Apazone dihydrate

• CAT Number: I022303
• CAS Number: 22304-30-9
• Molecular Formula: C16H24N4O4
• Molecular Weight: 336.39
• Purity: 98%
• Synonyms: Apazone dihydrate; Azapropazon dihydrate, MI 85, Prolixan, Rheumox, Tolyprin
• Solubility: Soluble in DMSO
• Appearance: Solid powder
• Storage: Dry, dark and at 0 - 4℃ for short term (days to weeks) or -20℃ for long term (months to years).
• IUPAC Name: 1H-Pyrazolo(1,2-a)(1,2,4)benzotriazine-1,3(2H)-dione, 5-(dimethylamino)-9-methyl-2-propyl-, dihydrate
• InChI: 1S/C16H20N4O2.2H2O/c1-5-6-11-14(21)19-13-9-10(2)7-8-12(13)17-16(18(3)4)20(19)15(11)22;;/h7-9,11H,5-6H2,1-4H3;2*1H2
• InChIKey: LLMGYOJUHDRDFJ-UHFFFAOYSA-N
• SMILES: CCCC1C(=O)N2c3cc(ccc3N=C(N2C1=O)N(C)C)C.O.O

Apazone dihydrate (Cat.No:I022303) is a nonsteroidal anti-inflammatory drug that was used to treat pain and inflammation. However, it has been largely discontinued due to its potential side effects and the availability of safer alternatives. 

Reference

1: Kim HS, Austin J, Hage DS. Screening major binding sites on human serum albumin by affinity capillary electrophoresis. Methods Mol Biol. 2004;276:169-87. PubMed PMID: 15163858.
2: García Rodríguez LA, Hernández-Díaz S. Relative risk of upper gastrointestinal complications among users of acetaminophen and nonsteroidal anti-inflammatory drugs. Epidemiology. 2001 Sep;12(5):570-6. PubMed PMID: 11505178.
3: Géher P, Gömör B. Repeated cyclosporine therapy of peripheral arthritis associated with ankylosing spondylitis. Med Sci Monit. 2001 Jan-Feb;7(1):105-7. PubMed PMID: 11208503.
4: Saenz A, Ausejo M, Shea B, Wells G, Welch V, Tugwell P. Pharmacotherapy for Behcet’s syndrome. Cochrane Database Syst Rev. 2000;(2):CD001084. Review. PubMed PMID: 10796413.
5: Gutgesell C, Fuchs T. Azapropazone in aspirin intolerance. Allergy. 1999 Aug;54(8):897-8. PubMed PMID: 10485401.
6: Lequesne MG. Is there preliminary in-vivo evidences of an influence of nonsteroidal antiinflammatory drug treatment on osteoarthritis progression? Part I. Osteoarthritis Cartilage. 1999 May;7(3):350. PubMed PMID: 10329328.
7: Chattopadhyay A, Tian T, Kortum L, Hage DS. Development of tryptophan-modified human serum albumin columns for site-specific studies of drug-protein interactions by high-performance affinity chromatography. J Chromatogr B Biomed Sci Appl. 1998 Sep 11;715(1):183-90. PubMed PMID: 9792509.
8: Rajaian H, Symonds HW, Bowmer CJ. Drug binding sites on chicken albumin: a comparison to human albumin. J Vet Pharmacol Ther. 1997 Dec;20(6):421-6. PubMed PMID: 9430764.
9: Lötsch J, Mohammadian P, Hummel T, Florin S, Brune K, Geisslinger G, Kobal G. Effects of azapropazone on pain-related brain activity in human subjects. Br J Clin Pharmacol. 1995 Dec;40(6):545-52. PubMed PMID: 8703660; PubMed Central PMCID: PMC1365209.
10: Moral F, Hamuryudan V, Yurdakul S, Yazici H. Inefficacy of azapropazone in the acute arthritis of Behçet’s syndrome: a randomized, double blind, placebo controlled study. Clin Exp Rheumatol. 1995 Jul-Aug;13(4):493-5. PubMed PMID: 7586783.
11: Smart JM, Caslake C, Gunn I. Positive interference by azapropazone (Rheumox) in the measurement of total thyroxine using the Ciba-Corning ACS:180 immunoassay analyser. Ann Clin Biochem. 1995 Jul;32 ( Pt 4):424-5. PubMed PMID: 7486806.
12: Pini LA, Sandrini M, Vitale G. Lack of activity of azapropazone in the hot-plate test and in 5-HT1A and 5-HT2 receptor subtypes in rat brain membranes. Drugs Exp Clin Res. 1995;21(5):181-6. PubMed PMID: 8846748.
13: Steffen P, Wiedemann S, Georgieff M, Hähnel J, Treiber H, Seeling W. [Combined intravenous administration of diclofenac and apazone for postoperative analgesia A randomized study of 112 patients with access to i. v. on-demand analgesia after minor orthopaedic operations.]. Schmerz. 1994 Dec;8(4):235-42. German. PubMed PMID: 18415463.
14: Pallapies D, Peskar BA, Brune K, Geisslinger G. Effects on platelet functions and pharmacokinetics of azapropazone and ketorolac tromethamine given as single parenteral doses. Br J Clin Pharmacol. 1994 Apr;37(4):335-9. PubMed PMID: 8018454; PubMed Central PMCID: PMC1364733.
15: Vargas F, Rivas C, Machado R, Sarabia Z, López I. Photoproducts of benzydamine and azapropazone: demonstration of their phototoxicity in vitro. J Photochem Photobiol B. 1993 Jan;17(1):41-5. PubMed PMID: 8433222.
16: Rainsford KD, James C, Johnson DM, Stetsko PI, Hill RE, Salena BJ, Hunt RH. Effects of chronic NSAIDs on gastric mucosal injury related to mucosal prostanoids, and plasma drug concentrations in human volunteers. Agents Actions. 1993;39 Spec No:C21-3. PubMed PMID: 8273571.
17: McCune KH, Allen D, Cranley B. Small bowel diaphragm disease–strictures associated with non-steroidal anti-inflammatory drugs. Ulster Med J. 1992 Oct;61(2):182-4. PubMed PMID: 1481311; PubMed Central PMCID: PMC2448949.
18: Meshali MM, el-Dien EZ, Omar SA, Luzzi LA. A new approach to encapsulating non-steroidal anti-inflammatory drugs. V. Biopharmaceutical study of microcapsules of azapropazone coated with pectin and rutin. J Microencapsul. 1992 Jan-Mar;9(1):67-72. PubMed PMID: 1613645.
19: Viani A, Pacifici GM. Quantitative contribution of endogenous compounds and hypoalbuminemia in reducing the binding of furosemide in the plasma of newborn infants. Dev Pharmacol Ther. 1992;18(1-2):39-43. PubMed PMID: 1483361.
20: Beró T, Nagy L, Jávor T, Vincze A. Measurement of non-steroid antiinflammatory drugs induced gastric microbleeding. Acta Physiol Hung. 1992;80(1-4):281-7. PubMed PMID: 1345197.