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Chemical Compound Review

decylate     decanoic acid

Synonyms: caprynate, decanoate, decoate, Dekansaeure, Kaprinsaeure, ...
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Disease relevance of decanoic acid

  • Safety and efficacy of nandrolone decanoate for treatment of wasting in patients with HIV infection [1].
  • Decanoate and unconjugated bile salts, which are present in the normal habitat of E. coli, were further shown to make the bacteria more resistant to lipophilic antibiotics, at least in part because of the induction of the AcrAB efflux pump [2].
  • Effect of nandrolone decanoate therapy on weight and lean body mass in HIV-infected women with weight loss: a randomized, double-blind, placebo-controlled, multicenter trial [3].
  • OBJECTIVE: This experiment evaluated enterally administered low molecular weight heparin (LMWH) combined with sodium N-[10-(2-hydroxybenzoyl)amino] decanoate (SNAD) for the treatment of induced venous thrombosis [4].
  • We conclude that the combination of low-dose rHuEPO and nandrolone decanoate is effective treatment for the anemia of end-stage renal failure [5].

Psychiatry related information on decanoic acid


High impact information on decanoic acid

  • OBJECTIVE: To assess the effects of an anabolic steroid, nandrolone decanoate, on lean body mass (LBM), functional status, and quality of life in dialysis patients [11].
  • We now report that melanocyte stimulation with phorbol 12-tetra decanoate 13-acetate (TPA), previously reported to induce p75 NGF receptor, also induces trk in melanocytes, and TPA effect is further potentiated by the presence of keratinocytes in culture [12].
  • Rapid exchange of fatty acid among binding sites obscures these sites at temperatures greater than 30 degrees C. Rate constants for exchange at 33 degrees C were 350 sec-1 for octanoate and 20 sec-1 for decanoate, corresponding to lifetimes in a binding site of 2.8 msec (octanoate) and 50 msec (decanoate) [13].
  • Derivatives of this mutant that can grow on decanoate (termed fadR) are capable of growth on medium-chain but not long-chain fatty acids [14].
  • A unique threonine at amino acid position 3 (Thr(3)) in bullfrog ghrelin differs from the serine present in the mammalian ghrelins; this Thr(3) is acylated by either n-octanoic or n-decanoic acid [15].

Chemical compound and disease context of decanoic acid


Biological context of decanoic acid


Anatomical context of decanoic acid


Associations of decanoic acid with other chemical compounds


Gene context of decanoic acid


Analytical, diagnostic and therapeutic context of decanoic acid


  1. Safety and efficacy of nandrolone decanoate for treatment of wasting in patients with HIV infection. Gold, J., High, H.A., Li, Y., Michelmore, H., Bodsworth, N.J., Finlayson, R., Furner, V.L., Allen, B.J., Oliver, C.J. AIDS (1996) [Pubmed]
  2. Bile salts and fatty acids induce the expression of Escherichia coli AcrAB multidrug efflux pump through their interaction with Rob regulatory protein. Rosenberg, E.Y., Bertenthal, D., Nilles, M.L., Bertrand, K.P., Nikaido, H. Mol. Microbiol. (2003) [Pubmed]
  3. Effect of nandrolone decanoate therapy on weight and lean body mass in HIV-infected women with weight loss: a randomized, double-blind, placebo-controlled, multicenter trial. Mulligan, K., Zackin, R., Clark, R.A., Alston-Smith, B., Liu, T., Sattler, F.R., Delvers, T.B., Currier, J.S. Arch. Intern. Med. (2005) [Pubmed]
  4. Treatment of experimentally induced caval thrombosis with oral low molecular weight heparin and delivery agent in a porcine model of deep venous thrombosis. Salartash, K., Lepore, M., Gonze, M.D., Leone-Bay, A., Baughman, R., Sternbergh, W.C., Bowen, J.C., Money, S.R. Ann. Surg. (2000) [Pubmed]
  5. A 6-month study of low-dose recombinant human erythropoietin alone and in combination with androgens for the treatment of anemia in chronic hemodialysis patients. Gaughan, W.J., Liss, K.A., Dunn, S.R., Mangold, A.M., Buhsmer, J.P., Michael, B., Burke, J.F. Am. J. Kidney Dis. (1997) [Pubmed]
  6. Prevalence of diabetes mellitus among outpatients with severe mental disorders receiving atypical antipsychotic drugs. Lamberti, J.S., Crilly, J.F., Maharaj, K., Olson, D., Wiener, K., Dvorin, S., Costea, G.O., Bushey, M.P., Dietz, M.B. The Journal of clinical psychiatry. (2004) [Pubmed]
  7. Efficacy and tolerability of flupenthixol decanoate in the treatment of depression and psychosomatic disorders: a multicenter trial in general practice. Budde, G. Prog. Neuropsychopharmacol. Biol. Psychiatry (1992) [Pubmed]
  8. A double-blind comparison of oral amitriptyline and low-dose intramuscular flupenthixol decanoate in depressive illness. Maragakis, B.P. Current medical research and opinion. (1990) [Pubmed]
  9. Therapeutic efficacy of flupenthixol decanoate in schizoaffective disorder: a clinical evaluation. Singh, A.N. J. Int. Med. Res. (1984) [Pubmed]
  10. Pharmacology of cis(Z)-clopenthixol decanoate, a depot neuroleptic. Pedersen, V., Svendsen, O., Danneskiold-Samsoe, P., Boeck, V., Nielsen, I.M. Acta pharmacologica et toxicologica. (1977) [Pubmed]
  11. Anabolic effects of nandrolone decanoate in patients receiving dialysis: a randomized controlled trial. Johansen, K.L., Mulligan, K., Schambelan, M. JAMA (1999) [Pubmed]
  12. The trk family of receptors mediates nerve growth factor and neurotrophin-3 effects in melanocytes. Yaar, M., Eller, M.S., DiBenedetto, P., Reenstra, W.R., Zhai, S., McQuaid, T., Archambault, M., Gilchrest, B.A. J. Clin. Invest. (1994) [Pubmed]
  13. Medium-chain fatty acid binding to albumin and transfer to phospholipid bilayers. Hamilton, J.A. Proc. Natl. Acad. Sci. U.S.A. (1989) [Pubmed]
  14. Transport of long-chain fatty acids by Escherichia coli: mapping and characterization of mutants in the fadL gene. Nunn, W.D., Simons, R.W. Proc. Natl. Acad. Sci. U.S.A. (1978) [Pubmed]
  15. Bullfrog ghrelin is modified by n-octanoic acid at its third threonine residue. Kaiya, H., Kojima, M., Hosoda, H., Koda, A., Yamamoto, K., Kitajima, Y., Matsumoto, M., Minamitake, Y., Kikuyama, S., Kangawa, K. J. Biol. Chem. (2001) [Pubmed]
  16. Effects of anabolic steroids on diaphragm impairment induced by methylprednisolone in emphysematous hamsters. van Balkom, R.H., Dekhuijzen, P.N., van der Heijden, H.F., Folgering, H.T., Fransen, J.A., van Herwaarden, C.L. Eur. Respir. J. (1999) [Pubmed]
  17. Synthesis and bioevaluation of a series of fatty acid esters of p-[N,N-bis(2-chloroethyl)amino]phenol. Wynn, J.E., Caldwell, M.L., Robinson, J.R., Beamer, R.L., Bauguess, C.T. Journal of pharmaceutical sciences. (1982) [Pubmed]
  18. Recurrent priapism as a side effect of zuclopenthixol decanoate. van Hemert, A.M., Meinhardt, W., Moehadjir, D., Kropman, R.F. International clinical psychopharmacology. (1995) [Pubmed]
  19. Effects of nandrolone decanoate and antiresorptive therapy on vertebral density in osteoporotic postmenopausal women. Need, A.G., Horowitz, M., Bridges, A., Morris, H.A., Nordin, B.E. Arch. Intern. Med. (1989) [Pubmed]
  20. Monitoring changes in fat-free mass in HIV-positive men with hypotestosteronemia and AIDS wasting syndrome treated with gonadal hormone replacement therapy. Van Loan, M.D., Strawford, A., Jacob, M., Hellerstein, M. AIDS (1999) [Pubmed]
  21. Effect of nortestosterone decanoate on red cell 2,3 diphosphoglycerate and hematocrit in hemodialysis patients. Goodman, J., Bessman, A.N. Clin. Pharmacol. Ther. (1975) [Pubmed]
  22. A practical loading dose method for converting schizophrenic patients from oral to depot haloperidol therapy. Wei, F.C., Jann, M.W., Lin, H.N., Piao-Chien, C., Chang, W.H. The Journal of clinical psychiatry. (1996) [Pubmed]
  23. Diacylglycerol is an effector of the clonal expansion of cells containing activated Ha-ras genes. Mills, K.J., Reynolds, S.H., Smart, R.C. Carcinogenesis (1993) [Pubmed]
  24. Effects of resistance exercise training and nandrolone decanoate on body composition and muscle function among patients who receive hemodialysis: A randomized, controlled trial. Johansen, K.L., Painter, P.L., Sakkas, G.K., Gordon, P., Doyle, J., Shubert, T. J. Am. Soc. Nephrol. (2006) [Pubmed]
  25. Haldol decanoate and thyroid disease. Jefferson, J.W. The Journal of clinical psychiatry. (1988) [Pubmed]
  26. Nandrolone decanoate causes pathologic changes in the uterus of surgically postmenopausal female cynomolgus macaques. Obasanjo, I.O., Cline, J.M., Schmotzer, S., Weaver, D.S. Menopause (New York, N.Y.) (1998) [Pubmed]
  27. Persistent antagonism of methamphetamine-induced dopamine release in rats pretreated with GBR12909 decanoate. Baumann, M.H., Ayestas, M.A., Sharpe, L.G., Lewis, D.B., Rice, K.C., Rothman, R.B. J. Pharmacol. Exp. Ther. (2002) [Pubmed]
  28. Location of the medium chain fatty acid site on human serum albumin. Residues involved and relationship to the indole site. Lee, I.Y., McMenamy, R.H. J. Biol. Chem. (1980) [Pubmed]
  29. Double-blind comparison of half-dose and standard-dose flupenthixol decanoate in the maintenance treatment of stabilised out-patients with schizophrenia. Johnson, D.A., Ludlow, J.M., Street, K., Taylor, R.D. The British journal of psychiatry : the journal of mental science. (1987) [Pubmed]
  30. Clopenthixol decanoate in the management of aggressive mentally handicapped patients. Mlele, T.J., Wiley, Y.V. The British journal of psychiatry : the journal of mental science. (1986) [Pubmed]
  31. Depressive symptoms in chronic schizophrenic patients after withdrawal of long-acting neuroleptics. Wistedt, B., Palmstierna, T. The Journal of clinical psychiatry. (1983) [Pubmed]
  32. Effects of the androgenic anabolic steroid, nandrolone decanoate, on adrenocorticotropin hormone, corticosterone and proopiomelanocortin, corticotropin releasing factor (CRF) and CRF receptor1 mRNA levels in the hypothalamus, pituitary and amygdala of the rat. Schlussman, S.D., Zhou, Y., Johansson, P., Kiuru, A., Ho, A., Nyberg, F., Kreek, M.J. Neurosci. Lett. (2000) [Pubmed]
  33. A controlled trial of recombinant human erythropoietin and nandrolone decanoate in the treatment of anemia in patients on chronic hemodialysis. Berns, J.S., Rudnick, M.R., Cohen, R.M. Clin. Nephrol. (1992) [Pubmed]
  34. Effect of unesterified cholesterol on the activity of cholesteryl ester transfer protein. Rajaram, O.V., Chan, R.Y., Sawyer, W.H. Biochem. J. (1994) [Pubmed]
  35. Maintenance therapy with zuclopenthixol decanoate: associations between plasma concentrations, neurological side effects and CYP2D6 genotype. Jaanson, P., Marandi, T., Kiivet, R.A., Vasar, V., Vään, S., Svensson, J.O., Dahl, M.L. Psychopharmacology (Berl.) (2002) [Pubmed]
  36. Synthesis of poly(3-hydroxyalkanoates) in Escherichia coli expressing the PHA synthase gene phaC2 from Pseudomonas aeruginosa: comparison of PhaC1 and PhaC2. Qi, Q., Rehm, B.H., Steinbüchel, A. FEMS Microbiol. Lett. (1997) [Pubmed]
  37. Calcium-deficient diet in ovariectomized dogs limits the effects of 17 beta-estradiol and nandrolone decanoate on bone. Geusens, P., Schot, L.P., Nijs, J., Dequeker, J. J. Bone Miner. Res. (1991) [Pubmed]
  38. Oxygenated analogues of 1-[2-(Diphenylmethoxy)ethyl]- and 1-[2-[Bis(4-fluorophenyl)methoxy]ethyl]-4-(3-phenylpropyl)piperazines (GBR 12935 and GBR 12909) as potential extended-action cocaine-abuse therapeutic agents. Lewis, D.B., Matecka, D., Zhang, Y., Hsin, L.W., Dersch, C.M., Stafford, D., Glowa, J.R., Rothman, R.B., Rice, K.C. J. Med. Chem. (1999) [Pubmed]
  39. Neuroleptic serum levels measured by radioreceptor assay in patients receiving intramuscular depot neuroleptics. Some preliminary findings. Turbott, J., Villiger, J., Hunter, L. The British journal of psychiatry : the journal of mental science. (1985) [Pubmed]
  40. Antipsychotic prescribing practices in Connecticut's public mental health system: rates of changing medications and prescribing styles. Covell, N.H., Jackson, C.T., Evans, A.C., Essock, S.M. Schizophrenia bulletin. (2002) [Pubmed]
  41. Behavioral effects produced by long-term administration of a neuroleptic drug (flupenthixol) upon social interaction in a group of eight rats. Hecht, A. Psychopharmacology (Berl.) (1979) [Pubmed]
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