5582. Lornoxicam

Nomenclature

CAS number: 70374-39-9
6-Chloro-4-hydroxy-2-methyl-N-2-pyridinyl-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide; 6-chloro-4-hydroxy-2-methyl-3-(2-pyridylcarbamoyl)-2H-thieno[2,3-e]-1,2-thiazine-1,1-dioxide; chlortenoxicam; Ro-13-9297; TS-110; Xefo (Nycomed).
C13H10ClN3O4S2; mol wt 371.82.
C 41.99%, H 2.71%, Cl 9.53%, N 11.30%, O 17.21%, S 17.25%.

Description and references

Cyclooxygenase inhibitor; structurally similar to tenoxicam, q.v. Prepn: R. Pfister et al., DE 2838851; eidem, US 4180662 (both 1979 to Hoffmann-La Roche). Clinical pharmacokinetics: S. I. Ankier et al., Postgrad. Med. J. 64, 752 (1988). Symposium on pharmacology and clinical experience: ibid. 66, Suppl. 4, S1-S50 (1990). Overview of pharmacology and safety assessment: T. P. Pruss et al., ibid. S18.

Chemical structure

Properties

Orange to yellow crystals, mp 225-230° (dec). pKa2 4.7. uv max: 371 nm. Partition coefficient (n-octanol/pH 7.4 buffer): 1.8. LD50 orally in mice, rats, rabbits, dogs, monkeys: >10 mg/kg (Pruss).

Therapeutic Category

Anti-inflammatory; analgesic.

Keywords

Anti-inflammatory (Nonsteroidal); Thiazinecarboxamides; Analgesic; Non-opioids