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Chemical Compound Review

Anchoate     nonanedioic acid

Synonyms: Skinorem, Skinoren, Azelaic, Finacea, Finevin, ...
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Disease relevance of nonanedioic acid


High impact information on nonanedioic acid


Chemical compound and disease context of nonanedioic acid


Biological context of nonanedioic acid


Anatomical context of nonanedioic acid


Associations of nonanedioic acid with other chemical compounds

  • In both P. acnes and S. epidermidis the addition of 30 mM azelaic acid and the membrane active inhibitors nigericin (150 microM) and CCCP (150 microM) resulted in a rapid release of [14C] label into the dialysate indicating the dissipation of delta pH between external pH values of 4.0-6 [17].
  • The agents tested were uniformly active against MRSA, mupirocin being the most active (MIC50 0.15 mg/L) followed by nitrofurazone (MIC50 19 mg/L), silver sulphadiazine (MIC50 85 mg/L) and azelaic acid (MIC50 850 mg/L) [18].
  • RESULTS: The dermal application of therapeutically used acids, such as salicylic acid and azelaic acid, caused a plain change of microacidity (pH) inside the skin [19].
  • A new quassinoid, yadanziolide S (1), was isolated from the seeds of the traditional Chinese medicinal herb, Brucea javanica, along with ten known compounds, flazin, bruceine D, yadanziolide B, bruceoside A, yadanziolide S, yadanzigan, glycerol 1,3-bisoleate, azelaic acid, (+/-)-8-hydroxyhexadecanoic acid, and vanillin [20].
  • Neither azelaic acid nor its monomethyl ester inhibit tyrosinase when catechol is used as a substrate instead of L-tyrosine [21].

Gene context of nonanedioic acid


Analytical, diagnostic and therapeutic context of nonanedioic acid


  1. Effect of azelaic acid on human malignant melanoma. Nazzaro-Porro, M., Passi, S., Zina, G., Bernengo, A., Breathnach, A., Gallagher, S., Morpurgo, G. Lancet (1980) [Pubmed]
  2. Inhibition of DNA synthesis of melanoma cells by azelaic acid. Leibl, H., Stingl, G., Pehamberger, H., Korschan, H., Konrad, K., Wolff, K. J. Invest. Dermatol. (1985) [Pubmed]
  3. Azelaic acid. A review of its pharmacological properties and therapeutic efficacy in acne and hyperpigmentary skin disorders. Fitton, A., Goa, K.L. Drugs (1991) [Pubmed]
  4. An evaluation of the effectiveness of azelaic acid as a depigmenting and chemotherapeutic agent. Pathak, M.A., Ciganek, E.R., Wick, M., Sober, A.J., Farinelli, W.A., Fitzpatrick, T.B. J. Invest. Dermatol. (1985) [Pubmed]
  5. The in-vitro antimicrobial effects of azelaic acid upon Propionibacterium acnes strain P37. Bojar, R.A., Holland, K.T., Cunliffe, W.J. J. Antimicrob. Chemother. (1991) [Pubmed]
  6. Pharmacokinetic analysis of azelaic acid disodium salt. A proposed substrate for total parenteral nutrition. Bertuzzi, A., Gandolfi, A., Salinari, S., Mingrone, G., Arcieri-Mastromattei, E., Finotti, E., Greco, A.V. Clinical pharmacokinetics. (1991) [Pubmed]
  7. Effects of azelaic acid on proliferation and ultrastructure of mouse keratinocytes in vitro. Detmar, M., Mayer-da-Silva, A., Stadler, R., Orfanos, C.E. J. Invest. Dermatol. (1989) [Pubmed]
  8. Effect of L-carnitine on cultured murine melanoma cells exposed to azelaic acid. Ward, B.J., Breathnach, A.S., Robins, E.J., Bhasin, Y.P., Ethridge, L., Nazzaro-Porro, M., Passi, S. J. Invest. Dermatol. (1986) [Pubmed]
  9. A comparison of topical azelaic acid 20% cream and topical metronidazole 0.75% cream in the treatment of patients with papulopustular rosacea. Maddin, S. J. Am. Acad. Dermatol. (1999) [Pubmed]
  10. Azelaic acid and glycolic acid combination therapy for facial hyperpigmentation in darker-skinned patients: a clinical comparison with hydroquinone. Kakita, L.S., Lowe, N.J. Clinical therapeutics. (1998) [Pubmed]
  11. Percutaneous absorption of azelaic acid in humans. Täuber, U., Weiss, C., Matthes, H. Exp. Dermatol. (1992) [Pubmed]
  12. Monoclonal anti-conjugated azelaic acid antibody production: application to multiple sclerosis. Chagnaud, J.L., Gosset, I., Brochet, B., Audhuy, S., Geffard, M. Neuroreport (1990) [Pubmed]
  13. Azelaic acid as a competitive inhibitor of thioredoxin reductase in human melanoma cells. Schallreuter, K.U., Wood, J.M. Cancer Lett. (1987) [Pubmed]
  14. Inhibitory effect of azelaic acid on neutrophil functions: a possible cause for its efficacy in treating pathogenetically unrelated diseases. Akamatsu, H., Komura, J., Asada, Y., Miyachi, Y., Niwa, Y. Arch. Dermatol. Res. (1991) [Pubmed]
  15. Activity of azelaic acid on cultures of lymphoma- and leukemia-derived cell lines, normal resting and stimulated lymphocytes and 3T3 fibroblasts. Picardo, M., Passi, S., Sirianni, M.C., Fiorilli, M., Russo, G.D., Cortesi, E., Barile, G., Breathnach, A.S., Nazzaro-Porro, M. Biochem. Pharmacol. (1985) [Pubmed]
  16. Topical azelaic acid and the treatment of acne: a clinical and laboratory comparison with oral tetracycline. Bladon, P.T., Burke, B.M., Cunliffe, W.J., Forster, R.A., Holland, K.T., King, K. Br. J. Dermatol. (1986) [Pubmed]
  17. Disruption of the transmembrane pH gradient--a possible mechanism for the antibacterial action of azelaic acid in Propionibacterium acnes and Staphylococcus epidermidis. Bojar, R.A., Cunliffe, W.J., Holland, K.T. J. Antimicrob. Chemother. (1994) [Pubmed]
  18. Comparison of the in-vitro activities of the topical antimicrobials azelaic acid, nitrofurazone, silver sulphadiazine and mupirocin against methicillin-resistant Staphylococcus aureus. Maple, P.A., Hamilton-Miller, J.M., Brumfitt, W. J. Antimicrob. Chemother. (1992) [Pubmed]
  19. Influence of drug treatment on the microacidity in rat and human skin--an in vitro electron spin resonance imaging study. Kroll, C., Hermann, W., Stösser, R., Borchert, H.H., Mäder, K. Pharm. Res. (2001) [Pubmed]
  20. Bioactive constituents of the seeds of Brucea javanica. Su, B.N., Chang, L.C., Park, E.J., Cuendet, M., Santarsiero, B.D., Mesecar, A.D., Mehta, R.G., Fong, H.H., Pezzuto, J.M., Kinghorn, A.D. Planta Med. (2002) [Pubmed]
  21. A possible mechanism of action for azelaic acid in the human epidermis. Schallreuter, K.U., Wood, J.W. Arch. Dermatol. Res. (1990) [Pubmed]
  22. Cell cycle inhibition of HTLV-I transformed T cell lines by retinoic acid: the possible therapeutic use of thioredoxin reductase inhibitors. U-Taniguchi, Y., Furuke, K., Masutani, H., Nakamura, H., Yodoi, J. Oncol. Res. (1995) [Pubmed]
  23. Alpha-adrenergic receptor-stimulated hypertrophy in adult rat ventricular myocytes is mediated via thioredoxin-1-sensitive oxidative modification of thiols on Ras. Kuster, G.M., Pimentel, D.R., Adachi, T., Ido, Y., Brenner, D.A., Cohen, R.A., Liao, R., Siwik, D.A., Colucci, W.S. Circulation (2005) [Pubmed]
  24. Effect of dicarboxylic acids (C6 and C9) on human choroidal melanoma in cell culture. Breathnach, A.S., Robins, E.J., Pätzold, H.C., Bhasin, Y.P., Ethridge, L.B., Garner, A., Nazzaro-Porro, M. Invest. Ophthalmol. Vis. Sci. (1989) [Pubmed]
  25. Azelaic acid in the treatment of papulopustular rosacea: a systematic review of randomized controlled trials. Liu, R.H., Smith, M.K., Basta, S.A., Farmer, E.R. Archives of dermatology. (2006) [Pubmed]
  26. Azelaic acid vs. placebo: effects on normal human keratinocytes and melanocytes. Electron microscopic evaluation after long-term application in vivo. Mayer-da Silva, A., Gollnick, H., Imcke, E., Orfanos, C.E. Acta Derm. Venereol. (1987) [Pubmed]
  27. Short-term infusion of azelaic acid vs intralipid in healthy subjects evaluated by indirect calorimetry. Tacchino, R.M., Mingrone, G., Marino, F., Arcieri-Mastromattei, E., Greco, A.V., Castagneto, M. JPEN. Journal of parenteral and enteral nutrition. (1990) [Pubmed]
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