WordNet

use recreational drugs (同)do drugs
administer a drug to; "They drugged the kidnapped tourist" (同)dose
a substance that is used as a medicine or narcotic
any agent that destroys or prevents the growth of fungi (同)antifungal_agent, fungicide, antimycotic, antimycotic_agent

PrepTutorEJDIC

『薬』,薬品,薬剤 / 『麻薬』,麻酔剤 / 〈人〉‘に'薬(特に麻酔剤)を与える / 〈飲食物〉‘に'(麻酔薬・毒薬などの)薬を混ぜる

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2013/06/12 06:01:52」(JST)

wiki en

An antifungal medication is a pharmaceutical fungicide used to treat mycoses 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.

1 Adverse effects
2 Classes
- 2.1 Polyene antifungals
- 2.2 Imidazole, triazole, and thiazole antifungals
  - 2.2.1 Imidazoles
  - 2.2.2 Triazoles
  - 2.2.3 Thiazoles
- 2.3 Allylamines
- 2.4 Echinocandins
- 2.5 Others
- 2.6 Alternatives
3 Mechanism of action
4 Antidandruff shampoos
5 See also
6 References
7 External links

Adverse effects[edit]

Apart from side effects like liver damage or affecting estrogen levels, many antifungal medicines can cause allergic reactions in people. For example, the azole group of drugs is known to have caused anaphylaxis.

There are also many drug interactions. Patients must read in detail the enclosed data sheet(s) of the medicine. For example, the azole antifungals such as ketoconazole or itraconazole can be both substrates and inhibitors of the P-glycoprotein, which (among other functions) excretes toxins and drugs into the intestines.^[1] Azole antifungals also are both substrates and inhibitors of the cytochrome P450 family CYP3A4,^[1] causing increased concentration when administering, for example, calcium channel blockers, immunosuppressants, chemotherapeutic drugs, benzodiazepines, tricyclic antidepressants, macrolides and SSRIs.

Classes[edit]

Polyene antifungals[edit]

Main article: Polyene antimycotic

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. (In ordinary circumstances membrane sterols increase the packing of the phospholipid bilayer making the plasma membrane more dense.) As a result, the cell's contents including monovalent ions (K+, Na+, H+, and Cl-), small organic molecules leak and this is regarded one of the primary ways cell dies.^[2] Animal cells contain cholesterol instead of ergosterol and so they are much less susceptible. However, at therapeutic doses, some amphotericin B may bind to animal membrane cholesterol, increasing the risk of human toxicity. Amphotericin B is nephrotoxic when given intravenously. As a polyene's hydrophobic chain is shortened, its sterol binding activity is increased. Therefore, further reduction of the hydrophobic chain may result in it binding to cholesterol, making it toxic to animals.

Amphotericin B
Candicidin
Filipin – 35 carbons, binds to cholesterol (toxic)
Hamycin
Natamycin – 33 carbons, binds well to ergosterol
Nystatin
Rimocidin

Imidazole, triazole, and thiazole antifungals[edit]

Azole antifungal drugs inhibit the enzyme lanosterol 14 α-demethylase; the enzyme necessary to convert lanosterol to ergosterol. Depletion of ergosterol in fungal membrane disrupts the structure and many functions of fungal membrane leading to inhibition of fungal growth.^[3]

Imidazoles[edit]

Canesten (clotrimazole) antifungal cream

Bifonazole
Butoconazole
Clotrimazole
Econazole
Fenticonazole
Isoconazole
Ketoconazole
Miconazole
Omoconazole
Oxiconazole
Sertaconazole
Sulconazole
Tioconazole

Triazoles[edit]

Albaconazole
Fluconazole
Isavuconazole
Itraconazole
Posaconazole
Ravuconazole
Terconazole
Voriconazole

Thiazoles[edit]

Abafungin

Allylamines[edit]

Allylamines inhibit squalene epoxidase, another enzyme required for ergosterol synthesis:

Amorolfin
Butenafine
Naftifine
Terbinafine

Echinocandins[edit]

Echinocandins may be used for systemic fungal infections in immunocompromised patients, they inhibit the synthesis of glucan in the cell wall via the enzyme 1,3-β glucan synthase:

Anidulafungin
Caspofungin
Micafungin

Echinocandins are poorly absorbed when administered orally. When administered by injection they will reach most tissues and organs with concentrations sufficient to treat localized and systemic fungal infections.^[4]

Others[edit]

Benzoic acid – has antifugal properties, but must be combined with a keratolytic agent such as in Whitfield's ointment^[5]
Ciclopirox – (ciclopirox olamine) – is a hydroxypyridone antifungal which interferes with active membrane transport, cell membrane integrity, and fungal respiratory processes. It is most useful against tinea versicolour. ^[6]
Flucytosine or 5-fluorocytosine – an antimetabolite pyrimidine analog
Griseofulvin – binds to polymerized microtubules and inhibits fungal mitosis
Haloprogin – discontinued due to the emergence of more modern antifungals with fewer side effects ^[7]
Polygodial ^[8]^[9] – strong and fast-acting in-vitroantifungal activity against Candida albicans.
Tolnaftate – a thiocarbamate antifungal, which inhibits fungal squalene epoxidase (similar mechanism to allylamines like terbinafine)
Undecylenic acid – an unsaturated fatty acid derived from natural castor oil; fungistatic, antibacterial, antiviral, and inhibits Candida morphogenesis^{[citation needed]}
Crystal violet – a triarylmethane dye, it has antibacterial, antifungal, and anthelmintic properties and was formerly important as a topical antiseptic.^[10]

Alternatives[edit]

Research conducted in 1996 indicated the following substances or essential oils had antifungal properties:^[11]

Oregano – the most powerful anti-fungal of the essential oils, and possess significant activity against Candida Albicans. The minimum inhibitory concentration against C. albicans has been found to be <0.1ug per ml. In contrast, caprylic acid (a mixture of calcium and magnesium salts, a natural anti-fungal fatty acid), is 0.5ug.
Allicin – created from crushing garlic
Citronella oil – obtained from the leaves and stems of different species of Cymbopogon (lemon grass)
Coconut oil – medium-chain triglycerides in the oil have antifungal activities
Iodine – Lugol's iodine
Lemon myrtle
Neem seed oil
Olive leaf
Orange oil
Palmarosa oil
Patchouli
Selenium – in dietary supplements or natural food sources, particularly Brazil nuts
Tea tree oil – ISO 4730 ("oil of melaleuca, terpinen-4-ol type")
Zinc – in dietary supplements or natural food sources, including pumpkin seeds and chickpeas
Horopito (Pseudowintera colorata) leaf contains the antifungal compound polygodial.^[8]
Turnip
Chives
Radish

Researchers at Tel Aviv University's Department of Plant Sciences published a study in 2009 indicating carnivorous plants, such as the Venus flytrap, contain compounds that may be useful in providing a new class of antifungal drugs for use in humans, for fungal infections that are resistant to current drugs.^[12]^[13]^[14]

Mechanism of action[edit]

Antifungals work by exploiting differences between mammalian and fungal cells to kill the fungal organism with fewer adverse effects to the host. Unlike bacteria, both fungi and humans are eukaryotes. Thus, fungal and human cells are similar at the biological level. This makes it more difficult to discover drugs that target fungi without affecting human cells. As a consequence, many antifungal drugs cause side effects. Some of these side effects can be life-threatening if the drugs are not used properly.

Antidandruff shampoos[edit]

Nizoral (ketoconazole) 2% shampoo

Antifungal agents (such as ketoconazole) are often found in antidandruff shampoos. The antifungal drugs inhibit the yeast Malassezia globosa which encourages seborrhoeic dermatitis and tinea versicolor.

Agent	Trade names	Medical applications
Ketoconazole^[15]	Nizoral, Fungoral and Sebizole	Preliminary findings, research and studies including the completion of a small controlled clinical trial have produced data suggesting ketoconazole shampoo is effective as a hair loss treatment in men with androgenic alopecia. Larger controlled clinical studies are still needed to evaluate the ideal dosage, formulation, and to determine the routine of treatment for this condition, thus ketoconazole shampoo is not FDA-approved for this indication.^[16]
Ciclopirox olamine	Loprox	The cream and lotion form of this agent is used to treat fungal infections of the skin. The lacquer form is used as part of a treatment plan to treat fungal infections of the nails. The shampoo form is used to treat and prevent dandruff or to treat seborrhoeic dermatitis.
Piroctone olamine	Octopirox^[17] and Nivea Complete Control^[18]	Piroctone olamine is sometimes used as an antifungal agent, and it often used in dandruff shampoos in lieu of zinc. Piroctone olamine is said to be less toxic than other antidandruff agents, often bypassing some of the normal FDA warnings, but still must be used with care, and only externally.
Zinc pyrithione^[19]	Head & Shoulders, Johnson and Johnson ZP-11, Clinic All Clear, Pantene Pro V and Sikkai Powder	An antifungal and antibacterial agent first reported in the 1930s, zinc pyrithione is best known for its use in the treatment of dandruff and seborrhoeic dermatitis. It also has antibacterial properties and is effective against many pathogens from the Streptococcus and Staphylococcus genera. Its other medical applications include treatments of psoriasis, eczema, ringworm, fungus, athletes foot, dry skin, atopic dermatitis, tinea, and vitiligo.
Selenium sulfide	Selsun Blue, Head & Shoulders and Vichy Dercos Anti-Dandruff Shampoo	Selenium sulfide is available as a 1% and 2.5% lotion and shampoo. In some countries, the higher-strength preparations require a doctor's prescription. The shampoo is used to treat dandruff and seborrhea of the scalp, and the lotion is used to treat tinea versicolor, a fungal infection of the skin.
Tar^[20]	Neutrogena T-Gel	Is effective as a therapeutic treatment to control scalp itching and flaking symptomatic of scalp psoriasis, eczema, seborrhoeic dermatitis and dandruff.
Tea tree oil^[21]	Dr. Bronner's Castile Soap	It is used topically as an ingredient in creams, ointments, lotions, soaps, and shampoos. In addition to antifungal properties, tea tree oil has antiseptic, antibacterial, and antiviral actions. It is also effective against mites (such as scabies), and lice (such as head lice).

References[edit]

^ ^a ^b doctorfungus > Antifungal Drug Interactions Content Director: Russell E. Lewis, Pharm.D. Retrieved on Jan 23, 2010
^ [Baginski M, Czub B. Amphotericin B and its new derivatives. Current Drug Metabolism. 2009 Jun;10(5) : 459-69]
^ > Sheehan D., Hitchcock C, Sibley C. Current and Emerging Azole Antifungal Agents
^ Echinocandins for the treatment of systemic fungal infection | Canadian Antimicrobial Resistance Alliance (CARA)
^ Wilson, Gisvold, Block, Beale (2004). Wilson and Gisvold's Textbook of Organic Medicinal and Pharmaceutical Chemistry. Philadelphia, Pa.: Lippincott Williams & Wilkins. ISBN 0-7817-3481-9.
^ "antifung". Archived from the original on 17 June 2008. Retrieved 2008-07-09.
^ accessdate = 2007-02-17 "Haloprogin". DrugBank. University of Alberta. November 6, 2006.
^ ^a ^b McCallion R F, Cole A L J, Walker J R L, Blunt J W, Monro M H G. (1982) Antibiotic Substances from New Zealand Plants, Planta Medica, vol 44, pp134-138
^ Lee S H, Lee J R, Lunde C S, Kubo I. (1999). In Vitro Antifungal Susceptibilities of Candida albicans and other Fungal Pathogens to Polygodial, a Sesquiterpene Dialdehyde, Planta Medica, vol 65, pp205-208
^ Docampo, R.; Moreno, S.N. (1990), "The metabolism and mode of action of gentian violet", Drug Metab. Rev. 22 (2–3): 161–178, doi:10.3109/03602539009041083, PMID 2272286
^ Pattnaik S, Subramanyam VR, Kole C (1996). "Antibacterial and antifungal activity of ten essential oils in vitro". Microbios 86 (349): 237–46. PMID 8893526.
^ Eilenberg, Haviva; Smadar Pnini-Cohen, Yocheved Rahamim, Edward Sionov, Esther Segal, Shmuel Carmeli and Aviah Zilberstein (December 2009). "Induced production of antifungal naphthoquinones in the pitchers of the carnivorous plant Nepenthes khasiana". Journal of Experimental Botany (Oxford University Press) 61 (3): 911–922. doi:10.1093/jxb/erp359. PMC 2814117. PMID 20018905. Archived from the original on 12 April 2010. Retrieved 2010-04-22.
^ "Carnivorous plants may save people". Israel 21c Innovation News Service. April 11, 2010. Archived from the original on 27 April 2010. Retrieved 2010-04-13.
^ "From carnivorous plants to the medicine cabinet". physorg.com. February 18, 2010. Retrieved 2010-04-13.
^ McGrath J, Murphy GM (1991). "The control of seborrhoeic dermatitis and dandruff by antipityrosporal drugs". Drugs 41 (2): 178–84. doi:10.2165/00003495-199141020-00003. PMID 1709848.
^ Ketoconazole Shampoo: Effect of Long-Term Use in Androgenic Alopecia
^ 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.
^ NIVEA
^ 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[edit]

Antifungal Drugs – Detailed information on antifungals from the Fungal Guide written by Drs. R. Thomas and K. Barber

UpToDate Contents

全文を閲覧するには購読必要です。 To read the full text you will need to subscribe.

1. 成人におけるカンジダ菌血症および侵襲性カンジダ症 treatment of candidemia and invasive candidiasis in adults
2. アゾールの薬理学 pharmacology of azoles
3. 皮膚糸状菌（白癬）感染症 dermatophyte tinea infections
4. 抗真菌剤感受性試験 antifungal susceptibility testing
5. クリプトコッカス髄膜脳炎を伴うHIV感染患者の抗真菌治療中の臨床的マネージメントおよびモニタリング clinical management and monitoring during antifungal therapy of the hiv infected patient with cryptococcal meningoencephalitis

English Journal

Impacts of chemical enhancers on skin permeation and deposition of terbinafine.

Erdal MS, Peköz AY, Aksu B, Araman A.Author information Department of Pharmaceutical Technology, Faculty of Pharmacy, Istanbul University, 34116 Beyazıt , Istanbul , Turkey and.AbstractAbstract Context/Objective: The addition of chemical enhancers into formulations is the most commonly employed approach to overcome the skin barrier. The objective of this work was to evaluate the effect of vehicle and chemical enhancers on the skin permeation and accumulation of terbinafine, an allylamine antifungal drug. Methods: Terbinafine (1% w/w) was formulated as a Carbopol 934 P gel formulation in presence and absence of three chemical enhancers, nerolidol, dl-limonene and urea. Terbinafine distribution and deposition in stratum corneum (SC) and skin following 8-h ex vivo permeation study was determined using a sequential tape stripping procedure. The conformational order of SC lipids was investigated by ATR-FTIR spectroscopy. Results and discussion: Nerolidol containing gel formulation produced significantly higher enhancement in terbinafine permeation through skin and its skin accumulation was increased. ATR-FTIR results showed enhancer induced lipid bilayer disruption in SC. Urea resulted in enhanced permeation of terbinafine across the skin and a balanced distribution to the SC was achieved. But, dl-limonene could not minimize the accumulation of terbinafine in the upper SC. Conclusion: Nerolidol dramatically improved the skin permeation and deposition of terbinafine in the skin that might help to optimize targeting of the drug to the epidermal sites as required for both of superficial and deep cutaneous fungal infections.
Pharmaceutical development and technology.Pharm Dev Technol.2014 Aug;19(5):565-70. doi: 10.3109/10837450.2013.813538. Epub 2013 Jul 10.
Abstract Context/Objective: The addition of chemical enhancers into formulations is the most commonly employed approach to overcome the skin barrier. The objective of this work was to evaluate the effect of vehicle and chemical enhancers on the skin permeation and accumulation of terbinafine, an all
PMID 23841559

Polymeric microparticles-based formulation for the eradication of cutaneous candidiasis: development and characterization.

Kumar L, Verma S, Jamwal S, Vaidya S, Vaidya B.Author information Department of Pharmaceutics .AbstractAbstract Cutaneous candidiasis is a common topical fungal infection which may be more prominent in patients associated with AIDS. It is usually treated by conventional formulations such as cream, gel, which show various adverse effects on skin along with systemic absorption. To overcome these drawbacks, various novel drug delivery systems have been explored. Poly(lactic-co-glycolic acid) (PLGA)-based microparticulate systems have shown good dermal penetration after topical application. Therefore, in the present study clotrimazole-loaded PLGA microspheres were prepared for targeted dermal delivery. Microspheres were prepared by using a single emulsification (oil-in-water, O/W) evaporation technique and characterized for different parameters. Prepared microparticulate systems were dispersed in Carbopol 934® gel and antifungal activity was carried out on experimentally induced cutaneous candidiasis in immunosuppressed guinea pigs. Particle size of optimized formulation was 2.9 µm along with 74.85% entrapment of drug. Skin retention studies revealed that drug accumulation in the skin was higher with microspheres gel as compared to marketed gel. Confocal microscopy of skin further confirmed penetration of microspheres up to 50 µm into the dermal region. In-vivo antifungal activity studies demonstrated that microsphere gel showed better therapeutic activity, lowest number of cfu/ml was recorded, as compared to marketed gel after 96 h of application. Based on the results of the study, it can be concluded that PLGA microparticles may be promising carriers to deliver clotrimazole intradermally for the treatment of invasive fungal infections.
Pharmaceutical development and technology.Pharm Dev Technol.2014 May;19(3):318-25. doi: 10.3109/10837450.2013.778874. Epub 2013 Apr 8.
Abstract Cutaneous candidiasis is a common topical fungal infection which may be more prominent in patients associated with AIDS. It is usually treated by conventional formulations such as cream, gel, which show various adverse effects on skin along with systemic absorption. To overcome these drawba
PMID 23560821

Centauries as underestimated food additives: antioxidant and antimicrobial potential.

Siler B, Zivković S, Banjanac T, Cvetković J, Nestorović Živković J, Cirić A, Soković M, Mišić D.Author information Institute for Biological Research "Siniša Stanković", University of Belgrade, Bulevar despota Stefana 142, 11060 Belgrade, Serbia.AbstractMethanol extracts of aerial parts and roots of five centaury species (Centaurium erythraea, C. tenuiflorum, C. littorale ssp. uliginosum, C. pulchellum, and Schenkia spicata) were analysed for their main secondary metabolites: secoiridoid glycosides, a group of monoterpenoid compounds, and phenolics (xanthones and flavonoids), and further investigated for antioxidant capacity and antimicrobial activity. The results of ABTS, DPPH, and FRAP assays showed that above ground parts generally displayed up to 13 times higher antioxidant activity compared to roots, which should be related to higher phenolics content, especially flavonoids, in green plant organs. Secoiridoid glycosides showed no antioxidant activity. All the tested extracts demonstrated appreciative antibacterial (0.05-0.5 mg ml(-1)) and strong antifungal activity (0.1-0.6 mg ml(-1)). Our results imply that above ground parts of all centaury species studied, could be recommended for human usage as a rich source of natural antioxidants and also in food industry as strong antimicrobial agents for food preservation.
Food chemistry.Food Chem.2014 Mar 15;147:367-76. doi: 10.1016/j.foodchem.2013.10.007. Epub 2013 Oct 11.
Methanol extracts of aerial parts and roots of five centaury species (Centaurium erythraea, C. tenuiflorum, C. littorale ssp. uliginosum, C. pulchellum, and Schenkia spicata) were analysed for their main secondary metabolites: secoiridoid glycosides, a group of monoterpenoid compounds, and phenolics
PMID 24206732

Japanese Journal

アレルギー性気管支肺アスペルギルス症 (特集高IgE血症を伴う難治疾患 : 基礎と臨床)

山崎章
臨床免疫・アレルギー科 63(3), 232-238, 2015-03
NAID 40020393264

ドラッグデリバリーシステム(4)放出制御製剤

岡田弘晃
日本防菌防黴学会誌 = Journal of Antibacterial and Antifungal
NAID 40020386440

ドラッグデリバリーシステム(3)抗がん剤内包ミセルの基礎から臨床

松村保広
日本防菌防黴学会誌 = Journal of Antibacterial and Antifungal
NAID 40020353311

Related Pictures

Antifungal - Wikipedia antimycotic Images, Stock Photos & Vectors | Shutterstock Ringworm Stock Vectors, Images & Vector Art | Shutterstock floccosum Images, Stock Photos & Vectors | Shutterstock

★リンクテーブル★

リンク元	「抗真菌薬」「antimycotic」「antimycotics」「antimycotic agent」「抗真菌剤」
関連記事	「antifungal」「antifungals」「drug」

「抗真菌薬」

　　[★]

英: antifungal drug, antifungal, antimycotic
関: 真菌、真菌症、抗真菌薬一覧

作用機序

作用部位	薬物	作用機序	スペクトル
細胞膜	キャンディン系抗真菌薬	1,3-β-D-グルカン合成阻害	カンジダとアスペルギウス。ムコール、クリプトコッカスには無効
細胞膜	アムホテリシンB	エルゴステロールに結合し細胞膜破壊、殺菌的	広スペクトル
細胞膜	アゾール系抗真菌薬	エルゴステロール合成阻害	カンジダとアスペルギウス
核	フルシトシン	核酸合成阻害	カンジダのみ