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.^[4]^[5]^[6] 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.^[1]^[6] Nitazoxanide has also been shown to have in vitro antiparasitic activity and clinical treatment efficacy for infections caused by other protozoa and helminths;^[4]^[7] evidence as of 2014^[update] suggested that it possesses efficacy in treating a number of viral infections as well.^[6]

Chemically, nitazoxanide is the prototype member of the thiazolides, a class of drugs which are synthetic nitrothiazolyl-salicylamide derivatives with antiparasitic and antiviral activity.^[4]^[6]^[8] Tizoxanide, an active metabolite of nitazoxanide in humans, is also an antiparasitic drug of the thiazolide class.^[4]^[9]

Nitazoxanide tablets were approved as a generic medication in the United States in 2020.^[10]

^ ^a ^b ^c ^d ^e ^f ^g Cite error: The named reference Alinia FDA label was invoked but never defined (see the help page).
^ ^a ^b ^c Stockis A, Allemon AM, De Bruyn S, Gengler C (May 2002). "Nitazoxanide pharmacokinetics and tolerability in man using single ascending oral doses". International Journal of Clinical Pharmacology and Therapeutics. 40 (5): 213–220. doi:10.5414/cpp40213. PMID 12051573.
^ "Nitazoxanide". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 3 January 2016.
^ ^a ^b ^c ^d Di Santo N, Ehrisman J (September 2013). "Research perspective: potential role of nitazoxanide in ovarian cancer treatment. Old drug, new purpose?". Cancers. 5 (3): 1163–1176. doi:10.3390/cancers5031163. PMC 3795384. PMID 24202339. Nitazoxanide [NTZ: 2-acetyloxy-N-(5-nitro-2-thiazolyl)benzamide] is a thiazolide antiparasitic agent with excellent activity against a wide variety of protozoa and helminths. ... Nitazoxanide (NTZ) is a main compound of a class of broad-spectrum anti-parasitic compounds named thiazolides. It is composed of a nitrothiazole-ring and a salicylic acid moiety which are linked together by an amide bond ... NTZ is generally well tolerated, and no significant adverse events have been noted in human trials [13]. ... In vitro, NTZ and tizoxanide function against a wide range of organisms, including the protozoal species Blastocystis hominis, C. parvum, Entamoeba histolytica, G. lamblia and Trichomonas vaginalis [13]
^ White CA (February 2004). "Nitazoxanide: a new broad spectrum antiparasitic agent". Expert Review of Anti-Infective Therapy. 2 (1): 43–49. doi:10.1586/14787210.2.1.43. PMID 15482170. S2CID 219184877.
^ ^a ^b ^c ^d Rossignol JF (October 2014). "Nitazoxanide: a first-in-class broad-spectrum antiviral agent". Antiviral Research. 110: 94–103. doi:10.1016/j.antiviral.2014.07.014. PMC 7113776. PMID 25108173. Originally developed and commercialized as an antiprotozoal agent, nitazoxanide was later identified as a first-in-class broad-spectrum antiviral drug and has been repurposed for the treatment of influenza. ... From a chemical perspective, nitazoxanide is the scaffold for a new class of drugs called thiazolides. These small-molecule drugs target host-regulated processes involved in viral replication. ... A new dosage formulation of nitazoxanide is presently undergoing global Phase 3 clinical development for the treatment of influenza. Nitazoxanide inhibits a broad range of influenza A and B viruses including influenza A(pH1N1) and the avian A(H7N9) as well as viruses that are resistant to neuraminidase inhibitors. ... Nitazoxanide also inhibits the replication of a broad range of other RNA and DNA viruses including respiratory syncytial virus, parainfluenza, coronavirus, rotavirus, norovirus, hepatitis B, hepatitis C, dengue, yellow fever, Japanese encephalitis virus and human immunodeficiency virus in cell culture assays. Clinical trials have indicated a potential role for thiazolides in treating rotavirus and norovirus gastroenteritis and chronic hepatitis B and chronic hepatitis C. Ongoing and future clinical development is focused on viral respiratory infections, viral gastroenteritis and emerging infections such as dengue fever.
^ Cite error: The named reference NTZ 2007 review was invoked but never defined (see the help page).
^ Cite error: The named reference Nitrothiazolyl-salicylamide was invoked but never defined (see the help page).
^ Cite error: The named reference pmid17888524 was invoked but never defined (see the help page).
^ "First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). Retrieved 13 February 2021.

[Alinia_FDA_label-1] ^ ^a ^b ^c ^d ^e ^f ^g Cite error: The named reference Alinia FDA label was invoked but never defined (see the help page).

[Primary:_Kinetics_and_OD-2] Stockis A, Allemon AM, De Bruyn S, Gengler C (May 2002). "Nitazoxanide pharmacokinetics and tolerability in man using single ascending oral doses". International Journal of Clinical Pharmacology and Therapeutics. 40 (5): 213–220. doi:10.5414/cpp40213. PMID 12051573.

[PubChem-3] "Nitazoxanide". PubChem. National Center for Biotechnology Information, U.S. National Library of Medicine. Retrieved 3 January 2016.

[Thiazolides-4] Di Santo N, Ehrisman J (September 2013). "Research perspective: potential role of nitazoxanide in ovarian cancer treatment. Old drug, new purpose?". Cancers. 5 (3): 1163–1176. doi:10.3390/cancers5031163. PMC 3795384. PMID 24202339. Nitazoxanide [NTZ: 2-acetyloxy-N-(5-nitro-2-thiazolyl)benzamide] is a thiazolide antiparasitic agent with excellent activity against a wide variety of protozoa and helminths. ... Nitazoxanide (NTZ) is a main compound of a class of broad-spectrum anti-parasitic compounds named thiazolides. It is composed of a nitrothiazole-ring and a salicylic acid moiety which are linked together by an amide bond ... NTZ is generally well tolerated, and no significant adverse events have been noted in human trials [13]. ... In vitro, NTZ and tizoxanide function against a wide range of organisms, including the protozoal species Blastocystis hominis, C. parvum, Entamoeba histolytica, G. lamblia and Trichomonas vaginalis [13]

[Nitazoxanide:_Broad-spectrum_antiparasitic-5] White CA (February 2004). "Nitazoxanide: a new broad spectrum antiparasitic agent". Expert Review of Anti-Infective Therapy. 2 (1): 43–49. doi:10.1586/14787210.2.1.43. PMID 15482170. S2CID 219184877.

[Broad-spectrum_antiviral_review-6] Rossignol JF (October 2014). "Nitazoxanide: a first-in-class broad-spectrum antiviral agent". Antiviral Research. 110: 94–103. doi:10.1016/j.antiviral.2014.07.014. PMC 7113776. PMID 25108173. Originally developed and commercialized as an antiprotozoal agent, nitazoxanide was later identified as a first-in-class broad-spectrum antiviral drug and has been repurposed for the treatment of influenza. ... From a chemical perspective, nitazoxanide is the scaffold for a new class of drugs called thiazolides. These small-molecule drugs target host-regulated processes involved in viral replication. ... A new dosage formulation of nitazoxanide is presently undergoing global Phase 3 clinical development for the treatment of influenza. Nitazoxanide inhibits a broad range of influenza A and B viruses including influenza A(pH1N1) and the avian A(H7N9) as well as viruses that are resistant to neuraminidase inhibitors. ... Nitazoxanide also inhibits the replication of a broad range of other RNA and DNA viruses including respiratory syncytial virus, parainfluenza, coronavirus, rotavirus, norovirus, hepatitis B, hepatitis C, dengue, yellow fever, Japanese encephalitis virus and human immunodeficiency virus in cell culture assays. Clinical trials have indicated a potential role for thiazolides in treating rotavirus and norovirus gastroenteritis and chronic hepatitis B and chronic hepatitis C. Ongoing and future clinical development is focused on viral respiratory infections, viral gastroenteritis and emerging infections such as dengue fever.

[NTZ_2007_review-7] Cite error: The named reference NTZ 2007 review was invoked but never defined (see the help page).

[Nitrothiazolyl-salicylamide-8] Cite error: The named reference Nitrothiazolyl-salicylamide was invoked but never defined (see the help page).

[pmid17888524-9] Cite error: The named reference pmid17888524 was invoked but never defined (see the help page).

[10] "First Generic Drug Approvals". U.S. Food and Drug Administration (FDA). Retrieved 13 February 2021.

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