ACS Medicinal Chemistry Letters
Letter
(
22) Akyel, A.; Alsancak, Y.; Yayla, C.; Sahinarslan, A.; Ozdemir, M.
REFERENCES
■
Acute inferior myocardial infarction with low atrial rhythm due to
propyphenazone: Kounis syndrome. Int. J. Cardiol. 2011, 148 (3),
(
1) Green, G. A. Understanding NSAIDs: from aspirin to COX-2.
Clin. Cornerstone 2001, 3 (5), 50−60.
2) Makhijia, D. T.; Somani, R. R. Improvement of GI tolerance of
NSAIDs using oral prodrug approach. Der Pharm. Lett. 2010, 2 (2),
00−309.
3) Allison, M. C.; Howatson, A. G.; Torrance, C. J.; Lee, F. D.;
3
(
52−353.
(
23) Goromaru, T.; Matsuura, H.; Furuta, T.; Baba, S. Identification
of isopropylantipyrine metabolites in rat and man by using stable
3
(
isotope tracer techniques. Chem. Pharm. Bull. 1984, 32 (8), 3179−
3
186.
Russell, R. I. Gastrointestinal damage associated with the use of
nonsteroidal antiinflammatory drugs. N. Engl. J. Med. 1992, 327 (11),
(
24) Perez, C.; Daniel, K. B.; Cohen, S. M. Evaluating prodrug
strategies for esterase-triggered release of alcohols. ChemMedChem
013, DOI: 10.1002/cmdc.201300255.
25) Lacour, M. Betahistine treatment in managing vertigo and
improving vestibular compensation: clarification. J. Vestibular Res.
013, 23 (3), 139−151.
26) Windsor, M. A.; Hermanson, D. J.; Kingsley, P. J.; Xu, S.; Crews,
7
(
49−754.
4) Wallace, J. L. How do NSAIDs cause ulcer disease? Bailliere's Best
Pract. Res., Clin. Anaesthesiol. 2000, 14 (1), 147−159.
5) Fromm, D. How do non-steroidal anti-inflammatory drugs affect
gastric mucosal defenses? Clin. Invest. Med. 1987, 10 (3), 251−258.
6) Somasundaram, S.; Hayllar, H.; Rafi, S.; Wrigglesworth, J. M.;
Macpherson, A. J.; Bjarnason, I. The biochemical basis of non-steroidal
anti-inflammatory drug-induced damage to the gastrointestinal tract: a
review and a hypothesis. Scand. J. Gastroenterol. 1995, 30 (4), 289−
2
(
(
2
(
(
B. C.; Ho, W.; Keenan, C. M.; Banerjee, S.; Sharkey, K. A.; Marnett, L.
J. Substrate-selective inhibition of cyclooxygenase-2: Development and
evaluation of achiral profen probes. ACS Med. Chem. Lett. 2012, 3 (9),
7
(
59−763.
299.
27) Cao, H.; Yu, R.; Tao, Y.; Nikolic, D.; van Breemen, R. B.
(
7) Yamaoka, S.; Urade, R.; Kito, M. Mitochondrial function in rats is
affected by modification of membrane phospholipids with dietary
sardine oil. J. Nutr. 1988, 118 (3), 290−296.
8) Rainsford, K. D.; Willis, C. Relationship of gastric mucosal
damage induced in pigs by antiinflammatory drugs to their effects on
prostaglandin production. Dig. Dis. Sci. 1982, 27 (7), 624−635.
9) Whittle, B. J. Temporal relationship between cyclooxygenase
Measurement of cyclooxygenase inhibition using liquid chromatog-
raphy-tandem mass spectrometry. J. Pharm. Biomed. Anal. 2011, 54
(
1), 230−235.
28) Koster, R. M.; Anderson, M.; Debeer, E. J. Acetic acid for
analgesic screening. Fed. Proc. 1959, 18, 412−416.
29) Sawraj, S.; Bhardawaj, T.; Sharma, P. Design, synthesis and
(
(
(
(
evaluation of novel indomethacin-flavonoid mutual prodrugs as safer
NSAIDs. Med. Chem. Res. 2011, 20, 687−694.
(
inhibition, as measured by prostacyclin biosynthesis, and the
gastrointestinal damage induced by indomethacin in the rat.
Gastroenterology 1981, 80 (1), 94−98.
30) Kurumbail, R. G.; Stevens, A. M.; Gierse, J. K.; McDonald, J. J.;
Stegeman, R. A.; Pak, J. Y.; Gildehaus, D.; Miyashiro, J. M.; Penning,
T. D.; Seibert, K.; Isakson, P. C.; Stallings, W. C. Structural basis for
selective inhibition of cyclooxygenase-2 by anti-inflammatory agents.
Nature 1996, 384 (6610), 644−648.
(
1
10) Abuo-Rahma Gel, D.; Abdel-Aziz, M.; Beshr, E. A.; Ali, T. F.
,2,4-Triazole/oxime hybrids as new strategy for nitric oxide donors:
Synthesis, anti-inflammatory, ulceroginicity and antiproliferative
activities. Eur. J. Med. Chem. 2014, 71, 185−198.
11) Abdel-Aziz, M.; Abuo-Rahma Gel, D.; Beshr, E. A.; Ali, T. F.
New nitric oxide donating 1,2,4-triazole/oxime hybrids: synthesis,
investigation of anti-inflammatory, ulceroginic liability and antiproli-
ferative activities. Bioorg. Med. Chem. 2013, 21 (13), 3839−3849.
12) Takeuchi, K.; Yasuhiro, T.; Asada, Y.; Sugawa, Y. Role of nitric
oxide in pathogenesis of aspirin-induced gastric mucosal damage in
rats. Digestion 1998, 59 (4), 298−307.
13) Holzer, P.; Pabst, M. A.; Lippe, I. T.; Peskar, B. M.; Peskar, B.
A.; Livingston, E. H.; Guth, P. H. Afferent nerve-mediated protection
against deep mucosal damage in the rat stomach. Gastroenterology
(
31) Luong, C.; Miller, A.; Barnett, J.; Chow, J.; Ramesha, C.;
(
Browner, M. F. Flexibility of the NSAID binding site in the structure of
human cyclooxygenase-2. Nat. Struct. Biol. 1996, 3 (11), 927−933.
(
Investigating substrate promiscuity in cyclooxygenase-2: The role of
Arg-120 and residues lining the hydrophobic groove. J. Biol. Chem.
32) Vecchio, A. J.; Orlando, B. J.; Nandagiri, R.; Malkowski, M. G.
(
2
(
012, 287 (29), 24619−24630.
33) Rao, P.; Knaus, E. E. Evolution of nonsteroidal anti-
(
inflammatory drugs (NSAIDs): cyclooxygenase (COX) inhibition
and beyond. J. Pharm. Pharm. Sci. 2008, 11 (2), 81s−110s.
1
990, 98 (4), 838−848.
14) Wallace, J. L.; Miller, M. J. Nitric oxide in mucosal defense: a
little goes a long way. Gastroenterology 2000, 119 (2), 512−520.
15) Halen, P. K.; Murumkar, P. R.; Giridhar, R.; Yadav, M. R.
Prodrug designing of NSAIDs. Mini Rev. Med. Chem. 2009, 9 (1),
24−139.
16) Calvi, E.; Picciola, G.; Carenini, G.; Gentili, P. Synthesis and
(
(
1
(
pharmacologic study of new esters of naproxen with derivatives of N-
oxyethylpiperazine. Il Farmaco; Edizione Scientifica 1985, 40 (5), 334−
346.
(
17) Sheha, M.; Khedr, A.; Elsherief, H. Biological and metabolic
study of naproxen-propyphenazone mutual prodrug. Eur. J. Pharm. Sci.
002, 17 (3), 121−130.
18) Hsiao, F. Y.; Tsai, Y. W.; Huang, W. F. Changes in physicians’
2
(
practice of prescribing cyclooxygenase-2 inhibitor after market
withdrawal of rofecoxib: a retrospective study of physician-patient
pairs in Taiwan. Clin. Ther. 2009, 31 (11), 2618−2627.
(
19) Zarraga, I. G.; Schwarz, E. R. Coxibs and heart disease: what we
have learned and what else we need to know. J. Am. Coll. Cardiol.
007, 49 (1), 1−14.
20) Boerlin, V.; Maeglin, B.; Hagler, W.; Kuhn, M.; Nuesch, E.
2
(
Analgesic activity of propyphenazone in patients with pain following
oral surgery. Eur. J. Clin. Pharmacol. 1986, 31 (2), 127−131.
(
21) Kraetsch, H. G.; Hummel, T.; Lotsch, J.; Kussat, R.; Kobal, G.
Analgesic effects of propyphenazone in comparison to its combination
with caffeine. Eur. J. Clin. Pharmacol. 1996, 49 (5), 377−382.
F
dx.doi.org/10.1021/ml500156v | ACS Med. Chem. Lett. XXXX, XXX, XXX−XXX