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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/12/12 11:40:00」(JST)
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Triclabendazole
|
| Clinical data |
| Trade names |
Fasinex, Egaten, others |
| AHFS/Drugs.com |
International Drug Names |
Routes of
administration |
by mouth |
| ATC code |
P02BX04 (WHO) QP52AC01 (WHO) |
| Pharmacokinetic data |
| Metabolism |
Oxidation to the sulfone and sulfoxide parent compound |
| Biological half-life |
22–24 hs |
| Excretion |
Feces (>95%), urine (2%), milk (<1%) |
| Identifiers |
IUPAC name
- 5-Chloro-6-(2,3-dichlorophenoxy)-2-(methylthio)-1H-benzimidazole
|
| CAS Number |
68786-66-3 N |
| PubChem (CID) |
50248 |
| ChemSpider |
45565 Y |
| UNII |
4784C8E03O Y |
| KEGG |
D07364 N |
| ChEMBL |
CHEMBL1086440 Y |
| ECHA InfoCard |
100.127.414 |
| Chemical and physical data |
| Formula |
C14H9Cl3N2OS |
| Molar mass |
359.658 |
| 3D model (Jmol) |
Interactive image |
SMILES
-
Clc3cccc(Oc2c(Cl)cc1c(nc(SC)n1)c2)c3Cl
|
InChI
-
InChI=1S/C14H9Cl3N2OS/c1-21-14-18-9-5-8(16)12(6-10(9)19-14)20-11-4-2-3-7(15)13(11)17/h2-6H,1H3,(H,18,19) Y
-
Key:NQPDXQQQCQDHHW-UHFFFAOYSA-N Y
|
| NY (what is this?) (verify) |
Triclabendazole, sold under the brand name Egaten among others, is a medication used to treat liver flukes, specifically fascioliasis and paragonimiasis. It is very effective for both conditions. Treatment in hospital may be required. It is taken by mouth with typically one or two doses being required.[1]
Side effects are generally few, but can include abdominal pain and headaches.[1] Biliary colic may occur due to dying worms. While no harms have been found with use during pregnancy, triclabendazole has not been well studied in this population.[2] It is a member of the benzimidazole family of medications for worms.[1]
It is on the World Health Organization's List of Essential Medicines, the most important medication needed in a basic health system.[3] It is not commercially avaliable in the United States.[4] For human use it can be gotten from the World Health Organization.[2] It is also used in other animals.[5]
Contents
- 1 Chemistry
- 2 History
- 3 References
- 4 Further reading
Chemistry
It is a member of the benzimidazole family of anthelmintics. The benzimidazole drugs share a common molecular structure, triclabendazole being the exception in having a chlorinated benzene ring but no carbamate group. Benzimidazoles such as triclabendazole are generally accepted to bind to beta-tubulin and prevent the polymerization of the microtubules of which they are part.
History
Since late 1990s, triclabendazole became available as a generic drug, as patents expired in many countries. Many products were developed then. Among them, Trivantel 15, a 15% triclabendazole suspension, was launched by Agrovet Market Animal Health in the early 2000s. In 2009, the first triclabendazole injectable solution (combined with ivermectin) was developed and launched, also by Agrovet Market Animal Health. The product, Fasiject Plus, a triclabendazole 36% and ivermectin 0.6% solution, is designed to treat infections by Fasciola hepatica (both immature and adult liver flukes), roundworms and ectoparasites, as well.
Fasinex is a brandname for veterinary use while Egaten is a brandname for human use.
References
- ^ a b c WHO Model Formulary 2008 (PDF). World Health Organization. 2009. p. 94, 96. ISBN 9789241547659. Retrieved 8 December 2016.
- ^ a b Wolfe, M. Michael; Lowe, Robert C. (2014). "Benzimidazoles". Pocket Guide to GastrointestinaI Drugs. John Wiley & Sons. p. PT173. ISBN 9781118481554.
- ^ "WHO Model List of EssentialMedicines" (PDF). World Health Organization. October 2013. Retrieved 22 April 2014.
- ^ "Praziquantel Monograph for Professionals - Drugs.com". www.drugs.com. Retrieved 10 December 2016.
- ^ "Triclabendazole - Drugs.com". www.drugs.com. Retrieved 10 December 2016.
Further reading
- "Report of the WHO Informal Meeting on use of triclabendazole in fascioliasis control" (PDF). who.int. 2006. Retrieved 10 December 2016.
|
Antiparasitics – Anthelmintics (P02) and Endectocides (QP54)
|
|
| Antiplatyhelmintic agents |
|
Antitrematodals
(schistosomicides)
|
|
Binds tubulin
|
|
|
|
AI
|
|
|
|
Other/unknown
|
- quinoline
- Praziquantel#
- Oxamniquine#
- phenol
- thiazole
- arylsulfonate
|
|
|
|
Anticestodals
(taeniacides)
|
|
Binds tubulin
|
|
|
|
Other/unknown
|
- quinoline
- salicylanilide
- aminoacridine
- butyrophenone
- chlorophenol
|
|
|
|
Antinematodal agents
(including
macrofilaricides) |
|
Binds tubulin
|
- benzimidazole
- Mebendazole#
- Albendazole#
- Tiabendazole
- Fenbendazole
- Ciclobendazole
- Flubendazole
|
|
|
Glutamate-gated chloride channel, GABA receptor
|
- avermectins
- Abamectin
- Doramectin
- Emamectin
- Ivermectin#
- Selamectin
- milbemycins
- Moxidectin
- Milbemycin oxime
|
|
|
NMDA
|
- tetrahydropyrimidine
- Pyrantel#
- Oxantel
- Morantel
- Carbantel
- Febantel (aka felsantel)
|
|
|
Other/unknown
|
- piperazine
- Piperazine
- Diethylcarbamazine#
- thiazole
- quinolinium
- benzylammonium
- naphthalenesulfonate
- Tribendimidine
|
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
|
UpToDate Contents
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English Journal
- Across intra-mammalian stages of the liver f luke Fasciola hepatica: a proteomic study.
- Di Maggio LS1,2, Tirloni L2,3, Pinto AF4,5, Diedrich JK5, Yates Iii JR5, Benavides U6, Carmona C1, da Silva Vaz I Jr2,3, Berasain P1.
- Scientific reports.Sci Rep.2016 Sep 7;6:32796. doi: 10.1038/srep32796.
- Fasciola hepatica is the agent of fasciolosis, a foodborne zoonosis that affects livestock production and human health. Although flukicidal drugs are available, re-infection and expanding resistance to triclabendazole demand new control strategies. Understanding the molecular mechanisms underlying t
- PMID 27600774
- Exploring and Expanding the Fatty-Acid-Binding Protein Superfamily in Fasciola Species.
- Morphew RM1, Wilkinson TJ1, Mackintosh N1, Jahndel V2, Paterson S3, McVeigh P4, Abbas Abidi SM5, Saifullah K5, Raman M6, Ravikumar G6, LaCourse J7, Maule A4, Brophy PM1.
- Journal of proteome research.J Proteome Res.2016 Sep 2;15(9):3308-21. doi: 10.1021/acs.jproteome.6b00331. Epub 2016 Aug 16.
- The liver flukes Fasciola hepatica and F. gigantica infect livestock worldwide and threaten food security with climate change and problematic control measures spreading disease. Fascioliasis is also a foodborne disease with up to 17 million humans infected. In the absence of vaccines, treatment depe
- PMID 27495901
- Simultaneous extraction and determination of albendazole and triclabendazole by a novel syringe to syringe dispersive liquid phase microextraction-solidified floating organic drop combined with high performance liquid chromatography.
- Asadi M1, Dadfarnia S2, Haji Shabani AM1.
- Analytica chimica acta.Anal Chim Acta.2016 Aug 17;932:22-8. doi: 10.1016/j.aca.2016.05.014. Epub 2016 May 20.
- A syringe to syringe dispersive liquid phase microextraction-solidified floating organic drop was introduced and used for the simultaneous extraction of trace amounts of albendazole and triclabendazole from different matrices. The extracted analytes were determined by high performance liquid chromat
- PMID 27286766
Japanese Journal
- Simultaneous determination of triclabendazole and its metabolites in bovine and goat tissues by liquid chromatography-tandem mass spectrometry
- CAI Chengyuan,ZHANG Lifang,XUE Feiqun,QIU Minqi,ZHENG Wenli
- Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 878(30), 3106-3112, 2010-11-15
- NAID 10028043821
- 牛肉中の駆虫剤(トリクラベンダゾール)分析法の改良
- 高速液体クロマトグラフィー/タンデム質量分析法による畜産物中のベンズイミダゾール系寄生虫駆虫剤の分析(<特集>「若手研究者の初論文」)
- 甲斐 茂美,赤星 猛,岸 美智子 [他],金澤 秀子,小林 静子
- 分析化学 54(9), 775-782, 2005-09-05
- 畜水産物に使用される動物用医薬品は, 生産性の向上や疾病予防や治療のため使用量が増大し, その残留の可能性が懸念されている.一方, 食品の安全性確保のため公布された「ポジティブリスト制」施行に向け, 動物用医薬品の一斉分析法の開発が急務となっている.そこで家畜用寄生虫駆除剤として広く使用されているベンズイミダゾール系薬剤について, 高感度測定と構造解析能を併せ持つイオントラップ-高速液体クロマトグ …
- NAID 110002910483
Related Links
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