clotrimazole

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2012/09/16 16:09:34」(JST)

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Clotrimazole

Systematic (IUPAC) name
1-[(2-chlorophenyl)(diphenyl)methyl]-1H-imidazole
Clinical data
Trade names	Lotrimin AF, Mycelex
AHFS/Drugs.com	monograph
MedlinePlus	a682753
Pregnancy cat.	A (AU) C (oral) and B (topical) (US)
Legal status	P (UK)
Routes	topical
Pharmacokinetic data
Bioavailability	Poorly and erratically absorbed orally
Protein binding	90%
Metabolism	hepatic
Half-life	2 hours
Identifiers
CAS number	23593-75-1 Y
ATC code	A01AB18 D01AC01 G01AF02 QJ02AB90
PubChem	CID 2812
DrugBank	DB00257
ChemSpider	2710 Y
UNII	G07GZ97H65 Y
KEGG	D00282 Y
ChEBI	CHEBI:3764 Y
ChEMBL	CHEMBL104 Y
Chemical data
Formula	C22H17ClN2
Mol. mass	344.837 g/mol
SMILES Clc1ccccc1C(c2ccccc2)(c3ccccc3)n4ccnc4
InChI InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H Y Key:VNFPBHJOKIVQEB-UHFFFAOYSA-N Y
Y (what is this?)  (verify)

Clotrimazole (brand name Canesten or Lotrimin) is an antifungal medication commonly used in the treatment of fungal infections (of both humans and other animals) such as vaginal yeast infections, oral thrush, and ringworm. It is also used to treat athlete's foot and the Dhobi itch, a.k.a. jock itch.

Medical uses

It is commonly available as an over-the-counter substance in various dosage forms, such as a cream, and also (especially in the case of ear infection) as a combination medicine. It is also available as a troche or throat lozenge (prescription only). For ear infection, it is often applied in liquid form, as ear drops. Fungal infections can be slow to clear up, so the usual course for an antifungal agent is, in general, longer than the typical three to seven days of an antibiotic. Clotrimazole is also commonly found in conjunction with betamethasone, known as Lotriderm, to add steroid properties. Additionally, clotrimazole is used to treat the sickling of cells (related to sickle cell anemia) by blocking ion channels in the red blood cell membrane, keeping ions and water within the cell.

Mechanism of action

The primary mechanism of action of clotrimazole is against the division and growing of fungi. Clotrimazole alters the permeability of the fungal cell wall and inhibits the activity of enzymes within the cell. It specifically inhibits the biosynthesis of ergosterol and other sterols required for cell membrane production. Studies show minimal concentrations of clotrimazole cause leakage of intracellular phosphorus compounds into the ambient medium, along with the breakdown of cellular nucleic acids and an accelerated K⁺ efflux. This leads eventually to the cell's death. It does not appreciably spread through the user's body, but remains at the point of application.

Drug interactions

Potential for drug interactions with clotrimazole oral exists, as it is a potent, specific inhibitor of cytochrome P450 oxidase and may alter the metabolism of other drugs.

Side effects

Side effects include skin rash, hives, blistering, burning, itching, peeling, redness, stinging, swelling, or other sign of skin irritation.

Production

This compound (3) is produced by alkylating imidazole (1) with o-chlorotrityl chloride (2) in acetone, with triethylamine as the base.

Environmental impact

Some research suggests clotrimazole, in combination with other commonly used chemicals, has negative effects on the ocean environment, in particular on microalgae.

References

External links

Canesten (clotrimazole) antifungal cream

• Clotrimazole | MedlinePlus

UpToDate Contents

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• 1. カンジダ性外陰膣炎 candida vulvovaginitis
• 2. 口腔咽頭および食道カンジダ症の治療 treatment of oropharyngeal and esophageal candidiasis
• 3. 皮膚糸状菌（白癬）感染症 dermatophyte tinea infections
• 4. マラセチア感染症 malassezia infection
• 5. 外耳炎：治療 external otitis treatment

English Journal

• Full spectrum and selected spectrum based multivariate calibration methods for simultaneous determination of betamethasone dipropionate, clotrimazole and benzyl alcohol: Development, validation and application on commercial dosage form.

• Darwish HW1, Elzanfaly ES2, Saad AS3, Abdelaleem Ael-B4.
• Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy.Spectrochim Acta A Mol Biomol Spectrosc.2016 Dec 5;169:50-7. doi: 10.1016/j.saa.2016.06.001. Epub 2016 Jun 3.
• Five different chemometric methods were developed for the simultaneous determination of betamethasone dipropionate (BMD), clotrimazole (CT) and benzyl alcohol (BA) in their combined dosage form (Lotriderm® cream). The applied methods included three full spectrum based chemometric techniques; namely
• PMID 27327260

• Is it possible to prevent recurrent vulvovaginitis? The role of Lactobacillus plantarum I1001 (CECT7504).

• Palacios S1, Espadaler J2, Fernández-Moya JM3, Prieto C4, Salas N1.
• European journal of clinical microbiology & infectious diseases : official publication of the European Society of Clinical Microbiology.Eur J Clin Microbiol Infect Dis.2016 Oct;35(10):1701-8. doi: 10.1007/s10096-016-2715-8. Epub 2016 Jul 9.
• The purpose of this study was to prospectively evaluate the impact of the use of L. plantarum I1001 applied vaginally on Vulvovaginal Candidiasis (VVC) time-until-recurrence after treatment with single-dose vaginal clotrimazole. This was a clinical open-label, prospective study of two non-randomized
• PMID 27393491

• Activation of p38 Mitogen-Activated Protein Kinase by Clotrimazole Induces Multidrug Resistance-Associated Protein 3 Activation through a Novel Transcriptional Element.

• Sasaki T1, Inami K1, Numata Y1, Funakoshi K1, Yoshida M1, Kumagai T1, Kanno S1, Matsui S1, Toriyabe T1, Yamazoe Y1, Yoshinari K1, Nagata K2.
• The Journal of pharmacology and experimental therapeutics.J Pharmacol Exp Ther.2016 Oct;359(1):102-9. doi: 10.1124/jpet.115.231589. Epub 2016 Aug 9.
• Multidrug resistance-associated protein 3 (MRP3) is a basolaterally localized transporter in the liver and contributes to the transport of various metabolites such as conjugates of endogenous compounds and drugs from hepatocytes. MRP3 expression in the human liver is low under normal physiologic con
• PMID 27507784

Japanese Journal

• Vaginal Chitosan Tablets with Clotrimazole-Design and Evaluation of Mucoadhesive Properties Using Porcine Vaginal Mucosa, Mucin and Gelatine

• Szymanska Emilia,Winnicka Katarzyna,Amelian Aleksandra [他]
• Chemical and pharmaceutical bulletin 62(2), 160-167, 2014-02
• NAID 40019956335

• P-44 高効率アルコール発酵のためのキシロース資化性酵母Pichia stipitisの改良(セルロースエタノール,Poster Session)

• 西田 孝伸,進藤 昌,佐々木 美希子,柏谷 香織,三橋 秀一
• バイオマス科学会議発表論文集 (9), 140-141, 2014-01-08
• … Clotrimazole-tolerant mutant CTM-2 was obtained by mutation in Pichia stipitis and adaptation of P stipitis against clotrimazole and ethanol. …
• NAID 110009820205

• セバシン酸ジエチルによる接触皮膚炎の1例

• 木村 友香,中川 浩一,岸田 大,木下 理恵,加藤 敦子,大迫 順子
• 皮膚の科学 13(4), 269-272, 2014
• 69歳，女性。クロトリマゾール外用剤を塗布した後，両足に重度の湿疹を生じ受診した。患者は10年前にも，セバシン酸ジエチルを含む塩酸ネチコナゾール外用液による接触皮膚炎の既往があった。我々はクロトリマゾール外用剤 (as is) とその各々の成分について48時間閉鎖貼付試験を施行した。結果はクロトリマゾール外用剤 (as is) とセバシン酸ジエチル（5％ pet) で陽性であった。従って，自験例を …
• NAID 130004706612

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