Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00473)
Name
Nitazoxanide
Synonyms    Click to Show/Hide the Synonyms of This API
NITAZOXANIDE; 55981-09-4; Alinia; Nitazoxamide; 2-((5-nitrothiazol-2-yl)carbamoyl)phenyl acetate; Nitazoxanidum [INN-Latin]; Nitazoxanida [INN-Spanish]; Benzamide, 2-(acetyloxy)-N-(5-nitro-2-thiazolyl)-; 2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl acetate; 2-(Acetolyloxy)-N-(5-nitro-2-thiazolyl)benzamide; C12H9N3O5S; [2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl] acetate; UNII-SOA12P041N; NSC697855; 2-Acetyloxy-N-[(5-nitro-2-thiazolyl)]benzamide; Nitazoxanide (Alinia, Annita); SOA12P041N; Nitazoxanida; 2-(Acetyloxy)-N-(5-nitro-2-thiazolyl)benzamide; MFCD00416599; NSC-697855; PH 5776; PH-5776; NCGC00090774-01; Nitazoxanid; Nitazoxanidum; Colufase; Cryptaz; Heliton; DSSTox_CID_13757; DSSTox_RID_79095; DSSTox_GSID_33757; Phavic-1; acetic acid [2-[[(5-nitro-2-thiazolyl)amino]-oxomethyl]phenyl] ester; SMR000466367; NSC 697855; Alinia (TN); AZT + Nitazoxanide; CAS-55981-09-4; EINECS 259-931-8; Nitazoxanide (USAN/INN); (2-((5-Nitro-2-thiazolyl)carbamoyl)phenyl)acetat; BRN 1225475; N-(5-Nitro-2-thiazolyl)salicylamide acetate (ester); Nitrazoxanide; Pacovanton; Dexidex; Kidonax; Nitazox; Paramix; Nitazoxanide [USAN:INN:BAN]; Alinia(TM); N-(5-Nitrothiazol-2-yl)salicylamide acetate ester; o-(N-(5-Nitrothiazol-2-yl)carbamoyl)phenyl acetate; Salicylamide, N-(5-nitro-2-thiazolyl)-, acetate (ester); CPD000466367; NCIMech_000843; CHEMBL1401; Oprea1_263587; SCHEMBL40981; MLS000759492; MLS001424074; MLS006010127; [2-[(5-nitrothiazol-2-yl)carbamoyl]phenyl] acetate; DTXSID5033757; CHEBI:94807; Nitazoxanide, >=98% (HPLC); NTZ;NSC 697855; HMS2051L04; HMS3393L04; HMS3655M11; HMS3715F10; Pharmakon1600-01503843; BCP13918; HY-B0217; ZINC3956788; Tox21_111018; Tox21_201226; BDBM50075050; CCG-35851; CN0040; MMV688991; NSC760057; STK395664; AKOS015915393; Tox21_111018_1; AC-1302; DB00507; KS-1160; MCULE-8701444531; NC00246; NSC-760057; NCGC00090774-02; NCGC00090774-03; NCGC00090774-04; NCGC00090774-05; NCGC00258778-01; AK-26130; BR-26130; NCI60_034935; AB0010620; FT-0601547; ST51059722; SW197626-2; 2-(5-nitrothiazol-2-ylcarbamoyl)phenyl acetate; D02486; J10428; S-3645; AB00639988-07; AB00639988-09; AB00639988_10; AB00639988_11; 981N094; A830877; Q-201475; Q2943789; NTZ; 2-(Acetyloxy)-N-(5-nitro-2-thiazolyl)benzamide; Salicylamide, N-(5-nitro-2-thiazolyl)- acetate (ester); Z1514087129; 2-[N-(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl acetate; [2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl]phenyl] ethanoate; Nitazoxanide, United States Pharmacopeia (USP) Reference Standard
Clinical Status
Approved
Disease Indication Irritable bowel syndrome ICD-11: DD91 [1]
PubChem CID
41684
Formula
C12H9N3O5S
Canonical SMILES
CC(=O)OC1=CC=CC=C1C(=O)NC2=NC=C(S2)[N+](=O)[O-]
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)
InChIKey
YQNQNVDNTFHQSW-UHFFFAOYSA-N
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=41684"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 307.28 Topological Polar Surface Area 142
XlogP 2 Complexity 428
Heavy Atom Count 21 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 7
Full List of Drug Formulations (DFMs) Containing This API
          Nitazoxanide 500 mg tablet Click to Show/Hide the Full List of Formulation(s):          2 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
D&c yellow no. 10; Fd&c blue no. 2; Fd&c yellow no. 6; Magnesium stearate; Sucrose; Talc; Titanium dioxide; Lecithin, soybean; Polyvinyl alcohol; Hypromelloses; Sodium starch glycolate type a potato; Starch, corn; Xanthan gum
                   Dosage Form Oral Tablet
                   Company Avera McKennan Hospital
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [6]
             Drug Formulation 2 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
D&c yellow no. 10; Fd&c blue no. 2; Fd&c yellow no. 6; Magnesium stearate; Sucrose; Talc; Titanium dioxide; Lecithin, soybean; Polyvinyl alcohol; Hypromelloses; Sodium starch glycolate type a potato; Starch, corn; Xanthan gum
                   Dosage Form Oral Tablet
                   Company Romark Laboratories
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
Sunset yellow FCF DIG Info Solute carrier SLCO2B1 (Ki = 68.4 uM) [2]
FD&C blue no. 2 DIG Info Adenosine receptor A3 (IC50 = 1 uM) [3]
Quinoline yellow WS DIG Info Estrogen receptor alpha (IC50 = 18 uM) [3]
Polyvinyl alcohol DIG Info Debrisoquine 4-hydroxylase (EC50 = 354.8 uM) [4]
Magnesium stearate DIG Info Albendazole monooxygenase (Protein expression downregulation) [5]
Soybean lecithin DIG Info Albendazole monooxygenase (IC50 = 6.61 mg.mL-1) [6]
References
1 FDA label for approved nitazoxanide from the official website of the U.S. Food and Drug Administration.
2 Bacterial metabolism rescues the inhibition of intestinal drug absorption by food and drug additives. Proc Natl Acad Sci U S A. 2020 Jul 7;117(27):16009-16018.
3 The activities of drug inactive ingredients on biological targets. Science. 2020 Jul 24;369(6502):403-413.
4 Mediation of in vitro cytochrome p450 activity by common pharmaceutical excipients. Mol Pharm. 2013 Jul 1;10(7):2739-48.
5 Effects of commonly used excipients on the expression of CYP3A4 in colon and liver cells. Pharm Res. 2010 Aug;27(8):1703-12.
6 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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