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Chemistry

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Also known as: 55981-09-4, Alinia, 2-((5-nitrothiazol-2-yl)carbamoyl)phenyl acetate, Nitazoxamide, Daxon, Nitazoxanidum [inn-latin]
Molecular Formula
C12H9N3O5S
Molecular Weight
307.28  g/mol
InChI Key
YQNQNVDNTFHQSW-UHFFFAOYSA-N
FDA UNII
SOA12P041N

Nitazoxanide
Nitazoxanide is a synthetic benzamide with antiprotozoal activity. Nitazoxanide exerts its antiprotozoal activity by interfering with the pyruvate ferredoxin/flavodoxin oxidoreductase dependent electron transfer reaction, which is essential to anaerobic energy metabolism. PFOR enzyme reduces nitazoxanide, thereby impairing the energy metabolism. However, interference with the PFOR enzyme-dependent electron transfer reaction may not be the only pathway by which nitazoxanide exhibits antiprotozoal activity. Nitazoxanide is active against Giardia lamblia and Cryptosporidium parvum.
Nitazoxanide is an Antiprotozoal.
1 2D Structure

Nitazoxanide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
[2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl] acetate
2.1.2 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)
2.1.3 InChI Key
YQNQNVDNTFHQSW-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC(=O)OC1=CC=CC=C1C(=O)NC2=NC=C(S2)[N+](=O)[O-]
2.2 Other Identifiers
2.2.1 UNII
SOA12P041N
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-(acetolyloxy)-n-(5-nitro-2-thiazolyl)benzamide

2. Alinia

3. Colufase

4. Cryptaz

5. Daxon

6. Heliton

7. Ntz

8. Taenitaz

2.3.2 Depositor-Supplied Synonyms

1. 55981-09-4

2. Alinia

3. 2-((5-nitrothiazol-2-yl)carbamoyl)phenyl Acetate

4. Nitazoxamide

5. Daxon

6. Nitazoxanidum [inn-latin]

7. Nitazoxanida [inn-spanish]

8. 2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl Acetate

9. Benzamide, 2-(acetyloxy)-n-(5-nitro-2-thiazolyl)-

10. [2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl] Acetate

11. 2-(acetolyloxy)-n-(5-nitro-2-thiazolyl)benzamide

12. Nsc 697855

13. Nsc697855

14. Ntz

15. 2-acetyloxy-n-[(5-nitro-2-thiazolyl)]benzamide

16. Nsc-697855

17. Nsc-760057

18. N-(5-nitrothiazol-2-yl)salicylamide Acetate Ester

19. Ph 5776

20. Ph-5776

21. Nitazoxanide (alinia, Annita)

22. Soa12p041n

23. Nitazoxanida

24. Cryptaz

25. [2-[(5-nitrothiazol-2-yl)carbamoyl]phenyl] Acetate

26. Ncgc00090774-01

27. Nitazoxanid

28. Nitazoxanidum

29. Colufase

30. Heliton

31. Dsstox_cid_13757

32. Dsstox_rid_79095

33. Dsstox_gsid_33757

34. Phavic-1

35. Smr000466367

36. Alinia (tn)

37. Azt + Nitazoxanide

38. Cas-55981-09-4

39. Einecs 259-931-8

40. Nitazoxanide (usan/inn)

41. (2-((5-nitro-2-thiazolyl)carbamoyl)phenyl)acetat

42. Brn 1225475

43. Unii-soa12p041n

44. N-(5-nitro-2-thiazolyl)salicylamide Acetate (ester)

45. Nitrazoxanide

46. Pacovanton

47. Dexidex

48. Kidonax

49. Nitazox

50. Paramix

51. Nitax

52. Toza

53. Nitazoxanide [usan:inn:ban]

54. Alinia(tm)

55. Mfcd00416599

56. O-(n-(5-nitrothiazol-2-yl)carbamoyl)phenyl Acetate

57. Nitazoxanide- Bio-x

58. Salicylamide, N-(5-nitro-2-thiazolyl)-, Acetate (ester)

59. Cpd000466367

60. Nitazoxanide [mi]

61. Nitazoxanide [inn]

62. Ncimech_000843

63. Nitazoxanide [usan]

64. Chembl1401

65. Nitazoxanide [vandf]

66. 2-(acetyloxy)-n-(5-nitro-2-thiazolyl)benzamide

67. Oprea1_263587

68. Schembl40981

69. Nitazoxanide [mart.]

70. Mls000759492

71. Mls001424074

72. Mls006010127

73. Nitazoxanide [usp-rs]

74. Nitazoxanide [who-dd]

75. Dtxsid5033757

76. Chebi:94807

77. Nitazoxanide [green Book]

78. Nitazoxanide, >=98% (hplc)

79. Ntz;nsc 697855

80. Hms2051l04

81. Hms3393l04

82. Hms3655m11

83. Hms3715f10

84. Nitazoxanide [orange Book]

85. Pharmakon1600-01503843

86. Bcp13918

87. Hy-b0217

88. Zinc3956788

89. Tox21_111018

90. Tox21_201226

91. Bdbm50075050

92. Ccg-35851

93. Mmv688991

94. Nsc760057

95. Stk395664

96. Akos015915393

97. Tox21_111018_1

98. Ac-1302

99. Db00507

100. Ks-1160

101. Nc00246

102. Ncgc00090774-02

103. Ncgc00090774-03

104. Ncgc00090774-04

105. Ncgc00090774-05

106. Ncgc00258778-01

107. Bn164151

108. Nci60_034935

109. Ft-0601547

110. N1031

111. Nitrazoxanide 100 Microg/ml In Acetonitrile

112. S1627

113. Sw197626-2

114. 2-(5-nitrothiazol-2-ylcarbamoyl)phenyl Acetate

115. D02486

116. Ab00639988-07

117. Ab00639988-09

118. Ab00639988_10

119. Ab00639988_11

120. 2-(acetyloxy)-n-(5-nitro-2-thiazolyl)-benzamide

121. 981n094

122. A830877

123. Sr-01000759418

124. Q-201475

125. Q2943789

126. Sr-01000759418-9

127. Salicylamide, N-(5-nitro-2-thiazolyl)- Acetate (ester)

128. Z1514087129

129. Nitazoxanide, United States Pharmacopeia (usp) Reference Standard

130. Acetic Acid [2-[[(5-nitro-2-thiazolyl)amino]-oxomethyl]phenyl] Ester

131. Zox

2.4 Create Date
2005-03-26
3 Chemical and Physical Properties
Molecular Weight 307.28 g/mol
Molecular Formula C12H9N3O5S
XLogP32
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count7
Rotatable Bond Count4
Exact Mass307.02629157 g/mol
Monoisotopic Mass307.02629157 g/mol
Topological Polar Surface Area142 Ų
Heavy Atom Count21
Formal Charge0
Complexity428
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameAlinia
PubMed HealthNitazoxanide (By mouth)
Drug ClassesAntiprotozoal
Drug LabelAlinia Tablets and Alinia for Oral Suspension contain the active ingredient, nitazoxanide, a synthetic antiprotozoal agent for oral administration. Nitazoxanide is a light yellow crystalline powder. It is poorly soluble in ethanol and practically ins...
Active IngredientNitazoxanide
Dosage FormTablet; For suspension
Routeoral; Oral
Strength100mg/5ml; 500mg
Market StatusPrescription
CompanyRomark

2 of 2  
Drug NameAlinia
PubMed HealthNitazoxanide (By mouth)
Drug ClassesAntiprotozoal
Drug LabelAlinia Tablets and Alinia for Oral Suspension contain the active ingredient, nitazoxanide, a synthetic antiprotozoal agent for oral administration. Nitazoxanide is a light yellow crystalline powder. It is poorly soluble in ethanol and practically ins...
Active IngredientNitazoxanide
Dosage FormTablet; For suspension
Routeoral; Oral
Strength100mg/5ml; 500mg
Market StatusPrescription
CompanyRomark

4.2 Drug Indication

For the treatment of diarrhea in adults and children caused by the protozoa Giardia lamblia, and for the treatment of diarrhea in children caused by the protozoan, Cryptosporidium parvum. Nitazoxanide has not been shown to be superior to placebo medication for the management of diarrhea caused by Cryptosporidium parvum in patients with HIV/immunodeficiency.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

The general effect of this medication is the prevention of microbe activity through disruption of important energy pathways for survival and proliferation. Nitazoxanide exhibits antiprotozoal activity by interfering with the pyruvate ferredoxin/flavodoxin oxidoreductase dependent electron transfer reaction, an essential reaction need for anaerobic energy metabolism of various microorganisms. Sporozoites of Cryptosporidium parvum and trophozoites of Giardia lamblia are therefore inhibited, relieving symptoms of diahrrea. Interference with the PFOR enzyme-dependent electron transfer reaction may only be one of the many pathways by which nitazoxanide exhibits antiprotozoal activity.


5.2 MeSH Pharmacological Classification

Antiparasitic Agents

Drugs used to treat or prevent parasitic infections. (See all compounds classified as Antiparasitic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
NITAZOXANIDE
5.3.2 FDA UNII
SOA12P041N
5.3.3 Pharmacological Classes
Antiprotozoal [EPC]
5.4 ATC Code

P - Antiparasitic products, insecticides and repellents

P01 - Antiprotozoals

P01A - Agents against amoebiasis and other protozoal diseases

P01AX - Other agents against amoebiasis and other protozoal diseases

P01AX11 - Nitazoxanide


5.5 Absorption, Distribution and Excretion

Absorption

The relative bioavailability of the suspension compared to the tablet was 70%. When administered with food the AUC and Cmax increased by two-fold and 50%, respectively, for the tablet and 45 to 50% and ≤ 10%, respectively, for the oral suspension.


Route of Elimination

Tizoxanide is excreted in the urine, bile and feces, and tizoxanide glucuronide is excreted in urine and bile. Approximately 2/3 of the oral dose of nitazoxanide is excreted in the faeces and 1/3 in the urine.


Clearance

Nitazoxanide is cleared in the urine and feces. The metabolite, tizoxanide, is also found in the urine, plasma, and breastmilk. The drug is not found unchanged in the urine.


5.6 Metabolism/Metabolites

The active metabolite of this drug is tizoxanide (desacetyl-nitazoxanide). The initial reaction in the metabolic pathway of Nitazoxanide is hydrolysis to tizoxanide, followed by conjugation, primarily by glucuronidation to tizoxanide glucuronide. The oral suspension bioavailability of this drug is not equivalent to that of the oral tablets. Compared to the to the tablet, the bioavailability of the suspension was 70%. When administered with food, the AUCt of tizoxanide and tizoxanide glucuronide in plasma is increased to almost two-fold and the maximum concentration is increased by almost 50% compared to when ingested without food. When the oral suspension was ingested with food, the AUC of tizoxanide and tizoxanide glucuronide increased by approximately 50% and the Cmax increased by less than 10%.


5.7 Biological Half-Life

7.3h


5.8 Mechanism of Action

The most widely accepted mechanism of NTZ is believed to be the disruption of the energy metabolism in anaerobic microbes by inhibition of the pyruvate: ferredoxin/flavodoxin oxidoreductase (PFOR) cycle. In parasitic-protozoa, Nitazoxanide also induces lesions in the cell membranes and depolarizes the mitochondrial membrane while inhibiting quinone oxidoreductase NQO1, nitroreductase-1 and protein disulphide isomerase enzymes. In addition, this drug also inhibits the glutathione-S-transferase (a major detoxifying enzyme) and modulates the Avr-14 gene, encoding for the alpha-type subunit of glutamate-gated chloride ion channel present in nematodes. Aside from its well understood non-competitive inhibition of the PFOR in anaerobic bacteria, NTZ also demonstrates various other antibacterial mechanisms. It inhibits pyruvate dehydrogenase in E Coli, disrupts the membrane potential and pH homeostasis in the Mycobacterium tuberculosis, suppresses the chaperone/usher (CU) pathway of the gram-negative bacteria, and stimulates host macrophage autophagy in tuberculosis patients. NTZ also suppresses viral replication by inhibiting the maturation of the viral hemagglutinin and the viral transcription factor immediate early 2 (IE2) as well as by activating the eukaryotic translation initiation factor 2 (an antiviral intracellular protein). Lastly, NTZ exhibits an inhibitory effect on tumor cell progression by altering drug detoxification (glutathione-S-transferase P1), unfolded protein response, autophagy, anti-cytokines activity, and c-Myc inhibition.


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24-Jul-2025
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DOSAGE - TABLET;ORAL - 500MG

USFDA APPLICATION NUMBER - 21497

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DOSAGE - FOR SUSPENSION;ORAL - 100MG/5ML

USFDA APPLICATION NUMBER - 21498

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ABOUT THIS PAGE

Looking for 55981-09-4 / Nitazoxanide API manufacturers, exporters & distributors?

Nitazoxanide manufacturers, exporters & distributors 1

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PharmaCompass offers a list of Nitazoxanide API manufacturers, exporters & distributors, which can be sorted by GMP, USDMF, JDMF, KDMF, CEP (COS), WC, Price,and more, enabling you to easily find the right Nitazoxanide manufacturer or Nitazoxanide supplier for your needs.

Send us enquiries for free, and we will assist you in establishing a direct connection with your preferred Nitazoxanide manufacturer or Nitazoxanide supplier.

PharmaCompass also assists you with knowing the Nitazoxanide API Price utilized in the formulation of products. Nitazoxanide API Price is not always fixed or binding as the Nitazoxanide Price is obtained through a variety of data sources. The Nitazoxanide Price can also vary due to multiple factors, including market conditions, regulatory modifications, or negotiated pricing deals.

API | Excipient name

Nitazoxanide

Synonyms

55981-09-4, Alinia, 2-((5-nitrothiazol-2-yl)carbamoyl)phenyl acetate, Nitazoxamide, Daxon, Nitazoxanidum [inn-latin]

Cas Number

55981-09-4

Unique Ingredient Identifier (UNII)

SOA12P041N

About Nitazoxanide

Nitazoxanide is a synthetic benzamide with antiprotozoal activity. Nitazoxanide exerts its antiprotozoal activity by interfering with the pyruvate ferredoxin/flavodoxin oxidoreductase dependent electron transfer reaction, which is essential to anaerobic energy metabolism. PFOR enzyme reduces nitazoxanide, thereby impairing the energy metabolism. However, interference with the PFOR enzyme-dependent electron transfer reaction may not be the only pathway by which nitazoxanide exhibits antiprotozoal activity. Nitazoxanide is active against Giardia lamblia and Cryptosporidium parvum.

Columbia Brand 1 of Nitazoxanide Manufacturers

A Columbia Brand 1 of Nitazoxanide manufacturer is defined as any person or entity involved in the manufacture, preparation, processing, compounding or propagation of Columbia Brand 1 of Nitazoxanide, including repackagers and relabelers. The FDA regulates Columbia Brand 1 of Nitazoxanide manufacturers to ensure that their products comply with relevant laws and regulations and are safe and effective to use. Columbia Brand 1 of Nitazoxanide API Manufacturers are required to adhere to Good Manufacturing Practices (GMP) to ensure that their products are consistently manufactured to meet established quality criteria.

click here to find a list of Columbia Brand 1 of Nitazoxanide manufacturers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PhamaCompass.

Columbia Brand 1 of Nitazoxanide Suppliers

A Columbia Brand 1 of Nitazoxanide supplier is an individual or a company that provides Columbia Brand 1 of Nitazoxanide active pharmaceutical ingredient (API) or Columbia Brand 1 of Nitazoxanide finished formulations upon request. The Columbia Brand 1 of Nitazoxanide suppliers may include Columbia Brand 1 of Nitazoxanide API manufacturers, exporters, distributors and traders.

click here to find a list of Columbia Brand 1 of Nitazoxanide suppliers with USDMF, JDMF, KDMF, CEP, GMP, COA and API Price related information on PharmaCompass.

Columbia Brand 1 of Nitazoxanide USDMF

A Columbia Brand 1 of Nitazoxanide DMF (Drug Master File) is a document detailing the whole manufacturing process of Columbia Brand 1 of Nitazoxanide active pharmaceutical ingredient (API) in detail. Different forms of Columbia Brand 1 of Nitazoxanide DMFs exist exist since differing nations have different regulations, such as Columbia Brand 1 of Nitazoxanide USDMF, ASMF (EDMF), JDMF, CDMF, etc.

A Columbia Brand 1 of Nitazoxanide DMF submitted to regulatory agencies in the US is known as a USDMF. Columbia Brand 1 of Nitazoxanide USDMF includes data on Columbia Brand 1 of Nitazoxanide's chemical properties, information on the facilities and procedures used, and details about packaging and storage. The Columbia Brand 1 of Nitazoxanide USDMF is kept confidential to protect the manufacturer’s intellectual property.

click here to find a list of Columbia Brand 1 of Nitazoxanide suppliers with USDMF on PharmaCompass.

Columbia Brand 1 of Nitazoxanide WC

A Columbia Brand 1 of Nitazoxanide written confirmation (Columbia Brand 1 of Nitazoxanide WC) is an official document issued by a regulatory agency to a Columbia Brand 1 of Nitazoxanide manufacturer, verifying that the manufacturing facility of a Columbia Brand 1 of Nitazoxanide active pharmaceutical ingredient (API) adheres to the Good Manufacturing Practices (GMP) regulations of the importing country. When exporting Columbia Brand 1 of Nitazoxanide APIs or Columbia Brand 1 of Nitazoxanide finished pharmaceutical products to another nation, regulatory agencies frequently require a Columbia Brand 1 of Nitazoxanide WC (written confirmation) as part of the regulatory process.

click here to find a list of Columbia Brand 1 of Nitazoxanide suppliers with Written Confirmation (WC) on PharmaCompass.

Columbia Brand 1 of Nitazoxanide NDC

National Drug Code is a comprehensive database maintained by the FDA that contains information on all drugs marketed in the US. This directory includes information about finished drug products, unfinished drug products, and compounded drug products, including those containing Columbia Brand 1 of Nitazoxanide as an active pharmaceutical ingredient (API).

Finished drug products

The FDA updates the NDC directory daily. The NDC numbers for Columbia Brand 1 of Nitazoxanide API and other APIs are published in this directory by the FDA.

Unfinished drugs

The NDC unfinished drugs database includes product listing information submitted for all unfinished drugs, such as active pharmaceutical ingredients (APIs), drugs intended for further processing and bulk drug substances for compounding.

Pharmaceutical companies that manufacture Columbia Brand 1 of Nitazoxanide as an active pharmaceutical ingredient (API) must furnish the FDA with an updated record of all drugs that they produce, prepare, propagate, compound, or process for commercial distribution in the US at their facilities.

Compounded drug products

The NDC directory also contains data on finished compounded human drug products that contain Columbia Brand 1 of Nitazoxanide and are produced by outsourcing facilities. While these outsourcing facilities are not mandated to assign a Columbia Brand 1 of Nitazoxanide NDC to their finished compounded human drug products, they may choose to do so.

click here to find a list of Columbia Brand 1 of Nitazoxanide suppliers with NDC on PharmaCompass.

Columbia Brand 1 of Nitazoxanide GMP

Columbia Brand 1 of Nitazoxanide Active pharmaceutical ingredient (API) is produced in GMP-certified manufacturing facility.

GMP stands for Good Manufacturing Practices, which is a system used in the pharmaceutical industry to make sure that goods are regularly produced and monitored in accordance with quality standards. The FDA’s current Good Manufacturing Practices requirements are referred to as cGMP or current GMP which indicates that the company follows the most recent GMP specifications. The World Health Organization (WHO) has its own set of GMP guidelines, called the WHO GMP. Different countries can also set their own guidelines for GMP like China (Chinese GMP) or the EU (EU GMP).

PharmaCompass offers a list of Columbia Brand 1 of Nitazoxanide GMP manufacturers, exporters & distributors, which can be sorted by USDMF, JDMF, KDMF, CEP (COS), WC, API price, and more, enabling you to easily find the right Columbia Brand 1 of Nitazoxanide GMP manufacturer or Columbia Brand 1 of Nitazoxanide GMP API supplier for your needs.

Columbia Brand 1 of Nitazoxanide CoA

A Columbia Brand 1 of Nitazoxanide CoA (Certificate of Analysis) is a formal document that attests to Columbia Brand 1 of Nitazoxanide's compliance with Columbia Brand 1 of Nitazoxanide specifications and serves as a tool for batch-level quality control.

Columbia Brand 1 of Nitazoxanide CoA mostly includes findings from lab analyses of a specific batch. For each Columbia Brand 1 of Nitazoxanide CoA document that a company creates, the USFDA specifies specific requirements, such as supplier information, material identification, transportation data, evidence of conformity and signature data.

Columbia Brand 1 of Nitazoxanide may be tested according to a variety of international standards, such as European Pharmacopoeia (Columbia Brand 1 of Nitazoxanide EP), Columbia Brand 1 of Nitazoxanide JP (Japanese Pharmacopeia) and the US Pharmacopoeia (Columbia Brand 1 of Nitazoxanide USP).

Inform the supplier about your product requirements, specifying if you need a product with particular monograph like EP (Ph. Eur.), USP, JP, BP, or any other quality. In addition, clarify whether you need hydrochloride (HCl), anhydricum, base, micronisatum or a specific level of purity. To find reputable suppliers, utilize the filters and select those certified by GMP, FDA, or any other certification as per your requirement.
For your convenience, we have listed synonyms and CAS numbers to help you find the best supplier. The use of synonyms and CAS numbers can be helpful in identifying potential suppliers, but it is crucial to note that they might not always indicate the exact same product. It is important to confirm the product details with the supplier before making a purchase to ensure that it meets your requirements.
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