Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H8Cl2N2O4.H2O |
Molecular Weight | 345.135 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.OC1=C(C=C(Cl)C=C1)C(=O)NC2=C(Cl)C=C(C=C2)[N+]([O-])=O
InChI
InChIKey=ZBXRPLQCPHTHLM-UHFFFAOYSA-N
InChI=1S/C13H8Cl2N2O4.H2O/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);1H2
Molecular Formula | C13H8Cl2N2O4 |
Molecular Weight | 327.12 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
DescriptionSources: http://www.drugbank.ca/drugs/DB06803Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/mmx/niclosamide.html
Sources: http://www.drugbank.ca/drugs/DB06803
Curator's Comment: Description was created based on several sources, including
https://www.drugs.com/mmx/niclosamide.html
Niclosamide is an antihelminth used against tapeworm infections. It may act by the uncoupling of the electron transport chain to ATP synthase. The disturbance of this crucial metabolic pathway prevents creation of adenosine tri-phosphate (ATP), an essential molecule that supplies energy for metabolism. Niclosamide works by killing tapeworms on contact. Adult worms (but not ova) are rapidly killed, presumably due to uncoupling of oxidative phosphorylation or stimulation of ATPase activity. The killed worms are then passed in the stool or sometimes destroyed in the intestine. Niclosamide may work as a molluscicide by binding to and damaging DNA. Niclosamide is used for the treatment of tapeworm and intestinal fluke infections: Taenia saginata (Beef Tapeworm), Taenia solium (Pork Tapeworm), Diphyllobothrium latum (Fish Tapeworm), Fasciolopsis buski (large intestinal fluke). Niclosamide is also used as a molluscicide in the control of schistosomiasis. Niclosamide was marketed under the trade name Niclocide, now discontinued.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL352 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25897961 |
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Target ID: CHEMBL357 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25897961 |
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Target ID: CHEMBL3356 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11124226 |
2.7 µM [Ki] | ||
Target ID: CHEMBL612450 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6841958 |
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Target ID: Taenia saginata Sources: https://www.ncbi.nlm.nih.gov/pubmed/3425963 |
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Target ID: CHEMBL387 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27545321 |
45.0 µM [IC50] | ||
Target ID: CHEMBL2366043 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12392939 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Curative | NICLOCIDE Approved UseDiphyllobothriasis (treatment)—Niclosamide is indicated in the treatment of diphyllobothriasis caused by Diphyllobothrium latum (broad or fish tapeworm).
Hymenolepiasis (treatment)—Niclosamide is indicated in the treatment of hymenolepiasis caused by Hymenolepis nana (dwarf tapeworm) and [H. diminuta (rat tapeworm)] .
Taeniasis (treatment)—Niclosamide is indicated in the treatment of taeniasis caused by Taenia saginata (beef tapeworm) and [T. solium (pork tapeworm)] .
[Dipylidiasis (treatment)]—Niclosamide is used in the treatment of dipylidiasis caused by Dipylidium caninum (dog and cat tapeworm). Launch Date3.90095995E11 |
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Curative | NICLOCIDE Approved UseDiphyllobothriasis (treatment)—Niclosamide is indicated in the treatment of diphyllobothriasis caused by Diphyllobothrium latum (broad or fish tapeworm).
Hymenolepiasis (treatment)—Niclosamide is indicated in the treatment of hymenolepiasis caused by Hymenolepis nana (dwarf tapeworm) and [H. diminuta (rat tapeworm)] .
Taeniasis (treatment)—Niclosamide is indicated in the treatment of taeniasis caused by Taenia saginata (beef tapeworm) and [T. solium (pork tapeworm)] .
[Dipylidiasis (treatment)]—Niclosamide is used in the treatment of dipylidiasis caused by Dipylidium caninum (dog and cat tapeworm). Launch Date3.90095995E11 |
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Curative | NICLOCIDE Approved UseDiphyllobothriasis (treatment)—Niclosamide is indicated in the treatment of diphyllobothriasis caused by Diphyllobothrium latum (broad or fish tapeworm).
Hymenolepiasis (treatment)—Niclosamide is indicated in the treatment of hymenolepiasis caused by Hymenolepis nana (dwarf tapeworm) and [H. diminuta (rat tapeworm)] .
Taeniasis (treatment)—Niclosamide is indicated in the treatment of taeniasis caused by Taenia saginata (beef tapeworm) and [T. solium (pork tapeworm)] .
[Dipylidiasis (treatment)]—Niclosamide is used in the treatment of dipylidiasis caused by Dipylidium caninum (dog and cat tapeworm). Launch Date3.90095995E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.665 μg/mL |
2 g single, oral dose: 2 g route of administration: Oral experiment type: SINGLE co-administered: |
NICLOSAMIDE plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1413 ng × h/mL |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NICLOSAMIDE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
6.7 h |
2 mg/kg single, intravenous dose: 2 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered: |
NICLOSAMIDE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
1000 mg 3 times / day steady, oral Dose: 1000 mg, 3 times / day Route: oral Route: steady Dose: 1000 mg, 3 times / day Co-administed with:: enzalutamide(160 mg, oral, daily) Sources: |
unhealthy n = 2 Health Status: unhealthy Condition: castration-resistant prostate cancer Sex: M Population Size: 2 Sources: |
DLT: Nausea, Vomiting... Dose limiting toxicities: Nausea (grade 3, 2 patients) Sources: Vomiting (grade 3, 2 patients) Diarrhea (grade 3, 2 patients) Colitis (grade 3, 2 patients) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Colitis | grade 3, 2 patients DLT |
1000 mg 3 times / day steady, oral Dose: 1000 mg, 3 times / day Route: oral Route: steady Dose: 1000 mg, 3 times / day Co-administed with:: enzalutamide(160 mg, oral, daily) Sources: |
unhealthy n = 2 Health Status: unhealthy Condition: castration-resistant prostate cancer Sex: M Population Size: 2 Sources: |
Diarrhea | grade 3, 2 patients DLT |
1000 mg 3 times / day steady, oral Dose: 1000 mg, 3 times / day Route: oral Route: steady Dose: 1000 mg, 3 times / day Co-administed with:: enzalutamide(160 mg, oral, daily) Sources: |
unhealthy n = 2 Health Status: unhealthy Condition: castration-resistant prostate cancer Sex: M Population Size: 2 Sources: |
Nausea | grade 3, 2 patients DLT |
1000 mg 3 times / day steady, oral Dose: 1000 mg, 3 times / day Route: oral Route: steady Dose: 1000 mg, 3 times / day Co-administed with:: enzalutamide(160 mg, oral, daily) Sources: |
unhealthy n = 2 Health Status: unhealthy Condition: castration-resistant prostate cancer Sex: M Population Size: 2 Sources: |
Vomiting | grade 3, 2 patients DLT |
1000 mg 3 times / day steady, oral Dose: 1000 mg, 3 times / day Route: oral Route: steady Dose: 1000 mg, 3 times / day Co-administed with:: enzalutamide(160 mg, oral, daily) Sources: |
unhealthy n = 2 Health Status: unhealthy Condition: castration-resistant prostate cancer Sex: M Population Size: 2 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [Ki 2.7 uM] | ||||
yes [Ki 6 uM] | ||||
yes |
Drug as victim
PubMed
Title | Date | PubMed |
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[Preliminary test of the effect of niclosamide-impregnated tissue for the prevention of Schistosoma japonicum infection]. | 2003 |
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Human Monieziasis expansa: the first Egyptian parastic zoonosis. | 2004 Aug |
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Nitazoxanide: a new broad spectrum antiparasitic agent. | 2004 Feb |
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Aqueous photolysis of niclosamide. | 2004 Feb 25 |
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Preparation and physicochemical properties of niclosamide anhydrate and two monohydrates. | 2004 Jan 28 |
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[Efficacy of the Russian anthelmintic agent trichlorophen]. | 2004 Jan-Mar |
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Molluscicidal effect of nicotinanilide and its intermediate compounds against a freshwater snail Lymnaea luteola, the vector of animal schistosomiasis. | 2004 Mar |
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Adverse drug reactions to anthelmintics. | 2004 Mar |
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Species identification after treatment for human taeniasis. | 2004 Mar 20 |
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Purging the worm: management of Taenia solium taeniasis. | 2004 Mar 20 |
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Infestation of the human intestine by the millipede, Nopoiulus kochii. | 2004 Sep |
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[Treatment of intestinal helminthiasis with albendazole]. | 2005 Apr-Jun |
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Impact of certain plants and synthetic molluscicides on some fresh water snails and fish. | 2005 Dec |
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Residues of the lampricides 3-trifluoromethyl-4-nitrophenol and niclosamide in muscle tissue of rainbow trout. | 2005 Jun 29 |
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Taeniasis and cysticercosis in housemaids working in affluent neighborhoods in Lima, Peru. | 2005 Sep |
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Effect of 4-sulphonato-calix[n]arenes and cyclodextrins on the solubilization of niclosamide, a poorly water soluble anthelmintic. | 2005 Sep 2 |
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Potential antivirals and antiviral strategies against SARS coronavirus infections. | 2006 Apr |
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Synthesis of furo-salicylanilides and their heterocyclic derivatives with anticipated molluscicidal activity. | 2006 Aug |
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Catalysis of NADH-->NADP+ transhydrogenation by adult Hymenolepis diminuta mitochondria. | 2006 Feb |
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[Cleaning and molluscicide treatment for schistosomiasis control]. | 2006 Jan-Mar |
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Prioritizing genomic drug targets in pathogens: application to Mycobacterium tuberculosis. | 2006 Jun 9 |
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Lower-rim substituted calixarenes and their applications. | 2007 |
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A studies on chemical control of S. mansoni intermediate host. | 2007 Aug 1 |
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Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus. | 2007 Aug 23 |
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[Study on molluscicidal effect of the extracts from sarcotesta of Ginkgo biloba]. | 2007 Feb 28 |
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Large water management projects and schistosomiasis control, Dongting Lake region, China. | 2007 Jul |
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5(6)-Carboxyfluorescein diacetate as an indicator of Caenorhabditis elegans viability for the development of an in vitro anthelmintic drug assay. | 2007 Mar 30 |
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[Study on molluscicidal effect of chlorosalicylicamide]. | 2007 Oct |
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Taeniasis and its socio-economic implication in Awassa town and its surroundings, Southern Ethiopia. | 2007 Oct |
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Community acceptability of the use of low-dose niclosamide (Bayluscide), as a molluscicide in the control of human schistosomiasis in Sahelian Cameroon. | 2007 Sep |
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Tribendimidine and albendazole for treating soil-transmitted helminths, Strongyloides stercoralis and Taenia spp.: open-label randomized trial. | 2008 |
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[Human infection due to Bertiella sp (cestode: Anoplocephalidae) in a man originating from Yemen in Algeria]. | 2008 Apr |
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In vitro trypanocidal activity of the anti-helminthic drug niclosamide. | 2008 Apr |
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[Snail control by using soil pasting mixed with niclosamide]. | 2008 Aug |
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Efficacy of temperature, and two commonly used molluscicides and fertilizers on Fasciola gigantica eggs. | 2008 Aug |
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Successful treatment of niclosamide- and praziquantel-resistant beef tapeworm infection with nitazoxanide. | 2008 Jan |
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A novel molluscicidal formulation of niclosamide. | 2008 Jul |
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Voltammetric Behavior of o-Nitrophenol and Damage to DNA. | 2008 Mar |
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Hymenolepis diminuta: mitochondrial transhydrogenase as an additional site for anaerobic phosphorylation. | 2008 May |
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Potential of some monoterpenoids and their new N-methyl carbamate derivatives against Schistosomiasis snail vector, Biomphalaria alexandrina. | 2008 Nov |
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Harnessing the wealth of Chinese scientific literature: schistosomiasis research and control in China. | 2008 Sep 30 |
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Taenia solium cysticercosis hotspots surrounding tapeworm carriers: clustering on human seroprevalence but not on seizures. | 2009 |
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A novel method for oral delivery of apolipoprotein mimetic peptides synthesized from all L-amino acids. | 2009 Aug |
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A retrospective analysis of prevalence of gastrointestinal parasites among school children in the Palajunoj Valley of Guatemala. | 2009 Feb |
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Spatial epidemiology in zoonotic parasitic diseases: insights gained at the 1st International Symposium on Geospatial Health in Lijiang, China, 2007. | 2009 Feb 4 |
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Drug discovery for schistosomiasis: hit and lead compounds identified in a library of known drugs by medium-throughput phenotypic screening. | 2009 Jul 14 |
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Diphyllobothrium latum identified by capsule endoscopy--an unusual cause of iron-deficiency anemia. | 2009 Jun |
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The autonomous notch signal pathway is activated by baicalin and baicalein but is suppressed by niclosamide in K562 cells. | 2009 Mar 1 |
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Multi-residue determination of phenolic and salicylanilide anthelmintics and related compounds in bovine kidney by liquid chromatography-tandem mass spectrometry. | 2009 Nov 13 |
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Halogenated pesticide transformation by a laccase-mediator system. | 2009 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.drugs.com/cons/niclosamide.html
Adults—2 grams as a single dose. Treatment may be repeated in seven days if needed.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3615395
Niclosamide (0.2 ug/ml) was effective against Diplozoon paradoxum after an exposure of 90 min and 45 min in vitro.
Substance Class |
Chemical
Created
by
admin
on
Edited
Thu Jul 06 02:05:54 UTC 2023
by
admin
on
Thu Jul 06 02:05:54 UTC 2023
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Record UNII |
20Z25R1145
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Record Status |
Validated (UNII)
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Record Version |
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-
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Code System | Code | Type | Description | ||
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NICLOSAMIDE MONOHYDRATE
Created by
admin on Thu Jul 06 02:05:54 UTC 2023 , Edited by admin on Thu Jul 06 02:05:54 UTC 2023
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PRIMARY | Description: A cream-coloured, crystalline powder; odourless. Solubility: Practically insoluble in water; soluble in 150 parts of ethanol (~750 g/L) TS; slightly soluble in ether R and acetone R. Category: Taeniacide. Storage: Niclosamide should be kept in a tightly closed container. Labelling: The designation on the container of Niclosamide should state whether the substance is the monohydrate or is in theanhydrous form.Additional information: Anhydrous Niclosamide is hygroscopic. Niclosamide monohydrate may exhibit polymorphism. Definition: Niclosamide contains not less than 98.0% and not more than 100.5% of C13H8Cl2N2O4, calculated with reference tothe dried substance. | ||
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73360-56-2
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SUB12175MIG
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DTXSID70223608
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100000079592
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12296604
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20Z25R1145
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PRIMARY |
Related Record | Type | Details | ||
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ANHYDROUS->SOLVATE | |||
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PARENT -> SALT/SOLVATE |
Related Record | Type | Details | ||
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ACTIVE MOIETY |