Levamisole

HCID 26879
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Basic information

CAS
14769-73-4
Standard SMILES
c1ccc([C@H]2CN3CCSC3=N2)cc1
InChIKey
HLFSDGLLUJUHTE-SNVBAGLBSA-N
Molecular formula
C11H12N2S
Average molar mass
204.29 g/mol
Monoisotopic mass
204.07211956

Names & identifiers

Preferred name
Levamisole
IUPAC
(6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole
English name
Levamisole
Molecular formula
C11H12N2S
Molecular weight
204.29

Names & synonyms

levamisole14769-73-4LevamisolKetraxL-TetramisoleLepuronLEVOMYSOLWormicid(S)-(-)-LevamisoleLevamisolum(-)-Tetramisole(6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole
Show more names
LEVAMISOLE BASE(S)-6-phenyl-2,3,5,6-tetrahydroiMidazo[2,1-b]thiazole(?)-LevamisoleLevamisole WickrLevamisole powder
Tetramisole, (s)-Totalon(6S)-6-phenyl-2H,3H,5H,6H-imidazo[2,1-b][1,3]thiazoleImidazo[2,1-b]thiazole, 2,3,5,6-tetrahydro-6-phenyl-, (6S)-(S)-2,3,5,6-Tetrahydro-6-phenylimidazo[2,1-b]thiazoleImidazo(2,1-b)thiazole, 2,3,5,6-tetrahydro-6-phenyl-, (S)-CHEBI:64322880D3468G

Database identifiers

CAS
14769-73-4
PubChem CID
26879
DTXSID
DTXSID4023206
ChEMBL
CHEMBL1454
ChEBI
CHEBI:6432
UNII
2880D3468G
EC Number
238-836-5
Nikkaji
J8.518I

Properties

Computed structural properties

XLogP
1.8
Topological polar surface area
40.9 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
2
Rotatable bonds
1
Heavy atoms
14

Physicochemical properties

Melting point
60 · 60-61.5°
alpha
25 · D25 -85.1° (c = 10 in chloroform)
Boiling point
344.4 · 344.4±45.0 °C(Predicted)
Density
1.32 · 1.32±0.1 g/cm3(Predicted)
storage temp.
2 · Sealed in dry,2-8°C
solubility
Chloroform (Slightly), Methanol (Slightly)

Safety & regulation

Safety data

Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302+H312+H332-H315-H319-H335
Precautionary statements
P261-P264b-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362+P364-P403+P233-P501c

Chemistry & industry

Applications · 2 items

UsesLevamisole is used for initial and secondary immunodeficient conditions, autoimmune diseases, chronic and reoccurring infections, large intestine adenocarcinoma, helmintosis, and rheumatoid arthritis. Synonyms of this drug are decaris, tetramizole, and others.Levimasole is also a drug of choice for ascardiasis. Numerous investigations show that a single dose of levamisole heals from 90 to 100% of patients with ascardiasis, in particular those infected with A. duodenale. It is less effective against ancylostomiasis and strongyloidiasis. However, it is not effective against N. americanus. It seems likely that it has a gangliostimulating effect on parasite tissues in both the parasympathetic and sympathetic regions. Moreover, it is presumed that this drug has an immunomodulatory effect on the host organism. Synonyms of this drug are decaris, solacil, ergamisol, tramisol, immunol, and others.

UsesBiological response modifier.

Upstream & downstream products

Downstream products

Suppliers100 total

北京华美互利生物化工010-56205725 · [email protected]
湖北万得化工有限公司15377098680 15377098680 · [email protected]
上海策嵘生物科技有限公司[email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
广州隽沐生物科技股份有限公司020-36607679; 13502246435 · [email protected]
Additional notes · 1 item

DefinitionChEBI: Levamisole is 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. It has a role as an antinematodal drug, an antirheumatic drug, an immunomodulator, an immunological adjuvant and an EC 3.1.3.1 (alkaline phosphatase) inhibitor. It is an enantiomer of a dexamisole.

Related reactions

13 records
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Compound notes

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