塩酸テルビナフィン、テルビナフィン塩酸塩

関: terbinafine

WordNet

an oral antifungal drug (trade name Lamisil) used to treat cases of fungal nail disease (同)Lamisil
a complex consisting of an organic base in association with hydrogen chloride

Wikipedia preview

出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/02/21 21:32:38」(JST)

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Terbinafine hydrochloride, also known under the trade name Lamisil,^[1] is a antifungal developed by Novartis. It is highly hydrophobic and tends to accumulate in hair, skin, nails, and fatty tissue.

It is on the WHO Model List of Essential Medicines, the most important medications needed in a basic health system.^[2]

Medical uses

Terbinafine is mainly effective on the dermatophyte group of fungi.

As a 1% cream or powder, it is used topically for superficial skin infections such as jock itch (tinea cruris), athlete's foot (tinea pedis), and other types of ringworm (tinea corporis). Terbinafine cream works in about half the time required by other antifungals.^[3]

Oral 250-mg tablets are often prescribed for the treatment of onychomycosis, a fungal nail infection, typically by a dermatophyte or Candida species. Fungal nail infections are located deep under the nail in the cuticle to which topically applied treatments are unable to penetrate in sufficient amounts. The tablets may, rarely, cause hepatotoxicity, so patients are warned of this and may be monitored with liver function tests. Alternatives to oral administration have been studied. In 2009, results from a clinical study of a new formulation (terbinafine in transfersomes, referred to as TDT-067) for topical treatment of onychomycosis were reported by Celtic Pharma.^[4]

Terbinafine hydrochloride may induce or exacerbate subacute cutaneous lupus erythematosus. Persons with lupus erythematosus should first discuss possible risks with their doctor before initiation of therapy.^[5]

FDA approval

Terbinafine first became available in Europe in 1991 and in the United States in 1996. The U.S. Food and Drug Administration has approved the first generic versions of prescription Lamisil (terbinafine hydrochloride) tablets. The remaining patent or exclusivity for Lamisil expired on June 30, 2007.

On September 28, 2007, the FDA stated that Lamisil (terbinafine hydrochloride, by Novartis AG) is a new treatment approved for use by children age four and up. The antifungal granules can be sprinkled on a child's food to treat ringworm of the scalp, tinea capitis.^[6]

Side effects

Many side effects and adverse drug reactions have been reported with oral terbinafine hydrochloride^[7]^[8]^[9] possibly due to its extensive biodistribution and the often extended durations involved in antifungal treatment (longer than two months). A comprehensive list of adverse events associated with terbinafine use includes:

Gastrointestinal problems: Diarrhea, constipation, nausea, sickness, fullness, abdominal pain, indigestion, dyspepsia, gastritis, cholestasis, flatulence, altered stool colour, abdominal muscular pain
Central nervous system or neurological problems: Headaches, dizziness, vertigo, light-headedness, decreased concentration levels, paraesthesia (pins and needles)
Hepatic problems: Raised liver enzyme levels, liver inflammation (hepatitis), liver damage, liver failure (leading to transplant — or death)
Immune system problems: Decreased white blood cell counts including pancytopenia, leukopenia, lymphopenia, thrombocytopenia, agranulocytosis, and neutropenia, autoimmune reactions such as lupus erythematosus
Psychological problems: Depression, anxiety, insomnia, increased or unusual dream activity, malaise
Sensory problems: Complete loss of taste (ageusia) (sometimes permanent after the treatment), decreased taste (hypogeusia) and distorted taste (dysgeusia) (sometimes permanent after the treatment) often involving a metallic taste sensation and dry mouth, visual disturbances including blurred vision, green vision and double vision
Skin problems: Rashes, hives (urticaria), skin irritation, itching (pruritis), jaundice, Stevens–Johnson syndrome
Other side effects: Fatigue, increased heart rate (tachycardia), hair loss (alopecia), decreased red blood cell count (anemia), muscle pain (myalgia), joint pain (arthralgia)

Pharmacology

Generic terbinafine hydrochloride pills

Terbinafine hydrochloride is a white fine crystalline powder that is freely soluble in methanol and dichloromethane, soluble in ethanol, and slightly soluble in water.

Like other allylamines, terbinafine inhibits ergosterol synthesis by inhibiting squalene epoxidase, an enzyme that is part of the fungal cell membrane synthesis pathway. Because terbinafine prevents conversion of squalene to lanosterol, ergosterol cannot be synthesized. This is thought to change cell membrane permeability, causing fungal cell lysis.

Brand names

Terbinafine is sold as Lamisil in Argentina, Australia, Belgium, Brazil, Canada, Chile, Croatia, Egypt, Czech, Denmark, Estonia, Finland, France, Germany, Greece, Hungary, Iceland, Ireland, Israel, Mexico, New Zealand, Norway, Pakistan (لیمسل), Peru, Romania, Russia, Slovakia, Slovenia, South Africa, Sweden, Thailand, the United Kingdom, the United States, and Venezuela; also it is sold under the name Corbinal and Terbisil in Turkey, and Undofen in Poland. As a generic oral medication, it is sold as Sebifin, Tinasil, Terbisil, Terbicor, and Tamsil in Australia, whilst the generic topical medication is sold there as SolvEasyTinea and Tamsil.^[10]^[11] It is also available as a generic medication in the United States, the United Kingdom, Belgium, Switzerland, Brazil and Mexico. In India, terbinafine hydrochloride is available in topical form under the brand names Sebifin (Ranbaxy Labs), Zimig (GSK Pharma), Tyza (Abbott Healthcare)^[12] and mycoCeaze (Progreś Laboratories). MycoVa, developed by Apricus Biosciences, is a topical nail solution of terbinafine and DDAIP, which has completed three phase-III studies for the treatment of onychomycosis. Other names include Terbinaforce (Mankind Pharma) and Tafine (Deurali Janta Pharmaceuticals Pvt Ltd.) Turbo (Apex Pharmaceuticals Pvt Ltd) in Nepal. The topical form is sold as LamisilAT in the United States.

References

^ Terbinafine - brand name list from Drugs.com
^ "19th WHO Model List of Essential Medicines (April 2015)" (PDF). WHO. April 2015. Retrieved May 10, 2015.
^ Markova, Tsveti (January 2002). "What is the most effective treatment for tinea pedis (athlete’s foot)?". The Journal of Family Practice (Frontline Medical Communications) 51 (1): 15–22. Retrieved 2013-11-09.
^ "Clinical Trials Update". Genetic Engineering & Biotechnology News 29 (8): 58. 2009.
^ Callen JP, Hughes AP, Kulp-Shorten C (September 2001). "Subacute cutaneous lupus erythematosus induced or exacerbated by terbinafine: a report of 5 cases". Arch Dermatol 137 (9): 1196–8. doi:10.1001/archderm.137.9.1196. PMID 11559217.
^ "US FDA approves oral granules for scalp ringworm". Reuters. 2007-09-28.
^ "Lamisil (terbinafine): Side Effects". Doublecheckmd.com. 2010-06-16. Retrieved 2013-11-09.
^ McGuire, Stephen (2008-02-05). "Australian regulators issue warning on Novartis' Lamisil". Medical Marketing and Media. Mmm-online.com. Retrieved 2013-11-09.
^ "Terbinafine-1 (Terbinafine Hydrochloride,Lamisil)". Drug Dosage and Side Effects. Healthline.com. 2009-02-27. Retrieved 2013-11-09.
^ "Terbinafine". Pharmaceutical Benefits Scheme: A-Z list. Australian Government.
^ "PI and CMI Trade Names and Active Ingredients containing Terbinafine". Therapeutic Goods Administration. Australian Government.
^ "Terbinafine brands in India". Brand index. DrugsUpdate India.

UpToDate Contents

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1. 爪真菌症 onychomycosis
2. 皮膚糸状菌（白癬）感染症 dermatophyte tinea infections
3. 癜風 tinea versicolor pityriasis versicolor
4. カンジダ性間擦疹 candidal intertrigo
5. フサリウム感染症の治療および予防 treatment and prevention of fusarium infection

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.AbstractCONTEXT/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.
Pharmaceutical development and technology.Pharm Dev Technol.2014 Aug;19(5):565-70. doi: 10.3109/10837450.2013.813538. Epub 2013 Jul 10.
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 a
PMID 23841559

In vitro susceptibility of dermatophytes isolated from patients with end-stage renal disease: a case-control study.

Irimie M, Tătaru A, Oantă A, Moga M.Author information Department of Dermatology, Transilvania University, Brasov, Romania.AbstractAlthough the therapeutic efficacy of antifungals is well known for dermatophytosis in general population, limited data exist for patients with chronic kidney disease. The objectives of this study were to determine the dermatophyte species causing infection in patients with end-stage renal disease (ESRD) and in vitro susceptibility of isolated dermatophytes to antifungals. A total of 87 patients with ESRD who undergoing haemodialysis and 105 patients with normal renal function suspected with dermatophytosis were included. Skin scrapings or nail clippings were examined by direct microscopy and cultured on Sabouraud agar. In vitro antifungal susceptibility tests were performed using a broth microdilution method. Dermatophyte infections were identified in 32.2% of haemodialysis patients and in 29.5% of controls (P > 0.05). In both groups, Trichophyton rubrum was the most frequently isolated. Mean MIC values of the all studied antifungals for all of isolated dermatophyte strains from patients with ESRD were similar to those obtained in control group (P > 0.05). Terbinafine (TBF) had the lowest mean MIC values for all tested dermatophytes in both groups. We consider that TBF should be the treatment of choice for dermatophytosis in patients with chronic kidney disease, but the dose should be adjusted according to creatinine clearance and should be monitored for side effects.
Mycoses.Mycoses.2014 Mar;57(3):129-34. doi: 10.1111/myc.12114. Epub 2013 Jul 25.
Although the therapeutic efficacy of antifungals is well known for dermatophytosis in general population, limited data exist for patients with chronic kidney disease. The objectives of this study were to determine the dermatophyte species causing infection in patients with end-stage renal disease (E
PMID 23889207

Comparison of the Antifungal Efficacy of Terbinafine Hydrochloride and Ciclopirox Olamine Containing Formulations against the Dermatophyte Trichophyton rubrum in an Infected Nail Plate Model.

Täuber A, Müller-Goymann CC.Author information Institut für Pharmazeutische Technologie, Technische Universität Braunschweig , Mendelssohnstraße 1, 38106 Braunschweig, Germany.AbstractOnychomycosis is a fungal infection mostly induced by dermatophytes such as Trichophyton rubrum. Due to slow nail growth, the treatment takes 3-9 months depending on the nail size and infected area. Hence, high efficacy of the active ingredient without systemic side effects is of major interest. To test the efficacy of an antifungal formulation, an appropriate in vitro model reflecting the in vivo situation as close as possible is required. In this study, a variety of antifungal formulations, i.e., commercial ones (Ciclopoli and Lamisil cream), those used in compounding pharmacies (Pentravan) as well as poloxamer 407-based systems, have been evaluated in an infected nail plate model. The active pharmaceutical ingredients (APIs) were ciclopirox olamine and terbinafine hydrochloride. The poloxamer 407-based formulations consisted of poloxamer 407, double distilled water, propylene glycol, isopropyl alcohol, medium chain triglycerides and either 1% ciclopirox olamine or 1% terbinafine hydrochloride as API, respectively. Former studies have shown high permeation rates of terbinafine hydrochloride from similar poloxamer 407-based formulations with dimethyl isosorbide instead of propylene glycol. The present contribution shows superior inhibition of T. rubrum growth from poloxamer 407-based formulations in comparison to the commercial Lamisil cream. Moreover, poloxamer 407-based formulations were equally effective as the nail lacquer Ciclopoli even though the poloxamer formulations contained only 1% of the drug instead of 8% in the marketed lacquer. Poloxamer 407-based systems containing ciclopirox olamine proved to be about as effective as similar terbinafine hydrochloride systems.
Molecular pharmaceutics.Mol Pharm.2014 Feb 12. [Epub ahead of print]
Onychomycosis is a fungal infection mostly induced by dermatophytes such as Trichophyton rubrum. Due to slow nail growth, the treatment takes 3-9 months depending on the nail size and infected area. Hence, high efficacy of the active ingredient without systemic side effects is of major interest. To
PMID 24490976

Japanese Journal

角質増殖性病変をともなう足白癬に対する IKD-382 クリームの使用経験

望月隆,阿部真也,田邊洋,牛上敢,小島清登,南部昌之,坂元とも子,川西絢子,八田順子,安澤数史,中村知矢,吉田直岐,小川和男
西日本皮膚科 75(5), 454-459, 2013
角質増殖性病変をともなう足白癬は外用療法に抵抗するとされ，従来外用抗真菌薬の臨床試験の対象にされることは少なかった。今回，この角質増殖性病変をともなう足白癬に対する 1.0％テルビナフィン塩酸塩と組織修復成分であるアラントイン，パンテノールを配合する IKD-382 クリームの有効性と安全性を評価した。本試験では試験期間を 8 週間に設定し，臨床症状 (皮膚症状ならびに自覚症状)，菌陰性化，安全性 …
NAID 130004475559

最近3年間に熊本の一診療所で経験された Microsporum canis 感染症25例の集計

榮仁子,野口博光,市之川悠子 [他],比留間政太郎
Medical mycology journal = / 日本医真菌学会 [編] 52(2), 139-144, 2011-04-30
最近3年間 (2008.1 - 2010.12) に熊本県の一診療所において <I>Microsporum canis</I> による白癬25例を経験した．当診療所を受診し直接鏡検で真菌要素を認め，真菌培養で <I>M. canis</I> と同定された白癬の25例を対象とした．症例は男性8例，女性17例で女性に多く，年齢は4歳から85歳，平均34. …
NAID 10029354584

バリカンより菌を分離し確定診断に至ったＴｒｉｃｈｏｐｈｙｔｏｎ　ｔｏｎｓｕｒａｎｓ感染症の１例

篠田英和,関山華子,西本勝太郎
西日本皮膚科 73(2), 166-169, 2011
14歳，男子，柔道部員。前頭，右側頭部の痒みがあり副腎皮質ホルモン外用剤で約20日間治療したが，紅斑と痒みが強くなり，白癬の診断で塩酸テルビナフィンの内服が行われた。1週間後同部の脱毛，発赤腫脹が著明となり，さらにイトラコナゾールの内服と抗真菌剤外用で追加治療するも発赤腫脹と脱毛巣の拡大を認め当院を受診した。右側頭部に発赤腫脹と膿疱を伴う径3cmの脱毛巣と脱毛巣内には数個の黒点がみられた。黒点のK …
NAID 130004831779

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リンク元	「テルビナフィン」
関連記事	「hydrochloride」

「テルビナフィン」

Terbinafine
Systematic (IUPAC) name
	[(2E)-6,6-dimethylhept-2-en-4-yn-1-yl](methyl)(naphthalen-1-ylmethyl)amine
Clinical data
Trade names	Lamisil
AHFS/Drugs.com	monograph
MedlinePlus	a699061
Pregnancy; category	B;
Legal status	Low-strength topical preparations available without prescription;
Routes of; administration	Oral and topical
Pharmacokinetic data
Bioavailability	Readily absorbed: 70–90%
Protein binding	>99%
Metabolism	Hepatic
Biological half-life	Highly variable
Identifiers
CAS Number	91161-71-6 78628-80-5
ATC code	D01AE15 D01BA02
PubChem	CID 1549008
DrugBank	DB00857
ChemSpider	1266005
UNII	G7RIW8S0XP
KEGG	D02375
ChEBI	CHEBI:9448
ChEMBL	CHEMBL822
Chemical data
Formula	C21H25N
Molar mass	291.43 g/mol
	SMILES C(#C\C=C\CN(C)Cc2cccc1ccccc12)C(C)(C)C ;
	InChI InChI=1S/C21H25N/c1-21(2,3)15-8-5-9-16-22(4)17-19-13-10-12-18-11-6-7-14-20(18)19/h5-7,9-14H,16-17H2,1-4H3/b9-5+ ; Key:DOMXUEMWDBAQBQ-WEVVVXLNSA-N ;
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英: terbinafine
化: テルビナフィン塩酸塩塩酸テルビナフィン terbinafine hydrochloride
商: ケルガー、テビーナ、テビナシール、テルビー、テルビナール、テルフィナビン、テルミシール、ネドリール、ビラス、ラミシール、ラミテクト、リプノール
関: 寄生性皮ふ疾患用剤

「hydrochloride」

　　[★] 塩酸塩、ハイドロクロライド　

[1] Terbinafine - brand name list from Drugs.com

[WHO2015E-2] "19th WHO Model List of Essential Medicines (April 2015)" (PDF). WHO. April 2015. Retrieved May 10, 2015.

[3] Markova, Tsveti (January 2002). "What is the most effective treatment for tinea pedis (athlete’s foot)?". The Journal of Family Practice (Frontline Medical Communications) 51 (1): 15–22. Retrieved 2013-11-09.

[Staff2009-4] "Clinical Trials Update". Genetic Engineering & Biotechnology News 29 (8): 58. 2009.

[5] Callen JP, Hughes AP, Kulp-Shorten C (September 2001). "Subacute cutaneous lupus erythematosus induced or exacerbated by terbinafine: a report of 5 cases". Arch Dermatol 137 (9): 1196–8. doi:10.1001/archderm.137.9.1196. PMID 11559217.

[6] "US FDA approves oral granules for scalp ringworm". Reuters. 2007-09-28.

[7] "Lamisil (terbinafine): Side Effects". Doublecheckmd.com. 2010-06-16. Retrieved 2013-11-09.

[8] McGuire, Stephen (2008-02-05). "Australian regulators issue warning on Novartis' Lamisil". Medical Marketing and Media. Mmm-online.com. Retrieved 2013-11-09.

[9] "Terbinafine-1 (Terbinafine Hydrochloride,Lamisil)". Drug Dosage and Side Effects. Healthline.com. 2009-02-27. Retrieved 2013-11-09.

[10] "Terbinafine". Pharmaceutical Benefits Scheme: A-Z list. Australian Government.

[11] "PI and CMI Trade Names and Active Ingredients containing Terbinafine". Therapeutic Goods Administration. Australian Government.

[12] "Terbinafine brands in India". Brand index. DrugsUpdate India.

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terbinafine hydrochloride