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Chemical Compound Review

Orthofen     2-[2-[(2,6-dichlorophenyl) amino]phenyl]eth...

Synonyms: Voltaren, Voltarol, Dicrofenac, Novapirina, diclofenac, ...
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Disease relevance of Diclophenac


Psychiatry related information on Diclophenac

  • METHODS: This was a randomized, double-blind, placebo-controlled study designed to compare the antihyperalgesic efficacy of topical (65 mg) and oral (93 mg) diclofenac via estimates of mechanical pain thresholds obtained at the site of induced inflammation with von Frey hairs [6].
  • The effect of treatment with riluzole on locomotor activity was greater than that of treatment with diclofenac and was dose-dependent [7].
  • The use of diclofenac was associated with a significantly more rapid return to calm wakefulness and had significantly less effect upon respiratory rate [8].
  • METHODS: The effect of diclofenac on the developing embryo during the critical period of organogenesis was investigated by using a whole rat embryo culture model [9].
  • The results showed that diclofenac sodium was significantly more effective than placebo in the treatment of nocturnal enuresis [10].

High impact information on Diclophenac


Chemical compound and disease context of Diclophenac


Biological context of Diclophenac


Anatomical context of Diclophenac

  • METHODS: Rats were treated orally with diclofenac (10-100 mg/kg) and killed after 1-24 hours, and their gastrointestinal (GI) tracts were evaluated for ulcer number and area [22].
  • CONCLUSIONS: This study provides both biochemical and direct evidence of macroscopic injury to the small intestine in 68%-75% of volunteers resulting from 2 weeks' ingestion of slow-release diclofenac [23].
  • One possibility is that reactive metabolites of diclofenac form adducts with enterocyte macromolecules, as previously shown for liver [22].
  • The case of a 61-year-old man who gradually developed similar inflammatory changes in the ascending colon during prolonged intake of a slow-release form of diclofenac is presented, and the literature on nonsteroidal antiinflammatory drug-induced intestinal strictures is briefly reviewed [24].
  • Diathermy DCH was performed without pedicle ligature or anal-canal dressing, and a diclofenac suppository was administered at the end of the procedure [25].

Associations of Diclophenac with other chemical compounds


Gene context of Diclophenac

  • Intriguingly, removal of the negative charge from either 216 or 301 produced enzymes (E216A, E216K, and D301Q) with elevated levels (50-75-fold) of catalytic activity toward diclofenac, a carboxylate-containing CYP2C9 substrate that lacks a basic nitrogen atom [28].
  • Determination of the crystal structure of a complex of diclofenac with murine COX-2 demonstrates that diclofenac binds to COX-2 in an inverted conformation with its carboxylate group hydrogen-bonded to Tyr-385 and Ser-530 [29].
  • This study investigated whether biotransformation to metabolites (4'-hydroxy-aceclofenac, diclofenac, 4'-hydroxy-diclofenac) contributes to inhibitory effects on the cyclooxygenase (COX) isozymes in vitro and ex vivo [30].
  • In conclusion, both COX-1-sparing and COX-2-inhibitory actions of aceclofenac may rest in its limited but sustained biotransformation to diclofenac [30].
  • The disappearance of MPA did not correlate with either the activity metabolized via CYP2C9 (diclofenac 4'-hydroxylase activity) or the activity metabolized via CYP2C19 (S-mephenytoin 4'-hydroxylase activity) [31].

Analytical, diagnostic and therapeutic context of Diclophenac


  1. Treatment of biliary colic with diclofenac: a randomized, double-blind, placebo-controlled study. Akriviadis, E.A., Hatzigavriel, M., Kapnias, D., Kirimlidis, J., Markantas, A., Garyfallos, A. Gastroenterology (1997) [Pubmed]
  2. Gastrointestinal safety and anti-inflammatory effects of a hydrogen sulfide-releasing diclofenac derivative in the rat. Wallace, J.L., Caliendo, G., Santagada, V., Cirino, G., Fiorucci, S. Gastroenterology (2007) [Pubmed]
  3. Celecoxib versus diclofenac in long-term management of rheumatoid arthritis: randomised double-blind comparison. Emery, P., Zeidler, H., Kvien, T.K., Guslandi, M., Naudin, R., Stead, H., Verburg, K.M., Isakson, P.C., Hubbard, R.C., Geis, G.S. Lancet (1999) [Pubmed]
  4. A nitric oxide-releasing nonsteroidal anti-inflammatory drug accelerates gastric ulcer healing in rats. Elliott, S.N., McKnight, W., Cirino, G., Wallace, J.L. Gastroenterology (1995) [Pubmed]
  5. Diclofenac reduces the incidence of acute pancreatitis after endoscopic retrograde cholangiopancreatography. Murray, B., Carter, R., Imrie, C., Evans, S., O'Suilleabhain, C. Gastroenterology (2003) [Pubmed]
  6. Peripheral and central antihyperalgesic effects of diclofenac in a model of human inflammatory pain. Burian, M., Tegeder, I., Seegel, M., Geisslinger, G. Clin. Pharmacol. Ther. (2003) [Pubmed]
  7. Riluzole restores motor activity in rats with post-traumatic peripheral neuropathy. Medico, M., Nicosia, A., Grech, M., Onesta, M., Sessa, G., Rampello, L., Drago, F. Neurosci. Lett. (2004) [Pubmed]
  8. A comparison of rectal diclofenac with intramuscular papaveretum or placebo for pain relief following tonsillectomy. Bone, M.E., Fell, D. Anaesthesia. (1988) [Pubmed]
  9. A study of diclofenac-induced teratogenicity during organogenesis using a whole rat embryo culture model. Chan, L.Y., Chiu, P.Y., Siu, S.S., Lau, T.K. Hum. Reprod. (2001) [Pubmed]
  10. Diclofenac sodium in the treatment of primary nocturnal enuresis: double-blind crossover study. Al-Waili, N.S. Clin. Exp. Pharmacol. Physiol. (1986) [Pubmed]
  11. Prevention of in vitro neutrophil-endothelial attachment through shedding of L-selectin by nonsteroidal antiinflammatory drugs. Díaz-González, F., González-Alvaro, I., Campanero, M.R., Mollinedo, F., del Pozo, M.A., Muñoz, C., Pivel, J.P., Sánchez-Madrid, F. J. Clin. Invest. (1995) [Pubmed]
  12. Genetic susceptibility to diclofenac-induced hepatotoxicity: contribution of UGT2B7, CYP2C8, and ABCC2 genotypes. Daly, A.K., Aithal, G.P., Leathart, J.B., Swainsbury, R.A., Dang, T.S., Day, C.P. Gastroenterology (2007) [Pubmed]
  13. Sulindac is excreted into bile by a canalicular bile salt pump and undergoes a cholehepatic circulation in rats. Bolder, U., Trang, N.V., Hagey, L.R., Schteingart, C.D., Ton-Nu, H.T., Cerrè, C., Elferink, R.P., Hofmann, A.F. Gastroenterology (1999) [Pubmed]
  14. Celecoxib versus diclofenac plus omeprazole in high-risk arthritis patients: results of a randomized double-blind trial. Chan, F.K., Hung, L.C., Suen, B.Y., Wong, V.W., Hui, A.J., Wu, J.C., Leung, W.K., Lee, Y.T., To, K.F., Chung, S.C., Sung, J.J. Gastroenterology (2004) [Pubmed]
  15. Coexpression of cyclooxygenases (COX-1, COX-2) and vascular endothelial growth factors (VEGF-A, VEGF-C) in esophageal adenocarcinoma. von Rahden, B.H., Stein, H.J., Pühringer, F., Koch, I., Langer, R., Piontek, G., Siewert, J.R., Höfler, H., Sarbia, M. Cancer Res. (2005) [Pubmed]
  16. Cyclooxygenase-2 is expressed in neuroblastoma, and nonsteroidal anti-inflammatory drugs induce apoptosis and inhibit tumor growth in vivo. Johnsen, J.I., Lindskog, M., Ponthan, F., Pettersen, I., Elfman, L., Orrego, A., Sveinbjörnsson, B., Kogner, P. Cancer Res. (2004) [Pubmed]
  17. A randomized, double-blind, crossover clinical trial of diclofenac plus misoprostol versus acetaminophen in patients with osteoarthritis of the hip or knee. Pincus, T., Koch, G.G., Sokka, T., Lefkowith, J., Wolfe, F., Jordan, J.M., Luta, G., Callahan, L.F., Wang, X., Schwartz, T., Abramson, S.B., Caldwell, J.R., Harrell, R.A., Kremer, J.M., Lautzenheiser, R.L., Markenson, J.A., Schnitzer, T.J., Weaver, A., Cummins, P., Wilson, A., Morant, S., Fort, J. Arthritis Rheum. (2001) [Pubmed]
  18. Diclofenac acyl glucuronide, a major biliary metabolite, is directly involved in small intestinal injury in rats. Seitz, S., Boelsterli, U.A. Gastroenterology (1998) [Pubmed]
  19. An endothelium-derived hyperpolarizing factor distinct from NO and prostacyclin is a major endothelium-dependent vasodilator in resistance vessels of wild-type and endothelial NO synthase knockout mice. Brandes, R.P., Schmitz-Winnenthal, F.H., Félétou, M., Gödecke, A., Huang, P.L., Vanhoutte, P.M., Fleming, I., Busse, R. Proc. Natl. Acad. Sci. U.S.A. (2000) [Pubmed]
  20. Induction of an acetaminophen-sensitive cyclooxygenase with reduced sensitivity to nonsteroid antiinflammatory drugs. Simmons, D.L., Botting, R.M., Robertson, P.M., Madsen, M.L., Vane, J.R. Proc. Natl. Acad. Sci. U.S.A. (1999) [Pubmed]
  21. Coronary hemodynamics in endothelial NO synthase knockout mice. Gödecke, A., Decking, U.K., Ding, Z., Hirchenhain, J., Bidmon, H.J., Gödecke, S., Schrader, J. Circ. Res. (1998) [Pubmed]
  22. Drug enterocyte adducts: possible causal factor for diclofenac enteropathy in rats. Atchison, C.R., West, A.B., Balakumaran, A., Hargus, S.J., Pohl, L.R., Daiker, D.H., Aronson, J.F., Hoffmann, W.E., Shipp, B.K., Treinen-Moslen, M. Gastroenterology (2000) [Pubmed]
  23. A quantitative analysis of NSAID-induced small bowel pathology by capsule enteroscopy. Maiden, L., Thjodleifsson, B., Theodors, A., Gonzalez, J., Bjarnason, I. Gastroenterology (2005) [Pubmed]
  24. Nonsteroidal antiinflammatory drug-induced colonic strictures: a case report. Huber, T., Ruchti, C., Halter, F. Gastroenterology (1991) [Pubmed]
  25. Double-blind randomised controlled trial of effect of metronidazole on pain after day-case haemorrhoidectomy. Carapeti, E.A., Kamm, M.A., McDonald, P.J., Phillips, R.K. Lancet (1998) [Pubmed]
  26. Cyclosporin and diclofenac interaction in rheumatoid arthritis. Branthwaite, J.P., Nicholls, A. Lancet (1991) [Pubmed]
  27. Pulsatile stretch in coronary arteries elicits release of endothelium-derived hyperpolarizing factor: a modulator of arterial compliance. Popp, R., Fleming, I., Busse, R. Circ. Res. (1998) [Pubmed]
  28. Residues glutamate 216 and aspartate 301 are key determinants of substrate specificity and product regioselectivity in cytochrome P450 2D6. Paine, M.J., McLaughlin, L.A., Flanagan, J.U., Kemp, C.A., Sutcliffe, M.J., Roberts, G.C., Wolf, C.R. J. Biol. Chem. (2003) [Pubmed]
  29. A novel mechanism of cyclooxygenase-2 inhibition involving interactions with Ser-530 and Tyr-385. Rowlinson, S.W., Kiefer, J.R., Prusakiewicz, J.J., Pawlitz, J.L., Kozak, K.R., Kalgutkar, A.S., Stallings, W.C., Kurumbail, R.G., Marnett, L.J. J. Biol. Chem. (2003) [Pubmed]
  30. Aceclofenac spares cyclooxygenase 1 as a result of limited but sustained biotransformation to diclofenac. Hinz, B., Rau, T., Auge, D., Werner, U., Ramer, R., Rietbrock, S., Brune, K. Clin. Pharmacol. Ther. (2003) [Pubmed]
  31. Role of human cytochrome P450 3A4 in metabolism of medroxyprogesterone acetate. Kobayashi, K., Mimura, N., Fujii, H., Minami, H., Sasaki, Y., Shimada, N., Chiba, K. Clin. Cancer Res. (2000) [Pubmed]
  32. Epidemiology of aplastic anemia in France: a case-control study. I. Medical history and medication use. The French Cooperative Group for Epidemiological Study of Aplastic Anemia. Baumelou, E., Guiguet, M., Mary, J.Y. Blood (1993) [Pubmed]
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