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20-September-2008 09:55:47 - Antifungal drug An antifungal drug is medication used to treat fungal infections such as athlete's foot, ringworm, candidiasis thrush, serious systemic infections such as cryptococcal meningitis, and others. Such drugs are usually obtained by a doctor's prescription or purchased over-the-counter. Contents 1 List of antifungal drugs 1.1 Polyene antifungals 1.2 Imidazole and Triazole antifungals 1.2.1 Imidazoles: 1.2.2 Triazoles: 1.3 Allylamines 1.4 Echinocandins 1.5 Others 1.6 Alternatives4 2 Anti-Dandruff shampoos 3 See also 4 References 5 External links List of antifungal drugs Antifungals work by exploiting differences between mammalian and fungal cells to kill off the fungal organism without dangerous effects on the host. Unlike bacteria, both fungi and humans are eukaryotes. Thus fungal and human cells are similar at the molecular level. This means it is more difficult to find a weakness in fungi to attack that does not also exist in human cells - so, if you attack the fungus, you may also attack the human cells the fungus lives on. Consequently, there are often side-effects to some of these drugs. Some of these side-effects can be life-threatening if not used properly. There are several classes of antifungal drugs. Polyene antifungals A polyene is a molecule with multiple conjugated double bonds. A polyene antifungal is a macrocyclic polyene with a heavily hydroxylated region on the ring opposite the conjugated system. This makes polyene antifungals amphiphilic. The polyene antimycotics bind with sterols in the fungal cell membrane, principally ergosterol. This changes the transition temperature Tg of the cell membrane, thereby placing the membrane in a less fluid, more crystalline state. As a result, the cell's contents leak out usually the hydrophilic contents and the cell dies. Animal cells contain cholesterol instead of ergosterol and so they are much less susceptible. Note: as a polyene's hydrophobic chain is shortened, its sterol binding activity is increased. Therefore, increased reduction of the hydrophobic chain may result in it binding to cholesterol, making it toxic to animals. Natamycin -- 33 Carbons, binds well to ergosterol. Rimocidin Filipin -- 35 Carbons, binds to cholesterol toxic. Nystatin Amphotericin B Candicin Imidazole and Triazole antifungals The imidazole and triazole are synthetic antifungal drugs inhibit the enzyme cytochrome P450 14α-demethylase. This enzyme converts lanosterol to ergosterol, and is required in fungal cell membrane synthesis. These drugs also block steroid synthesis in humans. Imidazoles: Miconazole - Miconazole nitrate. Ketoconazole Clotrimazole - marketed as Lotrimin or Lotrimin AF and Canesten in the UK. Econazole Bifonazole Butoconazole Fenticonazole Isoconazole Oxiconazole Sertaconazole - marketed as Ertaczo in North America. Sulconazole Tioconazole The triazoles are newer, and are less toxiccitation needed and more effectivecitation needed: Triazoles: Fluconazole Itraconazole Isavuconazole Ravuconazole Posaconazole Voriconazole Terconazole Allylamines Allylamines inhibit the enzyme squalene epoxidase, another enzyme required for ergosterol synthesis: Terbinafine - marketed as Lamisil in North America, Australia, the UK and Germany. Amorolfine Naftifine - marketed as Naftin in North America. Butenafine - marketed as Lotrimin Ultra. Echinocandins Echinocandins inhibit the synthesis of glucan in the cell wall, probably via the enzyme 1,3-β glucan synthase: Anidulafungin Caspofungin Micafungin Others Benzoic acid - has antifugal properties but must be combined with a keratolytic agent such as in Whitfield's Ointment1 Ciclopirox - ciclopirox olamine a fungicidal, It is most useful against Tinea versicolour 2. Tolnaftate - fungicidal, marketed as Tinactin, Desenex, Aftate, as well as other names. Undecylenic acid - organic unsaturated fatty acid derived from natural castor oil, fungistatic as well as anti-bacterial and anti-viral. Flucytosine, or 5-fluorocytosine, is an antimetabolite. Griseofulvin - binds to polymerized microtubules and inhibits fungal mitosis. Haloprogin - discontinued due to the emergence of more modern antifungals with fewer side effects 3. Alternatives4 Tea tree oil -- ISO 4730 Oil of Melaleuca, Terpinen-4-ol type. Citronella oil lemon grass orange oil palmarosa oil patchouli lemon myrtle Neem Seed Oil Coconut Oil -- medium chain triglycerides in the oil have antifungal activities. Zinc - zinc dietary supplements or natural food sources, including pumpkin seeds and chick peas. Selenium - selenium dietary supplements or natural food sources, particularly Brazil nuts. Anti-Dandruff shampoos Antifungal drugs are often found in Anti-dandruff shampoos, the antifungal drugs inhibit the yeast, Malassezia furfur formerly known as Pityrosporum ovale which encourage seborrhoeic dermatitis and Tinea versicolor. Active ingredient Example of product Comments Sodium bicarbonatecitation needed baking soda Ketoconazole5 Nizoral, or Fungoral There is a claim that Nizoral shampoo has hair loss benefits but Nizoral Shampoo does not have FDA approval as a hair loss remedy6 . Ciclopirox olamine Loprox Show similar efficacy to ketoconazole with a relative increase in subjective symptom relief due to its inherent anti-inflammatory properties7. Piroctone olamine Octopirox8 Nivea Complete Control9 a replacement for the commonly used compound zinc pyrithione Zinc pyrithione10 Head Shoulders, Johnson and Johnson ZP-11, Clinic All Clear, Pantene Pro V, Sikkai Powder An antifungal and antibacterial agent, was first reported in the 1930s. Selenium sulfide Selsun Blue, Vichy Dercos Anti-Dandruff shampoo, other varieties of Head Shoulders In USA, 1% strength is available over-the-counter, and a 2.5% strength is also available with a prescription Tar11 Neutrogena T/Gel Tea tree oil12 See also Fungicide Antimicrobial References ^ Wilson, Gisvold, Block, Beale. Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry. ISBN 0781734819. http://books.google.com/books?id=CIpWhgWV5q0Cpg=RA1-PA234lpg=RA1-PA234dq=%22benzoic+acid%22+antifungal+tineasource=webots=nK8OrzL8p3sig=AIzhJBiDYl1-sffvCRmynMan06Q ^ antifung. Retrieved on 2008-07-09. ^ Haloprogin. DrugBank. University of Alberta Nov 06, 2006. Retrieved on 2007-02-17. ^ Pattnaik S, Subramanyam VR, Kole C 1996. Antibacterial and antifungal activity of ten essential oils in vitro. Microbios 86 349: 237-46. PMID 8893526. ^ McGrath J, Murphy GM 1991. The control of seborrhoeic dermatitis and dandruff by antipityrosporal drugs. Drugs 41 2: 178-84. PMID 1709848. ^ Nizoral Shampoo as a Hair Loss Remedy? http://www.dermadoctor.com/pages/newsletter198.asp ^ Ratnavel RC, Squire RA, Boorman GC 2007. Clinical efficacies of shampoos containing ciclopirox olamine 1.5% and ketoconazole 2.0% in the treatment of seborrhoeic dermatitis. J Dermatolog Treat 18 2: 88-96. doi:10.1080/16537150601092944. PMID 17520465. ^ Dubini F, Bellotti MG, Frangi A, Monti D, Saccomani L 2005. In vitro antimycotic activity and nail permeation models of a piroctone olamine octopirox containing transungual water soluble technology. Arzneimittel-Forschung 55 8: 478-83. PMID 16149717. ^ http://products2.nivea.com/products.php?page_id=1298lan=com ^ Warner RR, Schwartz JR, Boissy Y, Dawson TL 2001. Dandruff has an altered stratum corneum ultrastructure that is improved with zinc pyrithione shampoo. J. Am. Acad. Dermatol. 45 6: 897-903. doi:10.1067/mjd.2001.117849. PMID 11712036. ^ Piérard-Franchimont C, Piérard GE, Vroome V, Lin GC, Appa Y 2000. Comparative anti-dandruff efficacy between a tar and a non-tar shampoo. Dermatology Basel 200 2: 181-4. doi:10.1159/000018362. PMID 10773717. ^ Prensner R 2003. Does 5% tea tree oil shampoo reduce dandruff?. The Journal of family practice 52 4: 285-6. PMID 12681088. External links Antifungal Drugs - Detailed information on antifungals from the Fungal Guide written by Drs. R. Thomas and K. Barber v d e Antifungals D01 and J02 Ergosterol inhibitors Azoles CYP51A1 inhibitors topical: imidazoles Bifonazole, Clomidazole, Clotrimazole, Croconazole, Econazole, Fenticonazole, Ketoconazole, Isoconazole, Miconazole, Neticonazole, Oxiconazole, Sertaconazole, Sulconazole, Tioconazole triazoles Fluconazole, Fosfluconazole benzimidazole Thiabendazole systemic: triazoles Itraconazole, Posaconazole, Voriconazole Polyene antimycotics ergosterol binding topical: Natamycin, Nystatin systemic: Amphotericin B Allylamines squalene monooxygenase inhibitors topical: Amorolfine, Butenafine, Naftifine, Terbinafine systemic: Terbinafine 1,3-beta-glucan synthase inhibitors echinocandins Anidulafungin, Caspofungin, Micafungin Intracellular Pyrimidine analogues/ Thymidylate synthase inhibitors Flucytosine Mitotic inhibitors Griseofulvin Others Ciclopirox Ethylparaben Salicylic acid Selenium sulfide Tolnaftate Undecylenic acid Tea tree oil citronella oil lemon grass orange oil patchouli lemon myrtle Whitfield's ointment v d e Major drug groups Gastrointestinal tract/metabolism A stomach acid Antacids, H2 antagonists, Proton pump inhibitors Antiemetics Laxatives Antidiarrhoeals/Antipropulsives Anti-obesity drugs Anti-diabetics Vitamins Dietary minerals Blood and blood forming organs B Antithrombotics Anticoagulants, Antiplatelets, Thrombolytics Antihemorrhagics Cardiovascular system C cardiac therapy/antianginals Cardiac glycosides, Antiarrhythmics, Cardiac stimulant Antihypertensives Diuretics Vasodilators Beta blockers renin-angiotensin system ACE inhibitors, Angiotensin II receptor antagonists, Renin inhibitors Antihyperlipidemics Skin D Emollients Cicatrizant Antipruritics Reproductive system G Hormonal contraception Fertility agents SERMs Sex hormones Endocrine system H Corticosteroids Sex hormones Thyroid hormones Antithyroid agent Infections and infestations J, P Antibiotics Antivirals Vaccines Antifungals Antiparasitic Antiprotozoals, Anthelmintics Malignant and immune disease L Anticancer agents Immunostimulators Immunosuppressants Muscles, bones, and joints M Anabolic steroids Anti-inflammatories NSAID Antirheumatics Corticosteroids Muscle relaxants Brain and nervous system N Anesthetics General, Local Analgesics Anticonvulsants Mood stabilizers Psycholeptic Anxiolytics, Antipsychotics, Hypnotics/Sedatives Psychoanaleptic Antidepressants, Stimulants/Psychostimulants Respiratory system R Bronchodilators Decongestants H1 antagonists Other ATC V Antidotes Contrast media Radiopharmaceuticals Dressing Retrieved from http://en..org/wiki/Antifungal_drug Categories: AntifungalsHidden categories: All articles with statements | Articles with statements since September 2007 | Articles with statements since July 2008 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Català Deutsch Français Nederlands 日本語 This page was last modified on 15 August 2008, at 20:37
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