Chemical substance record

Levamisole

14769-73-4C₁₁H₁₂N₂S204.298 g/mol

Organic/Inorganic Small MoleculeChEBI source record

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. — ChEBI

Safety references

Safety documents & references

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Identity & molecular properties

Source-linked values

CAS number	14769-73-4	ChEBI ↗
Molecular formula	C₁₁H₁₂N₂S	ChEBI ↗
Molar mass	204.298 g/mol	ChEBI ↗
Monoisotopic mass	204.07212 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:6432	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	204.29 g/mol	PubChem ↗
Exact mass	204.07211956 Da	PubChem ↗
Computed XLogP	1.8	PubChem ↗
Topological polar surface area (Å²)	40.9	PubChem ↗
H-bond donors	0	PubChem ↗
H-bond acceptors	2	PubChem ↗
Rotatable bonds	1	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

levamisole

IUPAC name

(6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazole

InChIKey

HLFSDGLLUJUHTE-SNVBAGLBSA-N

SMILES

[H][C@]1(c2ccccc2)CN2CCSC2=N1

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

Names & synonyms

(6S)-6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazoleKetraxLepuronlevamisollevamisolumLevomysolLevovermaxTotalonWormicid

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

6-phenyl-2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazoleChEBI parent class · 77278 ↗

organosulfur compound organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

antinematodal drugantirheumatic drugimmunomodulatorimmunological adjuvantEC 3.1.3.1 (alkaline phosphatase) inhibitor

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00489481 mol

Uses 204.298 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 11 atoms

64.67%

S

Sulfur · 1 atom

15.70%

N

Nitrogen · 2 atoms

13.71%

H

Hydrogen · 12 atoms

5.92%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

Miscellaneous treatments: thalidomide, potassium iodide, levamisole, clofazimine, colchicine, and D-penicillamine. ↗Clinics in dermatology · 2000 Jan-Feb · PMID 10701095

Differences in sialic acid residues among bone alkaline phosphatase isoforms: a physical, biochemical, and immunological characterization. ↗Calcified tissue international · 2002 Dec · PMID 12232676

US3274209 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

US3565907 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

US3579530 · Patent reference ↗Patent cross-reference supplied by ChEBI. Association alone does not establish claim scope.

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:6432

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 26879 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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