U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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
Structure of NICLOSAMIDE

SMILES

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

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

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
Measures for the prevention and control of Taenia solium taeniosis and cysticercosis.
2003 Jun
Piperazine N-substituted naphthyridines, pyridothienopyrimidines and pyridothienotriazines: new antiprotozoals active against Philasterides dicentrarchi.
2003 Mar
Overview of hymenolepis diminuta infection among Thai patients.
2004 Apr 22
The Hymenolepis diminuta-golden hamster (Mesocricetus auratus) model for the evaluation of gastrointestinal anticestode activity.
2004 Aug
Human Monieziasis expansa: the first Egyptian parastic zoonosis.
2004 Aug
Nitazoxanide: a new broad spectrum antiparasitic agent.
2004 Feb
Preparation and physicochemical characterization of 5 niclosamide solvates and 1 hemisolvate.
2004 Feb 23
Preparation and physicochemical properties of niclosamide anhydrate and two monohydrates.
2004 Jan 28
[Efficacy of the Russian anthelmintic agent trichlorophen].
2004 Jan-Mar
Bertiella studeri infection: resistance to niclosamide.
2004 Jun
Molluscicidal effect of nicotinanilide and its intermediate compounds against a freshwater snail Lymnaea luteola, the vector of animal schistosomiasis.
2004 Mar
Purging the worm: management of Taenia solium taeniasis.
2004 Mar 20
Influence of moisture on the crystal forms of niclosamide obtained from acetone and ethyl acetate.
2004 Mar 4
[Treatment of intestinal helminthiasis with albendazole].
2005 Apr-Jun
Impact of certain plants and synthetic molluscicides on some fresh water snails and fish.
2005 Dec
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
[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
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
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
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
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
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
Connectivity sustains disease transmission in environments with low potential for endemicity: modelling schistosomiasis with hydrologic and social connectivities.
2009 Jun 6
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 21:08:11 UTC 2021
Edited
by admin
on Fri Jun 25 21:08:11 UTC 2021
Record UNII
8KK8CQ2K8G
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NICLOSAMIDE
GREEN BOOK   HSDB   INN   ISO   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
DWRX2003 COMPONENT NICLOSAMIDE
Common Name English
NICLOSAMIDE [ISO]
Common Name English
NICLOSAMIDE [HSDB]
Common Name English
NICLOSAMIDE [EP MONOGRAPH]
Common Name English
NICLOSAMIDE COMPONENT OF DWRX2003
Common Name English
BAY 2353
Code English
NICLOCIDE
Brand Name English
BENZAMIDE, 5-CHLORO-N-(2-CHLORO-4-NITROPHENYL)-2-HYDROXY-
Systematic Name English
NICLOSAMIDE [INN]
Common Name English
BAY-2353
Code English
NICLOSAMIDE [ORANGE BOOK]
Common Name English
NICLOSAMIDE [USAN]
Common Name English
NICLOSAMIDE [MART.]
Common Name English
2',5-DICHLORO-4'-NITROSALICYLANILIDE
Systematic Name English
NICLOSAMIDE [VANDF]
Common Name English
NICLOSAMIDE ANHYDROUS [WHO-IP]
Common Name English
NICLOSAMIDE [MI]
Common Name English
DWRX-2003 COMPONENT NICLOSAMIDE
Common Name English
NICLOSAMIDE, ANHYDROUS [EP]
Common Name English
5-CHLORO-N-(2-CHLORO-4-NITROPHENYL)-2-HYDROXYBENZAMIDE
Systematic Name English
NICLOSAMIDUM ANHYDROUS [WHO-IP LATIN]
Common Name English
NICLOSAMIDE [WHO-DD]
Common Name English
NICLOSAMIDE, ANHYDROUS
EP  
Common Name English
WR 46234
Code English
NICLOSAMIDE [GREEN BOOK]
Common Name English
NSC-178296
Code English
NICLOSAMIDE (ANHYDROUS)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C250
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
EPA PESTICIDE CODE 77401
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
WHO-ESSENTIAL MEDICINES LIST 6.1.1
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
EPA PESTICIDE CODE 217800
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
WHO-ATC P02DA01
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
WHO-VATC QP52AG03
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
Code System Code Type Description
ECHA (EC/EINECS)
200-056-8
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
HSDB
1572
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
MERCK INDEX
M7874
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY Merck Index
ChEMBL
CHEMBL1448
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
EVMPD
SUB12176MIG
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
DRUG CENTRAL
1912
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
NCI_THESAURUS
C66240
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
WIKIPEDIA
NICLOSAMIDE
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
MESH
D009534
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
EVMPD
SUB09230MIG
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
FDA UNII
8KK8CQ2K8G
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
CAS
50-65-7
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
INN
1532
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
LACTMED
Niclosamide
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
DRUG BANK
DB06803
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
PUBCHEM
4477
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NICLOSAMIDE
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 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.
EPA CompTox
50-65-7
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY
RXCUI
7402
Created by admin on Fri Jun 25 21:08:11 UTC 2021 , Edited by admin on Fri Jun 25 21:08:11 UTC 2021
PRIMARY RxNorm
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ACTIVE MOIETY