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Niclosamide
Identification
- Name
- Niclosamide
- Accession Number
- DB06803
- Description
Niclosamide is an antihelminthic used for the treatment of tapeworm infections. Helminths (worms) are multicellular organisms that infect very large numbers of humans and cause a broad range of diseases. Over 1 billion people are infected with intestinal nematodes, and many millions are infected with filarial nematodes, flukes, and tapeworms. They are an even greater problem in domestic animals.
Niclosamide, once marketed in the US under the brand name Niclocide, was voluntarily withdrawn from market by Bayer in 1996.2
- Type
- Small Molecule
- Groups
- Approved, Investigational, Vet approved
- Structure
Structure for Niclosamide (DB06803)
- Weight
- Average: 327.12
Monoisotopic: 325.986112168 - Chemical Formula
- C13H8Cl2N2O4
- Synonyms
- Not Available
- External IDs
- BAY 2353
- NSC-178296
- WR 46234
Pharmacology
- Indication
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.
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- Pharmacodynamics
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.
- Mechanism of action
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.
Target Actions Organism UDNA antagonistHumans - Absorption
Niclosamide appears to be minimally absorbed from the gastrointestinal tract—neither the drug nor its metabolites have been recovered from the blood or urine.
- Volume of distribution
- Not Available
- Protein binding
- Not Available
- Metabolism
- Not Available
- Route of elimination
- Not Available
- Half-life
- Not Available
- Clearance
- Not Available
- Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More- Toxicity
Infrequent, mild, and transitory adverse events include nausea, vomiting, diarrhea, and abdominal discomfort.
- Affected organisms
- Helminthic Microorganisms
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Unlock Additional DataAbatacept The metabolism of Niclosamide can be increased when combined with Abatacept. Abiraterone The metabolism of Niclosamide can be decreased when combined with Abiraterone. Acenocoumarol The metabolism of Acenocoumarol can be decreased when combined with Niclosamide. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Niclosamide. Acetohexamide The metabolism of Niclosamide can be decreased when combined with Acetohexamide. Acetyl sulfisoxazole The metabolism of Niclosamide can be decreased when combined with Acetyl sulfisoxazole. Acetylsalicylic acid The metabolism of Niclosamide can be decreased when combined with Acetylsalicylic acid. Acyclovir The metabolism of Acyclovir can be decreased when combined with Niclosamide. Adalimumab The metabolism of Niclosamide can be increased when combined with Adalimumab. Agomelatine The metabolism of Agomelatine can be decreased when combined with Niclosamide. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- Food Interactions
- Not Available
Products
- International/Other Brands
- Niclocide
Categories
- ATC Codes
- P02DA01 — Niclosamide
- Drug Categories
- Agrochemicals
- Amides
- Amines
- Anilides
- Aniline Compounds
- Anthelmintics
- Anti-Infective Agents
- Anticestodal Agents
- Anticestodals
- Antinematodal Agents
- Antiparasitic Agents
- Antiparasitic Products, Insecticides and Repellents
- Antiplatyhelmintic Agents
- Compounds used in a research, industrial, or household setting
- Cytochrome P-450 CYP1A2 Inhibitors
- Cytochrome P-450 CYP1A2 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Molluscacides
- Pesticides
- Salicylamides
- Salicylanilides
- Salicylic Acid Derivatives
- Toxic Actions
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Anilides
- Direct Parent
- Benzanilides
- Alternative Parents
- Salicylamides / 3-halobenzoic acids and derivatives / Benzamides / Nitrobenzenes / P-chlorophenols / Benzoyl derivatives / Nitroaromatic compounds / 1-hydroxy-2-unsubstituted benzenoids / Chlorobenzenes / Aryl chlorides show 11 more
- Substituents
- 1-hydroxy-2-unsubstituted benzenoid / 3-halobenzoic acid or derivatives / 4-chlorophenol / 4-halophenol / Allyl-type 1,3-dipolar organic compound / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Benzamide / Benzanilide show 29 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- Not Available
Chemical Identifiers
- UNII
- 8KK8CQ2K8G
- CAS number
- 50-65-7
- InChI Key
- RJMUSRYZPJIFPJ-UHFFFAOYSA-N
- InChI
- 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)
- IUPAC Name
- 5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide
- SMILES
- OC1=C(C=C(Cl)C=C1)C(=O)NC1=C(Cl)C=C(C=C1)[N+]([O-])=O
References
- Synthesis Reference
- US3079297
- General References
- Thomson Micromedex (2007). Advice for the Patient Volume II (27th ed.). PDR Network, LLC. [ISBN:1-56363-575-5]
- Federal Register: Withdrawal of Approval of 29 NADA's (July 3, 1996) [Link]
- External Links
- Human Metabolome Database
- HMDB0015679
- KEGG Drug
- D00436
- PubChem Compound
- 4477
- PubChem Substance
- 99443295
- ChemSpider
- 4322
- BindingDB
- 11242
- 7402
- ChEBI
- 7553
- ChEMBL
- CHEMBL1448
- ZINC
- ZINC000003874496
- PharmGKB
- PA165958408
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Niclosamide
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Not Yet Recruiting Treatment Nephropathy, Diabetic 1 3 Not Yet Recruiting Treatment Novel Coronavirus Infectious Disease (COVID-19) 1 2 Not Yet Recruiting Treatment COVID / COVID - 19 / Novel Coronavirus Infectious Disease (COVID-19) 1 2 Not Yet Recruiting Treatment Novel Coronavirus Infectious Disease (COVID-19) 2 2 Recruiting Treatment Colorectal Cancers 1 2 Recruiting Treatment Familial Adenomatous Polyposis (FAP) 1 2 Recruiting Treatment Metastatic Hormone Refractory Prostate Cancer / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer 1 1 Completed Treatment Castration Levels of Testosterone / Castration-Resistant Prostate Carcinoma / Hormone-Resistant Prostate Cancer / Metastatic Hormone Refractory Prostate Cancer / Recurrent Prostate Carcinoma / Stage IV Prostate Adenocarcinoma 1 1 Recruiting Treatment Metastatic Hormone Refractory Prostate Cancer / Recurrent Prostate Carcinoma / Stage IV Prostate Cancer 1 1 Terminated Other Malignant Neoplasm of Colon 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Tablet 500 mg Tablet Oral 500 MG Tablet 0.5 g - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 230 °C PhysProp water solubility 1.6 mg/L (at 20 °C) TOMLIN,C (1997) - Predicted Properties
Property Value Source Water Solubility 0.00799 mg/mL ALOGPS logP 4.49 ALOGPS logP 3.91 ChemAxon logS -4.6 ALOGPS pKa (Strongest Acidic) 6.89 ChemAxon pKa (Strongest Basic) -4.4 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 4 ChemAxon Hydrogen Donor Count 2 ChemAxon Polar Surface Area 95.15 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 80.51 m3·mol-1 ChemAxon Polarizability 28.47 Å3 ChemAxon Number of Rings 2 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.7721 Blood Brain Barrier + 0.7259 Caco-2 permeable + 0.5 P-glycoprotein substrate Non-substrate 0.7857 P-glycoprotein inhibitor I Non-inhibitor 0.8671 P-glycoprotein inhibitor II Non-inhibitor 0.9349 Renal organic cation transporter Non-inhibitor 0.9267 CYP450 2C9 substrate Non-substrate 0.721 CYP450 2D6 substrate Non-substrate 0.8519 CYP450 3A4 substrate Substrate 0.5187 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Inhibitor 0.8948 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Inhibitor 0.6943 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.8442 Ames test AMES toxic 0.9107 Carcinogenicity Carcinogens 0.5513 Biodegradation Not ready biodegradable 0.9803 Rat acute toxicity 2.2390 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.914 hERG inhibition (predictor II) Non-inhibitor 0.8434
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
Unknown
Antagonist
References
- Abreu FC, Goulart MO, Brett AM: Detection of the damage caused to DNA by niclosamide using an electrochemical DNA-biosensor. Biosens Bioelectron. 2002 Dec;17(11-12):913-9. [PubMed:12392939]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Substrate
- General Function
- Steroid hydroxylase activity
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- Bapiro TE, Egnell AC, Hasler JA, Masimirembwa CM: Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5. [PubMed:11124226]
- Egnell AC, Eriksson C, Albertson N, Houston B, Boyer S: Generation and evaluation of a CYP2C9 heteroactivation pharmacophore. J Pharmacol Exp Ther. 2003 Dec;307(3):878-87. Epub 2003 Oct 13. [PubMed:14557374]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Data limited to in vitro studies.
- General Function
- Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, reduced flavin or flavoprotein as one donor, and incorporation of one atom of oxygen
- Specific Function
- Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
- Gene Name
- CYP1A2
- Uniprot ID
- P05177
- Uniprot Name
- Cytochrome P450 1A2
- Molecular Weight
- 58293.76 Da
References
- Bapiro TE, Egnell AC, Hasler JA, Masimirembwa CM: Application of higher throughput screening (HTS) inhibition assays to evaluate the interaction of antiparasitic drugs with cytochrome P450s. Drug Metab Dispos. 2001 Jan;29(1):30-5. [PubMed:11124226]
Drug created on September 14, 2010 10:21 / Updated on August 01, 2020 06:24
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