Details
Stereochemistry | ACHIRAL |
Molecular Formula | C13H8Cl2N2O4 |
Molecular Weight | 327.12 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC1=C(C=C(Cl)C=C1)C(=O)NC2=C(Cl)C=C(C=C2)[N+]([O-])=O
InChI
InChIKey=RJMUSRYZPJIFPJ-UHFFFAOYSA-N
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)
Molecular Formula | C13H8Cl2N2O4 |
Molecular Weight | 327.12 |
Charge | 0 |
Count |
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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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[Climbing-upward inhibition of Oncomelania hupensis by niclosamide combination]. | 2001 |
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Inhibition of stimulated Jurkat cell adenosine 3',5'-cyclic monophosphate synthesis by the immunomodulatory compound HR325. | 2001 Jan 15 |
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Effect of soil moisture and sample depth on pesticide photolysis. | 2002 Apr 24 |
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Transplasma membrane electron transport in Leishmania donovani promastigotes. | 2002 Jan-Feb |
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Antiprotozoals effective in vitro against the scuticociliate fish pathogen Philasterides dicentrarchi. | 2002 Jun 3 |
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Generation and evaluation of a CYP2C9 heteroactivation pharmacophore. | 2003 Dec |
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Measures for the prevention and control of Taenia solium taeniosis and cysticercosis. | 2003 Jun |
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Investigations on the influence of helminth parasites on vaccination of chickens against Newcastle disease virus under village conditions. | 2003 Oct |
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Human Monieziasis expansa: the first Egyptian parastic zoonosis. | 2004 Aug |
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Polymeric controlled release formulations of niclosamide for control of Biomphalaria alexandrina, the vector snail of schistosomiasis. | 2004 Feb 20 |
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Aqueous photolysis of niclosamide. | 2004 Feb 25 |
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Adverse drug reactions to anthelmintics. | 2004 Mar |
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Old drugs as lead compounds for a new disease? Binding analysis of SARS coronavirus main proteinase with HIV, psychotic and parasite drugs. | 2004 May 15 |
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[Treatment of intestinal helminthiasis with albendazole]. | 2005 Apr-Jun |
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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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Lower-rim substituted calixarenes and their applications. | 2007 |
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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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A novel method for oral delivery of apolipoprotein mimetic peptides synthesized from all L-amino acids. | 2009 Aug |
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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 |
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
Wed Jul 05 22:51:42 UTC 2023
by
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on
Wed Jul 05 22:51:42 UTC 2023
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Record UNII |
8KK8CQ2K8G
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C250
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EPA PESTICIDE CODE |
77401
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WHO-ESSENTIAL MEDICINES LIST |
6.1.1
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EPA PESTICIDE CODE |
217800
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WHO-ATC |
P02DA01
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WHO-VATC |
QP52AG03
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100000092044
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200-056-8
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1572
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M7874
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178296
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CHEMBL1448
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SUB12176MIG
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1912
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C66240
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NICLOSAMIDE
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D009534
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SUB09230MIG
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8KK8CQ2K8G
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50-65-7
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1532
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niclosamide
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Niclosamide
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DB06803
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4477
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NICLOSAMIDE
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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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DTXSID7040362
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7402
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PRIMARY | RxNorm |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
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SALT/SOLVATE -> PARENT |
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SOLVATE->ANHYDROUS |
Related Record | Type | Details | ||
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METABOLITE -> PARENT |
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METABOLITE -> PARENT |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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