7506. Piroxicam

Nomenclature

CAS number: 36322-90-4
4-Hydroxy-2-methyl-N-2-pyridinyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide; 3,4-dihydro-2-methyl-4-oxo-N-2-pyridyl-2H-1,2-benzothiazine-3-carboxamide 1,1-dioxide; CP-16171; Artroxicam (SoSe); Baxo (Toyama); Bruxicam (Bruschettini); Durapirox (Dura); Erazon (Krka); Feldene (Pfizer); Felden (Pfizer); Flexase (TAD); Geldene (Pfizer); Improntal (Rottapharm); Inflaced (Dexo); Larapam (Sandoz); Pirkam (Nycomed); Piroflex (Betapharm); Proxalyoc (Cephalon); Riacen (Chiesi); Roxiden (Pulitzer); Sasulen (Faes); Solocalm (Bernabó); Zunden (Luitpold).
C15H13N3O4S; mol wt 331.35.
C 54.37%, H 3.95%, N 12.68%, O 19.31%, S 9.68%.

Description and references

Non-steroidal anti-inflammatory with long half-life. Prepn (keto form): J. Lombardino, DE 1943265; idem, US 3591584 (1970, 1971 to Pfizer). Synthesis and biological properties: J. Lombardino, E. Wiseman, J. Med. Chem. 15, 848 (1972); J. Lombardino et al., ibid. 16, 493 (1973). Characterization of crystal modifications: F. Vrecer et al., Int. J. Pharm. 256, 3 (2003). HPLC determn in plasma: S. Dadashzadeh et al., J. Pharm. Biomed. Anal. 28, 1201 (2002). Pharmacology: E. Wiseman et al., Arzneim.-Forsch. 26, 1300 (1976). Evaluation of ulcerogenic effects: G. Palacios et al., Methods Find. Exp. Clin. Pharmacol. 9, 353 (1987). Antitumor effects in canine squamous cell carcinoma: B. R. Schmidt et al., J. Am. Vet. Med. Assoc. 218, 1783 (2001). Review of pharmacology and therapeutic efficacy: R. N. Brogden et al., Drugs 22, 165-187 (1981); eidem, ibid. 28, 292-323 (1984). Symposium on clinical efficacy and safety: Am. J. Med. 81, Suppl. 5B, 1-55 (1986). Comprehensive description: M. Mihalic et al., Anal. Profiles Drug Subs. 15, 509-531 (1986). Review of therapeutic potential of β-cyclodextrin complex: C. R. Lee, J. A. Balfour, Drugs 48, 907-929 (1994).

Chemical structure

Properties

Crystals from methanol, mp 198-200°. Sparingly sol in water, dilute acid, most organic solvents. Slightly sol in alcohol, aq solns. Pyridyl nitrogen pKa 1.8. 4-Hydroxy pKa 5.1. LD50 orally in mice: 360 mg/kg (Wiseman).

Derivative

Cinnamic acid ester.

Nomenclature

CAS number: 87234-24-0
Piroxicam cinnamate; cinnoxicam; SPA-S-510; Sinartrol (SPA); Zelis (Pharma Italia); Zen (Prophin).
C24H19N3O5S; mol wt 461.49.
C 62.46%, H 4.15%, N 9.11%, O 17.33%, S 6.95%.

Derivative

Compd with β-cyclodextrin.

Nomenclature

CAS number: 121696-62-6
Brexidol (Chiesi); Brexin (Chiesi); Cicladol (Master); Cycladol (Kiesi).
C57H83N3O39S; mol wt 1466.33.
C 46.69%, H 5.71%, N 2.87%, O 42.55%, S 2.19%.

Therapeutic Category

Anti-inflammatory.

Therapeutic Category (Veterinary)

Treatment of carcinoma in dogs; anti-inflammatory.

Keywords

Anti-inflammatory (Nonsteroidal); Thiazinecarboxamides