ethyl 1-({2-methyl-1,1-dioxo-3-[(pyridin-2-yl)carbamoyl]-2H-1λ6,2-benzothiazin-4-yl}oxy)ethyl carbonate

• ChemBase ID: 160595
• Molecular Formular: C20H21N3O7S
• Molecular Mass: 447.46164
• Monoisotopic Mass: 447.11002103
• SMILES: c1cccc2c1C(=C(N(S2(=O)=O)C)C(=O)Nc1ncccc1)OC(OC(=O)OCC)C
• Canonical SMILES: CCOC(=O)OC(OC1=C(C(=O)Nc2ccccn2)N(C)S(=O)(=O)c2c1cccc2)C
• InChI: InChI=1S/C20H21N3O7S/c1-4-28-20(25)30-13(2)29-18-14-9-5-6-10-15(14)31(26,27)23(3)17(18)19(24)22-16-11-7-8-12-21-16/h5-13H,4H2,1-3H3,(H,21,22,24)
• InChIKey: LSNWBKACGXCGAJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl 1-({2-methyl-1,1-dioxo-3-[(pyridin-2-yl)carbamoyl]-2H-1λ^6,2-benzothiazin-4-yl}oxy)ethyl carbonate
• IUPAC Traditional name: ampiroxicam
• Synonyms: Carbonic Acid Ethyl 1-[[2-Methyl-1,1-dioxido-3-[(2-pyridinylamino)carbonyl]-2H-1,2-benzothiazin-4-yl]oxy]ethyl Ester; CP 65703; Flucam; Nasil; Ampiroxicam

Database IDs

• CAS Number: 99464-64-9
• PubChem SID: 162254730
• PubChem CID: 2176

CALCULATED PROPERTIES

• Acid pKa: 11.6014
• H Acceptors: 7
• H Donor: 1
• LogD (pH = 5.5): 2.1561484
• LogD (pH = 7.4): 2.1678681
• Log P: 2.1680465
• Molar Refractivity: 113.2625 cm^3
• Polarizability: 43.44205 Å^3
• Polar Surface Area: 124.13 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: White Solid
• Melting Point: 159-161°C

Safety Information

• Storage Condition: -20°C Freezer

Pharmacology Properties

• Target: COX

Product Information

• Salt Data: Free Base

DETAILS

Toronto Research Chemicals - A634350

Prodrug of Piroxicam. Anti-inflammatory.

REFERENCES

• Kurita, K., et al.: Oral. Ther. Pharmacol., 10, 138 (1991)
• Chen, M., et al.: Pharm. Res., 18, 1645 (1991)
• Davis, A., et al.: Curr. Opin. Chem. Biol., 8, 378 (1991)
• Votano, J., et al.: J. Med. Chem., 49, 7169 (1991)