Clotrimazole

From Wikipedia, the free encyclopedia - View original article

Clotrimazole
Systematic (IUPAC) name
1-[(2-chlorophenyl)(diphenyl)methyl]-1H-imidazole
Clinical data
Trade namesLotrimin AF, Mycelex, Fungicip
AHFS/Drugs.commonograph
MedlinePlusa682753
Pregnancy cat.A (AU) C (oral) and B (topical) (US)
Legal statusP (UK)
Routestopical
Pharmacokinetic data
BioavailabilityPoorly and erratically absorbed orally
Protein binding90%
Metabolismhepatic
Half-life2 hours
Identifiers
CAS number23593-75-1 YesY
ATC codeA01AB18 D01AC01 G01AF02 QJ02AB90
PubChemCID 2812
DrugBankDB00257
ChemSpider2710 YesY
UNIIG07GZ97H65 YesY
KEGGD00282 YesY
ChEBICHEBI:3764 YesY
ChEMBLCHEMBL104 YesY
Chemical data
FormulaC22H17ClN2 
Mol. mass344.837 g/mol
 YesY (what is this?)  (verify)
 
Jump to: navigation, search
Clotrimazole
Systematic (IUPAC) name
1-[(2-chlorophenyl)(diphenyl)methyl]-1H-imidazole
Clinical data
Trade namesLotrimin AF, Mycelex, Fungicip
AHFS/Drugs.commonograph
MedlinePlusa682753
Pregnancy cat.A (AU) C (oral) and B (topical) (US)
Legal statusP (UK)
Routestopical
Pharmacokinetic data
BioavailabilityPoorly and erratically absorbed orally
Protein binding90%
Metabolismhepatic
Half-life2 hours
Identifiers
CAS number23593-75-1 YesY
ATC codeA01AB18 D01AC01 G01AF02 QJ02AB90
PubChemCID 2812
DrugBankDB00257
ChemSpider2710 YesY
UNIIG07GZ97H65 YesY
KEGGD00282 YesY
ChEBICHEBI:3764 YesY
ChEMBLCHEMBL104 YesY
Chemical data
FormulaC22H17ClN2 
Mol. mass344.837 g/mol
 YesY (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 jock itch.

Medical uses[edit]

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 compared to bacterial infections, 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 used in conjunction with betamethasone. Additionally, clotrimazole is used to treat the sickling of cells (related to sickle cell anemia) by blocking ion channels or clocip B channels in the red blood cell membrane, keeping ions and water within the cell.[1][2]

Mechanism of action[edit]

The primary mechanism of action of clotrimazole is against the division and growing of fungi.[3] 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.[3] 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.[4]

Drug interactions[edit]

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[edit]

Side effects include skin rash, hives, blistering, burning, itching, peeling, redness, stinging, swelling, or other signs of skin irritation.[5]

Production[edit]

This compound (3) is produced by alkylating imidazole (1) with o-chlorotrityl chloride (2) in acetone, with triethylamine as the base.[6]

Clotrimazole synthesis.svg

Environmental impact[edit]

Some research suggests clotrimazole, in combination with other commonly used chemicals, has negative effects on the ocean environment, in particular on microalgae.[7]

References[edit]

  1. ^ Marieb & Hoehn, (2010). Human Anatomy and Physiology, p. 643. Toronto: Pearson
  2. ^ http://www.rxmed.com/b.main/b2.pharmaceutical/b2.1.monographs/CPS-%20Monographs/CPS-%20%28General%20Monographs-%20L%29/LOTRIDERM.html
  3. ^ a b "Clotrimazole Official FDA information, side effects, and uses". FDA. Retrieved 28 December 2011. 
  4. ^ "Clotrimazole". Fungal Guide .ca. Vancouver , B.C. Canada. Retrieved 15 February 2011. 
  5. ^ Canesten Topical consumer information from Drugs.com
  6. ^ OSPAR Commission: Hazardous Substances Series: OSPAR background document on clotrimazole. possable interaction with some hiv meds. OSPAR Publication 2005/199, 2005, ISBN 1-904426-38-7 (pdf, engl.)
  7. ^ Krister Svahn (2009-03-24). (Press release). University of Gothenburg title = Drug used to treat skin conditions is a marine pollutant http://www.eurekalert.org/pub_releases/2009-03/uog-dut032409.php title = Drug used to treat skin conditions is a marine pollutant.  Missing or empty |title= (help)

External links[edit]

Canesten (clotrimazole) antifungal cream