate Cream usp 0.05

Not to be confused with Clostebol propionate.

Clobetasol propionate

Clinical data
Pronunciation| /kloʊˈbeɪtəsɒl/[1]
Trade names| Dermovate, Temovate, Clovate, others
AHFS/Drugs.com| Monograph
License data|

* US DailyMed: Clobetasol_propionate

Pregnancy
category|

* AU: B3

Routes of
administration| Topical
ATC code|

* D07AD01 (WHO)

Legal status
Legal status|

* US: WARNING[2]
* In general: ℞ (Prescription only)

Identifiers

IUPAC name

* [17-(2'-Chloroacetyl)-9-fluoro-11-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-17-yl] propanoate

CAS Number|

* 25122-46-7 Y

PubChem CID|

* 32798

IUPHAR/BPS|

* 7062

DrugBank|

* DB01013 Y

ChemSpider|

* 30399 Y

UNII|

* 779619577M

KEGG|

* D01272

ChEBI|

* CHEBI:31414 Y

ChEMBL|

* ChEMBL1159650 Y

CompTox Dashboard (EPA)|

* DTXSID6045907

ECHA InfoCard| 100.042.380
Chemical and physical data
Formula| C25H32ClFO5
Molar mass| 466.97 g·mol−1
3D model (JSmol)|

* Interactive image

SMILES

* ClCC(=O)[C@]3(OC(=O)CC)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)CC[C@H]4[C@@H]2C[C@@H]3C)C)C

InChI

* InChI=1S/C25H32ClFO5/c1-5-21(31)32-25(20(30)13-26)14(2)10-18-17-7-6-15-11-16(28)8-9-22(15,3)24(17,27)19(29)12-23(18,25)4/h8-9,11,14,17-19,29H,5-7,10,12-13H2,1-4H3/t14-,17-,18-,19-,22-,23-,24-,25-/m0/s1 Y

* Key:CBGUOGMQLZIXBE-XGQKBEPLSA-N Y

(verify)

Clobetasol propionate is a corticosteroid used to treat skin conditions such as eczema, contact dermatitis, seborrheic dermatitis, and psoriasis.[3] It is applied to the skin as a cream, ointment, or shampoo.[3][4] Use should be short term and only if other weaker corticosteroids are not effective.[4] Use is not recommended in rosacea or perioral dermatitis.[3]

Common side effects include skin irritation, dry skin, redness, pimples, and telangiectasia.[3] Serious side effects may include adrenal suppression, allergic reactions, cellulitis, and Cushing's syndrome.[3] Use in pregnancy and breastfeeding is of unclear safety.[5] Clobetasol is believed to work by activating steroid receptors.[3] It is a US Class I (Europe: class IV) corticosteroid, making it one of the strongest available.

Clobetasol propionate was patented in 1968 and came into medical use in 1978.[6] It is available as a generic medication.[4] In 2020, it was the 171st most commonly prescribed medication in the United States, with more than 3 million prescriptions.[7][8]

## Medical uses[edit]

Clobetasol propionate is used for the treatment of various skin disorders including eczema, herpes labialis,[9] psoriasis, and lichen sclerosus. It is also used to treat several auto-immune diseases including alopecia areata, lichen planus (auto immune skin nodules), and mycosis fungoides (T-cell skin lymphoma). It is used as first-line treatment for both acute and chronic GVHD of the skin.[10]

Clobetasol propionate is used cosmetically for skin whitening, although this use is controversial. The U.S. Food and Drug Administration has not approved it for that purpose, and sales without a prescription are illegal in the U.S. Nonetheless, skin-whitening creams containing this ingredient can sometimes be found in beauty supply stores in New York City and on the internet. It is also sold internationally, and does not require a prescription in some countries. Whitening creams with clobetasol propionate, such as Hyprogel, can make skin thin and easily bruised, with visible capillaries, and acne. It can also lead to hypertension, elevated blood sugar, suppression of the body's natural steroids, and stretch marks, which may be permanent.[11]

Clobetasol propionate is, along with mercury and hydroquinone, "amongst the most toxic and most used agents in lightening products." Many products sold illegally have higher concentrations of clobetasol propionate than is permitted for prescription drugs.[12]

## Contraindications[edit]

According to the California Environmental Protection Agency, clobetasol propionate should not be used by pregnant women, or women expecting to become pregnant soon, as studies with rats shows a risk of birth defects:[13]

> "Studies in the rat following oral administration at dosage levels up to 50 mcg/kg per day revealed that the females exhibited an increase in the number of resorbed embryos and a decrease in the number of living fetuses at the highest dose. Pregnancy: Teratogenic Effects (i.e., possibility of causing abnormalities in fetuses): Pregnancy Category C: Clobetasol propionate has not been tested for teratogenicity when applied topically; however, it is absorbed percutaneously, and when administered subcutaneously it was a significant teratogen in both the rabbit and mouse. Clobetasol propionate has greater teratogenic potential than steroids that are less potent. There are no adequate and well-controlled studies of the teratogenic effects of clobetasol propionate in pregnant women. Temovate Cream and Ointment should be used during pregnancy only if the potential benefit justifies the potential risk to the fetus."

## Forms[edit]

Clobetasol propionate is marketed and sold worldwide under numerous names, including Clobex, Clob-x (Colombia), Clovate, Clobet (Biolab Thailand) Clonovate (T.O. Chemicals, Thailand), Cormax (Watson, US), Haloderm (Switzerland, by ELKO Org), Pentasol (Colombia), Cosvate, Clop (Cadila Healthcare, India), Propysalic (India), Temovate (US), Dermovate[14] (GlaxoSmithKline, Canada, Estonia, Pakistan, Switzerland, Portugal, Romania, Israel), Olux, ClobaDerm, Tenovate, Dermatovate (Brazil, Mexico), Butavate, Movate, Novate, Salac (Argentina), and Powercort, Lotasbat and Kloderma (Indonesia), Lemonvate and Clobesol (Italy), Dovate (South Africa), Delor (Ethiopia), Psovate (Turkey), Skineal(Nigeria).

## References[edit]

1. ^ "Clobetasol Propionate Topical Ointment 0.05% Information". Drug Encyclopedia. Kaiser Permanente.
2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
3. ^ a b c d e f "Clobetasol Propionate Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Retrieved 13 April 2019.
4. ^ a b c British National Formulary: BNF 76 (76th ed.). Pharmaceutical Press. 2018. p. 1210\. ISBN 978-0-85711-338-2.
5. ^ "Clobetasol topical Use During Pregnancy". Drugs.com. Retrieved 13 April 2019.
6. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 487\. ISBN 9783527607495.
7. ^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
8. ^ "Clobetasol - Drug Usage Statistics". ClinCalc. Retrieved 7 October 2022.
9. ^ Hull C, McKeough M, Sebastian K, Kriesel J, Spruance S (March 2009). "Valacyclovir and topical clobetasol gel for the episodic treatment of herpes labialis: a patient-initiated, double-blind, placebo-controlled pilot trial". Journal of the European Academy of Dermatology and Venereology. 23 (3): 263–7. doi:10.1111/j.1468-3083.2008.03047.x. PMID 19143902. S2CID 205588376.
10. ^ E. Fougera and Co. "Clobetasol Propionate Cream Usp, 0.05% Clobetasol Propionate Ointment USP, 0.05%". Daily Med. U.S. National Library of Medicine.
11. ^ Saint Louis C (January 15, 2010). "Creams Offering Lighter Skin May Bring Risks". New York Times.
12. ^ Gbetoh MH, Amyot M (October 2016). "Mercury, hydroquinone and clobetasol propionate in skin lightening products in West Africa and Canada". Environmental Research. 150: 403–410. Bibcode:2016ER....150..403G. doi:10.1016/j.envres.2016.06.030. hdl:1866/19006. PMID 27372064.
13. ^ Office of Environmental Health Hazard Assessment (August 22, 1997). "Chemicals Under Consideration For Possible Listing Via The "Formally Required To Be Labeled Or Identified" Mechanism". California Environmental Protection Agency. Archived from the original on 2001-07-20. Retrieved 2007-05-06.
14. ^ "Dermovate 0.05% W/V Ointment - Clobetasol Topical(0.05% W/V)". Glaxo SmithKline Pharmaceuticals Ltd. GNHIndia.com. Archived from the original on 2021-07-16. Retrieved 2021-07-16.

## External links[edit]

* "Clobetasol propionate". Drug Information Portal. U.S. National Library of Medicine.

* v
* t
* e

Glucocorticoids and antiglucocorticoids (D07, H02)

Glucocorticoids|

| Natural|

* Cortisone
* Cortisone acetate
* Cortodoxone (cortexolone, 11-deoxycortisol)
* Desoxycortone (deoxycortone, cortexone, 11-deoxycorticosterone)
* Desoxycortone esters
* Hydrocortisone (cortisol)#
* Hydrocortisone esters
* Prebediolone acetate
* Pregnenolone
* Pregnenolone acetate
* Pregnenolone succinate

|

Synthetic|

* Cortisol-like and related (16-unsubstituted): Chloroprednisone
* Cloprednol
* Difluprednate
* Fludrocortisone
* Flugestone acetate (flurogestone acetate)
* Fluocinolone
* Fluorometholone
* Fluorometholone acetate
* Fluperolone
* Fluperolone acetate
* Fluprednisolone
* Fluprednisolone esters
* Loteprednol
* Medrysone
* Methylprednisolone
* Methylprednisolone esters
* Prednicarbate
* Prednisolone#
* Prednisone
* Tixocortol
* Tixocortol pivalate

* Methasones and related (16-substituted): Alclometasone
* Beclometasone
* Beclometasone esters
* Betamethasone#
* Betamethasone esters
* Clobetasol
* Clobetasol propionate
* Clobetasone
* Clocortolone
* Clocortolone esters
* Cortivazol
* Desoximetasone
* Dexamethasone#
* Dexamethasone esters
* Diflorasone
* Diflucortolone
* Diflucortolone valerate
* Fluclorolone
* Flumetasone
* Fluocortin
* Fluocortolone
* Fluocortolone esters
* Fluprednidene acetate
* Fluticasone
* Fluticasone furoate
* Fluticasone propionate
* Halometasone
* Meprednisone
* Mometasone
* Mometasone furoate
* Paramethasone
* Prednylidene
* Rimexolone
* Triamcinolone
* Ulobetasol (halobetasol)

* Cyclic ketals (16,17-cyclized): Amcinonide
* Budesonide
* Ciclesonide
* Deflazacort
* Desonide
* Fluclorolone acetonide (flucloronide)
* Fludroxycortide (flurandrenolone, flurandrenolide)
* Flunisolide
* Fluocinolone acetonide
* Fluocinonide
* Formocortal (fluoroformylone)
* Halcinonide
* Triamcinolone acetonide
* Triamcinolone acetonide esters

Antiglucocorticoids|

* Antagonists: Aglepristone
* Ketoconazole
* Mifepristone
* Ulipristal acetate

Synthesis modifiers|

* Acetoxolone
* Aminoglutethimide
* Carbenoxolone
* Enoxolone
* Ketoconazole
* Metyrapone
* Mitotane
* Trilostane

* #WHO-EM
* ‡Withdrawn from market
* Clinical trials:
* †Phase III
* §Never to phase III

See also
Glucocorticoid receptor modulators
Mineralocorticoids and antimineralocorticoids
List of corticosteroids

* v
* t
* e

Glucocorticoid receptor modulators

GR|

| Agonists|

* Cortisol-like and related (16-unsubstituted): 3α,5α-Tetrahydrocorticosterone
* 5α-Dihydrocorticosterone
* 9α-Fluorocortisone (alfluorone)
* 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone)
* 11-Dehydrocorticosterone acetate
* 11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone)
* Desoxycortone esters
* 11-Deoxycortisol (cortodoxone, cortexolone)
* Cortifen (cortiphen, kortifen)
* Cortodoxone acetate
* 21-Deoxycortisol
* Δ7-Prednisolone
* Δ7-Prednisolone 21-acetate
* Amebucort
* Chloroprednisone
* Chloroprednisone acetate
* Cloprednol
* Cloprednol acetate
* Corticosterone
* Corticosterone acetate
* Corticosterone benzoate
* Cortisol (hydrocortisone)
* Benzodrocortisone (hydrocortisone benzoate)
* Hydrocortamate (hydrocortisone diethylaminoacetate)
* Hydrocortisone esters
* Cortisone
* Cortisone acetate
* Deprodone
* Deprodone propionate
* Dichlorisone
* Dichlorisone acetate
* Dichlorisone diacetate
* Difluprednate
* Endrisone (endrysone)
* Etiprednol
* Etiprednol dicloacetate (etiprednol dichloroacetate)
* Fludrocortisone (fludrocortone)
* Fludrocortisone acetate
* Fluorometholone
* Fluorometholone acetate
* Fluperolone
* Fluperolone acetate
* Fluprednisolone
* Fluprednisolone esters
* Halopredone
* Halopredone acetate (halopredone diacetate)
* Isoflupredone (9α-fluoroprednisolone)
* Isoflupredone acetate
* Loteprednol
* Mazipredone (depersolone)
* Medrysone
* Methylprednisolone
* Methylprednisolone esters
* Prebediolone
* Prebediolone acetate
* Prednisolone
* Prednazate
* Prednazoline
* Prednicarbate (prednisolone ethylcarbonate propionate)
* Prednimustine
* Prednisolamate (prednisolone diethylaminoacetate)
* Prednisolone esters
* Prednisone
* Prednisone esters
* Pregnenolone
* Pregnenolone acetate
* Pregnenolone succinate (pregnenolone hemisuccinate)
* Resocortol
* Tipredane
* Tixocortol
* Butixocort (tixocortol butyrate)
* Butixocort propionate
* Tixocortol pivalate

* Methasones and related (16-substituted): 16α-Methyl-11-oxoprednisolone
* Alclometasone
* Alclometasone dipropionate
* Amelometasone
* Beclometasone (beclomethasone)
* Beclometasone esters
* Betamethasone (betametasone)
* Betamethasone esters
* Cortobenzolone (betamethasone salicylate)
* Ciclometasone (ciclomethasone, cyclomethasone)
* Clobetasol
* Clobetasol propionate
* Clobetasone
* Clobetasone butyrate
* Clocortolone
* Clocortolone esters
* Cloticasone
* Cloticasone propionate
* Cormetasone (cormethasone)
* Cormetasone acetate
* Descinolone
* Desoximetasone (desoxymethasone)
* Dexamethasone (dexametasone)
* Dexamethasone esters
* Diflorasone
* Diflorasone diacetate
* Diflucortolone
* Diflucortolone pivalate
* Diflucortolone valerate
* Dimesone
* Dimesone acetate
* Doxibetasol (doxybetasol)
* Fluclorolone
* Flumetasone (flumethasone)
* Flumetasone acetate
* Flumetasone pivalate
* Fluocinolone
* Fluocortin
* Fluocortin butyl (fluocortin butylate)
* Fluocortolone
* Fluocortolone esters
* Fluprednidene (fluprednylidene)
* Fluprednidene acetate
* Fluticasone
* Fluticasone furoate
* Fluticasone propionate
* Halocortolone
* Halometasone
* Icometasone
* Icometasone enbutate (icometasone butyrate acetate)
* Isoprednidene
* Locicortolone (locicortone)
* Locicortolone dicibate (locicortone dicibate)
* Meclorisone
* Meclorisone dibutyrate
* Meprednisone (methylprednisone)
* Meprednisone acetate
* Meprednisone hydrogen succinate (methylprednisone hemisuccinate)
* Mometasone
* Mometasone furoate
* Paramethasone
* Paramethasone acetate
* Paramethasone disodium phosphate
* Paramethasone phosphate
* Prednylidene
* Prednylidene diethylaminoacetate
* Rimexolone
* Ticabesone
* Ticabesone propionate
* Timobesone
* Timobesone acetate
* Triamcinolone
* Triamcinolone diacetate
* Ulobetasol (halobetasol)
* Ulobetasol propionate
* Vamorolone

* Cyclic ketals (16,17-cyclized): Acrocinonide (triamcinolone acroleinide)
* Amcinafal (triamcinolone pentanonide)
* Amcinafide (triamcinolone acetophenide)
* Amcinonide (triamcinolone acetate cyclopentanonide)
* Budesonide
* Ciclesonide
* Cicortonide
* Deflazacort (azacort)
* Descinolone acetonide
* Desonide (hydroxyprednisolone acetonide)
* Desonide disodium phosphate
* Desonide pivalate
* Dexbudesonide
* Drocinonide
* Drocinonide phosphate
* Fluazacort
* Fluclorolone acetonide (flucloronide)
* Fludroxycortide (flurandrenolone, flurandrenolide)
* Flumoxonide
* Flunisolide
* Flunisolide acetate
* Fluocinolone acetonide
* Ciprocinonide (fluocinolone acetonide cyclopropylcarboxylate)
* Fluocinonide (fluocinolide, fluocinolone acetonide acetate)
* Procinonide (fluocinolone acetonide propionate)
* Formocortal
* Halcinonide
* Itrocinonide
* Rofleponide
* Rofleponide palmitate
* Tralonide
* Triamcinolone acetonide
* Flupamesone (triamcinolone acetonide metembonate)
* Triamcinolone acetonide esters
* Triamcinolone aminobenzal benzamidoisobutyrate (TBI-PAB)
* Triclonide

* Others/atypical (other expanded steroid ring systems, homosteroids, and non-pregnane steroids): Cortisuzol
* Cortivazol
* Domoprednate
* Naflocort
* Nicocortonide
* Nicocortonide acetate
* Nivacortol (nivazol)
* Oxisopred
* RU-26988
* RU-28362

* Non-corticosteroids with some glucocorticoid activity: 15β-Hydroxycyproterone acetate
* 17α-Hydroxyprogesterone
* Bromoketoprogesterone
* Chlormadinone acetate
* Cyproterone
* Cyproterone acetate
* Danazol
* Delmadinone acetate
* Desogestrel
* DU-41165
* Etonogestrel
* Flugestone
* Flugestone acetate (flurogestone acetate)
* Fluoromedroxyprogesterone acetate
* Fluoxymesterone
* Gestodene
* Medrogestone
* Medroxyprogesterone acetate
* Megestrol acetate
* Metribolone
* Norgestomet
* Osaterone acetate
* Progesterone
* Promegestone
* RU-2309
* Quingestrone
* Segesterone acetate (nestorone)
* Tetrahydrogestrinone

* Nonsteroidal glucocorticoids: AZD-5423
* GSK-9027

|

Mixed
(SEGRMs)|

* Dagrocorat
* Fosdagrocorat
* Mapracorat

Antagonists|

* 7α-Hydroxy-DHEA
* 17α-Methylprogesterone
* Aglepristone
* Asoprisnil
* Asoprisnil ecamate
* C108297
* C113176
* CORT-108297
* Cyproterone acetate
* Dazucorilant
* Exicorilant (CORT-125281)
* Guggulsterone
* Ketoconazole
* Lilopristone
* LLY-2707
* Metapristone (RU-42633)
* Miconazole
* Mifepristone (RU-486)
* Miricorilant (CORT-118335)
* Onapristone
* ORG-34116
* ORG-34517 (SCH-900636)
* ORG-34850
* Pregnenolone 16α-carbonitrile
* Relacorilant (CORT-125134)
* RTI 3021–012
* RTI 3021–022
* Telapristone
* Tibolone
* Toripristone
* Ulipristal acetate
* Zavacorilant

Others|

* Antisense oligonucleotides: IONIS-GCCRRx (ISIS-426115)

See also
Receptor/signaling modulators
Glucocorticoids and antiglucocorticoids
Mineralocorticoid receptor modulators
List of corticosteroids

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