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Substance Name: Levamisole [INN:BAN]
RN: 14769-73-4
UNII: 2880D3468G
InChIKey: HLFSDGLLUJUHTE-SNVBAGLBSA-N

Note

  • 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 Formula

  • C11-H12-N2-S

Molecular Weight

  • 204.2958
 

Classification Codes

  • Adjuvants, Immunologic
  • Anthelmintics
  • Anti-Infective Agents
  • Antinematodal Agents
  • Antiparasitic Agents
  • Antirheumatic Agents
  • Antiviral (COVID-19)
  • Drug / Therapeutic Agent
  • Immunologic Factors
  • Mutation Data
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Names and Synonyms

Name of Substance

  • Levamisole
  • Levamisole [INN:BAN]

MeSH Heading

  • Levamisole

Synonyms

  • (-)-Tetramisole
  • (S)-(-)-Levamisole
  • EINECS 238-836-5
  • Ergamisol
  • Ketrax
  • L-2,3,5,6-Tetrahyro-6-phenylimidazo(2,1-b)thiazole
  • L-Tetramisole
  • Lepuron
  • Levamisol
  • Levamisol [INN-Spanish]
  • Levamisole
  • Levamisolum
  • Levamisolum [INN-Latin]
  • Levomysol
  • UNII-2880D3468G
  • Vermisol 150
  • Wormicid

Systematic Names

  • Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, (6S)-
  • Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, (S)-
  • Levamisole

Registry Numbers

CAS Registry Number

  • 14769-73-4

FDA UNII

  • 2880D3468G

Other Registry Number

  • 53096-13-2

Related Registry Number

  • 16595-80-5 (hydrochloride)

System Generated Number

  • 0014769734

Structure Descriptors

InChI

InChI=1S/C11H12N2S/c1-2-4-9(5-3-1)10-8-13-6-7-14-11(13)12-10/h1-5,10H,6-8H2/t10-/m1/s1

InChIKey

HLFSDGLLUJUHTE-SNVBAGLBSA-N

Smiles

C1CN2C[C@@H](N=C2S1)c3ccccc3

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
mouse LD50 intraperitoneal 43mg/kg (43mg/kg)   Pharmaceutical Chemistry Journal Vol. 30, Pg. 448, 1996.
mouse LD50 intravenous 22mg/kg (22mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979.
mouse LD50 oral 210mg/kg (210mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE		 Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979.
mouse LD50 subcutaneous 84mg/kg (84mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979.
rabbit LD50 intravenous 15mg/kg (15mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE		 Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979.
rabbit LD50 oral 700mg/kg (700mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: EXCITEMENT		 Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979.
rat LD50 intravenous 24mg/kg (24mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE

BEHAVIORAL: EXCITEMENT		 Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979.
rat LD50 oral 480mg/kg (480mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

SENSE ORGANS AND SPECIAL SENSES: OTHER: EYE		 Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 407, 1979.
rat LD50 subcutaneous 120mg/kg (120mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD		 MBI, Mediko Biologicheskaya Informatsiya. Medical-Biological Information. Vol. (6), Pg. 27, 1985.

Physical Properties

Physical Property Value Units Temp (deg C) Source
log P (octanol-water) 1.84 (none)   EXP
Water Solubility 1120 mg/L 25 EST
Vapor Pressure 1.11E-04 mm Hg 25 EST
Henry's Law Constant 4.03E-10 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 3.33E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.