Levamisole

Levamisole
Clinical data
Trade names	Decaris, Ergamisol
AHFS/Drugs.com	Micromedex Detailed Consumer Information
MedlinePlus	a697011
License data	US DailyMed: Levamisole;
Routes of; administration	By mouth
ATC code	P02CE01 (WHO) QP52AE01 (WHO);
Legal status
Legal status	CA: Withdrawn[citation needed]; US: Withdrawn[citation needed]; Rx-only (RU);
Pharmacokinetic data
Metabolism	Liver
Elimination half-life	3–4 hours
Excretion	Kidney (70%)
Identifiers
	IUPAC name (S)-6-Phenyl-2,3,5,6-tetrahydroimidazo[2,1-b] [1,3]thiazole;
CAS Number	14769-73-4 ;
PubChem CID	26879;
IUPHAR/BPS	7210;
DrugBank	DB00848 ;
ChemSpider	25037 ;
UNII	2880D3468G;
KEGG	D08114 ;
ChEBI	CHEBI:6432 ;
ChEMBL	ChEMBL1454 ;
CompTox Dashboard (EPA)	DTXSID4023206 ;
ECHA InfoCard	100.035.290
Chemical and physical data
Formula	C11H12N2S
Molar mass	204.29 g·mol−1
3D model (JSmol)	Interactive image;
Density	1.31 g/cm3
Melting point	60 °C (140 °F)
Solubility in water	hydrochloride: 210 mg/mL (20 °C)
	SMILES N\2=C1/SCCN1C[C@@H]/2c3ccccc3;
	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 ; Key:HLFSDGLLUJUHTE-SNVBAGLBSA-N ;
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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.^[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]

^ 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.
^ ^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.
^ ^a ^b "Levamisole Advanced Patient Information - Drugs.com". www.drugs.com. Archived from the original on 20 December 2016. Retrieved 8 December 2016.
^ 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.
^ 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.
^ Cite error: The named reference Valcor FDA label was invoked but never defined (see the help page).
^ Taylor MA, Coop RL, Wall RL (2015). Veterinary Parasitology. John Wiley & Sons. p. 329. ISBN 9781119073673. Archived from the original on 10 September 2017.

[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.

[WHO2008-2] 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.

[Cons2016-3] "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.

[WHO21st-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.

[Valcor_FDA_label-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.

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