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Chemical Compound Review

Muramyl Dipeptide     (4R)-4-[[(2S)-2-[[(2R)-2- [(2R,3R,4R,5S,6R)...

Synonyms: SureCN41814, CHEMBL369794, CHEBI:59414, AC1L9PSS, 53678-77-6, ...
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Disease relevance of N-Acetylmuramyl-L-alanyl-D-isoglutamine


Psychiatry related information on N-Acetylmuramyl-L-alanyl-D-isoglutamine


High impact information on N-Acetylmuramyl-L-alanyl-D-isoglutamine


Chemical compound and disease context of N-Acetylmuramyl-L-alanyl-D-isoglutamine


Biological context of N-Acetylmuramyl-L-alanyl-D-isoglutamine


Anatomical context of N-Acetylmuramyl-L-alanyl-D-isoglutamine


Associations of N-Acetylmuramyl-L-alanyl-D-isoglutamine with other chemical compounds


Gene context of N-Acetylmuramyl-L-alanyl-D-isoglutamine

  • If this hypothesis is correct, then inhibition of endogenous IL-1 should reduce both normal sleep and N-acetylmuramyl-L-alanyl-D-isoglutamine (MDP)-induced sleep [34].
  • Also IL-4 and IFN-gamma are released by PA in quantities higher than those induced by TA and MDP [35].
  • At concentration of 10 micrograms/ml; PA induces roughly +180% release of TNF with respect to controls, while release of IL-1 alpha is about 500% control values, and is higher than those obtained when cells are treated with TA and MDP; IL-6 release is higher than that stimulated by Con A, used as standard challenge [35].
  • Two muramyl dipeptides, N-acetylmuramyl-L-alanyl-D-isoglutamine and its adjuvant-inactive isomer N-acetylmuramyl-D-alanyl-D-isoglutamine, were examined for their ability to protect mice carrying the CBA/N immune deficiency gene (xid) against lethal bacterial challenge [36].
  • Muramyl dipeptide (MDP) and Escherichia coli LPS also stimulated TNF-alpha and IL-6 mRNA expression [37].

Analytical, diagnostic and therapeutic context of N-Acetylmuramyl-L-alanyl-D-isoglutamine


  1. Adjuvant polyarthritis. V. Induction by N-acetylmuramyl-L-alanyl-D-isoglutamine, the smallest peptide subunit of bacterial peptidoglycan. Chang, Y.H., Pearson, C.M., Chedid, L. J. Exp. Med. (1981) [Pubmed]
  2. Enhancement of nonspecific immunity to Klebsiella pneumoniae infection by a synthetic immunoadjuvant (N-acetylmuramyl-L-alanyl-D-isoglutamine) and several analogs. Chedid, L., Parant, M., Parant, F., Lefrancher, P., Choay, J., Lederer, E. Proc. Natl. Acad. Sci. U.S.A. (1977) [Pubmed]
  3. Potentiation of the immune response to influenza virus subunit vaccines. Webster, R.G., Glezen, W.P., Hannoun, C., Laver, W.G. J. Immunol. (1977) [Pubmed]
  4. Structural requirements of muramylpeptides for induction of necrosis at sites primed with Mycobacterium tuberculosis in guinea pigs. Nagao, S., Takada, H., Yagawa, K., Kutsukake, H., Shiba, T., Kusumoto, S., Kawata, S., Hasegawa, A., Kiso, M., Azuma, I. Infect. Immun. (1987) [Pubmed]
  5. Immunotherapy of experimental cancer with a mixture of synthetic muramyl dipeptide and trehalose dimycolate. Yarkoni, E., Lederer, E., Rapp, H.J. Infect. Immun. (1981) [Pubmed]
  6. Muramyl dipeptide does not induce slow-wave sleep or fever in rats. Fornal, C., Markus, R., Radulovacki, M. Peptides (1984) [Pubmed]
  7. Dengue type 2 virus infection in human peripheral blood monocyte cultures. Hotta, H., Wiharta, A.S., Hotta, S., Homma, M. Microbiol. Immunol. (1984) [Pubmed]
  8. Muramyl dipeptide and sleep in rat. Kadlecová, O., Masek, K. Methods and findings in experimental and clinical pharmacology. (1986) [Pubmed]
  9. Immunological castration of male mice by a totally synthetic vaccine administered in saline. Carelli, C., Audibert, F., Gaillard, J., Chedid, L. Proc. Natl. Acad. Sci. U.S.A. (1982) [Pubmed]
  10. Activation of murine Kupffer cell tumoricidal activity by liposomes containing lipophilic muramyl dipeptide. Phillips, N.C., Rioux, J., Tsao, M.S. Hepatology (1988) [Pubmed]
  11. Surface calreticulin mediates muramyl dipeptide-induced apoptosis in RK13 cells. Chen, D., Texada, D.E., Duggan, C., Liang, C., Reden, T.B., Kooragayala, L.M., Langford, M.P. J. Biol. Chem. (2005) [Pubmed]
  12. Epithelioid granuloma formation by a synthetic bacterial cell wall component, muramyl dipeptide (MDP). Tanaka, A., Emori, K. Am. J. Pathol. (1980) [Pubmed]
  13. Efficient induction of collagen arthritis by the use of a synthetic muramyl dipeptide. Koga, T., Sakamoto, S., Onoue, K., Kotani, S., Sumiyoshi, A. Arthritis Rheum. (1980) [Pubmed]
  14. Arthritogenic activity of a synthetic immunoadjuvant, muramyl dipeptide. Zídek, Z., Maśek, K., Jiricka, Z. Infect. Immun. (1982) [Pubmed]
  15. Enhancement by murabutide of the immune response to natural and synthetic hepatitis B surface antigens. Audibert, F.M., Przewlocki, G., Leclerc, C.D., Jolivet, M.E., Gras-Masse, H.S., Tartar, A.L., Chedid, L.A. Infect. Immun. (1984) [Pubmed]
  16. Adjuvant activity of carbohydrate analogs of N-acetylmuramyl-L-alanyl-D-isoglutamine on the induction of delayed-type hypersensitivity to azobenzenearsonate-N-acetyl-L-tyrosine in guinea pigs. Azuma, I., Okumura, H., Saiki, I., Kiso, M., Hasegawa, A., Tanio, Y., Yamamura, Y. Infect. Immun. (1981) [Pubmed]
  17. Detection of bacterial pyrogens on the basis of their effects on gamma interferon-mediated formation of neopterin or nitrite in cultured monocyte cell lines. Werner-Felmayer, G., Baier-Bitterlich, G., Fuchs, D., Hausen, A., Murr, C., Reibnegger, G., Werner, E.R., Wachter, H. Clin. Diagn. Lab. Immunol. (1995) [Pubmed]
  18. Immunopharmacologic agents in the amelioration of hepatic injuries. Farghali, H., Masek, K. Int. J. Immunopharmacol. (1998) [Pubmed]
  19. Inhibition of mitogen-induced polyclonal activation by by a synthetic adjuvant, muramyl dipeptide (MDP). Löwy, I., Leclerc, C., Bourgeois, E., Chedid, L. J. Immunol. (1980) [Pubmed]
  20. Possible chemotaxis of human monocytes by N-acetylmuramyl-L-alanyl-D-isoglutamine. Ogawa, T., Kotani, S., Kusumoto, S., Shiba, T. Infect. Immun. (1983) [Pubmed]
  21. Kinetics of the humoral and cellular immune response of guinea pigs after injection of the synthetic adjuvant N-acetylmuramyl L-alanyl-D-isoglutamine: comparison with Freund complete adjuvant. Souvannavong, V., Adam, A., Lederer, E. Infect. Immun. (1978) [Pubmed]
  22. Protection against experimental Pseudomonas aeruginosa infection in mice by active immunization with exotoxin A toxoids. Pavlovskis, O.R., Edman, D.C., Leppla, S.H., Wretlind, B., Lewis, L.R., Martin, K.E. Infect. Immun. (1981) [Pubmed]
  23. Amyloidosis and the serum amyloid A protein response to muramyl dipeptide analogs and different mycobacterial species. McAdam, K.P., Foss, N.T., Garcia, C., DeLellis, R., Chedid, L., Rees, R.J., Wolff, S.M. Infect. Immun. (1983) [Pubmed]
  24. Macrophage activation by mycobacterial water soluble compounds and synthetic muramyl dipeptide. Wahl, S.M., Wahl, L.M., McCarthy, J.B., Chedid, L., Mergenhagen, S.E. J. Immunol. (1979) [Pubmed]
  25. Enhancement of carrier-specific helper T cell function by the synthetic adjuvant, N-acetyl muramyl-L-alanyl-D-isoglutamine (MDP). Sugimoto, M., Germain, R.N., Chedid, L., Benacerraf, B. J. Immunol. (1978) [Pubmed]
  26. Macrophage stimulation in vitro by an inactive muramyl dipeptide derivative after conjugation to a multi-poly(DL-alanyl)-poly(L-lysine) carrier. Galelli, A., Le Garrec, Y., Chedid, L., Lefrancier, P., Derrien, M., Level, M. Infect. Immun. (1980) [Pubmed]
  27. Opposite effects of the synthetic adjuvant N-acetyl-muramyl-L-alanyl-D-isoglutamine on the immune response in mice depending on experimental conditions. Souvannavong, V., Adam, A. Eur. J. Immunol. (1980) [Pubmed]
  28. Contractile effects of bacterial cell walls, their enzymatic digests, and muramyl dipeptides on ileal strips from guinea pigs. Ogawa, T., Kotani, S., Tsujimoto, M., Kusumoto, S., Shiba, T., Kawata, S., Yokogawa, K. Infect. Immun. (1982) [Pubmed]
  29. Evidence for a hyperexcitability state of staggerer mutant mice macrophages. Kopmels, B., Mariani, J., Delhaye-Bouchaud, N., Audibert, F., Fradelizi, D., Wollman, E.E. J. Neurochem. (1992) [Pubmed]
  30. Correction of defective tumoricidal activity of macrophages from A/J mice by liposomal immunomodulators. Phillips, N.C., Skamene, E., Chedid, L. Immunopharmacology (1988) [Pubmed]
  31. Myelin-stimulated macrophages release neurotrophic factors for adult dorsal root ganglion neurons in culture. Hikawa, N., Takenaka, T. Cell. Mol. Neurobiol. (1996) [Pubmed]
  32. Effect of methyl esterification of isoglutamine residue in 6-O-acylated muramyl dipeptides on expression of immunopharmacological activities. Furuya, T., Kumazawa, Y., Takimoto, H., Nagumo, T., Kiso, M., Hasegawa, A., Nomoto, K. Int. J. Immunopharmacol. (1991) [Pubmed]
  33. Kinetics and parameters of the induction of interleukin 1 secretion by rat Kupffer cells. Shirahama, M., Ishibashi, H., Tsuchiya, Y., Kurokawa, S., Okumura, Y., Niho, Y. Journal of clinical & laboratory immunology. (1988) [Pubmed]
  34. An interleukin-1 receptor fragment inhibits spontaneous sleep and muramyl dipeptide-induced sleep in rabbits. Takahashi, S., Kapás, L., Fang, J., Seyer, J.M., Wang, Y., Krueger, J.M. Am. J. Physiol. (1996) [Pubmed]
  35. Protein A and other surface components of Staphylococcus aureus stimulate production of IL-1 alpha, IL-4, IL-6, TNF and IFN-gamma. Tufano, M.A., Cipollaro de l'Ero, G., Ianniello, R., Galdiero, M., Galdiero, F. Eur. Cytokine Netw. (1991) [Pubmed]
  36. Anti-infectious activity of liposomal muramyl dipeptides in immunodeficient CBA/N mice. Phillips, N.C., Chedid, L. Infect. Immun. (1987) [Pubmed]
  37. Ex vivo induction of TNF-alpha and IL-6 mRNA in bovine whole blood by Mycobacterium paratuberculosis and mycobacterial cell wall components. Adams, J.L., Czuprynski, C.J. Microb. Pathog. (1995) [Pubmed]
  38. Muramyl dipeptide-induced adjuvant arthritis. Nagao, S., Tanaka, A. Infect. Immun. (1980) [Pubmed]
  39. N-acetylmuramyl-L-alanyl-D-isoglutamine stimulates the immune response of B cells. Use of fast protein liquid chromatography to purify a novel monokine involved in this effect. Souvannavong, V., Adam, A. J. Chromatogr. (1988) [Pubmed]
  40. Oral adjuvants enhance IgA responses to Streptococcus mutans. Michalek, S.M., Morisaki, I., Gregory, R.L., Kiyono, H., Hamada, S., McGhee, J.R. Mol. Immunol. (1983) [Pubmed]
  41. Enhancement of quiet sleep in rabbit neonates by muramyl dipeptide. Davenne, D., Krueger, J.M. Am. J. Physiol. (1987) [Pubmed]
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