levamisole Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1561 14769-73-4

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • levamisole hydrochloride
  • levamisole
  • tetramisole
  • levamisol
  • levamizol
  • tetramisole hydrochloride
  • levamisole HCl
  • tetramisole HCl
An antihelminthic drug that has been tried experimentally in rheumatic disorders where it apparently restores the immune response by increasing macrophage chemotaxis and T-lymphocyte function. Paradoxically, this immune enhancement appears to be beneficial in rheumatoid arthritis where dermatitis, leukopenia, and thrombocytopenia, and nausea and vomiting have been reported as side effects. (From Smith and Reynard, Textbook of Pharmacology, 1991, p435-6)
  • Molecular weight: 204.29
  • Formula: C11H12N2S
  • CLOGP: 1.84
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 15.60
  • ALOGS: -2.15
  • ROTB: 1

  • Status: OFM

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

DoseUnitRoute
0.15 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 1 Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 4.08 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 65 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
June 18, 1990 FDA

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Toxicity to various agents 111.65 98.26 39 165 211727 46474131

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Toxicity to various agents 164.83 87.06 66 315 177117 29774980

Pharmacologic Action:

SourceCodeDescription
ATC P02CE01 ANTIPARASITIC PRODUCTS, INSECTICIDES AND REPELLENTS
ANTHELMINTICS
ANTINEMATODAL AGENTS
Imidazothiazole derivatives
MeSH PA D000276 Adjuvants, Immunologic
MeSH PA D000871 Anthelmintics
MeSH PA D000890 Anti-Infective Agents
MeSH PA D000969 Antinematodal Agents
MeSH PA D000977 Antiparasitic Agents
MeSH PA D018501 Antirheumatic Agents
MeSH PA D007155 Immunologic Factors
CHEBI has role CHEBI:35444 antinematodals
CHEBI has role CHEBI:35842 antirheumatic agent
CHEBI has role CHEBI:50846 biomodulator
CHEBI has role CHEBI:50847 immunostimulant
CHEBI has role CHEBI:63332 alkaline phosphatase inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Ascariasis indication 2435008 DOID:456
Ancylostomiasis indication 63479002 DOID:12841

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 8.2 Basic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Alkaline phosphatase, tissue-nonspecific isozyme Enzyme Ki 4.80 CHEMBL
Nicotinic acetylcholine receptor alpha subunit Ion channel AGONIST CHEMBL CHEMBL
Acetylcholine receptor subunit alpha-type unc-63 Ion channel WOMBAT-PK
Membrane-associated progesterone receptor component 1 Membrane receptor Ki 5.57 DRUG MATRIX
Alkaline phosphatase, tissue-nonspecific isozyme Unclassified IC50 4.72 CHEMBL

External reference:

IDSource
D00750 KEGG_DRUG
16595-80-5 SECONDARY_CAS_RN
4019531 VANDF
C0023556 UMLSCUI
CHEBI:6432 CHEBI
CHEMBL1454 ChEMBL_ID
CHEMBL1770 ChEMBL_ID
CHEMBL277775 ChEMBL_ID
CHEMBL554891 ChEMBL_ID
D007978 MESH_DESCRIPTOR_UI
D013773 MESH_DESCRIPTOR_UI
DB00848 DRUGBANK_ID
7210 IUPHAR_LIGAND_ID
2643 INN_ID
1973 INN_ID
2880D3468G UNII
26879 PUBCHEM_CID
227227 RXNORM
4967 MMSL
d00276 MMSL
003546 NDDF
004809 NDDF
387296006 SNOMEDCT_US
54391004 SNOMEDCT_US
81365005 SNOMEDCT_US

Pharmaceutical products:

None