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

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)

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
[Climbing-upward inhibition of Oncomelania hupensis by niclosamide combination].
2001
Inhibition of stimulated Jurkat cell adenosine 3',5'-cyclic monophosphate synthesis by the immunomodulatory compound HR325.
2001 Jan 15
Effect of soil moisture and sample depth on pesticide photolysis.
2002 Apr 24
Transplasma membrane electron transport in Leishmania donovani promastigotes.
2002 Jan-Feb
Antiprotozoals effective in vitro against the scuticociliate fish pathogen Philasterides dicentrarchi.
2002 Jun 3
Generation and evaluation of a CYP2C9 heteroactivation pharmacophore.
2003 Dec
Measures for the prevention and control of Taenia solium taeniosis and cysticercosis.
2003 Jun
Investigations on the influence of helminth parasites on vaccination of chickens against Newcastle disease virus under village conditions.
2003 Oct
Human Monieziasis expansa: the first Egyptian parastic zoonosis.
2004 Aug
Polymeric controlled release formulations of niclosamide for control of Biomphalaria alexandrina, the vector snail of schistosomiasis.
2004 Feb 20
Aqueous photolysis of niclosamide.
2004 Feb 25
Adverse drug reactions to anthelmintics.
2004 Mar
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
[Treatment of intestinal helminthiasis with albendazole].
2005 Apr-Jun
Effect of 4-sulphonato-calix[n]arenes and cyclodextrins on the solubilization of niclosamide, a poorly water soluble anthelmintic.
2005 Sep 2
Lower-rim substituted calixarenes and their applications.
2007
Potential of some monoterpenoids and their new N-methyl carbamate derivatives against Schistosomiasis snail vector, Biomphalaria alexandrina.
2008 Nov
A novel method for oral delivery of apolipoprotein mimetic peptides synthesized from all L-amino acids.
2009 Aug
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
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 Wed Jul 05 22:51:42 UTC 2023
Edited
by admin
on Wed Jul 05 22:51:42 UTC 2023
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
NICLOSAMIDE [ISO]
Common Name English
NICLOSAMIDE [HSDB]
Common Name English
NICLOSAMIDE [EP MONOGRAPH]
Common Name English
BAY 2353
Code English
NICLOCIDE
Brand Name English
Niclosamide [WHO-DD]
Common 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, ANHYDROUS [EP IMPURITY]
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
5-CHLORO-N-(2-CHLORO-4-NITROPHENYL)-2-HYDROXYBENZAMIDE
Systematic Name English
NICLOSAMIDUM ANHYDROUS [WHO-IP LATIN]
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 Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
EPA PESTICIDE CODE 77401
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
WHO-ESSENTIAL MEDICINES LIST 6.1.1
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
EPA PESTICIDE CODE 217800
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
WHO-ATC P02DA01
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
WHO-VATC QP52AG03
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
Code System Code Type Description
SMS_ID
100000092044
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-056-8
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
HSDB
1572
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
MERCK INDEX
M7874
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY Merck Index
NSC
178296
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
ChEMBL
CHEMBL1448
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
EVMPD
SUB12176MIG
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
DRUG CENTRAL
1912
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
NCI_THESAURUS
C66240
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
WIKIPEDIA
NICLOSAMIDE
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
MESH
D009534
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
EVMPD
SUB09230MIG
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
FDA UNII
8KK8CQ2K8G
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
CAS
50-65-7
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
INN
1532
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
ALANWOOD
niclosamide
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
LACTMED
Niclosamide
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
DRUG BANK
DB06803
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
PUBCHEM
4477
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
NICLOSAMIDE
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
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
DTXSID7040362
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY
RXCUI
7402
Created by admin on Wed Jul 05 22:51:42 UTC 2023 , Edited by admin on Wed Jul 05 22:51:42 UTC 2023
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
SOLVATE->ANHYDROUS
Related Record Type Details
METABOLITE -> PARENT
METABOLITE -> PARENT
Related Record Type Details
ACTIVE MOIETY