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{{short description|Chemical compound}}
{{drugbox
{{Drugbox
⚫
| UNII_Ref = {{fdacite|correct|FDA}}
| Verifiedfields = changed
⚫
| UNII = 9N42CW7I54
| Watchedfields = changed
| verifiedrevid = 395741812
| verifiedrevid = 451222675
| drug_name = Climbazole
| IUPAC_name = (''RS'')-1-(4-chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one <ref>[http://www.uchem.com.cn/products_detail.asp?id=59 Chemical Properties of Climbazole]</ref>
| IUPAC_name = (''RS'')-1-(4-Chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one<ref>[http://www.uchem.com.cn/products_detail.asp?id=59 Chemical Properties of Climbazole] {{webarchive|url=https://web.archive.org/web/20071113142005/http://www.uchem.com.cn/products_detail.asp?id=59 |date=2007-11-13 }}</ref>
| image = Climbazole.svg
| image = Climbazole.svg
⚫
| width = 200
| imagename = 1 : 1 mixture (racemate)
| chirality = [[Racemic mixture]]
⚫
| width=200
| ATC_prefix = none
| drug_name =
<!--Clinical data-->
⚫
| CAS_number = 38083-17-9
| tradename =
| molecular_weight = 292.76
⚫
| C=15 | H=17 | Cl=1 | N=2 | )=2
| routes_of_administration = [[topical]]
| routes_of_administration = [[topical]]
<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
⚫
| CAS_number = 38083-17-9
| ATC_prefix = none
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 83499
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1437764
⚫
| UNII_Ref = {{fdacite|correct|FDA}}
⚫
| UNII = 9N42CW7I54
| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
| ChemSpiderID = 34752
| PubChem = 37907
<!--Chemical data-->
⚫
| C=15 | H=17 | Cl=1 | N=2 | O=2
| smiles = CC(C)(C)C(=O)C(n1ccnc1)Oc2ccc(cc2)Cl
| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
| StdInChI = 1S/C15H17ClN2O2/c1-15(2,3)13(19)14(18-9-8-17-10-18)20-12-6-4-11(16)5-7-12/h4-10,14H,1-3H3
| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
| StdInChIKey = OWEGWHBOCFMBLP-UHFFFAOYSA-N

}}
}}


'''Climbazole''' is a topical [[antifungal]] agent commonly used in the treatment of human fungal skin infections such as [[Seborrhoeic dermatitis|dandruff]]<ref>{{cite journal | last1 = Wigger-Alberti | first1 = W | last2 = Kluge | first2 = K | last3 = Elsner | first3 = P | title = Clinical effectiveness and tolerance of climbazole containing dandruff shampoo in patients with seborrheic scalp eczema | journal = Praxis | volume = 90 | issue = 33 | pages = 1346–9 | year = 2001 | pmid = 11534318}}</ref> and [[eczema]]. Climbazole has shown a high ''in vitro'' and ''in vivo'' efficacy against ''Pityrosporum ovale'' that appears to play an important role in the pathogenesis of dandruff.<ref name="web reference">[http://www.ncbi.nlm.nih.gov/pubmed/11534318 Clinical effectiveness and tolerance of climbazole containing dandruff shampoo in patients with seborrheic scalp eczema] Praxis (Bern 1994). 2001 Aug 16;90(33):1346-9 </ref> Its chemical structure and properties are similar to other fungicides such as [[ketoconazole]] and [[miconazole]].
'''Climbazole''' is a topical [[Antifungal medication|antifungal]] agent commonly used in the treatment of human fungal skin infections such as [[dandruff]], [[seborrhoeic dermatitis]] and [[eczema]].<ref name=pmid11534318>{{cite journal | vauthors = Wigger-Alberti W, Kluge K, Elsner P | title = [Clinical effectiveness and tolerance of climbazole containing dandruff shampoo in patients with seborrheic scalp eczema] | journal = Praxis | volume = 90 | issue = 33 | pages = 1346–9 | date = August 2001 | pmid = 11534318 }}</ref> Climbazole has shown a high ''in vitro'' and ''in vivo'' efficacy against ''[[Malassezia spp.]]'' that appear to play an important role in the pathogenesis of dandruff.<ref name=pmid11534318/> Its chemical structure and properties are similar to other [[azole]] fungicides such as [[ketoconazole]], [[clotrimazole]] and [[miconazole]].
__TOC__


==Indications and formulations==
==Indications and formulations==
It is most commonly found as an active ingredient in [[over-the-counter substance|OTC]] anti-dandruff and anti-fungal products, including shampoos, lotions and conditioners. It may be accompanied by other active ingredients such as [[zinc pyrithione]] or [[triclosan]].
It is most commonly found as an active ingredient in [[over-the-counter substance|OTC]] anti-dandruff and anti-fungal products, including shampoos, lotions and conditioners. It may be accompanied by other active ingredients such as [[zinc pyrithione]] or [[triclosan]].{{cn|date=December 2022}}


==Side effects==
==Side effects==
May cause localized irritation of the skin with symptoms including redness, rashes and itching.{{Citation needed|date=October 2010}}
It may cause localized irritation of the skin with symptoms including redness, rashes and itching.{{Citation needed|date=October 2010}}


== References ==
== References ==
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{{Antifungals}}
{{Antifungals}}


[[Category:Antifungals]]
[[Category:Imidazoles]]
[[Category:Phenol ethers]]
[[Category:Phenol ethers]]
[[Category:Organochlorides]]
[[Category:4-Chlorophenyl compounds]]
[[Category:Ketones]]
[[Category:Ketones]]
[[Category:Imidazole antifungals]]

[[de:Climbazol]]
[[pl:Klimbazol]]

Latest revision as of 18:00, 7 September 2024

Climbazole
Clinical data
Routes of
administration		topical
ATC code
  • none
Identifiers
  • (RS)-1-(4-Chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one[1]
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.048.870 Edit this at Wikidata
Chemical and physical data
FormulaC15H17ClN2O2
Molar mass292.76 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • CC(C)(C)C(=O)C(n1ccnc1)Oc2ccc(cc2)Cl
  • InChI=1S/C15H17ClN2O2/c1-15(2,3)13(19)14(18-9-8-17-10-18)20-12-6-4-11(16)5-7-12/h4-10,14H,1-3H3 ☒N
  • Key:OWEGWHBOCFMBLP-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

Climbazole is a topical antifungal agent commonly used in the treatment of human fungal skin infections such as dandruff, seborrhoeic dermatitis and eczema.[2] Climbazole has shown a high in vitro and in vivo efficacy against Malassezia spp. that appear to play an important role in the pathogenesis of dandruff.[2] Its chemical structure and properties are similar to other azole fungicides such as ketoconazole, clotrimazole and miconazole.

Indications and formulations

[edit]

It is most commonly found as an active ingredient in OTC anti-dandruff and anti-fungal products, including shampoos, lotions and conditioners. It may be accompanied by other active ingredients such as zinc pyrithione or triclosan.[citation needed]

Side effects

[edit]

It may cause localized irritation of the skin with symptoms including redness, rashes and itching.[citation needed]

References

[edit]
  1. ^ Chemical Properties of Climbazole Archived 2007-11-13 at the Wayback Machine
  2. ^ a b Wigger-Alberti W, Kluge K, Elsner P (August 2001). "[Clinical effectiveness and tolerance of climbazole containing dandruff shampoo in patients with seborrheic scalp eczema]". Praxis. 90 (33): 1346–9. PMID 11534318.
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