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

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
Antituberculosis activity of certain antifungal and antihelmintic drugs.
1999
Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s.
2001 Jan
Biochemical and metabolic peculiarities of some parasites availing as targets for therapy.
2001 Jul-Aug
Effect of soil moisture and sample depth on pesticide photolysis.
2002 Apr 24
Per oral removal of tapeworm following vomiting after surgery.
2002 Oct
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
Physical transformation of niclosamide solvates in pharmaceutical suspensions determined by DSC and TG analysis.
2004 Jul
Adverse drug reactions to anthelmintics.
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
Metabolism of niclosamide in sediment and water systems.
2004 Sep 22
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
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
In vitro trypanocidal activity of the anti-helminthic drug niclosamide.
2008 Apr
Successful treatment of niclosamide- and praziquantel-resistant beef tapeworm infection with nitazoxanide.
2008 Jan
Voltammetric Behavior of o-Nitrophenol and Damage to DNA.
2008 Mar
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.
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