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Substance Name: Levamisole hydrochloride [USAN:USP]
RN: 16595-80-5
UNII: DL9055K809
InChIKey: LAZPBGZRMVRFKY-HNCPQSOCSA-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.Cl-H

Molecular Weight

  • 240.7567
 

Classification Codes

  • Biological Response Modifier
  • Drug / Therapeutic Agent
  • Human Data
  • Immunomodulator
  • Mutation Data
  • Reproductive Effect
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Names and Synonyms

Name of Substance

  • Levamisole hydrochloride [USAN:USP]

Synonyms

  • (-)-2,3,5,6-Tetrahydro-6-phenylimidazo(2,1-b)thiazole monohydrochloride
  • Ascaridil
  • Citarin L
  • Decaris
  • Dekaris
  • EINECS 240-654-6
  • Ergamisol
  • Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, (S)-
  • KW 2LE-T
  • KW-2-LE-T
  • L-(-)-2,3,5,6-Tetrahydro-6-phenyl-imidazo(2,1-b)thiazole hydrochloride
  • Levacide
  • Levadin
  • Levamisole HCl
  • Levamisole hydrochloride
  • Levasole
  • Levomysol hydrochloride
  • Meglum
  • Nemicide
  • Nilverm forte
  • Niratic hydrochloride
  • Niratic-puron hydrochloride
  • NSC-177023
  • R 12,564
  • R 12564
  • R-12,564
  • Ripercol-L
  • Solaskil
  • Spartakon
  • Stimamizol hydrochloride
  • Tramisol
  • Tramisole
  • UNII-DL9055K809
  • Worm-chek

Systematic Names

  • Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, (-)- (8CI)
  • Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, (6S)-
  • Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, (S)-
  • Imidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, monohydrochloride, L-(-)-
  • Levamisole hydrochloride

Registry Numbers

CAS Registry Number

  • 16595-80-5

FDA UNII

  • DL9055K809

Other Registry Numbers

  • 24593-45-1
  • 39170-95-1
  • 74191-78-9

Related Registry Number

  • 14769-73-4 (Parent)

System Generated Number

  • 0016595805

Molecular Formulas

Molecular Formula

  • C11-H12-N2-S.Cl-H

Molecular Formula Fragments

  • C11-H12-N2-S
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

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

InChIKey

LAZPBGZRMVRFKY-HNCPQSOCSA-N

Smiles

c1ccc(cc1)[C@H]2CN3CCSC3=N2.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
frog LD50 parenteral 363mg/kg (363mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 289, Pg. 278, 1987.
mouse LD50 intramuscular 121mg/kg (121mg/kg)   Fortschritte der Medizin. Vol. 94, Pg. 793, 1976.
mouse LD50 intraperitoneal 34mg/kg (34mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982.
mouse LD50 intravenous 18mg/kg (18mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982.
mouse LD50 oral 223mg/kg (223mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982.
mouse LD50 subcutaneous 52mg/kg (52mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: TREMOR
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982.
rat LD50 intraperitoneal 42mg/kg (42mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: TREMOR

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982.
rat LD50 intravenous 26mg/kg (26mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982.
rat LD50 oral 180mg/kg (180mg/kg)   Archives of Toxicology. Vol. 54, Pg. 275, 1983.
rat LD50 subcutaneous 80mg/kg (80mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: TREMOR
Yakuri to Chiryo. Pharmacology and Therapeutics. Vol. 10, Pg. 3141, 1982.
women TDLo oral 180mg/kg/36D (180mg/kg) BLOOD: THROMBOCYTOPENIA British Medical Journal. Vol. 2, Pg. 555, 1977.