Clobetasone: Difference between revisions

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{{drugbox |
{{Drugbox
| IUPAC_name = (''8S,9R,10S,13S,14S,16S,17R'')-17-(2-Chloroacetyl)-9-fluoro-17-hydroxy-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-''6H''-cyclopenta[a]phenanthrene-3,11-dione
| Watchedfields = changed
| verifiedrevid = 447609987
| IUPAC_name = (1''R'',2''S'',10''S'',11''S'',13''S'',14''R'',15''S'')-14-(2-chloroacetyl)-1-fluoro-14-hydroxy-2,13,15-trimethyltetracyclo[8.7.0.0<sup>2,7</sup>.0<sup>11,15</sup>]heptadeca-3,6-diene-5,17-dione
| image = clobetasone.png
| image = clobetasone.png
<!--Clinical data-->
| tradename = Eumovate
| Drugs.com = {{drugs.com|CONS|clobetasone}}
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B            / C / D / X -->
| pregnancy_category = 
| legal_AU = <!-- Unscheduled / S2 / S3 / S4  / S8 -->
| legal_UK = <!-- GSL        / P      / POM / CD -->
| legal_US = <!-- OTC                  / Rx-only  -->
| legal_status = 
| routes_of_administration = topical
<!--Pharmacokinetic data-->
| bioavailability = 
| protein_bound = 
| metabolism = 
| elimination_half-life = 
| excretion =
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 54063-32-0
| CAS_number = 54063-32-0
| ATC_prefix = D07
| ATC_prefix = D07
| ATC_suffix = AB01
| ATC_suffix = AB01
| ATC_supplemental = {{ATC|S01|BA09}}
| ATC_supplemental = {{ATC|S01|BA09}}
| PubChem = 71387
| PubChem = 71387
| DrugBank =  
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 64482
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = LT69WY1J6D
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07717
 
<!--Chemical data-->
| C=22 | H=26 | Cl=1 | F=1 | O=4  
| C=22 | H=26 | Cl=1 | F=1 | O=4  
| molecular_weight = 408.891
| molecular_weight = 408.891 g/mol
| bioavailability =  
| smiles = ClCC(=O)[C@@]2(O)[C@@H](C)C[C@H]1[C@H]4[C@](F)(C(=O)C[C@@]12C)[C@@]/3(/C(=C\C(=O)\C=C\3)CC4)C
| protein_bound =  
| InChI = 1/C22H26ClFO4/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/h6-7,9,12,15-16,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,19-,20-,21-,22-/m0/s1
| metabolism =  
| InChIKey = XXIFVOHLGBURIG-OZCCCYNHBL
| elimination_half-life =  
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| excretion =  
| StdInChI = 1S/C22H26ClFO4/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/h6-7,9,12,15-16,28H,4-5,8,10-11H2,1-3H3/t12-,15-,16-,19-,20-,21-,22-/m0/s1
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| pregnancy_US =  <!-- A / B            / C / D / X -->
| StdInChIKey = XXIFVOHLGBURIG-OZCCCYNHSA-N
| pregnancy_category =
| synonyms = (8''S'',9''R'',10''S'',13''S'',14''S'',16''S'',17''R'')-17-(2-Chloroacetyl)-9-fluoro-17-hydroxy-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6''H''-cyclopenta[''a'']phenanthrene-3,11-dione
| legal_AU =     <!-- Unscheduled / S2 / S3 / S4  / S8 -->
| legal_UK =      <!-- GSL        / P      / POM / CD -->
| legal_US =      <!-- OTC                  / Rx-only  -->
| legal_status =  
| routes_of_administration = topical
}}
}}
__NOTOC__
{{SI}}
{{SI}}


{{CMG}}
==Overview==
'''Clobetasone''' ([[International Nonproprietary Name|INN]]<ref>[http://unstats.un.org/unsd/cr/registry/regcia.asp?Cl=18&Lg=1&Co=C&p=310 United Nations Statistics Division - Classifications Registry - Alphabetical index for HS 2002 Entries starting with 'C' (page 310 of 422)]</ref>) 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]].<ref>{{cite pmid|1164639}}</ref>
It is available as clobetasone butyrate under the brand names '''Eumosone''' or '''Eumovate'''<ref>[http://www.netdoctor.co.uk/medicines/100000982.html Eumovate cream/ointment, NetDoctor.co.uk]</ref> both manufactured by [[GlaxoSmithKline]].
'''Trimovate''' also contains [[Oxytetracycline]], an [[antibiotic]], and [[nystatin]], an [[Antifungal medication|antifungal]].<ref name="TRI-Box">30g Trimovate Cream Box, GSK</ref><ref name="MED-ORG">[http://www.medicines.org.uk/guides/trimovate/ Medicines.org.uk - Trimovate info]</ref><ref>[http://www.netdoctor.co.uk/medicines/100002649.html Trimovate cream, NetDoctor.co.uk]</ref>


'''Clobetasone''' is a [[corticosteroid]] used in [[dermatology]], for treating such skin inflammation as seen in [[eczema]] and other forms of [[dermatitis]], and [[ophthalmology]].
==Uses==
In [[dermatology]], topical clobestasone butyrate helps to reduce the itchiness and [[erythema]] associated with [[eczema]] and [[dermatitis]].<ref>[http://public.gsk.co.uk/products/eumovate.html Euvomate Medication Guide, GlaxoSmithKline]</ref>


It is available as clobetasone butyrate under the brand name '''Eumovate''' manufactured by [[GlaxoSmithKline]].
In [[ophthalmology]], clobetasone butyrate 0.1% eye drops have been shown to be safe and effective in the treatment of dry eyes in [[Sjögren's Syndrome]]. Sjögren's Syndrome is an autoimmune disorder that affects the moisture producing glands of the body causing many symptoms including dry eyes.<ref>{{cite pmid|23225089}}</ref> When compared to other corticosteroid eye drops; clobetasone butyrate showed only minimal rises in intraocular pressure. Increased pressure within the eye can lead to [[glaucoma]].<ref>{{cite pmid|6986899}}</ref><ref>{{cite pmid|7032579}}</ref><ref>{{cite pmid|7028089}}</ref>


{{Corticosteroids}}
==Adverse effects==
Side effects associated with clobetasone cream and ointment include: burning, irritation, itching, thinning of the skin, and changes in skin color.<ref>[http://drugs.webmd.boots.com/drugs/drug-107-Clobetasone+Butyrate.aspx Clobetason Butyrate, WebMD]</ref><ref>[http://public.gsk.co.uk/products/eumovate.html Euvomate Medication Guide, GlaxoSmithKline]</ref>


==References==
{{Reflist|2}}


{{Glucocorticoids}}
{{Glucocorticoidics}}


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Revision as of 14:55, 9 April 2015

Clobetasone
Clinical data
Trade namesEumovate
Synonyms(8S,9R,10S,13S,14S,16S,17R)-17-(2-Chloroacetyl)-9-fluoro-17-hydroxy-10,13,16-trimethyl-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthrene-3,11-dione
AHFS/Drugs.comMicromedex Detailed Consumer Information
Routes of
administration
topical
ATC code
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC22H26ClFO4
Molar mass408.891 g/mol
3D model (JSmol)
  (verify)


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Editor-In-Chief: C. Michael Gibson, M.S., M.D. [1]

Overview

Clobetasone (INN[1]) 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.[2]

It is available as clobetasone butyrate under the brand names Eumosone or Eumovate[3] both manufactured by GlaxoSmithKline.

Trimovate also contains Oxytetracycline, an antibiotic, and nystatin, an antifungal.[4][5][6]

Uses

In dermatology, topical clobestasone butyrate helps to reduce the itchiness and erythema associated with eczema and dermatitis.[7]

In ophthalmology, clobetasone butyrate 0.1% eye drops have been shown to be safe and effective in the treatment of dry eyes in Sjögren's Syndrome. Sjögren's Syndrome is an autoimmune disorder that affects the moisture producing glands of the body causing many symptoms including dry eyes.[8] When compared to other corticosteroid eye drops; clobetasone butyrate showed only minimal rises in intraocular pressure. Increased pressure within the eye can lead to glaucoma.[9][10][11]

Adverse effects

Side effects associated with clobetasone cream and ointment include: burning, irritation, itching, thinning of the skin, and changes in skin color.[12][13]

References

  1. United Nations Statistics Division - Classifications Registry - Alphabetical index for HS 2002 Entries starting with 'C' (page 310 of 422)
  2. PMID 1164639 (PMID 1164639)
    Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
  3. Eumovate cream/ointment, NetDoctor.co.uk
  4. 30g Trimovate Cream Box, GSK
  5. Medicines.org.uk - Trimovate info
  6. Trimovate cream, NetDoctor.co.uk
  7. Euvomate Medication Guide, GlaxoSmithKline
  8. PMID 23225089 (PMID 23225089)
    Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
  9. PMID 6986899 (PMID 6986899)
    Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
  10. PMID 7032579 (PMID 7032579)
    Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
  11. PMID 7028089 (PMID 7028089)
    Citation will be completed automatically in a few minutes. Jump the queue or expand by hand
  12. Clobetason Butyrate, WebMD
  13. Euvomate Medication Guide, GlaxoSmithKline

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