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an antifungal agent and anthelmintic

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/06/01 23:01:51」(JST)

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Tiabendazole (INN, BAN), thiabendazole (AAN, USAN), TBZ and the trade names Mintezol, Tresaderm, and Arbotect) is a fungicide and parasiticide.

Uses

Fungicide

It is used primarily to control mold, blight, and other fungally caused diseases in fruits (e.g. oranges) and vegetables; it is also used as a prophylactic treatment for Dutch elm disease.

Use in treatment of aspergillosis has been reported.^[1]

Parasiticide

As an antiparasitic, it is able to control roundworms (such as those causing strongyloidiasis),^[2] hookworms, and other helminth species which attack wild animals, livestock and humans.^[3]

Angiogenesis Inhibitor

Genes responsible for the maintenance of cell walls in yeast have been shown to be responsible for angiogenesis in vertebrates. Tiabendazole serves to block angiogenesis in both frog embryos and human cells. It has also been shown to serve as a vascular disrupting agent to reduce newly established blood vessels. Tiabendazole has been shown to effectively do this in certain cancer cells ^[4]

Pharmacodynamics

TBZ works by inhibition of the mitochondrial, helminth-specific enzyme, fumarate reductase, with possible interaction with endogenous quinone.^[5]

Other

Medicinally, thiabendazole is also a chelating agent, which means that it is used medicinally to bind metals in cases of metal poisoning, such as lead, mercury or antimony poisoning.

In dogs and cats, thiabendazole is used to treat ear infections.

Thiabendazole is also used as a food additive,^[6]^[7] a preservative with E number E233 (INS number 233). For example, it is applied to bananas to ensure freshness, and is a common ingredient in the waxes applied to the skins of citrus fruits. It is not approved as a food additive in the EU,^[8] Australia and New Zealand.^[9]

Safety

The substance appears to have a slight toxicity in higher doses, with effects such as liver and intestinal disorders at high exposure in test animals (just below LD₅₀ level).^{[citation needed]} Some reproductive disorders and decreasing weaning weight have been observed, also at high exposure. Effects on humans from use as a drug include nausea, vomiting, loss of appetite, diarrhea, dizziness, drowsiness, or headache; very rarely also ringing in the ears, vision changes, stomach pain, yellowing eyes and skin, dark urine, fever, fatigue, increased thirst and change in the amount of urine.^{[citation needed]} Carcinogenic effects have been shown at higher doses.^[10]

References

^ Upadhyay MP, West EP, Sharma AP (January 1980). "Keratitis due to Aspergillus flavus successfully treated with thiabendazole". Br J Ophthalmol 64 (1): 30–2. doi:10.1136/bjo.64.1.30. PMC 1039343. PMID 6766732.
^ Igual-Adell R, Oltra-Alcaraz C, Soler-Company E, Sánchez-Sánchez P, Matogo-Oyana J, Rodríguez-Calabuig D (December 2004). "Efficacy and safety of ivermectin and thiabendazole in the treatment of strongyloidiasis". Expert Opin Pharmacother 5 (12): 2615–9. doi:10.1517/14656566.5.12.2615. PMID 15571478.
^ Portugal R, Schaffel R, Almeida L, Spector N, Nucci M (June 2002). "Thiabendazole for the prophylaxis of strongyloidiasis in immunosuppressed patients with hematological diseases: a randomized double-blind placebo-controlled study". Haematologica 87 (6): 663–4. PMID 12031927.
^ Cha, HJ; Byrom M, Mead PE, Ellington AD, Wallingford JB, et al. (August 2012). "Evolutionarily Repurposed Networks Reveal the Well-Known Antifungal Drug Thiabendazole to Be a Novel Vascular Disrupting Agent". PLoS Biology 10 (8). doi:10.1371/journal.pbio.1001379. Retrieved 2012-08-21. Cite uses deprecated parameters (help)
^ Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 970
^ Rosenblum C (March 1977). "Non-drug-related residues in tracer studies". Journal of Toxicology and Environmental Health 2 (4): 803–14. doi:10.1080/15287397709529480. PMID 853540. |accessdate= requires |url= (help)
^ Sax, N.I. Dangerous Properties of Industrial Materials. Vol 1-3 7th ed. New York, NY: Van Nostrand Reinhold, 1989., p. 3251
^ UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27.
^ Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27.
^ "Reregistration Eligibility Decision THIABENDAZOLE". Environmental Protection Agency. Retrieved 8 January 2013.

Thiabendazole, Extension Toxicology Network
Medicinenet: Thiabendazole - Oral

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. 駆虫薬療法 anthelminthic therapies
2. 糞線虫症 strongyloidiasis
3. 皮膚幼虫移行症（皮膚爬行症） cutaneous larva migrans creeping eruption
4. その他の線虫 miscellaneous nematodes
5. 有機食品と小児 organic foods and children

English Journal

Mutations of β-tubulin codon 198 or 200 indicate thiabendazole resistance among isolates of Penicillium digitatum collected from citrus in Taiwan.

Lee MH, Pan SM, Ng TW, Chen PS, Wang LY, Chung KR.SourceDepartment of Plant Pathology, National Chung-Hsing University, 250 Kuo-Kuang Rd., Taichung 402, Taiwan.
International journal of food microbiology.Int J Food Microbiol.2011 Nov 1;150(2-3):157-63. Epub 2011 Aug 4.
Penicillium digitatum causes green mold on citrus, resulting in severe postharvest fruit decay and economic losses in many citrus-producing areas of the world. Forty isolates of P. digitatum were cultured from citrus groves, packinghouses, and local markets in Taiwan, and assessed quantitatively for
PMID 21868117

In situ analysis of agrochemical residues on fruit using ambient ionization on a handheld mass spectrometer.

Soparawalla S, Tadjimukhamedov FK, Wiley JS, Ouyang Z, Cooks RG.SourceDepartment of Chemistry Purdue University, 560 Oval Drive, West Lafayette, IN 47907, United States.
The Analyst.Analyst.2011 Oct 10;136(21):4392-6. Epub 2011 Sep 2.
We describe a rapid in situ method for detecting agrochemicals on the surface or in the tissue of fruit using a portable mass spectrometer equipped with an ambient ionization source. Two such ionization methods, low temperature plasma (LTP) and paper spray (PS), were employed in experiments performe
PMID 21892448

Japanese Journal

LC-MS/MSによる味付け海苔中のチアベンダゾールの分析法の検討

福田弘美,植田勤,大仲輝男,佐藤伸哉,神藤正則,田中智之
食品衛生学雑誌 52(2), 117-120, 2011
苦情検体の味付け海苔からチアベンダゾール(TBZ)が検出された事例を経験した．原因調査の結果，味付け工程で調味液を塗布する機械に使用されるスポンジロールに，抗菌目的で使用されていたTBZが海苔に移行したことが判明した．今回，LC-MS/MSを用いて味付け海苔中のTBZの定量法を検討した．味付け海苔の製造工程でこのスポンジロールが広く普及していたことから，改良した定量方法を用いて同時期と翌年の市販品 …
NAID 130000671821

Solubility Behavior and Prediction for Antihelmintics at Several Temperatures in Aqueous and Nonaqueous Mixtures

Bustamante Pilar,Muela Susana,Escalera Begoña,Peña Ángeles
CHEMICAL & PHARMACEUTICAL BULLETIN 58(5), 644-649, 2010
… The solubility of the drugs was measured in ethanol–water and ethanol–ethyl acetate mixtures at 15—35 °C (mebendazole) and at 25 °C (thiabendazole and metronidazole). … Markedly different solubility profile shapes were obtained against the solubility parameter of the mixtures: two symmetrical peaks (metronidazole), two maxima of different height (mebendazole) and a single peak (thiabendazole). …
NAID 130000255822

Related Pictures

★リンクテーブル★

リンク元	「蠕虫」「駆虫薬」「チアベンダゾール」「tiabendazole」

「蠕虫」

Tiabendazole
Systematic (IUPAC) name
	4-(1H-1,3-benzodiazol-2-yl)-1,3-thiazole
Clinical data
Trade names	Mintezol
AHFS/Drugs.com	International Drug Names
Pregnancy cat.	B3 (AU)
Legal status	Prescription Only (S4) (AU)
Pharmacokinetic data
Metabolism	GI tract. Peak plasma 1-2 hours through oral admin.
Half-life	8 hours
Excretion	90% Urine
Identifiers
CAS number	148-79-8
ATC code	D01AC06 P02CA02 QP52AC10
PubChem	CID 5430
DrugBank	DB00730
ChemSpider	5237
UNII	N1Q45E87DT
KEGG	D00372
ChEMBL	CHEMBL625
NIAID ChemDB	007903
Chemical data
Formula	C10H7N3S
Mol. mass	201.249 g/mol
	SMILES [nH]1c2ccccc2nc1c3cscn3;
	InChI InChI=1S/C10H7N3S/c1-2-4-8-7(3-1)12-10(13-8)9-5-14-6-11-9/h1-6H,(H,12,13) ; Key:WJCNZQLZVWNLKY-UHFFFAOYSA-N ;
Physical data
Density	1.103 g/cm³
Melt. point	293–305 °C (559–581 °F)
(what is this?) (verify)

　　[★]

英: helminth, worms
ラ: helminthen
関: 微生物学、蠕虫症、家畜伝染病予防法

蠕虫類

吸虫類 trematoda
条虫類 cestoda
線虫類 nematoda
鉤頭虫類 acanthocephala

蠕虫類と感染症

蠕虫類	病原体名		病名	感染経路	寄生部位	症状	診断	治療
線虫類	Ancylostoma duodenale	ズビニ鉤虫	鈎虫症/十二指腸虫症	F型幼虫経口感染、経皮	空腸上部	皮膚炎、若菜病、貧血	飽和食塩水浮遊法、遠心沈降法	pyrantel pamoate、鉄剤
	Necator americanus	アメリカ鉤虫	鈎虫症/十二指腸虫症	F型幼虫経口感染、経皮	空腸上部	皮膚炎、若菜病、貧血	飽和食塩水浮遊法、遠心沈降法	pyrantel pamoate、鉄剤
	Strongyloides stercoralis	糞線虫	糞線虫症	F型幼虫経皮感染	小腸上部	Loffler症候群	糞便塗沫、普通寒天平板培養による R型、F型幼虫の検出	thiabendazole, ivermectin
	Enterobius vermicularis	蟯虫	蟯虫症	虫卵経口感染	盲腸～大腸	夜間の掻痒、不眠、情緒不安定	肛囲検査法「柿の種」	pyrantel pamoate
	Ascaris lumbricoides	回虫	回虫症	虫卵経口感染	小腸孵化→門脈→ 肺発育→食道嚥下→小腸	Loffler症候群。急性腹痛	糞便虫の虫卵の証明	pyrantel pamoate
	Toxocara canis	イヌ回虫	幼虫移行症	生後1-2ヶ月の感染犬の糞から経口感染	なし	幼虫移行症→失明	免疫診断	治療法無し？
	Wuchereria bancrofti	バンクロフト糸状虫	フィラリア症/糸状虫症	アカイエカ	リンパ系	急性期：リンパ肝炎、リンパ腺炎を伴う熱発作(filarial fever) 慢性期：乳糜尿、リンパ管瘤、陰嚢水腫、象皮病	急性期：夜間のmicrofilariaの検出慢性期：特有の症状を考慮	diethylcarbamazine & ivermectin
	Brugia malayi	マレー糸状虫	フィラリア症/糸状虫症	アカイエカ	リンパ系		急性期：夜間のmicrofilariaの検出慢性期：特有の症状を考慮	diethylcarbamazine & ivermectin
	Dirofilaria immitis	イヌ糸状虫		アカイエカ	なし	幼虫移行症→肺血管閉塞→胸部X線画像銭形陰影
	Gnathostoma spinigerum	有棘顎口虫	顎口虫症	ドジョウ、雷魚、ヘビの生食		消化管壁貫通→皮下移動による腫瘤や線状皮膚炎	移動性腫瘤、皮膚爬行疹雷魚やドジョウの生殖の問診免疫血清診断	なし
	Gnathostoma hispidum	剛棘顎口虫
	Gnathostoma doloresi	ドロレス顎口虫
	Gnathostoma nipponicum	日本顎口虫
	Anisakis simplex, larva	アニキサス幼虫	アニサキス症 (1)胃アニサキス症、 (2)腸アニサキス症、 (3)異所性アニサキス症	経口感染終宿主：クジラ、イルカ。中間宿主：オキアミ。待機宿主：サバ、ニシン、アジ、タラなど	胃や腸	(1)急激な上腹部痛"胃けいれん" (2)腹痛、急性虫垂炎、イレウス様。劇症型と緩和型がある (3)腹腔内の炎症性肉芽腫	胃内視鏡検査	内視鏡による虫体摘出
	Pseudoterranova decipiens	アニキサス幼虫	アニサキス症 (1)胃アニサキス症、 (2)腸アニサキス症、 (3)異所性アニサキス症	経口感染終宿主：クジラ、イルカ。中間宿主：オキアミ。待機宿主：サバ、ニシン、アジ、タラなど	胃や腸		胃内視鏡検査	内視鏡による虫体摘出
	Trichinella spiralis	旋毛虫	旋毛虫症	経口感染豚肉、クマ肉の生食		(1)成虫侵襲期：下痢、腹痛 (2)幼虫筋肉移行期：顔面浮腫、心筋障害など (3)幼虫被嚢期：全身浮腫、衰弱		急性期：ステロイド殺虫：mebendazole
			鞭虫症		盲腸	慢性下痢、腹痛、異食症、貧血	セロファン重層塗沫法、ホルマリンエーテル法	mebendazole
	Spirurin nematode larva	旋尾線虫	旋尾線虫幼虫	ホタルイカの生食	なし	皮膚爬行疹、イレウス様症状	予防：-30℃24時間。生食には-30℃4日間以上	摘出
吸虫類	Shistosoma japonicum	日本住血吸虫	日本住血吸虫症	糞便虫の虫卵→ミラシジウム→ ミヤイリガイ体内でセルカリア→ 人畜の皮膚より浸入→循環系→ 門脈に寄生	門脈	(1)潜伏期：侵入部の掻痒性皮膚炎。肺移行期：咳、発熱 (2)急性期：虫卵の門脈系寄生、産卵。住血吸虫性赤痢。 (3)慢性期：虫卵の肝、脳などの塞栓。肝硬変。脾腫、腹水	糞便虫の虫卵の検出。直腸粘膜層掻爬法、肝穿刺による組織内虫卵の検出。補助診断として免疫血清学的検査。	praziquantel
	Paragonimus westermani	ウェステルマン肺吸虫	肺吸虫症/肺ジストマ症	経口感染淡水産のカニ、イノシシ肉の生食	肺	痰、咳、胸痛、時に喀血	痰や便の虫卵検査、胸部写真、断層写真で明らかな虫嚢。免疫学血清検査
	Paragonimus miyazakii	宮崎肺吸虫	肺吸虫症/肺ジストマ症	経口感染淡水産のカニ、イノシシ肉の生食	肺	気胸、胸水貯留、膿胸、好酸球増加		praziquantel
	Clonorchis sinensis	肝吸虫	肝吸虫症/肝ジストマ症	経口感染虫卵→(マメタニシ:セルカリア)→ セルカリア→(魚:メタセルカリア)→ 摂取→(ヒト:成虫)→虫卵	胆管	胆汁流出障害による肝障害→肝硬変	糞便、胆汁(十二指腸ゾンデ法)。肝吸虫卵の検出。CT像。エコー検査。	praziquantel
			横川吸虫症	淡水魚(アユ、フナ、ウグイ、シラウオ)の生食	小腸粘膜	下痢、腹痛	糞便虫の虫卵	praziquantel
条虫類	Taeniarhynchus saginatus	無鉤条虫	腸管条虫症	経口感染。中間宿主：ウシ	小腸	無症状。下痢。広節裂頭条虫感染では悪性貧血。	糞便虫の虫卵と体節により診断	praziquantel。有鉤条虫の場合はガストログラフィン。有鉤条虫の駆虫の際、虫体を破壊しない →虫体の融解による嚢虫症
	Taenia solium	有鉤条虫		経口感染。中間宿主：ブタ
	Diphyllobothrium latum	広節裂頭条虫		経口感染。中間宿主：サケ、マス
		日本海裂頭条虫		経口感染。中間宿主：サケ
			腸管外条虫症
			有鉤嚢虫症	有鉤条虫の虫卵の経口摂取	皮下、筋肉内脳、脊髄、眼球	皮下、筋肉内：小指頭大の無症状腫瘤脳、脊髄、眼球：Jacksonてんかん。痙性麻痺など	皮下の虫嚢	外科的摘出。成虫寄生がなければ、praziquantel, albendazole + ステロイド
	Echinococcus granulosus	単包虫	包虫症/ エキノコックス症 (単包虫症)	終宿主：イヌ、キツネなど。中間宿主：ヒト、ブタ、野ネズミなど。終宿主の糞便虫の虫卵を中間宿主が接種して発症	肝、肺、まれに脳、腎、筋肉	肝寄生：肝部疼痛、満腹、時に黄疸、下肢浮腫肺寄生：胸部圧迫感、胸痛、咳、血痰、時に喀血	肝や肺の嚢胞形成から疑う。早期に診断に皮内反応→ CT、エコー→ 生検。免疫血清学的診断法	外科的切除。 albendazoleの長期投与
	Echinococcus multilocularis	多包虫	包虫症/ エキノコックス症 (多包虫症)	終宿主：イヌ、キツネなど。中間宿主：ヒト、ブタ、野ネズミなど。終宿主の糞便虫の虫卵を中間宿主が接種して発症	肝、肺、まれに脳、腎、筋肉	肝寄生：肝部疼痛、満腹、時に黄疸、下肢浮腫肺寄生：胸部圧迫感、胸痛、咳、血痰、時に喀血	肝や肺の嚢胞形成から疑う。早期に診断に皮内反応→ CT、エコー→ 生検。免疫血清学的診断法	外科的切除。 albendazoleの長期投与

「駆虫薬」

　　[★]

英: anthelmintic, anthelmintics
ラ: anthelmintica
関

http://en.wikipedia.org/wiki/Anthelmintic

antiplatyhelmintic agents	Antitrematodals (schistosomicides)	binds tubulin	benzimidazole (Triclabendazole#)
		acetylcholinesterase inhibitor	phosphonic acid (metrifonate)
		Other/unknown	quinoline (praziquantel#, oxamniquine#) · phenol (bithionol) · thiazole ([[niridazole]) · arylsulfonate (stibophen)
	anticestodals (taeniacides)	binds tubulin	benzimidazole (albendazole#)
	anticestodals (taeniacides)	Other/unknown	salicylanilide (niclosamide)# · aminoacridine (quinacrine) · butyrophenone (desaspidin) · chlorophenol (dichlorophen)
antinematodal agents (macrofilaricides)		binds tubulin	benzimidazole (mebendazole#, thiabendazole, albendazole#, fenbendazole, ciclobendazole, flubendazole)
		chloride channel	macrolide (ivermectin#)
		NMDA	tetrahydropyrimidine (pyrantel#, pyrantel pamoate, oxantel)
		Other/unknown	piperazine (piperazine · diethylcarbamazine#) · thiazole (levamisole#) · quinolinium (pyrvinium) · benzylammonium (bephenium) · naphthalenesulfonate (suramin#) · tribendimidine

「チアベンダゾール」

　　[★]

英: thiabendazole、tiabendazole
商: ミンテゾール
関: trichinosis

「tiabendazole」

　　[★]

チアベンダゾール

関: thiabendazole

[pmid6766732-1] Upadhyay MP, West EP, Sharma AP (January 1980). "Keratitis due to Aspergillus flavus successfully treated with thiabendazole". Br J Ophthalmol 64 (1): 30–2. doi:10.1136/bjo.64.1.30. PMC 1039343. PMID 6766732.

[pmid15571478-2] Igual-Adell R, Oltra-Alcaraz C, Soler-Company E, Sánchez-Sánchez P, Matogo-Oyana J, Rodríguez-Calabuig D (December 2004). "Efficacy and safety of ivermectin and thiabendazole in the treatment of strongyloidiasis". Expert Opin Pharmacother 5 (12): 2615–9. doi:10.1517/14656566.5.12.2615. PMID 15571478.

[pmid12031927-3] Portugal R, Schaffel R, Almeida L, Spector N, Nucci M (June 2002). "Thiabendazole for the prophylaxis of strongyloidiasis in immunosuppressed patients with hematological diseases: a randomized double-blind placebo-controlled study". Haematologica 87 (6): 663–4. PMID 12031927.

[4] Cha, HJ; Byrom M, Mead PE, Ellington AD, Wallingford JB, et al. (August 2012). "Evolutionarily Repurposed Networks Reveal the Well-Known Antifungal Drug Thiabendazole to Be a Novel Vascular Disrupting Agent". PLoS Biology 10 (8). doi:10.1371/journal.pbio.1001379. Retrieved 2012-08-21. Cite uses deprecated parameters (help)

[5] Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 970

[pmid853540-6] Rosenblum C (March 1977). "Non-drug-related residues in tracer studies". Journal of Toxicology and Environmental Health 2 (4): 803–14. doi:10.1080/15287397709529480. PMID 853540. |accessdate= requires |url= (help)

[7] Sax, N.I. Dangerous Properties of Industrial Materials. Vol 1-3 7th ed. New York, NY: Van Nostrand Reinhold, 1989., p. 3251

[8] UK Food Standards Agency: "Current EU approved additives and their E Numbers". Retrieved 2011-10-27.

[9] Australia New Zealand Food Standards Code"Standard 1.2.4 - Labelling of ingredients". Retrieved 2011-10-27.

[10] "Reregistration Eligibility Decision THIABENDAZOLE". Environmental Protection Agency. Retrieved 8 January 2013.

匿名

検索

案内

案内

thiabendazole