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Chemical Compound Review

Damme     2-[2-[2-[[2-amino-3-(4...

Synonyms: AGN-PC-00FKDH, Sandoz 33-824, NSC-310410, NSC310410, LS-105735, ...
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Disease relevance of FK 33-824


Psychiatry related information on FK 33-824


High impact information on FK 33-824

  • Previously, using the Met-enkephalin analogue FK 33-824 (Sandoz), we determined that brain opioid binding sites could be visualized by electron microscopic autoradiography [9].
  • Infusion of 1 mg DAMME into water-deprived volunteers produced a diuresis which was attenuated by naloxone; there was no change in water excretion when subjects were hydrated [10].
  • DAMME and other substances with opiate-like activity, such as morphine and beta-endorphin, affect carbohydrate metabolism and insulin secretion [11].
  • An enkephalin analogue [D-Ala2, MePhe4, Met(o)-ol] enkephalin (DAMME), given intravenously to normal subjects raised serum prolactin and growth-hormone levels but lowered serum levels of luteinising hormone, follicle-stimulating hormone, cortisol, and corticotrophin [12].
  • Here, Ghislain Opdenakker and Jo Van Damme propose the REGA-model (Remnant Epitope Generates Autoimmunity) to explain the generation of autoantigens and their interaction with the T-cell receptor complex [13].

Chemical compound and disease context of FK 33-824


Biological context of FK 33-824

  • Blood pressure following tilt was significantly decreased by DAMME but not influenced by naloxone, the effect being most marked at 3 hours (placebo = 110 +/- 6/78 +/- 7 mm Hg; naloxone = 106 +/- 10/79 +/- 5 mm Hg; DAMME = 96 +/- 16/67 +/- 8 mm Hg (p less than 0.01) [16].
  • Heart rates at 3 hours were: placebo = 87 +/- 16 bpm; naloxone = 88 +/- 19 bpm; DAMME = 89 +/- 23 bpm [16].
  • 1. The electrophysiological action of the mu-opioid receptor-preferring agonist D-Ala2, MePhe4, Met(O)5-ol-enkephalin (FK 33-824) on synaptic transmission has been studied in area CA3 of organotypic rat hippocampal slice cultures [17].
  • We have examined (1) the effects of naloxone and an opiate peptide, FK 33-824, on LH and FSH secretion in immature male and female rats and (2) the influence of sexual maturation on the ability of this peptide to inhibit LH secretion [18].
  • The effect of the synthetic enkephalin analogue Sandoz FK33-824 (DAMME) on gastric emptying and the postprandial secretion of upper gastrointestinal and pancreatic hormones was investigated in six healthy subjects [19].

Anatomical context of FK 33-824

  • Effects of an enkephalin analogue (DAMME) on insulin release from cultured rat islets of Langerhans [20].
  • 3. FK 33-824 (10 nM to 10 microM) reduced the amplitude of monosynaptic inhibitory postsynaptic potentials (IPSPs) that were elicited in pyramidal cells with local stimulation after pharmacological blockade of excitatory amino acid receptors [17].
  • The purpose of this study was to investigate the cardiorespiratory effects of the synthetic Met-enkephalin, D-Ala-2-Me-Phe-4-Met-(0)-ol enkephalin (FK 33-824) after its administration into the anterior hypothalamic area, paraventricular hypothalamic nuclei and third ventricle [21].
  • Gamma interferon (IFN-gamma) can be cytolytic for normal mouse fibroblasts isolated from embryonic or adult tissue (R. Dijkmas, B. Decock, H. Heremans, J. Van Damme, and A. Billiau, Lymphokine Res. 8:25-34, 1989) [22].
  • 4. The PIP was prolonged by the GABA-uptake blocker nipecotic acid, was reduced by hyperpolarizing interneurons with the opioid agonist FK 33-824, and was abolished by the GABAB-receptor antagonist CGP 35 348 [23].

Associations of FK 33-824 with other chemical compounds

  • Inhibition of glucose-stimulated insulin release by trifluoperazine, an inhibitor of calmodulin, was not overcome by DAMME [20].
  • In the first study, nine normal subjects received infusions of DAMME (a metenkephalin analog), naloxone, or saline, and blood pressure, heart rate, and plasma norepinephrine concentration were determined supine and following 5 minutes of 70 degrees head-up tilt at intervals for 6 hours [16].
  • 9. In the second study, seven normal subjects had blood pressure reduced by incremental infusions of sodium nitroprusside, and the effects of placebo, naloxone, and DAMME on the slope of the heart period/blood pressure relationship investigated [16].
  • Blockade of muscarinic cholinergic receptors by atropine (0.5 mg SC) or histaminergic H1 receptors by diphenhydramine (50 mg IV bolus plus 50 mg infusion) completely suppressed the GH release induced by FK 33-824, without significantly altering the PRL rise induced by the peptide [24].
  • Phentolamine failed to alter the PRL rise induced by FK 33-824, while combined FK 33-824-metoclopramide administration induced a greater PRL increase than FK 33-824 alone [24].

Gene context of FK 33-824

  • Tumor necrosis factor-alpha (TNF-alpha) has been shown to enhance the synthesis of interleukin-6 (IL-6) and collagenase in human omental microvascular endothelial (HOME) cell (Mawatari, M., Kohno, K., Mizoguchi, H., Matsuda, T., Asoh, K., Van Damme, J. V., Welgus, H. G., and Kuwano, M. (1989) J. Immunol. 143, 1619-1627) [25].
  • In this study we investigated the effects of the guanyl derivative of DAMME (G-DAMME) on the serum GH response to an analog of GHRH in normal men [26].
  • FK 33-824 increased PRL and GH (p less than 0.001) [27].
  • NC28 cDNA encodes a new member of the chemokine family, MCP-3, recently purified from MG-63 osteosarcoma cells by Van Damme et al [28].
  • FK 33-824 produced a pronounced and concomitant fall in IR-Nt, IR-EP, IR-LPH, and IR-ACTH levels [29].

Analytical, diagnostic and therapeutic context of FK 33-824

  • 2. Most experiments were carried out with a synthetic, stable enkephalin analogue (FK 33-824) administered either by perfusion or by local administration (ionophoresis or pressure application from micropipettes) [30].
  • Naloxone or FK 33-824 did not modify LHRH-stimulated release of gonadotropins from organ cultures of anterior pituitary obtained from immature rats [18].
  • The synthetic enkephalin, FK 33-824 (FK), is less susceptible to metabolic breakdown and produces long-lasting analgesia in animals [5].
  • 7. FK 33-824 produced a decrease in the frequency of miniature, action potential-independent, spontaneous inhibitory synaptic currents (mIPSCs) recorded with whole-cell voltage-clamp techniques, but did not change their mean amplitude [17].
  • Naloxone, given alone or with FK 33-824, had a small, but significant, stimulatory effect on cortisol from 60-120 min posttreatment compared to the control group [31].


  1. Plasma pituitary hormone responses to the synthetic enkephalin analog (FK 33-824) in normal subjects and patients with pituitary diseases. Demura, R., Suda, T., Wakabayashi, I., Yoshimura, M., Jibiki, K., Odagiri, E., Demura, H., Shizume, K. J. Clin. Endocrinol. Metab. (1981) [Pubmed]
  2. Effects of a met-enkephalin analog on adrenocorticotropin (ACTH), growth hormone, and prolactin in patients with ACTH hypersecretion. Allolio, B., Winkelmann, W., Hipp, F.X., Kaulen, D., Mies, R. J. Clin. Endocrinol. Metab. (1982) [Pubmed]
  3. FK 33-824, a met-enkephalin analog, blocks corticotropin-releasing hormone-induced adrenocorticotropin secretion in normal subjects but not in patients with Cushing's disease. Allolio, B., Deuss, U., Kaulen, D., Leonhardt, U., Kallabis, D., Hamel, E., Winkelmann, W. J. Clin. Endocrinol. Metab. (1986) [Pubmed]
  4. Dose-related effects of the synthetic met-enkephalin analogue FK 33-824 on esophageal motor activity in healthy humans. Stacher, G., Bauer, P., Steinringer, H., Schmierer, G., Langer, B., Winklehner, S. Gastroenterology (1982) [Pubmed]
  5. Effects of the synthetic enkephalin analogue FK 33-824 on pain threshold and pain tolerance in man. Stacher, G., Bauer, P., Steinringer, H., Schreiber, E., Schmierer, G. Pain (1979) [Pubmed]
  6. Enkephalin analogue in schizophrenia. Double blind cross-over trial. Joergensen, A., Fog, R. Acta psychiatrica Scandinavica. (1986) [Pubmed]
  7. Dopamine-mediated behavior produced by the enkephalin analogue FK 33-824. Extein, I., Lo, C., Goodwin, F.K., Schoenfeld, R.I. Psychiatry research. (1979) [Pubmed]
  8. Acute effects of the synthetic analogue of methionine enkephalin FK 33-824 on depressive symptoms. Jungkunz, G., Nedopil, N., Rüther, E. Pharmacopsychiatria. (1983) [Pubmed]
  9. Electron microscopic autoradiographic localization of opioid receptors in rat neostriatum. Hamel, E., Beaudet, A. Nature (1984) [Pubmed]
  10. Inhibition of vasopressin release in man by an opiate peptide. Grossman, A., Besser, G.M., Milles, J.J., Baylis, P.H. Lancet (1980) [Pubmed]
  11. Sensitivity to enkephalin as a cause of non-insulin dependent diabetes. Leslie, R.D., Pyke, D.A., Stubbs, W.A. Lancet (1979) [Pubmed]
  12. Hormonal and metabolic responses to an enkephalin analogue in normal man. Stubbs, W.A., Delitala, G., Jones, A., Jeffcoate, W.J., Edwards, C.R., Ratter, S.J., Besser, G.M., Bloom, S.R., Alberti, K.G. Lancet (1978) [Pubmed]
  13. Cytokine-regulated proteases in autoimmune diseases. Opdenakker, G., Van Damme, J. Immunol. Today (1994) [Pubmed]
  14. Hyperthermic effects of centrally injected (D-ala2, N-Me-Phe4, Met-(O)5-ol)-enkephalin (FK 33-824) in rabbits and guinea-pigs. Kandasamy, S.B., Williams, B.A. Neuropharmacology (1983) [Pubmed]
  15. Disturbed prolactin responses to dopamine-related substances in patients with acromegaly and hyperprolactinemia. Sekiya, K., Karashima, T., Ikuyama, S., Muta, K., Kato, K., Ibayashi, H. Endocrinol. Jpn. (1985) [Pubmed]
  16. Endogenous opioids and baroreflex control in humans. Rubin, P.C., McLean, K., Reid, J.L. Hypertension (1983) [Pubmed]
  17. Mechanism of mu-opioid receptor-mediated presynaptic inhibition in the rat hippocampus in vitro. Capogna, M., Gähwiler, B.H., Thompson, S.M. J. Physiol. (Lond.) (1993) [Pubmed]
  18. Opiatergic control of gonadotropin secretion during puberty in the rat: a neurochemical basis for the hypothalamic 'gonadostat'? Bhanot, R., Wilkinson, M. Endocrinology (1983) [Pubmed]
  19. The effect of a synthetic enkephalin analogue on postprandial gastrointestinal and pancreatic hormone secretion. Sullivan, S.N., Bloom, S.R., Adrian, T.E., Lamki, L., McDonald, T., Corcoran, P. Am. J. Gastroenterol. (1983) [Pubmed]
  20. Effects of an enkephalin analogue (DAMME) on insulin release from cultured rat islets of Langerhans. Pierluissi, R., Pierluissi, J., Ashcroft, S.J. Diabetologia (1981) [Pubmed]
  21. Cardiorespiratory effects of D-Ala-2-Me-Phe-4-Met-(0)-ol enkephalin in the third ventricle, and in anterior hypothalamic and paraventricular areas of the rat brain. Rabkin, S.W. Cardiovasc. Res. (1989) [Pubmed]
  22. Bacterial lipopolysaccharide potentiates gamma interferon-induced cytotoxicity for normal mouse and rat fibroblasts. Dijkmans, R., Van Damme, J., Cornette, F., Heremans, H., Billiau, A. Infect. Immun. (1990) [Pubmed]
  23. Paroxysmal inhibitory potentials mediated by GABAB receptors in partially disinhibited rat hippocampal slice cultures. Scanziani, M., Gähwiler, B.H., Thompson, S.M. J. Physiol. (Lond.) (1991) [Pubmed]
  24. Cholinergic and histaminergic involvement in the growth hormone releasing effect of an enkephalin analog FK 33-824 in man. Peñalva, A., Villanueva, L., Casanueva, F., Cavagnini, F., Gomez-Pan, A., Müller, E.E. Psychopharmacology (Berl.) (1983) [Pubmed]
  25. Endogenous basic fibroblast growth factor-dependent induction of collagenase and interleukin-6 in tumor necrosis factor-treated human microvascular endothelial cells. Okamura, K., Sato, Y., Matsuda, T., Hamanaka, R., Ono, M., Kohno, K., Kuwano, M. J. Biol. Chem. (1991) [Pubmed]
  26. Opioids stimulate growth hormone (GH) release in man independently of GH-releasing hormone. Delitala, G., Tomasi, P.A., Palermo, M., Ross, R.J., Grossman, A., Besser, G.M. J. Clin. Endocrinol. Metab. (1989) [Pubmed]
  27. Endocrine effect of a methionine-enkephalin derivative (FK 33-824) in man. del Pozo, E., von Graffenried, B., Brownell, J., Derrer, F., Marbach, P. Horm. Res. (1980) [Pubmed]
  28. Molecular cloning of the MCP-3 chemokine gene and regulation of its expression. Minty, A., Chalon, P., Guillemot, J.C., Kaghad, M., Liauzun, P., Magazin, M., Miloux, B., Minty, C., Ramond, P., Vita, N. Eur. Cytokine Netw. (1993) [Pubmed]
  29. Effects of ovine corticotropin-releasing hormone and FK 33-824 (met-enkephalin analogue) on the secretions of proopiomelanocortin-derived N-terminal peptide, beta-lipotropin, beta-endorphin and adrenocorticotropin in patients with Addison's disease. Sekiya, K., Nawata, H., Kato, K., Motomatsu, T., Ibayashi, H. Endocrinol. Jpn. (1986) [Pubmed]
  30. Is excitation by enkephalins of hippocampal neurones in the rat due to presynaptic facilitation or to disinhibition? Haas, H.L., Ryall, R.W. J. Physiol. (Lond.) (1980) [Pubmed]
  31. Effects of naloxone and an enkephalin analog on serum prolactin, cortisol, and gonadotropins in the chimpanzee. Gosselin, R.E., Blankstein, J., Dent, D.W., Hobson, W.C., Fuller, G.B., Reyes, F.I., Winter, J.S., Faiman, C. Endocrinology (1983) [Pubmed]
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