2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl](2H4)phenyl acetate

• ChemBase ID: 175152
• Molecular Formular: C12H9N3O5S
• Molecular Mass: 307.28196
• Monoisotopic Mass: 307.0262914
• SMILES: c1c(c(ccc1)OC(=O)C)C(=O)Nc1sc(cn1)[N+](=O)[O-]
• Canonical SMILES: CC(=O)Oc1ccccc1C(=O)Nc1ncc(s1)[N+](=O)[O-]
• 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)
• InChIKey: YQNQNVDNTFHQSW-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl](^2H₄)phenyl acetate
• IUPAC Traditional name: 2-[(5-nitro-1,3-thiazol-2-yl)carbamoyl](^2H₄)phenyl acetate
• Synonyms: 2-(Acetyloxy)-N-(5-nitro-2-thiazolyl)benzamide-d4; Alinia-d4; BRN 1225475-d4; Cryptaz-d4; DRG 0242-d4; N-(5-Nitro-2-thiazolyl)salicylamide-d4 Acetate Ester; Nitacure-d4; Nitarid-d4; Nitazoxanida-d4; Nixide-d4; Nixoran-d4; Nizonide-d4; PH 5776-d4; Nitazoxanide-d4

Database IDs

• PubChem SID: 164231062
• PubChem CID: 71751033

CALCULATED PROPERTIES

• Acid pKa: 8.299088
• H Acceptors: 5
• H Donor: 1
• LogD (pH = 5.5): 2.1207597
• LogD (pH = 7.4): 2.0725367
• Log P: 2.1214147
• Molar Refractivity: 73.8902 cm^3
• Polarizability: 27.305815 Å^3
• Polar Surface Area: 114.11 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - N490102

Labelled Nitazoxanide. An anthelmintic (cestodes), antiprotozoal (cryptosporidium). Kills Mycobacterium tuberculosis.

REFERENCES

• Cavier, R., et al.: Eur. J. Med. Chem.-Chim. Ther., 13, 539 (1978)
• Dubreuil, L., et al.: Antimicrob. Ag. Chemother., 40, 2266 (1978)
• Stockis, A., et al.: Int. J. Clin. Pharmacol. Ther., 34, 349 (1978)
• Nathan, C., et al.: J. Med. Chem. 52, 5789 (2009):