Clobetasol propionate
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| Systematic (IUPAC) name |
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[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
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| Clinical data |
| AHFS/Drugs.com |
monograph |
Pregnancy
category |
- US: C (Risk not ruled out)
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| Legal status |
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Routes of
administration |
Topical |
| Identifiers |
| CAS Registry Number |
25122-46-7 Y |
| ATC code |
D07AD01 |
| PubChem |
CID: 32798 |
| IUPHAR/BPS |
7062 |
| DrugBank |
DB01013 Y |
| ChemSpider |
30399 Y |
| UNII |
779619577M Y |
| ChEBI |
CHEBI:31414 Y |
| ChEMBL |
CHEMBL1159650 Y |
| Chemical data |
| Formula |
C25H32ClFO5 |
| Molecular mass |
466.97 g/mol |
SMILES
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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
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InChI
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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
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Key:CBGUOGMQLZIXBE-XGQKBEPLSA-N Y
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| Y (what is this?) (verify) |
Clobetasol propionate [1] is a corticosteroid of the glucocorticoid class used to treat various skin disorders including eczema and psoriasis. It is also highly effective for contact dermatitis caused by exposure to poison ivy/oak. Clobetasol belongs to US Class I (Europe: class IV) of the corticosteroids, making it one of the most potent available. It comes in shampoo, mousse, ointment and emollient cream presentations. It has very high potency and typically should not be used with occlusive dressings, or for extended continuous use (beyond two weeks). It is also used to treat several auto-immune diseases including alopecia areata, vitiligo and lichen planus (auto immune skin nodules).[2]
Clobetasol propionate is marketed and sold worldwide under numerous names including Clobex, Clob-x (Colombia), Clovate, Cormax (Watson, US), Pentasol (Colombia), Cosvate (India), Temovate (US), Dermovate (GlaxoSmithKline, Pakistan, Portugal, Israel), Olux, Tenovate, Dermatovate, Butavate, Movate, Novate, and Powercort.[3]
Contents
- 1 Uses
- 2 Possible side effects
- 3 Contraindications
- 4 Forms
- 5 See also
- 6 References
- 7 External links
Uses
Clobetasol propionate is used for the treatment of various skin disorders including eczema, herpes labialis,[4] psoriasis, and lichen sclerosus. It is also used to treat several auto-immune diseases including alopecia areata, vitiligo, 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.
Possible side effects
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This section needs additional citations for verification. Please help improve this article by adding citations to reliable sources. Unsourced material may be challenged and removed. (November 2013) |
- Osteoporosis
- Acneiform eruptions
- Allergic contact dermatitis
- Burning sensation
- Cracking and fissuring
- Cushing's syndrome
- Dizziness
- Dryness
- Erythema
- Glaucoma
- Folliculitis
- Hypertrichosis
- Hypopigmentation
- Itching
- Irritation
- Numbness of fingers
- Perioral dermatitis
- Pruritus
- Secondary infection
- Skin atrophy
- Skin maceration
- Stinging
- Striae
- [Rise in intensity] If stacking this with any other treatment especially bio-logic's all effects of the topical steroid will magnify greatly.
- Telangiectasia[5]
Contraindications
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:[6]
"Studies in the rat following oral administration at dosage levels up to 50 mg/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
- Clobetasol propionate ointment USP 0.05%, supplied in Olux 15 g, 30 g, 45 g, and 60 g tubes.
- Temovate & emollient 0.05%, supplied in 15 g (NDC 0173-0454-01), 30 g (NDC 0173-0454-02) and 60 g (NDC 0173-0454-03) tubes.
- Clobetasol propionate foam 0.05%
- Clobetasol propionate foam 0.10%
- Clobetasol propionate cream 0.05%
- Clobetasol propionate gel 0.05%
- Clobetasol propionate scalp application 0.05%
- Clobetasol propionate spray 0.05%
- Dermovate cream and ointment, containing clobetasol propionate 0.05% (UK)
- Dermol cream and ointment (NZ)
See also
References
- ^ Clobetasol Propionate Topical Ointment 0.05% Information - Drug Encyclopedia
- ^ CLOBETASOL PROPIONATE CREAM USP, 0.05% CLOBETASOL PROPIONATE OINTMENT USP, 0.05%
- ^ • Ulotka Novate / Clobetasoli propionas - leki i suplementy diety, dawkowanie, skład, zastosowanie, opis - DOZ.pl
- ^ Hull C, McKeough M, Sebastian K, Kriesel J, Spruance S. Valacyclovir and topical clobetasol gel for the episodic treatment of herpes labialis: a patient-initiated, double- blind, placebo-controlled pilot trial. J Eur Acad Derma- tol Venereol. 2009;23(3):263-267
- ^ Temovate E Top Precautions and Side Effects
- ^ Chemicals Under Consideration For Possible Listing Via The "Formally Required To Be Labeled Or Identified" Mechanism, Office of Environmental Health Hazard Assessment, California Environmental Protection Agency
External links
- Material Safety Data Sheet(MSDS)
- Manufacturers Product Information Sheet
- Manufacturers Product Web Page
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Glucocorticoids and antiglucocorticoids (H02)
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| Agonists |
| Pregnene |
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| Pregnenedione |
- Hydrocortisone (cortisol)# (Hydrocortisone aceponate
- Hydrocortisone buteprate
- Hydrocortisone butyrate)
- Budesonide
- Ciclesonide
- Deflazacort
- Medrysone
- Tixocortol
- HALOGENATED AT 6: Cloprednol
- HALOGENATED, WITH FG AT 16: Halcinonide
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|
| Pregnadiene |
- Rimexolone
- HALOGENATED, WITH FG AT 16: Flunisolide
- Triamcinolone
- Amcinonide
- Fluocinolone acetonide (Fluocinonide)
|
|
| Pregnadienediol |
- Prednisone (Meprednisone)
- HALOGENATED AT 9: Fluorometholone
- HALOGENATED, WITH FG AT 16: Fluocortolone (Clocortolone
- Diflucortolone
- Fluocortin)
- Desoximetasone
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|
| Pregnadienetriol |
- Prednisolone# (Methylprednisolone
- Methylprednisolone aceponate
- Prednicarbate
- Prednylidene)
- Desonide
- HALOGENATED: Fluprednisolone (Difluprednate
- Fluperolone)
- HALOGENATED, WITH FG AT 16: Dexamethasone#
- Betamethasone (Clobetasol
- Clobetasone
- Diflorasone
- Halometasone
- Ulobetasol)
- Beclometasone
- Paramethasone
- Alclometasone
- Fluclorolone acetonide
- Flumetasone
- Fluprednidene
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| Pregnatriene |
|
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| Androstene |
- HALOGENATED, WITH FG AT 16: Fluticasone (Fluticasone propionate
- Fluticasone furoate)
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| Others/unsorted |
- HALOGENATED: Loteprednol
- HALOGENATED, WITH FG AT 16: Fludroxycortide
- Formocortal
- Mometasone furoate
- Promestriene
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Antagonists /
SGRMs |
- Antagonists: Mifepristone
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| Synthesis modifiers |
- Acetoxolone
- Aminoglutethimide
- Carbenoxolone
- Enoxolone
- Ketoconazole
- Metyrapone
- Mitotane
- Trilostane
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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Index of hormones
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|
| Description |
- Glands
- Hormones
- thyroid
- mineralocorticoids
- Physiology
- Development
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|
| Disease |
- Diabetes
- Congenital
- Neoplasms and cancer
- Other
- Symptoms and signs
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|
| Treatment |
- Procedures
- Drugs
- calcium balance
- corticosteroids
- oral hypoglycemics
- pituitary and hypothalamic
- thyroid
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Glucocorticoid signaling
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Receptor
(ligands) |
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GR
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Agonists
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|
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Mixed (SEGRAs)
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- Dagrocorat
- Fosdagrocorat
- Mapracorat
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|
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Antagonists
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- 3α-Hydroxytibolone
- 3β-Hydroxytibolone
- Aglepristone
- Asoprisnil
- C108297
- C113176
- CORT-108297
- Cyproterone acetate
- Ketoconazole
- Lilopristone
- LLY-2707
- Mifepristone
- Onapristone
- Org 34850
- PCN
- Telapristone
- Tibolone
- Toripristone
- Ulipristal acetate
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Enzyme
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Modulators
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- 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 11β-HSD, 21-hydroxylase, 11β-hydroxylase, and 18-hydroxylase) (see also Steroid hormone metabolism modulators)
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| Others |
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Precursors/prohormones
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- Cholesterol
- 22R-Hydroxycholesterol
- 20α,22R-Dihydroxycholesterol
- Pregnenolone
- Pregnenolone sulfate
- 17-Hydroxypregnenolone
- Progesterone
- 17-Hydroxyprogesterone
- 11-Deoxycorticosterone
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Indirect
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- ACTH (corticotropin)
- CRH
- DHEA
- DHEA sulfate
- Plasma proteins (albumin, transcortin)
- Vasopressin
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See also: Androgenics • Estrogenics • Mineralocorticoids • Progestogenics
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