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Details

Stereochemistry ACHIRAL
Molecular Formula C13H8Cl2N2O4.H2O
Molecular Weight 345.1353
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NICLOSAMIDE MONOHYDRATE

SMILES

c1cc(c(cc1Cl)C(=Nc2ccc(cc2Cl)N(=O)=O)O)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

HIDE SMILES / InChI

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

Description
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.

Originator

Curator's Comment:: developed by Bayer and first marketed in 1962 # Bayer

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Curative
NICLOCIDE

Approved Use

Diphyllobothriasis (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 Date

3.90095995E11
Curative
NICLOCIDE

Approved Use

Diphyllobothriasis (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 Date

3.90095995E11
Curative
NICLOCIDE

Approved Use

Diphyllobothriasis (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 Date

3.90095995E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
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

AUC

ValueDoseCo-administeredAnalytePopulation
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

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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)
Vomiting (grade 3, 2 patients)
Diarrhea (grade 3, 2 patients)
Colitis (grade 3, 2 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
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:
OverviewDrug as perpetrator​

Drug as perpetrator​

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
no
no
no
no
no
no
no
no
no
no
no
no
no
no
yes
yes
yes
yes
yes
yes
yes
yes
yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Nitazoxanide: a new broad spectrum antiparasitic agent.
2004 Feb
Polymeric controlled release formulations of niclosamide for control of Biomphalaria alexandrina, the vector snail of schistosomiasis.
2004 Feb 20
Comparison of the physical and chemical stability of niclosamide crystal forms in aqueous versus nonaqueous suspensions.
2004 Jul
[Treatment of intestinal helminthiasis with albendazole].
2005 Apr-Jun
Residues of the lampricides 3-trifluoromethyl-4-nitrophenol and niclosamide in muscle tissue of rainbow trout.
2005 Jun 29
Transport of Schistosoma japonicum cercariae and the feasibility of niclosamide for cercariae control.
2005 Mar
Effect of 4-sulphonato-calix[n]arenes and cyclodextrins on the solubilization of niclosamide, a poorly water soluble anthelmintic.
2005 Sep 2
[Case report: taeniasis, is it a cause of psychiatric and neural symptoms?].
2006
Role of chemotherapy of taeniasis in prevention of neurocysticercosis.
2006
Potential antivirals and antiviral strategies against SARS coronavirus infections.
2006 Apr
[A study on the effect of Oncomelania hupensis hupensiss killed with niclosamide in China].
2006 Aug
Synthesis of furo-salicylanilides and their heterocyclic derivatives with anticipated molluscicidal activity.
2006 Aug
Influence of certain fertilizers on the activity of some molluscicides against Biomphalaria alexandrina and Lymnaea natalensis snails.
2006 Dec
[Cleaning and molluscicide treatment for schistosomiasis control].
2006 Jan-Mar
[Synergic effects of synthesis arecoline in combination with snail-killing drugs niclosamide].
2006 Jul
Field trials of low dose Bayluscide on snail hosts of schistosome and selected non-target organisms in sahelian Cameroon.
2006 Jun
Prioritizing genomic drug targets in pathogens: application to Mycobacterium tuberculosis.
2006 Jun 9
Lower-rim substituted calixarenes and their applications.
2007
A studies on chemical control of S. mansoni intermediate host.
2007 Aug 1
Specific plant terpenoids and lignoids possess potent antiviral activities against severe acute respiratory syndrome coronavirus.
2007 Aug 23
Effect of niclosamide on the tegumental surface of Haplorchis taichui using scanning electron microscopy.
2007 Dec
[Study on molluscicidal effect of the extracts from sarcotesta of Ginkgo biloba].
2007 Feb 28
Large water management projects and schistosomiasis control, Dongting Lake region, China.
2007 Jul
Cream formulations protecting against cercarial dermatitis by Trichobilharzia.
2007 Jun
5(6)-Carboxyfluorescein diacetate as an indicator of Caenorhabditis elegans viability for the development of an in vitro anthelmintic drug assay.
2007 Mar 30
[Study on molluscicidal effect of chlorosalicylicamide].
2007 Oct
Taeniasis and its socio-economic implication in Awassa town and its surroundings, Southern Ethiopia.
2007 Oct
Sympatric occurrence of Taenia solium, T. saginata, and T. asiatica, Thailand.
2007 Sep
Community acceptability of the use of low-dose niclosamide (Bayluscide), as a molluscicide in the control of human schistosomiasis in Sahelian Cameroon.
2007 Sep
Tribendimidine and albendazole for treating soil-transmitted helminths, Strongyloides stercoralis and Taenia spp.: open-label randomized trial.
2008
[Human infection due to Bertiella sp (cestode: Anoplocephalidae) in a man originating from Yemen in Algeria].
2008 Apr
In vitro trypanocidal activity of the anti-helminthic drug niclosamide.
2008 Apr
[Snail control by using soil pasting mixed with niclosamide].
2008 Aug
Efficacy of temperature, and two commonly used molluscicides and fertilizers on Fasciola gigantica eggs.
2008 Aug
Successful treatment of niclosamide- and praziquantel-resistant beef tapeworm infection with nitazoxanide.
2008 Jan
A novel molluscicidal formulation of niclosamide.
2008 Jul
Voltammetric Behavior of o-Nitrophenol and Damage to DNA.
2008 Mar
Hymenolepis diminuta: mitochondrial transhydrogenase as an additional site for anaerobic phosphorylation.
2008 May
Potential of some monoterpenoids and their new N-methyl carbamate derivatives against Schistosomiasis snail vector, Biomphalaria alexandrina.
2008 Nov
Harnessing the wealth of Chinese scientific literature: schistosomiasis research and control in China.
2008 Sep 30
Taenia solium cysticercosis hotspots surrounding tapeworm carriers: clustering on human seroprevalence but not on seizures.
2009
A novel method for oral delivery of apolipoprotein mimetic peptides synthesized from all L-amino acids.
2009 Aug
A retrospective analysis of prevalence of gastrointestinal parasites among school children in the Palajunoj Valley of Guatemala.
2009 Feb
Spatial epidemiology in zoonotic parasitic diseases: insights gained at the 1st International Symposium on Geospatial Health in Lijiang, China, 2007.
2009 Feb 4
Drug discovery for schistosomiasis: hit and lead compounds identified in a library of known drugs by medium-throughput phenotypic screening.
2009 Jul 14
Diphyllobothrium latum identified by capsule endoscopy--an unusual cause of iron-deficiency anemia.
2009 Jun
Connectivity sustains disease transmission in environments with low potential for endemicity: modelling schistosomiasis with hydrologic and social connectivities.
2009 Jun 6
The autonomous notch signal pathway is activated by baicalin and baicalein but is suppressed by niclosamide in K562 cells.
2009 Mar 1
Multi-residue determination of phenolic and salicylanilide anthelmintics and related compounds in bovine kidney by liquid chromatography-tandem mass spectrometry.
2009 Nov 13
Halogenated pesticide transformation by a laccase-mediator system.
2009 Oct
Patents

Patents

Sample Use Guides

Adults—2 grams as a single dose. Treatment may be repeated in seven days if needed.
Route of Administration: Oral
In Vitro Use Guide
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 Fri Jun 25 21:16:55 UTC 2021
Edited
by admin
on Fri Jun 25 21:16:55 UTC 2021
Record UNII
20Z25R1145
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NICLOSAMIDE MONOHYDRATE
EP   MART.   WHO-DD   WHO-IP  
Common Name English
NICLOSAMIDE MONOHYDRATE [WHO-IP]
Common Name English
2',5-DICHLORO-4'-NITROSALICYLANILIDE MONOHYDRATE
Systematic Name English
5-CHLORO-N-(2-CHLORO-4-NITROPHENYL)-2-HYDROXYBENZAMIDE MONOHYDRATE
Systematic Name English
NICLOSAMIDE MONOHYDRATE [EP]
Common Name English
BENZAMIDE, 5-CHLORO-N-(2-CHLORO-4-NITROPHENYL)-2-HYDROXY-, HYDRATE (1:1)
Systematic Name English
NICLOSAMIDE MONOHYDRATE [WHO-DD]
Common Name English
NICLOSAMIDE MONOHYDRATE [EP MONOGRAPH]
Common Name English
NICLOSAMIDE MONOHYDRATE [MART.]
Common Name English
Code System Code Type Description
WHO INTERNATIONAL PHARMACOPEIA
NICLOSAMIDE MONOHYDRATE
Created by admin on Fri Jun 25 21:16:55 UTC 2021 , Edited by admin on Fri Jun 25 21:16:55 UTC 2021
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.
CAS
73360-56-2
Created by admin on Fri Jun 25 21:16:55 UTC 2021 , Edited by admin on Fri Jun 25 21:16:55 UTC 2021
PRIMARY
EVMPD
SUB12175MIG
Created by admin on Fri Jun 25 21:16:55 UTC 2021 , Edited by admin on Fri Jun 25 21:16:55 UTC 2021
PRIMARY
EPA CompTox
73360-56-2
Created by admin on Fri Jun 25 21:16:55 UTC 2021 , Edited by admin on Fri Jun 25 21:16:55 UTC 2021
PRIMARY
PUBCHEM
12296604
Created by admin on Fri Jun 25 21:16:55 UTC 2021 , Edited by admin on Fri Jun 25 21:16:55 UTC 2021
PRIMARY
FDA UNII
20Z25R1145
Created by admin on Fri Jun 25 21:16:55 UTC 2021 , Edited by admin on Fri Jun 25 21:16:55 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
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ACTIVE MOIETY