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.
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Formula C11H12N2S
Net Charge 0
Average Mass 204.29100
Monoisotopic Mass 204.072
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 Waiting for Citations Types Sources
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Last Modified
22 February 2017