Nitazoxanide

Nitazoxanide
Clinical data
Trade names	Alinia, Nizonide, others
AHFS/Drugs.com	Monograph
MedlinePlus	a603017
License data	US DailyMed: Nitazoxanide;
Routes of; administration	By mouth
Drug class	Antiprotozoal; Broad-spectrum antiparasitic; Broad-spectrum antiviral
ATC code	P01AX11 (WHO) ;
Legal status
Legal status	US: ℞-only;
Pharmacokinetic data
Protein binding	Nitazoxanide: ?; Tizoxanide: over 99%
Metabolism	Rapidly hydrolyzed to tizoxanide
Metabolites	tizoxanide; tizoxanide glucuronide
Elimination half-life	3.5 hours
Excretion	Kidney, bile duct, and fecal
Identifiers
	IUPAC name [2-[(5-Nitro-1,3-thiazol-2-yl)carbamoyl]phenyl]ethanoate;
CAS Number	55981-09-4 ;
PubChem CID	41684;
DrugBank	DB00507 ;
ChemSpider	38037 ;
UNII	SOA12P041N;
KEGG	D02486 ;
ChEMBL	ChEMBL1401 ;
NIAID ChemDB	057131;
CompTox Dashboard (EPA)	DTXSID5033757 ;
ECHA InfoCard	100.054.465
Chemical and physical data
Formula	C12H9N3O5S
Molar mass	307.28 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(Nc1ncc(s1)[N+]([O-])=O)c2ccccc2OC(=O)C;
	InChI InChI=1S/C12H9N3O5S/c1-7(16)20-9-5-3-2-4-8(9)11(17)14-12-13-6-10(21-12)15(18)19/h2-6H,1H3,(H,13,14,17) ; Key:YQNQNVDNTFHQSW-UHFFFAOYSA-N ;
	(verify)

Nitazoxanide, sold under the brand name Alinia among others, is a broad-spectrum antiparasitic and broad-spectrum antiviral medication that is used in medicine for the treatment of various helminthic, protozoal, and viral infections. It is indicated for the treatment of infection by Cryptosporidium parvum and Giardia lamblia in immunocompetent individuals and has been repurposed for the treatment of influenza. Nitazoxanide has also been shown to have in vitro antiparasitic activity and clinical treatment efficacy for infections caused by other protozoa and helminths; evidence as of 2014 suggested that it possesses efficacy in treating a number of viral infections as well.

Chemically, nitazoxanide is the prototype member of the thiazolides, a class of drugs which are synthetic nitrothiazolyl-salicylamide derivatives with antiparasitic and antiviral activity. Tizoxanide, an active metabolite of nitazoxanide in humans, is also an antiparasitic drug of the thiazolide class.

Nitazoxanide tablets were approved as a generic medication in the United States in 2020.

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