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Chemical Compound Review

Koloxo     2-[4-[(2-oxocyclopentyl) methyl]phenyl]prop...

Synonyms: Loxoprofen, Loxoprofene, Loxoprofeno, Loxoprofenum, CHEMBL19299, ...
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Disease relevance of Loxoprofen


High impact information on Loxoprofen

  • The dihydrodiol dehydrogenases also showed lower Km values for haloperidol and loxoprofen than did carbonyl reductase [5].
  • Results were compared with those for loxoprofen, a non-selective COX inhibitor [6].
  • Comparison of pharmacokinetics of loxoprofen and its active metabolites after an intravenous, intramuscular, and oral administration of loxoprofen in rats: evidence for extrahepatic metabolism [7].
  • After the intragastric, intravenous, or intramuscular administration, AUC for loxoprofen and the metabolites at a dose of 10 mg/kg were not statistically different for the different routes of administration [7].
  • The objective of this study was to characterize the extent of the formation of the active (trans-alcohol form) and inactive (cis-alcohol) metabolites of loxoprofen and to compare the kinetics after its intragastric, intravenous, and intramuscular administrations in rats [7].

Chemical compound and disease context of Loxoprofen

  • The cause of hyperkalemia was considered to be several doses of loxoprofen, a nonsteroidal anti-inflammatory drug (NSAID), prescribed for her lumbago by an orthopedic specialist, in addition to the long-term intake of imidapril, an angiotensin-converting enzyme inhibitor (ACEI), prescribed for her hypertension by a cardiologist [8].

Biological context of Loxoprofen

  • Thus, approximately 22% of the loxoprofen may have been converted to the active metabolite in the liver and the extraheptic tissue(s) and the pharmacokinetics of the active metabolite was independent of the route of administration [7].
  • Decreased oral bioavailability of loxoprofen at second administration in human subjects [9].
  • The intramuscular ED50 values of loxoprofen sodium in carrageenan edema and vascular permeability tests are 1.15 and 7.8 mg/kg, respectively, which represent more potent than in case of oral application [10].

Anatomical context of Loxoprofen


Associations of Loxoprofen with other chemical compounds

  • A method for simultaneously quantitating the enantiomers in the alpha-substituted propionic acid moiety of loxoprofen and its two monohydroxy metabolites, trans- and cis-alcohols, by column liquid chromatography was described [14].
  • The drugs were given by twice daily oral administration for 10 days beginning 15 days after adjuvant injection, with celecoxib at 0.01-3 mg/kg/day and loxoprofen at 0.01-3 mg/kg/day [6].
  • A controlled double blind study on the incidence of nonsteroidal antiinflammatory drug (NSAID) gastropathy was performed in 29 healthy volunteers administered diclofenac Na (10 subjects) or a prodrug (loxoprofen Na in 10 subjects and proglumetacin maleate in 9 subjects) [15].
  • Loxoprofen sodium (sodium 2[4-(2-oxocyclopentylmethyl) phenyl] dehydrate; CAS #68767-14-6) is a nonsteroidal, inflammatory drug marketed only in Japan. A case report describes its association with an acute asthmatic death with features resembling those evoked by similar drugs [16].
  • These findings suggest that loxoprofen retards the elimination of methotrexate, at least in part, by inhibiting hOAT1 and hOAT3 [17].

Gene context of Loxoprofen


Analytical, diagnostic and therapeutic context of Loxoprofen


  1. Loxoprofen sodium and survival in older people with advanced non-small cell lung cancer. Kanda, A., Ebihara, S., Okazaki, T., Yasuda, H., Sasaki, H. Journal of the American Geriatrics Society. (2004) [Pubmed]
  2. Loxoprofen sodium suppresses mouse tumor growth by inhibiting vascular endothelial growth factor. Kanda, A., Ebihara, S., Takahashi, H., Sasaki, H. Acta oncologica (Stockholm, Sweden) (2003) [Pubmed]
  3. Study on the mechanism of photosensitive dermatitis caused by ketoprofen in the guinea pig. Nakazawa, T., Shimo, T., Chikamatsu, N., Igarashi, T., Nagata, O., Yamamoto, M. Arch. Toxicol. (2006) [Pubmed]
  4. Effectiveness of an anti-inflammatory drug, loxoprofen, for patients with nocturia. Saito, M., Kawatani, M., Kinoshita, Y., Satoh, K., Miyagawa, I. International journal of urology : official journal of the Japanese Urological Association. (2005) [Pubmed]
  5. Reduction of drug ketones by dihydrodiol dehydrogenases, carbonyl reductase and aldehyde reductase of human liver. Ohara, H., Miyabe, Y., Deyashiki, Y., Matsuura, K., Hara, A. Biochem. Pharmacol. (1995) [Pubmed]
  6. Effect of celecoxib, a cyclooxygenase-2 inhibitor, on the pathophysiology of adjuvant arthritis in rat. Noguchi, M., Kimoto, A., Kobayashi, S., Yoshino, T., Miyata, K., Sasamata, M. Eur. J. Pharmacol. (2005) [Pubmed]
  7. Comparison of pharmacokinetics of loxoprofen and its active metabolites after an intravenous, intramuscular, and oral administration of loxoprofen in rats: evidence for extrahepatic metabolism. Koo, T.S., Kim, D.H., Ahn, S.H., Kim, K.P., Kim, I.W., Seo, S.Y., Suh, Y.G., Kim, D.D., Shim, C.K., Chung, S.J. Journal of pharmaceutical sciences. (2005) [Pubmed]
  8. Syncope caused by nonsteroidal anti-inflammatory drugs and angiotensin-converting enzyme inhibitors. Kurata, C., Uehara, A., Sugi, T., Yamazaki, K. Jpn. Circ. J. (1999) [Pubmed]
  9. Decreased oral bioavailability of loxoprofen at second administration in human subjects. Kim, I.W., Choo, K.S., Han, T.G., Kim, K.S., Chung, S.J., Lee, M.H., Shim, C.K. International journal of clinical pharmacology and therapeutics. (2000) [Pubmed]
  10. Anti-inflammatory, analgesic and antipyretic activities of loxoprofen sodium given intramuscularly in animals. Hyun, J.E., Li, D.W., Lee, E.B., Jeong, C.S. Arch. Pharm. Res. (2001) [Pubmed]
  11. Purification and some properties of ketone reductase forming an active metabolite of sodium 2-[4-(2-oxocyclopentylmethyl)-phenyl]propionate dihydrate (loxoprofen sodium), a new anti-inflammatory agent, in rabbit liver cytosol. Tanaka, Y., Nishikawa, Y., Matsuda, K., Yamazaki, M., Hayashi, R. Chem. Pharm. Bull. (1984) [Pubmed]
  12. Ulcerogenicity and effect on inhibition of prostaglandin generation of indometacin farnesil, a prodrug of indomethacin, in rat gastric mucosa: comparison with indomethacin or loxoprofen. Arakawa, T., Fukuda, T., Nakagawa, K., Higuchi, K., Watanabe, T., Tominaga, K., Kobayashi, K. Drugs under experimental and clinical research. (1995) [Pubmed]
  13. A case of complex regional pain syndrome type II after transradial coronary intervention. Sasano, N., Tsuda, T., Sasano, H., Ito, S., Sobue, K., Katsuya, H. Journal of anesthesia. (2004) [Pubmed]
  14. Column liquid chromatography for the simultaneous determination of the enantiomers of loxoprofen sodium and its metabolites in human urine. Nagashima, H., Tanaka, Y., Hayashi, R. J. Chromatogr. (1985) [Pubmed]
  15. Possible mechanisms of gastroduodenal mucosal damage in volunteers treated with nonsteroidal antiinflammatory drugs--the usefulness of prodrugs. Yanagawa, A., Fukumura, T., Matsui, H., Uemura, H., Endo, T., Nakagawa, T., Mizushima, Y. J. Rheumatol. (1992) [Pubmed]
  16. Loxoprofen--another NSAID associated with acute asthmatic death. Watanabe, T., Sakata, M., Shimabukuro, R., Sakata, K., Tabata, N., Azumi, J., Morita, M., Itaya, K. J. Toxicol. Clin. Toxicol. (1993) [Pubmed]
  17. Methotrexate-loxoprofen interaction: involvement of human organic anion transporters hOAT1 and hOAT3. Uwai, Y., Taniguchi, R., Motohashi, H., Saito, H., Okuda, M., Inui, K. Drug Metab. Pharmacokinet. (2004) [Pubmed]
  18. Evaluation of loxoprofen and its alcohol metabolites for potency and selectivity of inhibition of cyclooxygenase-2. Riendeau, D., Salem, M., Styhler, A., Ouellet, M., Mancini, J.A., Li, C.S. Bioorg. Med. Chem. Lett. (2004) [Pubmed]
  19. Enzymologic and pharmacologic profile of loxoprofen sodium and its metabolites. Noguchi, M., Kimoto, A., Gierse, J.K., Walker, M.C., Zweifel, B.S., Nozaki, K., Sasamata, M. Biol. Pharm. Bull. (2005) [Pubmed]
  20. Retroperitoneal fibrosis with periaortic and pericardial involvement. Amiya, E., Ishizaka, N., Watanabe, A., Endo, Y., Itou, R., Yoshida, S., Nangaku, M., Nagai, R. Circ. J. (2005) [Pubmed]
  21. Stereospecific analysis of loxoprofen in plasma by chiral column liquid chromatography with a circular dichroism-based detector. Kanazawa, H., Tsubayashi, A., Nagata, Y., Matsushima, Y., Mori, C., Kizu, J., Higaki, M. Journal of chromatography. A. (2002) [Pubmed]
  22. Altered metabolism of orally administered loxoprofen in human subjects after an oral administration of loxoprofen for three consecutive days followed by a seven-day washout. Kim, I.W., Chung, S.J., Shim, C.K. Journal of pharmaceutical sciences. (2002) [Pubmed]
  23. Premedication with cyclooxygenase-2 inhibitor meloxicam reduced postoperative pain in patients after oral surgery. Aoki, T., Yamaguchi, H., Naito, H., Shiiki, K., Izawa, K., Ota, Y., Sakamoto, H., Kaneko, A. International journal of oral and maxillofacial surgery. (2006) [Pubmed]
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