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Niclosamide
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Systematic (IUPAC) name |
5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide |
Clinical data |
AHFS/Drugs.com |
Micromedex Detailed Consumer Information |
Pregnancy cat. |
? |
Legal status |
? |
Identifiers |
CAS number |
50-65-7 N |
ATC code |
P02DA01 QP52AG03 |
PubChem |
CID 4477 |
DrugBank |
DB06803 |
ChemSpider |
4322 Y |
UNII |
8KK8CQ2K8G Y |
KEGG |
D00436 Y |
ChEMBL |
CHEMBL1448 Y |
Chemical data |
Formula |
C13H8Cl2N2O4 |
Mol. mass |
327.119 g/mol |
SMILES
- Clc2cc(ccc2NC(=O)c1cc(Cl)ccc1O)[N+]([O-])=O
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InChI
-
InChI=1S/C13H8Cl2N2O4/c14-7-1-4-12(18)9(5-7)13(19)16-11-3-2-8(17(20)21)6-10(11)15/h1-6,18H,(H,16,19) Y
Key:RJMUSRYZPJIFPJ-UHFFFAOYSA-N Y
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N (what is this?) (verify)
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Niclosamide (trade name Niclocide) is a teniacide ("tenia-" referring to tapeworm) in the anthelmintic family especially effective against cestodes that infect humans. It is also used as a piscicide. It is stressed that while antihelmintics are a drug family used to treat worm infections, Niclosamide is used specifically to treat tapeworms and is not effective against other worms such as pinworms or roundworms. It is a chewable tablet taken orally, dosage depending on type of worm and patient's age and/or weight. Niclosamide molecules are lethal to tapeworms upon contact.
Contents
- 1 Side effects
- 2 Potential efficacy against colon cancer
- 3 Mechanism of action
- 4 References
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Side effects
The medication can have side effects such as abdominal pain, anorexia, diarrhea, and emesis. Rarely, dizziness, skin rash, drowsiness, perianal itching, and an unpleasant taste.
Potential efficacy against colon cancer
Niclosamide has been shown to inhibit the spread of colon cancer in animal studies. The drug works by blocking the expression of gene called S100A4/metastasin, which can prompt colon cancer metastasis.[1]
Mechanism of action
According to an article in Nature,[2] niclosamide uncouples oxidative phosphorylation in the tapeworm.
References
- ^ http://www.emaxhealth.com/1275/spread-colon-cancer-stopped-tapeworm-drug
- ^ Weinbach EC, Garbus J (1969). "Mechanism of action of reagents that uncouple oxidative phosphorylation". Nature 221 (5185): 1016–8. doi:10.1038/2211016a0. PMID 4180173.
- Taber, Clarence Wilbur; Venes, Donald; Thomas, Clayton L. (2001). Taber's cyclopedic medical dictionary. Philadelphia: F.A.Davis Co.
- Additional Medication Information:Medline
- http://www.drugs.com/cons/Niclosamide.html
Antiparasitics – Anthelmintics (P02) and Endectocides (QP54)
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Antiplatyhelmintic agents |
Antitrematodals
(schistosomicides)
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Binds tubulin
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AI
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Other/unknown
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- quinoline
- Praziquantel#
- Oxamniquine#
- phenol
- thiazole
- arylsulfonate
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Anticestodals
(taeniacides)
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Binds tubulin
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Other/unknown
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- salicylanilide
- aminoacridine
- butyrophenone
- chlorophenol
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Antinematodal agents
(including
macrofilaricides) |
Binds tubulin
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- benzimidazole
- Mebendazole#
- Albendazole#
- Thiabendazole
- Fenbendazole
- Ciclobendazole
- Flubendazole
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Glutamate-gated chloride channel, GABA receptor
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- avermectins
- Abamectin
- Doramectin
- Emamectin
- Ivermectin
- Selamectin
- milbemycins
- Moxidectin
- Milbemycin oxime
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NMDA
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- tetrahydropyrimidine
- Pyrantel#
- Pyrantel pamoate
- Oxantel
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Other/unknown
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- piperazine
- Piperazine
- Diethylcarbamazine#
- thiazole
- quinolinium
- benzylammonium
- naphthalenesulfonate
- Tribendimidine
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- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
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UpToDate Contents
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- 1. 腸管条虫 intestinal tapeworms
- 2. 肺吸虫症 paragonimiasis
- 3. 腸管寄生虫症 intestinal flukes
English Journal
- Effects of Bayluscide on Bithynia siamensis goniomphalos, the first intermediate host of the human liver fluke, Opisthorchis viverrini, in laboratory and field trials.
- Tesana S, Thapsripair P, Thammasiri C, Prasopdee S, Suwannatrai A, Harauy S, Piratae S, Khampoosa P, Kulsantiwong J, Donthaisong C, Chalokepanrat P, Viyanant V, Malone JB.SourceFood-Borne Parasite Research Group, Department of Parasitology, Faculty of Medicine, Khon Kaen University, Khon Kaen province 40002, Thailand.
- Parasitology international.Parasitol Int.2011 Aug 16. [Epub ahead of print]
- The molluscicidal effects of Bayluscide (niclosamide) were investigated on Bithynia siamensis goniomphalos, the first intermediate host of human liver fluke, Opisthorchis viverrini. Lethal concentrations of 50% (LC(50)) and 95% (LC(95)) against young and adult males were 0.38 and 0.80, 0.42 and 0.86
- PMID 21864711
- Niclosamide induces mitochondria fragmentation and promotes both apoptotic and autophagic cell death.
- Park SJ, Shin JH, Kang H, Hwang JJ, Cho DH.SourceGraduate School of East-West Medical Science, Kyung Hee University, Yongin, Korea.
- BMB reports.BMB Rep.2011 Aug;44(8):517-22.
- Mitochondrial dynamics not only involves mitochondrial morphology but also mitochondrial biogenesis, mitochondrial distribution, and cell death. To identify specific regulators to mitochondria dynamics, we screened a chemical library and identified niclosamide as a potent inducer of mitochondria fis
- PMID 21871175
Japanese Journal
- 伊藤 亮,Craig P
- Current Opinion in Infectious Diseases 20(5), 524-532, 2007-Oct
- … Most human intestinal cestode infections can be treated with a single oral dose of praziquantel or niclosamide. …
- NAID 120003203337
- Transport of Schistosoma japonicum cercariae and the feasibility of niclosamide for cercariae control
- LOWE Debbie,XI Jinyu,MENG Xianhong,WU Zisong,QIU Dongchuan,SPEAR Robert
- Parasitology international : official journal of the Japanese Society of Parasitology 54(1), 83-89, 2005-03-01
- NAID 10015455278
Related Links
- Niclosamide (trade name Niclocide) is a teniacide ("tenia-" referring to tapeworm) in the anthelmintic family especially effective against cestodes that infect humans. It is also used as a piscicide.It is stressed that while antihelmintics are a drug ...
Related Pictures
★リンクテーブル★
[★]
- 英
- anthelmintic, anthelmintics
- ラ
- anthelmintica
- 関