Clobetasol propionate

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Clobetasol propionate
Clobetasol Propionate.svg
Clinical data
Pronunciation /klˈbtəsɒl/ [1]
Trade names Dermovate, Temovate, Clovate, others
AHFS/Drugs.com Monograph
License data
Pregnancy
category
  • AU:B3
Routes of
administration
Topical
ATC code
Legal status
Legal status
  • US: WARNING [2]
  • In general: ℞ (Prescription only)
Identifiers
  • [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
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.042.380 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C25H32ClFO5
Molar mass 466.97 g·mol−1
3D model (JSmol)
  • 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=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 Yes check.svgY
  • Key:CBGUOGMQLZIXBE-XGQKBEPLSA-N Yes check.svgY
   (verify)

Clobetasol propionate is a corticosteroid used to treat skin conditions such as eczema, contact dermatitis, seborrheic dermatitis, steroid responsive dermatosis, and psoriasis (including scalp and plaque-type). [3] [4] [5]

Contents

It is applied to the skin as a cream, foam, gel, liquid, solution, ointment, or shampoo. [4] [6] [5] Use should be short term and only if other weaker corticosteroids are not effective. [6] Use is not recommended in rosacea or perioral dermatitis. [4]

Common side effects include skin irritation, dry skin, redness, pimples, and telangiectasia. [4] Serious side effects may include adrenal suppression, allergic reactions, cellulitis, and Cushing's syndrome. [4] Use in pregnancy and breastfeeding is of unclear safety. [7] Clobetasol is believed to work by activating steroid receptors. [4]

Clobetasol propionate was patented in 1968 and came into medical use in 1978. [8] It is available as a generic medication. [6] In 2021, it was the 162nd most commonly prescribed medication in the United States, with more than 3 million prescriptions. [9] [10]

Medical uses

Clobetasol propionate is used for the treatment of various skin disorders including eczema, herpes labialis, [11] 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. [12]

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. [13]

Clobetasol propionate is, along with mercury and hydroquinone, "amongst the most toxic, the latter in higher concentrations, and most used agents in lightening products." Many products sold illegally have higher concentrations of clobetasol propionate than is permitted for prescription drugs. [14]

Clobetasol 0.05% is considered a member of the "Super-high potency" (Group 1) group of topical corticosteroids [5] out of 7 total groups in the United States classification system of topical corticosteroids. The weaker strength formulation of 0.025% belongs to Group 2 (“High Potency”).

Society and culture

Brand names

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 [15] (GlaxoSmithKline, Canada, Estonia, Pakistan, Switzerland, Ukraine, 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) or Skineal (Nigeria).

Related Research Articles

<span class="mw-page-title-main">Dermatitis</span> Inflammatory disease of the skin

Dermatitis is a term used for different types of skin inflammation, typically characterized by itchiness, redness and a rash. In cases of short duration, there may be small blisters, while in long-term cases the skin may become thickened. The area of skin involved can vary from small to covering the entire body. Dermatitis is also called eczema but the same term is often used for the most common type of skin inflammation, atopic dermatitis.

<span class="mw-page-title-main">Pimecrolimus</span> Immunosuppressive drug

Pimecrolimus is an immunosuppressant drug of the calcineurin inhibitor class used in the treatment of atopic dermatitis (eczema).

<span class="mw-page-title-main">Betamethasone</span> Steroid medication

Betamethasone is a steroid medication. It is used for a number of diseases including rheumatic disorders such as rheumatoid arthritis and systemic lupus erythematosus, skin diseases such as dermatitis and psoriasis, allergic conditions such as asthma and angioedema, preterm labor to speed the development of the baby's lungs, Crohn's disease, cancers such as leukemia, and along with fludrocortisone for adrenocortical insufficiency, among others. It can be taken by mouth, injected into a muscle, or applied to the skin, typically in cream, lotion, or liquid forms.

<span class="mw-page-title-main">Desonide</span> Chemical compound

Desonide (INN) is a low-potency topical corticosteroid anti-inflammatory that has been available since the 1970s. It is primarily used to treat atopic dermatitis (eczema), seborrheic dermatitis, contact dermatitis and psoriasis in both adults and children. It has a fairly good safety profile and is available as a cream, ointment, lotion, and as a foam under the tradename Verdeso Foam. Other trade names for creams, lotions, and ointments include Tridesilon, DesOwen, Desonate. It is a group VI corticosteroid under US classification, the second least potent group.

<span class="mw-page-title-main">Fluticasone propionate</span> Medication

Fluticasone propionate, sold under the brand names Flovent and Flonase among others, is a glucocorticoid steroid medication. When inhaled it is used for the long term management of asthma and COPD. In the nose it is used for hay fever and nasal polyps. It can also be used for mouth ulcers. It works by decreasing inflammation.

<span class="mw-page-title-main">Betamethasone dipropionate</span> Glucocorticoid steroid (chemical compound)

Betamethasone dipropionate is a glucocorticoid steroid with anti-inflammatory and immunosuppressive properties. It is applied as a topical cream, ointment, lotion or gel (Diprolene) to treat itching and other skin conditions such as eczema. Minor side effects include dry skin and mild, temporary stinging when applied. Betamethasone dipropionate is a "super high potency" corticosteroid used to treat inflammatory skin conditions such as dermatitis, eczema and psoriasis. It is a synthetic analog of the adrenal corticosteroids. Although its exact mechanism of action is not known, it is effective when applied topically to cortico-responsive inflammatory dermatoses. It is available as a generic medication.

<span class="mw-page-title-main">Betamethasone valerate</span> Chemical compound

Betamethasone valerate is a synthetic glucocorticoid ester. It is the 17-valerate ester of betamethasone. Betamethasone valerate is often used to treat mild eczema with good efficacy and lower incidence of steroid induced adverse effects due to its lower potency compared to other glucocorticoids. Betamethasone-17-valerate is available in cream, ointment, lotion, and foam preparations for topical use.

<span class="mw-page-title-main">Fluocinonide</span> Chemical compound

Fluocinonide is a potent glucocorticoid used topically as an anti-inflammatory agent for the treatment of skin disorders such as eczema and seborrhoeic dermatitis. It relieves itching, redness, dryness, crusting, scaling, inflammation, and discomfort.

<span class="mw-page-title-main">Desoximetasone</span> Chemical compound

Desoximetasone is a medication belonging to the family of medications known as topical corticosteroids. It is used for the relief of various skin conditions, including rashes. It helps to reduce redness, itching, and irritation. Desoximetasone is a synthetic corticosteroid, a class of primarily synthetic steroids used as anti-inflammatory and anti-pruritic agents.

<span class="mw-page-title-main">Alclometasone</span> Chemical compound

Alclometasone is a synthetic corticosteroid for topical dermatologic use, possessing anti-inflammatory, antipruritic, and vasoconstrictive properties.

<span class="mw-page-title-main">Mometasone</span> Steroid medication

Mometasone, also known as mometasone y 3 s, is a steroid medication used to treat certain skin conditions, hay fever, and asthma. Specifically it is used to prevent rather than treat asthma attacks. It can be applied to the skin, inhaled, or used in the nose. Mometasone furoate, not mometasone, is used in medical products.

<span class="mw-page-title-main">Clobetasone</span> Chemical compound

Clobetasone (INN) is a corticosteroid used in dermatology, for treating such skin inflammation as seen in eczema, psoriasis and other forms of dermatitis, and ophthalmology. Topical clobetasone butyrate has shown minimal suppression of the hypothalamic–pituitary–adrenal axis.

<span class="mw-page-title-main">Diflorasone diacetate</span> Chemical compound and topical steroid

Diflorasone diacetate is a topical steroid that comes in the form of a cream. It is manufactured by E. Fougera & Co. and is used as an anti-inflammatory and anti-itching agent, like other topical corticosteroids. It is prescribed for psoriasis and atopic dermatitis, among other conditions. With respect to potency, it is regarded as a Class I corticosteroid [of classes I – VII] in the United States.

<span class="mw-page-title-main">Amcinonide</span> Chemical compound

Amcinonide is a topical glucocorticoid used to treat itching, redness and swelling associated with several dermatologic conditions such as atopic dermatitis and allergic contact dermatitis. Amcinonide can also be classified as a multi-functional small molecule corticosteroid, which has been approved by the FDA and is currently marketed as an ointment, lotion, or cream. It acts as both a transcription factor for responses to glucocorticoids and modulator for other transcription factors while also regulating phospholipase A2 activity.

In medicine, a finger tip unit (FTU) is defined as the amount of ointment, cream or other semi-solid dosage form expressed from a tube with a 5 mm diameter nozzle, applied from the distal skin-crease to the tip of the index finger of an adult. The "distal skin-crease" is the skin crease over the joint nearest the end of the finger. One FTU is enough to treat an area of skin twice the size of the flat of an adult's hand with the fingers together, i.e. a "handprint". Two FTUs are approximately equivalent to 1 g of topical steroid.

<span class="mw-page-title-main">Steroid-induced skin atrophy</span> Medical condition

Steroid-induced skin atrophy is thinning of the skin as a result of prolonged exposure to topical steroids. In people with psoriasis using topical steroids it occurs in up to 5% of people after a year of use. Intermittent use of topical steroids for atopic dermatitis is safe and does not cause skin thinning.

Topical steroids are the topical forms of corticosteroids. Topical steroids are the most commonly prescribed topical medications for the treatment of rash and eczema. Topical steroids have anti-inflammatory properties and are classified based on their skin vasoconstrictive abilities. There are numerous topical steroid products. All the preparations in each class have the same anti-inflammatory properties but essentially differ in base and price.

EpiCeram is a topical non-steroidal skin cream. Based on the research of Peter M. Elias, it is made up of ceramides, free fatty acids, and cholesterol, and is designed to treat atopic dermatitis, a type of eczema. Ceragenix obtained marketing clearance from the U.S. Food and Drug Administration in April 2006. This prescription medical device works as a moisturizer and barrier cream. In the US, it requires prescription and was launched in October 2008 by Promius Pharma. EpiCeram was acquired by PuraCap Pharmaceutical LLC in 2010.

<span class="mw-page-title-main">Topical glucocorticoids</span>

Topical glucocorticoids are the topical forms of glucocorticoids. Topical glucocorticoids are used in the treatment of many skin conditions. They provide anti-inflammatory, antimitotic, and immune-system suppressing actions through various mechanisms.

<span class="mw-page-title-main">Topical hydrocortisone</span> Pharmaceutical drug

Topical hydrocortisone is a drug under the class of corticosteroids, which is used for the treatment of skin inflammation, itchiness and allergies. Some examples include insect bites, dermatitis and rash.

References

  1. "Clobetasol Propionate Topical Ointment 0.05% Information". Drug Encyclopedia. Kaiser Permanente. Archived from the original on 28 August 2021. Retrieved 9 October 2009.
  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 October 2023.
  3. "DailyMed: Betasol dipropionate". NIH.gov.
  4. 1 2 3 4 5 6 "Clobetasol Propionate Monograph for Professionals". Drugs.com. American Society of Health-System Pharmacists. Archived from the original on 28 August 2021. Retrieved 13 April 2019.
  5. 1 2 3 "Clobetasol (topical): Drug information". UpToDate. 2024.
  6. 1 2 3 British National Formulary: BNF 76 (76th ed.). Pharmaceutical Press. 2018. p. 1210. ISBN   978-0-85711-338-2.
  7. "Clobetasol topical Use During Pregnancy". Drugs.com. Archived from the original on 28 August 2021. Retrieved 13 April 2019.
  8. Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 487. ISBN   9783527607495. Archived from the original on 28 November 2023. Retrieved 3 September 2020.
  9. "The Top 300 of 2021". ClinCalc. Archived from the original on 15 January 2024. Retrieved 14 January 2024.
  10. "Clobetasol – Drug Usage Statistics". ClinCalc. Archived from the original on 18 January 2024. Retrieved 14 January 2024.
  11. 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.
  12. E. Fougera and Co. "Clobetasol Propionate Cream Usp, 0.05% Clobetasol Propionate Ointment USP, 0.05%". Daily Med. U.S. National Library of Medicine. Archived from the original on 23 May 2009. Retrieved 3 July 2009.
  13. Saint Louis C (15 January 2010). "Creams Offering Lighter Skin May Bring Risks". New York Times. Archived from the original on 19 February 2017. Retrieved 24 February 2017.
  14. 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.
  15. "Dermovate 0.05% W/V Ointment – Clobetasol Topical(0.05% W/V)". Glaxo SmithKline Pharmaceuticals Ltd. GNHIndia.com. Archived from the original on 16 July 2021. Retrieved 16 July 2021.