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Chemical Compound Review

Thamnosmonin     6-(1,2-dihydroxy-3-methyl- but-3-enyl)-7...

Synonyms: COUMARIN (I), CHEMBL498094, AG-G-14843, NSC-220196, NSC-284685, ...
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Disease relevance of coumarin


Psychiatry related information on coumarin


High impact information on coumarin

  • Here we show that the uptake, storage and release of organic molecules in MCM-41 can be regulated through the photocontrolled and reversible intermolecular dimerization of coumarin derivatives attached to the pore outlets [6].
  • We report that the activities of both cytochromes depend critically on the identities of the amino acids at positions 117, 209 and 365 and, moreover, that a single mutation in which Phe 209 is substituted by Leu is sufficient to convert the specificity of P450coh from coumarin to steroid hydroxylation [7].
  • Patients with atrial fibrillation should be treated prophylactically with coumarin agents, but only if underlying organic heart disease is demonstrable [8].
  • CONCLUSIONS: These coumarin antibiotics, particularly novobiocin, represent a first-generation alternative to other Hsp90-targeting drugs that are not as well tolerated [9].
  • Effects of the coumarin antibiotics novobiocin, chlorobiocin, and coumermycin A1 on several proteins interacting with Hsp90 were assessed in vitro and in vivo [9].

Chemical compound and disease context of coumarin


Biological context of coumarin


Anatomical context of coumarin


Associations of coumarin with other chemical compounds


Gene context of coumarin

  • These variant alleles were found in individuals who were deficient in their ability to metabolize the CYP2A6 probe drug coumarin [27].
  • The structure-activity studies have revealed that three functional groups (i.e. 3-(4'-chlorophenyl), 4-benzyl, and 7-methoxyl) of this coumarin are important in its inhibition of aromatase [28].
  • We propose that binding of resveratrol to SIRT1 promotes a conformational change that better accommodates the attached coumarin group [29].
  • Other coumarin derivatives failed to block SAPK activation, but other inhibitors of quinone reductases, particularly menadione, similarly blocked SAPK activation [30].
  • Biotransformation of coumarin by rodent and human cytochromes P-450: metabolic basis of tissue-selective toxicity in olfactory mucosa of rats and mice [31].

Analytical, diagnostic and therapeutic context of coumarin

  • The rate of events was similar between sexes, coumarin type, size of enrolling centre, and target INR [32].
  • A peptide corresponding to the N-terminal 17 amino acids of bovine rhodanese was fluorescently labeled with a coumarin derivative at its primary amino group(s) and then purified by high performance liquid chromatography [33].
  • It hydrolyzed benzyloxylcarbonyl-Gly-Gly-Arg-amino-4-trifluoromethyl coumarin, and a Km of 53 microM and a Vmax of 63 mumol/min/mg of enzyme were obtained at pH 8.0 and 37 degrees C. The enzyme cleaved kininogen substrates to produce kinin which was measured by bioassay or radioimmunoassay [34].
  • Coumarin agents provide adequate protection against thromboembolism during pregnancy in patients with mechanical valve prostheses [35].
  • Here we describe a coumarin-phosphine dye that undergoes activation of coumarin fluorescence upon Staudinger ligation with azides [36].


  1. Lack of effect of coumarin in women with lymphedema after treatment for breast cancer. Loprinzi, C.L., Kugler, J.W., Sloan, J.A., Rooke, T.W., Quella, S.K., Novotny, P., Mowat, R.B., Michalak, J.C., Stella, P.J., Levitt, R., Tschetter, L.K., Windschitl, H. N. Engl. J. Med. (1999) [Pubmed]
  2. Risks of anticoagulant therapy in pregnant women with artificial heart valves. Iturbe-Alessio, I., Fonseca, M.C., Mutchinik, O., Santos, M.A., Zajarías, A., Salazar, E. N. Engl. J. Med. (1986) [Pubmed]
  3. Maternal and fetal sequelae of anticoagulation during pregnancy. Hall, J.G., Pauli, R.M., Wilson, K.M. Am. J. Med. (1980) [Pubmed]
  4. AD6, a coumarin derivative, and other pharmacological approaches to splanchnic artery occlusion (SAO) shock therapy. Squadrito, F., Sturniolo, R., Altavilla, D., Caputi, A.P. Journal of chemotherapy (Florence, Italy) (1989) [Pubmed]
  5. Comparison of the hepatotoxicity of coumarin in the rat, mouse, and Syrian hamster: a dose and time response study. Lake, B.G., Grasso, P. Fundamental and applied toxicology : official journal of the Society of Toxicology. (1996) [Pubmed]
  6. Photocontrolled reversible release of guest molecules from coumarin-modified mesoporous silica. Mal, N.K., Fujiwara, M., Tanaka, Y. Nature (2003) [Pubmed]
  7. Alteration of mouse cytochrome P450coh substrate specificity by mutation of a single amino-acid residue. Lindberg, R.L., Negishi, M. Nature (1989) [Pubmed]
  8. Drug prophylaxis for arterial thromboembolism--1981. Wessler, S. JAMA (1981) [Pubmed]
  9. Novobiocin and related coumarins and depletion of heat shock protein 90-dependent signaling proteins. Marcu, M.G., Schulte, T.W., Neckers, L. J. Natl. Cancer Inst. (2000) [Pubmed]
  10. Cimetidine and coumarin therapy of melanoma. Thornes, R.D., Lynch, G., Sheehan, M.V. Lancet (1982) [Pubmed]
  11. The nature of inhibition of DNA gyrase by the coumarins and the cyclothialidines revealed by X-ray crystallography. Lewis, R.J., Singh, O.M., Smith, C.V., Skarzynski, T., Maxwell, A., Wonacott, A.J., Wigley, D.B. EMBO J. (1996) [Pubmed]
  12. Association of congenital deficiency of multiple vitamin K-dependent coagulation factors and the phenotype of the warfarin embryopathy: clues to the mechanism of teratogenicity of coumarin derivatives. Pauli, R.M., Lian, J.B., Mosher, D.F., Suttie, J.W. Am. J. Hum. Genet. (1987) [Pubmed]
  13. Randomized comparison of low molecular weight heparin and coumarin derivatives on the survival of patients with cancer and venous thromboembolism. Lee, A.Y., Rickles, F.R., Julian, J.A., Gent, M., Baker, R.I., Bowden, C., Kakkar, A.K., Prins, M., Levine, M.N. J. Clin. Oncol. (2005) [Pubmed]
  14. Phase II study of coumarin and cimetidine in patients with metastatic renal cell carcinoma. Dexeus, F.H., Logothetis, C.J., Sella, A., Fitz, K., Amato, R., Reuben, J.M., Dozier, N. J. Clin. Oncol. (1990) [Pubmed]
  15. Heparins, coumarin, and bone density. Monreal, M., Olive, A., Lafoz, E., del Rio, L. Lancet (1991) [Pubmed]
  16. Assembly and exchange of intermediate filament proteins of neurons: neurofilaments are dynamic structures. Angelides, K.J., Smith, K.E., Takeda, M. J. Cell Biol. (1989) [Pubmed]
  17. Armand J. Quick: pioneer and prophet of coagulation research. Dirckx, J.H. Ann. Intern. Med. (1980) [Pubmed]
  18. cDNA and protein sequence of polymorphic macaque albumins that differ in bilirubin binding. Watkins, S., Sakamoto, Y., Madison, J., Davis, E., Smith, D.G., Dwulet, J., Putnam, F.W. Proc. Natl. Acad. Sci. U.S.A. (1993) [Pubmed]
  19. Loss of the MYC gene amplified in human HL-60 cells after treatment with inhibitors of poly(ADP-ribose) polymerase or with dimethyl sulfoxide. Shima, H., Nakayasu, M., Aonuma, S., Sugimura, T., Nagao, M. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  20. Effect of coumarin on the normal rat prostate and on the R-3327H prostatic adenocarcinoma. Omarbasha, B., Fair, W.R., Heston, W.D. Cancer Res. (1989) [Pubmed]
  21. Genetic regulation of coumarin hydroxylase activity in mice. Biochemical characterization of the enzyme from two inbred strains and their F1 hybrid. Wood, A.W. J. Biol. Chem. (1979) [Pubmed]
  22. Regression of melanoma nodules in a patient treated with ranitidine. Smith, T., Clark, J.W., Popp, M.B. Arch. Intern. Med. (1987) [Pubmed]
  23. Destabilization of the non-pathogenic, cellular prion-protein by a small molecular drug. Ochel, H.J., Gademann, G. Antivir. Ther. (Lond.) (2004) [Pubmed]
  24. Dicoumarol: a unique microtubule stabilizing natural product that is synergistic with Taxol. Madari, H., Panda, D., Wilson, L., Jacobs, R.S. Cancer Res. (2003) [Pubmed]
  25. Chemoprevention of aflatoxin B1 hepatocarcinogenesis by coumarin, a natural benzopyrone that is a potent inducer of aflatoxin B1-aldehyde reductase, the glutathione S-transferase A5 and P1 subunits, and NAD(P)H:quinone oxidoreductase in rat liver. Kelly, V.P., Ellis, E.M., Manson, M.M., Chanas, S.A., Moffat, G.J., McLeod, R., Judah, D.J., Neal, G.E., Hayes, J.D. Cancer Res. (2000) [Pubmed]
  26. Identification and characterization of liver nonparenchymal cells by flow cytometry. Doolittle, M., Bohman, R., Durstenfeld, A., Cascarano, J. Hepatology (1987) [Pubmed]
  27. A genetic polymorphism in coumarin 7-hydroxylation: sequence of the human CYP2A genes and identification of variant CYP2A6 alleles. Fernandez-Salguero, P., Hoffman, S.M., Cholerton, S., Mohrenweiser, H., Raunio, H., Rautio, A., Pelkonen, O., Huang, J.D., Evans, W.E., Idle, J.R. Am. J. Hum. Genet. (1995) [Pubmed]
  28. Biochemical and biological characterization of a novel anti-aromatase coumarin derivative. Chen, S., Cho, M., Karlsberg, K., Zhou, D., Yuan, Y.C. J. Biol. Chem. (2004) [Pubmed]
  29. Mechanism of human SIRT1 activation by resveratrol. Borra, M.T., Smith, B.C., Denu, J.M. J. Biol. Chem. (2005) [Pubmed]
  30. Quinone reductase inhibitors block SAPK/JNK and NFkappaB pathways and potentiate apoptosis. Cross, J.V., Deak, J.C., Rich, E.A., Qian, Y., Lewis, M., Parrott, L.A., Mochida, K., Gustafson, D., Vande Pol, S., Templeton, D.J. J. Biol. Chem. (1999) [Pubmed]
  31. Biotransformation of coumarin by rodent and human cytochromes P-450: metabolic basis of tissue-selective toxicity in olfactory mucosa of rats and mice. Zhuo, X., Gu, J., Zhang, Q.Y., Spink, D.C., Kaminsky, L.S., Ding, X. J. Pharmacol. Exp. Ther. (1999) [Pubmed]
  32. Bleeding complications of oral anticoagulant treatment: an inception-cohort, prospective collaborative study (ISCOAT). Italian Study on Complications of Oral Anticoagulant Therapy. Palareti, G., Leali, N., Coccheri, S., Poggi, M., Manotti, C., D'Angelo, A., Pengo, V., Erba, N., Moia, M., Ciavarella, N., Devoto, G., Berrettini, M., Musolesi, S. Lancet (1996) [Pubmed]
  33. Binding of an N-terminal rhodanese peptide to DnaJ and to ribosomes. Kudlicki, W., Odom, O.W., Kramer, G., Hardesty, B. J. Biol. Chem. (1996) [Pubmed]
  34. Purification and characterization of rat urinary esterase A, a plasminogen activator. Chao, J. J. Biol. Chem. (1983) [Pubmed]
  35. Failure of adjusted doses of subcutaneous heparin to prevent thromboembolic phenomena in pregnant patients with mechanical cardiac valve prostheses. Salazar, E., Izaguirre, R., Verdejo, J., Mutchinick, O. J. Am. Coll. Cardiol. (1996) [Pubmed]
  36. A fluorogenic dye activated by the staudinger ligation. Lemieux, G.A., De Graffenried, C.L., Bertozzi, C.R. J. Am. Chem. Soc. (2003) [Pubmed]
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