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Clobetasol
Clobetasol
Clobetasol
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Clobetasol
Clinical data
Other names9α-Fluoro-11β,17α-dihydroxy-16β-methyl-21-chloropregna-1,4-diene-3,20-dione
Pregnancy
category
Drug classCorticosteroid; Glucocorticoid
ATC code
  • None
Identifiers
  • (8S,9R,10S,11S,13S,14S,16S,17R)-17-(2-Chloroacetyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.042.379 Edit this at Wikidata
Chemical and physical data
FormulaC22H28ClFO4
Molar mass410.91 g·mol−1
3D model (JSmol)
  • C[C@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CCl)O)C)O)F)C
  • InChI=1S/C22H28ClFO4/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,24)17(26)10-20(16,3)22(12,28)18(27)11-23/h6-7,9,12,15-17,26,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,17-,19-,20-,21-,22-/m0/s1
  • Key:FCSHDIVRCWTZOX-DVTGEIKXSA-N

Clobetasol is a synthetic glucocorticoid corticosteroid. A propionate ester of clobetasol, clobetasol propionate, has also been marketed, and is far more widely used in comparison.[2][3]

References

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Revisions and contributorsEdit on WikipediaRead on Wikipedia

Clobetasol

View on Grokipedia
from Grokipedia
Clobetasol propionate is a synthetic formulated for topical application, classified as a super-high potency agent used primarily to alleviate the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses, including moderate to severe forms of and eczema. It exerts its effects through binding to receptors, which leads to the inhibition of pro-inflammatory signals and the promotion of anti-inflammatory responses in the , while also demonstrating immunosuppressive and antimitotic properties that influence , differentiation, and function. Originally developed in the late 1960s, it received initial U.S. (FDA) approval for topical use in 1985, with various formulations such as creams, ointments, gels, lotions, foams, shampoos, sprays, and an ophthalmic suspension (approved 2024) becoming available to target specific areas like the , , and eyes. Available in a 0.05% concentration across most formulations, is indicated for short-term treatment—typically up to two weeks for adults and less for children—to reduce symptoms such as itching, redness, dryness, crusting, scaling, and discomfort associated with conditions like plaque psoriasis, , and other inflammatory scalp and skin disorders. Due to its high potency, it can suppress the hypothalamic-pituitary-adrenal (HPA) axis even at low doses (as little as 2 grams per day), potentially leading to systemic absorption and side effects including skin atrophy, , , and increased risk of infections if overused or applied to large areas. Common local adverse reactions include burning, stinging, irritation, dryness, and , while precautions emphasize avoiding application near the eyes, mouth, or genital areas, not using occlusive dressings unless directed, and monitoring for signs of HPA axis suppression through cosyntropin stimulation testing in prolonged use. Brand names for products include Clobex, Cormax, Embeline, Olux, and Temovate, though some formulations like Temovate have been discontinued in certain markets. It is contraindicated in patients with primary skin infections, , , or , and should be used cautiously in those with , , cataracts, or during due to potential fetal risks. Overall, its efficacy in rapidly controlling severe dermatological inflammation is balanced against the need for strict adherence to dosing guidelines to minimize risks, making it a cornerstone therapy in when lower-potency alternatives prove insufficient.

Medical uses

Indications

Clobetasol propionate is a super-high potency (Class I) topical indicated for the short-term relief of the inflammatory and pruritic manifestations of corticosteroid-responsive dermatoses. Its primary indications encompass a range of inflammatory skin conditions, including (eczema), plaque , , seborrheic dermatitis, , , and . In these conditions, clobetasol effectively reduces redness, swelling, itching, and scaling, particularly in moderate to severe or resistant cases where lower-potency agents prove inadequate. Secondary uses include the treatment of autoimmune dermatoses such as and (a form of ), where it serves as an initial topical therapy to manage localized lesions. It is also recommended as a first-line agent for acute and chronic cutaneous (GVHD) following , helping to control skin involvement in this complication. Off-label applications extend to the short-term of severe pruritus and other steroid-responsive dermatoses unresponsive to milder treatments, leveraging its potent effects while limiting use to avoid potential risks. Clinical guidelines from dermatological societies, such as the , endorse clobetasol for short durations (typically 2-4 weeks) in resistant inflammatory conditions like and , emphasizing its role in flare control rather than long-term maintenance.

Administration

Clobetasol propionate is available in several topical formulations, each suited to different application needs, including cream (0.05%), ointment (0.05%), lotion (0.05%), gel (0.05%), foam (0.05%), shampoo (0.05%), and scalp solution (0.05%). These forms are designed for dermatologic use on the skin and scalp, with the cream and ointment being the most commonly prescribed for general inflammatory conditions. For adults, the standard dosing involves applying a thin layer of the formulation to the affected areas once or twice daily, depending on the product, for no more than two weeks to minimize risks of adverse effects. The maximum weekly dose should not exceed 50 grams to avoid systemic absorption issues. Treatment should be discontinued once symptoms are controlled, and therapy should not be restarted without medical advice if symptoms recur. In pediatric patients aged 12 years and older, dosing mirrors adult guidelines but with caution due to higher absorption risks; use is generally not recommended for children under 12 years unless directed by a physician, often opting for lower-potency alternatives or shorter durations. Adjustments may include reducing frequency to once daily or limiting the treated area. Application should be limited to the affected areas, rubbing gently and completely into the skin while avoiding the eyes, , and other mucous membranes. For scalp formulations like or solution, apply to wet , lather if needed, and leave on for 15 minutes before rinsing, typically once daily. Occlusive dressings are not recommended unless specified by a healthcare provider, as they can increase absorption; similarly, avoid covering treated areas tightly. To prevent rebound effects, taper usage gradually under medical supervision after the initial course. Monitoring during treatment includes regular clinical assessments for therapeutic response and early signs of side effects, such as skin thinning or lack of improvement after two weeks, prompting reevaluation or discontinuation. Patients should report any changes promptly to their healthcare provider.

Adverse effects

Local effects

Clobetasol, a high-potency topical , commonly induces local adverse reactions at the site of application, primarily affecting the skin's structure and appearance. These include skin atrophy, characterized by thinning of the and due to inhibition of synthesis; , manifesting as visible dilated blood vessels; striae, or resulting from dermal tearing; acneiform eruptions, resembling lesions; and , inflammation of hair follicles. Such local effects occur in approximately 1-10% of users, with skin atrophy reported in 4.2% and in 3.2% of patients using lotion in clinical trials. Risk factors that increase their incidence include prolonged application beyond 2 weeks, use of occlusive dressings to enhance penetration, application of this high-potency agent on thin-skinned areas such as the face, genitals, or regions, and higher cumulative doses. Management of these local effects involves prompt discontinuation of clobetasol upon appearance of signs, as early intervention allows reversibility in many cases through natural skin recovery or supportive care. However, chronic exposure can lead to permanent changes, such as irreversible striae or scarring, necessitating avoidance of long-term use without medical supervision. In topical formulations like creams, ointments, or shampoos, irritation may also arise from excipients such as propylene glycol or alcohol, exacerbating burning, dryness, or contact dermatitis at the application site, particularly in sensitive individuals.

Systemic effects

Systemic absorption of clobetasol, a super-potent topical corticosteroid, can lead to hypothalamic-pituitary-adrenal (HPA) axis suppression, resulting in adrenal insufficiency, particularly with prolonged use or application over large areas of skin. This suppression manifests through symptoms such as fatigue, hypotension, and Cushingoid features including moon face, buffalo hump, and central obesity. Biochemical evidence of HPA suppression, such as reduced serum cortisol levels, has been observed in 15-20% of patients after 2-4 weeks of treatment, though clinical adrenal insufficiency is less common. Other systemic risks associated with clobetasol absorption include , which may exacerbate ; ; due to interference with ; , especially with periorbital application; and that increases susceptibility to infections. Prolonged use has been linked to an increased risk of major osteoporotic fractures, with potent topical corticosteroids showing a of 1.20 compared to milder agents. Periorbital use elevates and may lead to ; has been reported in 0.63% of adverse events associated with clobetasol in data. Rare but serious effects include iatrogenic from excessive absorption, growth retardation in children due to interference with linear growth, and or other complications from misuse in skin lightening practices, which can also rarely contribute to exogenous when combined with other agents. Children are particularly vulnerable, with growth suppression reported in cases of extensive application, and clobetasol is generally not recommended for those under 12 years. The incidence of clinically significant systemic effects is low, less than 1% with recommended dosing, but rises in , elderly patients, or with extensive/occlusive use; transient HPA suppression may occur in up to 48% of cases but is often asymptomatic. This suppression is usually reversible upon discontinuation, with mean recovery times of approximately 3.5 months in children and 3.8 months in adults. For high-risk cases, such as prolonged therapy or pediatric use, laboratory monitoring of levels and ACTH stimulation tests is recommended to detect HPA suppression early.

Pharmacology

Pharmacodynamics

Clobetasol propionate, a synthetic corticosteroid, exerts its effects primarily by binding to intracellular glucocorticoid receptors (GR) in the cytoplasm of target cells, such as keratinocytes and immune cells in the skin. Upon binding, the ligand-receptor complex dissociates from chaperone proteins like heat shock protein 90 (HSP90) and translocates to the nucleus, where it dimerizes and binds to glucocorticoid response elements (GREs) on DNA. This interaction modulates gene transcription by activating the expression of anti-inflammatory proteins, such as annexin A1 and interleukin-10 (IL-10), while repressing pro-inflammatory pathways. A key aspect of clobetasol's action involves the inhibition of (), a that drives the expression of pro-inflammatory genes. By interacting with and its co-activators, the complex prevents from binding to DNA, thereby suppressing the production of cytokines including interleukin-1 (IL-1), interleukin-6 (IL-6), and tumor necrosis factor-alpha (TNF-α). Additionally, clobetasol induces the synthesis of lipocortin-1 (), which inhibits (PLA2) activity. This inhibition reduces the release of from phospholipids, subsequently decreasing the formation of pro-inflammatory mediators such as prostaglandins and leukotrienes via the and pathways, respectively. Clobetasol demonstrates exceptional potency, classified as a superpotent (Class I) topical due to its high affinity for the and resistance to local metabolism, making it up to 600 times more potent than in skin assays. This potency profile contributes to its rapid and vasoconstrictive effects in dermatological conditions. Furthermore, clobetasol acts as a selective agonist at the with minimal activity at the , minimizing unwanted effects on electrolyte balance.

Pharmacokinetics

Clobetasol propionate demonstrates limited systemic exposure following topical application due to low percutaneous absorption, which is influenced by formulation, , and application method. Systemic absorption is minimal, typically ranging from 1% to 6% of the applied dose in adults under normal conditions, with peak plasma concentrations achieved within 1 to 3 hours post-application. Absorption increases significantly with occlusive dressings, application to areas of thin or inflamed skin (such as regions), or treatment of large body surface areas exceeding 10-20% of total skin. Once absorbed, distributes widely to and other tissues and is highly bound to plasma proteins, primarily to and , as is typical for corticosteroids. It readily crosses the , potentially leading to fetal exposure, and is detectable in in trace quantities following maternal use. This distribution profile contributes to its localized therapeutic effects while minimizing widespread systemic accumulation. Metabolism of absorbed occurs primarily in the liver via 3A4 () enzymes, yielding inactive metabolites such as hydroxylated and conjugated forms. In the skin, rapid local inactivation by () enzymes further restricts the amount available for systemic circulation, enhancing the drug's safety for topical use. These metabolic pathways ensure quick deactivation, reducing the duration of activity. Excretion of clobetasol propionate and its metabolites occurs primarily through the feces via biliary elimination and urine. The plasma elimination half-life is short, typically 1-2 hours for systemically absorbed drug, though retention in skin layers can extend local exposure to several hours or more. Overall clearance is hepatic-dependent, with total recovery of administered dose approaching 70-90% within 96 hours in absorption studies. In special populations, may vary. Patients with hepatic impairment exhibit reduced clearance and prolonged half-life due to diminished metabolic capacity, necessitating dose adjustments or monitoring for systemic effects. Children experience higher relative absorption owing to their larger surface area-to-body weight ratio and thinner epidermal barrier, increasing the risk of HPA axis suppression with extensive use.

Chemistry

Structure

Clobetasol is a synthetic with the molecular formula C22H28ClFO4 for its base form. Its systematic name is 21-chloro-9-fluoro-11β,17-dihydroxy-16β-methylpregna-1,4-diene-3,20-dione. The molecule features a skeleton, which is a four-ring structure consisting of three six-membered rings (A, B, C) and one five-membered ring (D), characteristic of many . This core includes a Δ1,4-3-keto configuration, with a group at the C3 position and double bonds between C1-C2 and C4-C5 in ring A, enhancing its binding affinity to glucocorticoid receptors. Key substituents contribute to its superpotent activity: a 9α-fluoro group increases potency by improving receptor interaction, a 21-chloro group replaces the typical 21-hydroxy for greater , a 16β-methyl group reduces hepatic to prolong duration of action, and 11β- and 17α-hydroxy groups support its hormonal functionality. These modifications distinguish clobetasol from (11β,17α,21-trihydroxypregn-4-ene-3,20-dione), which lacks the system, , methyl, and chloro substitutions, resulting in clobetasol's markedly higher topical potency. In clinical use, clobetasol is primarily administered as the 17-propionate ester, clobetasol 17-propionate, with the molecular formula C25H32ClFO5, where a propionyl group (CH3CH2COO-) is esterified at the 17α-hydroxy position to enhance penetration and . The structure can be visualized with the backbone, the C3 and Δ1,4 unsaturation in ring A, the 9α-fluoro and 11β-hydroxy in ring C, the 16β-methyl and 17α-propionyloxy with adjacent 20-keto and 21-chloroacetyl side chain in ring D.

Properties

Clobetasol propionate appears as a to practically crystalline powder. Its ranges from 190°C to 200°C. The compound exhibits a logP value of approximately 3.5, reflecting its lipophilic nature that facilitates penetration through the skin. Clobetasol propionate is poorly soluble in water, with solubility below 0.1 mg/mL, but it is freely soluble in acetone and chloroform, and sparingly soluble in ethanol. It has a pKa of about 12.9, classifying it as a weak acid. The compound is sensitive to light, heat, and alkaline conditions, where it undergoes significant degradation, while remaining relatively stable under neutral pH. Clobetasol propionate is classified in Group I (super-high potency) according to the system for topical corticosteroids, determined via the vasoconstrictor assay. It is approximately 600 times more potent than in this context.

History

Development

Clobetasol propionate was synthesized in the late 1960s by researchers at Glaxo Laboratories in the , as part of a broader program to develop more potent synthetic corticosteroids for topical application. The compound emerged from modifications to betamethasone, specifically through the introduction of a atom at the 21-position and retention of the at the 9-position, which enhanced its potency while minimizing systemic absorption. This optimization was driven by structure-activity relationship studies aimed at improving efficacy in dermatological conditions. Preclinical evaluation in the late involved animal models to assess activity. These studies highlighted the role of substitutions—particularly the 21-chloro and 9-fluoro groups—in conferring superior vasoconstrictor and antiproliferative effects, establishing clobetasol as a candidate for superpotent topical . Early clinical trials, conducted primarily in the 1970s, included phase I and II studies that demonstrated clobetasol propionate's efficacy in , with rapid clearance of plaques observed in bilateral lesion comparisons against standard treatments like . An international multicenter trial involving 1,150 patients with or eczema confirmed its status as one of the first superpotent topical corticosteroids, showing high response rates in moderate to severe cases while noting the need for short-term use to avoid side effects. Key milestones included the filing of a by Glaxo Laboratories in 1968 ( Patent 3,721,687 granted in ) and the initial marketing of as Dermovate ointment in , marking its entry into clinical practice.

Regulatory approval

Clobetasol propionate received initial approval from the U.S. Food and Drug Administration (FDA) on December 27, 1985, as Temovate (clobetasol propionate cream and ointment, 0.05%) for the short-term topical treatment of moderate to severe corticosteroid-responsive dermatoses of the non-scalp, non-facial regions. The drug first entered medical use in the UK as Dermovate in 1973, with wider availability across in the late , receiving national authorizations such as for Dermovate ointment and cream in the UK. Over the and , indications and formulations expanded to address specific dermatoses. For instance, approvals were granted for applications, including solutions and s for , with the FDA approving Clobex (clobetasol propionate , 0.05%) in 2004 for moderate to severe . Use for vulvar was supported by and incorporated into labeling in the , emphasizing short-term to minimize risks like skin atrophy. In the , FDA updated class labeling for topical corticosteroids, including clobetasol, with strengthened warnings for pediatric use due to risks of hypothalamic-pituitary-adrenal (HPA) axis suppression, limiting application to no more than 10-20% of and short durations in children over 12 years. Clobetasol propionate is classified as a prescription-only medicine worldwide to ensure supervised use given its potency. In the and , it requires a prescription for all formulations; in the , it is designated as Prescription Only Medicine (POM); and in , it falls under , mandating a doctor's prescription. Its inclusion in over-the-counter cosmetics is prohibited in many countries, including the , , , and , due to potential endocrine disruption and skin damage from unsupervised potent exposure; regulatory actions have targeted illegal skin-lightening products containing it. As of 2025, no major changes to core approvals have occurred, though guidelines have heightened focus on long-term safety. The American Academy of Dermatology's 2023 guidelines for management recommend high-potency topical corticosteroids like clobetasol for short-term flares in adults but caution against prolonged use to avoid adverse effects, prioritizing proactive maintenance therapy. In March 2024, the FDA approved a new ophthalmic suspension formulation (0.05%) for postoperative and , marking the first novel indication in over 15 years. is used in in the and for treating inflammatory dermatoses in animals, such as in dogs and cats, often through compounded formulations.

Society and culture

Brand names

Clobetasol is most commonly available as , the primary ester form used in topical formulations, with fewer products featuring the butyrate ester. In the United States, major current brand names include Clobex (by Galderma Laboratories) and Impoyz, while former brands such as Temovate (developed by GlaxoSmithKline and now available as generic equivalents), Olux (foam formulation), Cormax, and Embeline have been discontinued. In the and , prominent brands are Dermovate (GlaxoSmithKline), ClobaDerm (Accord Healthcare), and Etrivex (scalp application). In and other Asian markets, notable brands include Tenovate (GlaxoSmithKline), Topinate (Systopic Laboratories), and Hexiderm, often in combination products with antibiotics or antifungals for dermatological use. Globally, over 50 brand names exist for clobetasol products, including generics such as Clobetasol Topical Solution or Ointment, manufactured by companies like Teva Pharmaceuticals, Perrigo, Lupin, and Taro Pharmaceuticals.

Availability

Clobetasol propionate has been widely available as a generic medication in the United States and many other countries since the early 2000s, following the expiration of patents on branded versions. In 2023, it was the 129th most commonly prescribed drug in the US, with more than 4 million outpatient prescriptions dispensed, primarily for dermatological conditions. Despite its potency, it is obtainable over-the-counter in some low-regulation regions, including parts of Africa and Asia, where misuse for non-medical purposes like skin lightening has raised significant health concerns due to risks of skin atrophy and systemic absorption; as of 2025, cases of topical steroid-induced dermatitis from such products continue to be reported. In terms of pricing, a 45 g tube of generic cream typically costs $20 to $50 in the as of 2025, though this can be lower with manufacturer coupons or discounts; branded foam formulations command higher prices, often exceeding $100 for equivalent quantities. In the , access is facilitated through national health systems that subsidize costs for eligible patients, making it more affordable in countries like and the where pharmaceutical benefit schemes cover a substantial portion of expenses. Access to clobetasol faces regulatory restrictions beyond prescription use, particularly in ; it is illegal to market or use it for skin bleaching in the and , as prohibited by FDA guidelines and EU Regulation 1223/2009, due to severe adverse effects like dermal thinning and adrenal suppression. Veterinary formulations are readily available in both the and for treating inflammatory skin conditions in pets, such as allergies and in dogs and cats. challenges have occasionally led to shortages, including manufacturing disruptions in 2022 that affected ointment availability in , prompting temporary reliance on alternative suppliers.

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