CHEBI:6432 - levamisole

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ChEBI Name levamisole
ChEBI ID CHEBI:6432
Definition A 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole that has S configuration. It is used (generally as the monohydrochloride salt) to treat parasitic worm infections in pigs, sheep and cattle and was formerly used in humans as an adjuvant to chemotherapy for the treatment of various cancers. It is also widely used as an adulterant to coccaine.
Stars This entity has been manually annotated by the ChEBI Team.
Supplier Information eMolecules:29542986, ZINC000000119839
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Levamisole, sold under the brand name Ergamisol among others, is a medication used to treat parasitic worm infections, specifically ascariasis and hookworm infections. It is taken by mouth. Side effects may include abdominal pain, vomiting, headache, and dizziness. Use is not recommended during breastfeeding or the third trimester of pregnancy. Serious side effects may include an increased risk of infection. It belongs to the anthelmintic class of medications. Levamisole was invented in 1966 in Belgium by Janssen Pharmaceuticals. It is on the World Health Organization's List of Essential Medicines. Levamisole is also used as a dewormer for cattle.
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Formula C11H12N2S
Net Charge 0
Average Mass 204.29100
Monoisotopic Mass 204.07212
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)c1ccccc1
Roles Classification
Chemical Role(s): environmental contaminant
Any minor or unwanted substance introduced into the environment that can have undesired effects.
(via 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole )
Biological Role(s): immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
immunological adjuvant
A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
EC 3.1.3.1 (alkaline phosphatase) inhibitor
An EC 3.1.3.* (phosphoric monoester hydrolase) inhibitor that interferes with the action of alkaline phosphatase (EC 3.1.3.1).
xenobiotic
A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
(via 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole )
Application(s): antinematodal drug
A substance used in the treatment or control of nematode infestations.
antirheumatic drug
A drug used to treat rheumatoid arthritis.
immunomodulator
Biologically active substance whose activity affects or plays a role in the functioning of the immune system.
immunological adjuvant
A substance that augments, stimulates, activates, potentiates, or modulates the immune response at either the cellular or humoral level. A classical agent (Freund's adjuvant, BCG, Corynebacterium parvum, et al.) contains bacterial antigens. It could also be endogenous (e.g., histamine, interferon, transfer factor, tuftsin, interleukin-1). Its mode of action is either non-specific, resulting in increased immune responsiveness to a wide variety of antigens, or antigen-specific, i.e., affecting a restricted type of immune response to a narrow group of antigens. The therapeutic efficacy is related to its antigen-specific immunoadjuvanticity.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing levamisole (CHEBI:6432) has role antinematodal drug (CHEBI:35444)
levamisole (CHEBI:6432) has role antirheumatic drug (CHEBI:35842)
levamisole (CHEBI:6432) has role EC 3.1.3.1 (alkaline phosphatase) inhibitor (CHEBI:63332)
levamisole (CHEBI:6432) has role immunological adjuvant (CHEBI:50847)
levamisole (CHEBI:6432) has role immunomodulator (CHEBI:50846)
levamisole (CHEBI:6432) is a 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole (CHEBI:77278)
levamisole (CHEBI:6432) is enantiomer of dexamisole (CHEBI:77282)
Incoming tetramisole (CHEBI:77289) has part levamisole (CHEBI:6432)
dexamisole (CHEBI:77282) is enantiomer of levamisole (CHEBI:6432)
IUPAC Name
(6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole
INNs Sources
levamisol WHO MedNet
lévamisole WHO MedNet
levamisole WHO MedNet
levamisolum WHO MedNet
Synonyms Sources
(−)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole ChEBI
(−)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole ChEBI
(−)-tetramisole ChemIDplus
(S)-(−)-levamisole ChemIDplus
(S)-(−)-tetramisole ChEBI
(S)-2,3,5,6-tetrahydro-6-phenylimidazo[2,1-b]thiazole ChEBI
Brand Names Sources
Ketrax KEGG DRUG
Lepuron ChemIDplus
Levomysol ChemIDplus
Levovermax ChEBI
Totalon ChEBI
Wormicid ChemIDplus
Manual Xrefs Databases
1561 DrugCentral
1798 VSDB
C07070 KEGG COMPOUND
D08114 KEGG DRUG
DB00848 DrugBank
HMDB0014986 HMDB
Levamisole Wikipedia
LSM-6655 LINCS
US3274209 Patent
US3565907 Patent
US3579530 Patent
View more database links
Registry Numbers Types Sources
14769-73-4 CAS Registry Number KEGG COMPOUND
14769-73-4 CAS Registry Number ChemIDplus
4233256 Reaxys Registry Number Reaxys
Citations
Michaud K, Grabherr S, Shiferaw K, Doenz F, Augsburger M, Mangin P (2014)
Acute coronary syndrome after levamisole-adultered cocaine abuse.
Journal of forensic and legal medicine 21, 48-52 [PubMed:24365689]
[show Abstract]
Xiao Y, Li J, Fu C (2014)
A sensitive method for the determination of levamisole in serum by electrochemiluminescence.
Luminescence : the journal of biological and chemical luminescence 29, 183-187 [PubMed:23649929]
[show Abstract]
Tallarida CS, Egan E, Alejo GD, Raffa R, Tallarida RJ, Rawls SM (2014)
Levamisole and cocaine synergism: a prevalent adulterant enhances cocaine's action in vivo.
Neuropharmacology 79, 590-595 [PubMed:24440755]
[show Abstract]
Suran J, Flajs D, Peraica M, Prevendar Crnić A, Speranda M, Božić F (2013)
Pharmacokinetics of an immunomodulating dose of levamisole in weaned pigs.
Acta veterinaria Hungarica 61, 376-382 [PubMed:23921349]
[show Abstract]
Shea JL (2013)
Bioanalytical methods for quantitation of levamisole, a widespread cocaine adulterant.
Clinical chemistry and laboratory medicine 51, 205-212 [PubMed:23152411]
[show Abstract]
Sanadgol H (2013)
Levamisole usage as an adjuvant to hepatitis B vaccine in hemodialysis patients, yes or no?
Nephro-urology monthly 5, 673-678 [PubMed:23577329]
[show Abstract]
Abdul-Karim R, Ryan C, Rangel C, Emmett M (2013)
Levamisole-induced vasculitis.
Proceedings (Baylor University. Medical Center) 26, 163-165 [PubMed:23543977]
[show Abstract]
Casale JF, Colley VL, Legatt DF (2012)
Determination of phenyltetrahydroimidazothiazole enantiomers (Levamisole/Dexamisole) in illicit cocaine seizures and in the urine of cocaine abusers via chiral capillary gas chromatography-flame-ionization detection: clinical and forensic perspectives.
Journal of analytical toxicology 36, 130-135 [PubMed:22337783]
[show Abstract]
Dy IA, Wiernik PH (2012)
Cocaine-levamisole thrombotic vasculopathy.
Seminars in thrombosis and hemostasis 38, 780-782 [PubMed:23041983]
[show Abstract]
Martin RJ, Robertson AP, Buxton SK, Beech RN, Charvet CL, Neveu C (2012)
Levamisole receptors: a second awakening.
Trends in parasitology 28, 289-296 [PubMed:22607692]
[show Abstract]
Martin RJ, Robertson AP (2007)
Mode of action of levamisole and pyrantel, anthelmintic resistance, E153 and Q57.
Parasitology 134, 1093-1104 [PubMed:17608969]
[show Abstract]
Scheinfeld N, Rosenberg JD, Weinberg JM (2004)
Levamisole in dermatology : a review.
American journal of clinical dermatology 5, 97-104 [PubMed:15109274]
[show Abstract]
Kutzler MA, Solter PF, Hoffman WE, Volkmann DH (2003)
Characterization and localization of alkaline phosphatase in canine seminal plasma and gonadal tissues.
Theriogenology 60, 299-306 [PubMed:12749943]
[show Abstract]
Magnusson P, Farley JR (2002)
Differences in sialic acid residues among bone alkaline phosphatase isoforms: a physical, biochemical, and immunological characterization.
Calcified tissue international 71, 508-518 [PubMed:12232676]
[show Abstract]
Sanchez MR (2000)
Miscellaneous treatments: thalidomide, potassium iodide, levamisole, clofazimine, colchicine, and D-penicillamine.
Clinics in dermatology 18, 131-145 [PubMed:10701095]
Amery WK, Bruynseels JP (1992)
Levamisole, the story and the lessons.
International journal of immunopharmacology 14, 481-486 [PubMed:1618599]
[show Abstract]
Janssen PA (1991)
Levamisole as an adjuvant in cancer treatment.
Journal of clinical pharmacology 31, 396-400 [PubMed:2050823]
Drannik GN, Kolesnik NA (1982)
[Use of levamisole in nephrological practice (a review of the literature)].
Vrachebnoe delo12-16 [PubMed:7051554]
Spreafico F (1980)
Use of levamisole in cancer patients.
Drugs 20, 105-116 [PubMed:6995092]
Miller MJ (1980)
Use of levamisole in parasitic infections.
Drugs 20, 122-130 [PubMed:6995094]
[show Abstract]
Symoens J, Veys E, Mielants M, Pinals R (1978)
Adverse reactions to levamisole.
Cancer treatment reports 62, 1721-1730 [PubMed:365327]
[show Abstract]
Hozumi T, Iwaguchi T, Kitagawa H, Ozawa H (1978)
Anticancer activity of isomers of 6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole.
Gan 69, 339-343 [PubMed:669135]
[show Abstract]
Wilton JM (1978)
Levamisole in chronic inflammatory diseases.
The Journal of rheumatology. Supplement 4, 101-113 [PubMed:366135]
[show Abstract]
Amery WK, Verhaegen H (1978)
Effects of levamisole treatment in cancer patients.
The Journal of rheumatology. Supplement 4, 123-135 [PubMed:366137]
[show Abstract]
Vanhoutte PM, Van Nueten JM, Verbeuren TJ, Laduron PM (1977)
Differential effects of the isomers of tetramisole on adrenergic neurotransmission in cutaneous veins of dog.
The Journal of pharmacology and experimental therapeutics 200, 127-140 [PubMed:189006]
[show Abstract]
Janssen PA (1976)
The levamisole story.
Progress in drug research. Fortschritte der Arzneimittelforschung. Progres des recherches pharmaceutiques 20, 347-383 [PubMed:827785]
Last Modified
22 February 2017