Climbazole: Difference between revisions

Climbazole
Clinical data
Routes of; administration	topical
ATC code	none;
Identifiers
	IUPAC name (RS)-1-(4-Chlorophenoxy)-1-imidazol-1-yl-3,3-dimethylbutan-2-one;
CAS Number	38083-17-9 ;
PubChem CID	37907;
ChemSpider	34752 ;
UNII	9N42CW7I54;
ChEBI	CHEBI:83499 ;
ChEMBL	ChEMBL1437764 ;
CompTox Dashboard (EPA)	DTXSID6046555 ;
ECHA InfoCard	100.048.870
Chemical and physical data
Formula	C15H17ClN2O2
Molar mass	292.76 g·mol−1
3D model (JSmol)	Interactive image;
Chirality	Racemic mixture
	SMILES CC(C)(C)C(=O)C(n1ccnc1)Oc2ccc(cc2)Cl;
	InChI 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 ; Key:OWEGWHBOCFMBLP-UHFFFAOYSA-N ;
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Latest revision as of 18:00, 7 September 2024

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

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

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

References

^ Chemical Properties of Climbazole Archived 2007-11-13 at the Wayback Machine
^ ^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.

[1] Chemical Properties of Climbazole Archived 2007-11-13 at the Wayback Machine

[pmid11534318-2] 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.

[1]

[2]

@@ Line 1: / Line 1: @@
+{{short description|Chemical compound}}
 {{Drugbox
 | Verifiedfields = changed
@@ Line 26: / Line 27: @@
 <!--Chemical data-->
 | C=15 | H=17 | Cl=1 | N=2 | O=2
-| molecular_weight = 292.76
 | smiles            = CC(C)(C)C(=O)C(n1ccnc1)Oc2ccc(cc2)Cl
 | StdInChI_Ref = {{stdinchicite|changed|chemspider}}
@@ Line 35: / Line 35: @@
 }}
-'''Climbazole''' is a [[bioactive]] [[molecule]] of imidazol-1-yl group that inhibits [[sterol 14-demethylase|sterol 14α-demethylase]].<ref name="10.3389/fphar.2019.00835">{{cite journal|first1=Abed|last1=Forouzesh|first2=Sadegh|last2=Samadi Foroushani|first3=Fatemeh|last3=Forouzesh|first4=Eskandar|last4=Zand|title=Reliable target prediction of bioactive molecules based on chemical similarity without employing statistical methods|journal=Frontiers in Pharmacology|date=2019|doi=10.3389/fphar.2019.00835|volume=10|pages=835|pmid=31404334|pmc=6676798}}</ref> Climbazole is a topical [[Antifungal medication|antifungal]] agent commonly used in the treatment of human fungal skin infections such as [[Seborrhoeic dermatitis|dandruff]]<ref name=pmid11534318>{{cite journal |pmid=11534318 |year=2001 |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 |volume=90 |issue=33 |pages=1346–9 |journal=Praxis}}</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=pmid11534318/> 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==
-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==
-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 ==
@@ Line 49: / Line 50: @@
 [[Category:Phenol ethers]]
-[[Category:Chloroarenes]]
+[[Category:4-Chlorophenyl compounds]]
 [[Category:Ketones]]
 [[Category:Imidazole antifungals]]