Levamisole

Levamisole
Skeletal formula of levamisole
Ball-and-stick model of the levamisole molecule
Clinical data
Trade namesDecaris, Ergamisol
AHFS/Drugs.comMicromedex Detailed Consumer Information
MedlinePlusa697011
License data
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
MetabolismLiver
Elimination half-life3–4 hours
ExcretionKidney (70%)
Identifiers
  • (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b] [1,3]thiazole
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.035.290 Edit this at Wikidata
Chemical and physical data
FormulaC11H12N2S
Molar mass204.29 g·mol−1
3D model (JSmol)
Density1.31 g/cm3
Melting point60 °C (140 °F)
Solubility in waterhydrochloride: 210 mg/mL (20 °C)
  • N\2=C1/SCCN1C[C@@H]/2c3ccccc3
  • 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 checkY
  • Key:HLFSDGLLUJUHTE-SNVBAGLBSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Levamisole, sold under the brand name Ergamisol among others, is a medication used to treat parasitic worm infections, specifically ascariasis and hookworm infections.[1] It is taken by mouth.[2]

Side effects may include abdominal pain, vomiting, headache, and dizziness.[2] Use is not recommended during breastfeeding or the third trimester of pregnancy.[2] Serious side effects may include an increased risk of infection.[3] It belongs to the anthelmintic class of medications.[3]

Levamisole was invented in 1966 in Belgium by Janssen Pharmaceuticals.[4] It is on the World Health Organization's List of Essential Medicines.[5] Levamisole is also used as a dewormer for cattle.[6][7]

  1. ^ Keiser J, Utzinger J (April 2008). "Efficacy of current drugs against soil-transmitted helminth infections: systematic review and meta-analysis". JAMA. 299 (16): 1937–48. doi:10.1001/jama.299.16.1937. PMID 18430913.
  2. ^ a b c World Health Organization (2009). Stuart MC, Kouimtzi M, Hill SR (eds.). WHO Model Formulary 2008. World Health Organization. pp. 86, 590. hdl:10665/44053. ISBN 9789241547659.
  3. ^ a b "Levamisole Advanced Patient Information - Drugs.com". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
  4. ^ Prevenier W, Howelland M (2001). From reliable sources : an introduction to historical methods (1st ed.). Ithaca: Cornell university press. p. 77. ISBN 9780801485602. Archived from the original on 10 September 2017.
  5. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  6. ^ Cite error: The named reference Valcor FDA label was invoked but never defined (see the help page).
  7. ^ Taylor MA, Coop RL, Wall RL (2015). Veterinary Parasitology. John Wiley & Sons. p. 329. ISBN 9781119073673. Archived from the original on 10 September 2017.