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Chemical Compound Review

CHEMBL38763     1-[(3R)-3-(3,4- dichlorophenyl)-3-[2-(4...

Synonyms: SureCN1650319, CHEBI:156436, AC1L33GN, SR 140333, SR 140603, ...
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Disease relevance of 1-[(3S)-3-(3,4-dichlorophenyl)-3-[2-(4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl)ethyl]-1-piperidyl]-2-(3-isopropoxyphenyl)ethanone


Psychiatry related information on 1-[(3S)-3-(3,4-dichlorophenyl)-3-[2-(4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl)ethyl]-1-piperidyl]-2-(3-isopropoxyphenyl)ethanone

  • Administration of [Sar9,Met(O2)11]substance P induced increased locomotor activity, as well as face washing, grooming and wet-dog shake behaviours, all of which were inhibited by the neurokinin-1 receptor antagonist, SR 140333, indicating the involvement of neurokinin-1 receptors [4].

High impact information on 1-[(3S)-3-(3,4-dichlorophenyl)-3-[2-(4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl)ethyl]-1-piperidyl]-2-(3-isopropoxyphenyl)ethanone


Biological context of 1-[(3S)-3-(3,4-dichlorophenyl)-3-[2-(4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl)ethyl]-1-piperidyl]-2-(3-isopropoxyphenyl)ethanone


Anatomical context of 1-[(3S)-3-(3,4-dichlorophenyl)-3-[2-(4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl)ethyl]-1-piperidyl]-2-(3-isopropoxyphenyl)ethanone


Associations of 1-[(3S)-3-(3,4-dichlorophenyl)-3-[2-(4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl)ethyl]-1-piperidyl]-2-(3-isopropoxyphenyl)ethanone with other chemical compounds

  • The response to septide was prevented by intraperitoneal administration of the nonpeptide NK1 antagonist SR 140333 (1-3 mg/kg) but not by the nonpeptide NK2 receptor antagonist SR 48968, indicating that the effect was mediated specifically by NK1 receptors [17].
  • Relaxations of the guinea pig trachea elicited by antidromic stimulation of capsaicin-sensitive vagal afferent nerves were markedly inhibited by 0.3 microM SR 142801 and were abolished by a combination of SR 142801 and either of the NK1-selective receptor antagonists SR 140333 and CP 99994 (0.3 microM each) [18].
  • NK1 receptors played a secretory role as receptor agonists stimulated secretion and SR-140333 antagonized the response to SP response (pK(b) = 9.2) [19].
  • The effect of intra-arterial NKA could not be blocked by the NK1 receptor selective antagonist SR 140,333 or the NK2 receptor selective antagonist SR 48,968, but by their combination [20].
  • The tachykinin NK1 receptor antagonist, SR 140333 ((S)1-[2-[3-(3,4-dichlorophenyl)-1-(3-isopropoxyphenylacetyl)pi peridin-3-yl]ethyl]-4-phenyl-1-azoniabicyclo[2.2.2.]octane, chloride), not only inhibited mustard oil-induced plasma extravasation but also blocked the enhancement by phosphoramidon of the response to mustard oil [21].

Gene context of 1-[(3S)-3-(3,4-dichlorophenyl)-3-[2-(4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl)ethyl]-1-piperidyl]-2-(3-isopropoxyphenyl)ethanone


Analytical, diagnostic and therapeutic context of 1-[(3S)-3-(3,4-dichlorophenyl)-3-[2-(4-phenyl-1-azoniabicyclo[2.2.2]oct-1-yl)ethyl]-1-piperidyl]-2-(3-isopropoxyphenyl)ethanone

  • The potent neurokinin receptor 1 (NK1) antagonist SR-140333 has previously been shown to reduce castor oil-induced secretion in animal models [19].
  • Furthermore, SR 140333 significantly (p < 0.001) suppressed ear oedema in response to intradermal injection of substance P (SP) (100 pmol/site) by i.v. administration (0.1 mg/kg,) and co-injection (50 pmol/site) [26].


  1. Proteinases and proteinase-activated receptor 2: a possible role to promote visceral hyperalgesia in rats. Coelho, A.M., Vergnolle, N., Guiard, B., Fioramonti, J., Bueno, L. Gastroenterology (2002) [Pubmed]
  2. SR 140333, a novel, selective, and potent nonpeptide antagonist of the NK1 tachykinin receptor: characterization on the U373MG cell line. Oury-Donat, F., Lefevre, I.A., Thurneyssen, O., Gauthier, T., Bordey, A., Feltz, P., Emonds-Alt, X., Le Fur, G., Soubrie, P. J. Neurochem. (1994) [Pubmed]
  3. Effect of SR 140333, a selective NK1 antagonist, on antigen-induced oedema formation in rat skin. Herbert, J.M., Bernat, A. Journal of lipid mediators and cell signalling. (1996) [Pubmed]
  4. Distribution of Fos-like immunoreactivity in guinea-pig brain following administration of the neurokinin-1 receptor agonist, [SAR9,MET(O2)11]substance P. Yip, J., Chahl, L.A. Neuroscience (1999) [Pubmed]
  5. Passive smoke effects on cough and airways in young guinea pigs: role of brainstem substance P. Joad, J.P., Munch, P.A., Bric, J.M., Evans, S.J., Pinkerton, K.E., Chen, C.Y., Bonham, A.C. Am. J. Respir. Crit. Care Med. (2004) [Pubmed]
  6. Neutrophil recruitment by interleukin-17 into rat airways in vivo. Role of tachykinins. Hoshino, H., Lötvall, J., Skoogh, B.E., Lindén, A. Am. J. Respir. Crit. Care Med. (1999) [Pubmed]
  7. Acute ACE inhibition causes plasma extravasation in mice that is mediated by bradykinin and substance P. Emanueli, C., Grady, E.F., Madeddu, P., Figini, M., Bunnett, N.W., Parisi, D., Regoli, D., Geppetti, P. Hypertension (1998) [Pubmed]
  8. Chronic low-level administration of diquat increases the nociceptive response to gastric distension in rats: role of mast cells and tachykinin receptor activation. Anton, P.M., Theodorou, V., Fioramonti, J., Bueno, L. Pain (2001) [Pubmed]
  9. Involvement of neurokinins in antidromic vasodilatation in hairy and hairless skin of the rat hindlimb. Häbler, H.J., Timmermann, L., Stegmann, J.U., Jänig, W. Neuroscience (1999) [Pubmed]
  10. An NK1 receptor-dependent component of the slow excitation recorded intracellularly from rat motoneurons following dorsal root stimulation. Baranauskas, G., Traversa, U., Rosati, A.M., Nistri, A. Eur. J. Neurosci. (1995) [Pubmed]
  11. Further evidence that central tachykinin NK-1 receptors mediate the inhibitory effect of tachykinins on angiotensin-induced drinking in rats. Polidori, C., Ciccocioppo, R., De Caro, G., Massi, M. Peptides (1998) [Pubmed]
  12. Role of tachykinins in the bronchoconstriction induced by HCl intraesophageal instillation in the rabbit. Gallelli, L., D'Agostino, B., Marrocco, G., De Rosa, G., Filippelli, W., Rossi, F., Advenier, C. Life Sci. (2003) [Pubmed]
  13. Protease-activated receptor-2 peptides activate neurokinin-1 receptors in the mouse isolated trachea. Abey, H.T., Fairlie, D.P., Moffatt, J.D., Balzary, R.W., Cocks, T.M. J. Pharmacol. Exp. Ther. (2006) [Pubmed]
  14. Effect of the tachykinin NK1 receptor antagonists, RP 67580 and SR 140333, on electrically-evoked substance P release from rat spinal cord. Malcangio, M., Bowery, N.G. Br. J. Pharmacol. (1994) [Pubmed]
  15. Effects of SR 140333 and SR 48968 on antigen and substance P-induced activation of guinea-pig alveolar macrophages. Boichot, E., Germain, N., Emonds-Alt, X., Advenier, C., Lagente, V. Clin. Exp. Allergy (1998) [Pubmed]
  16. Role of tachykinin NK1 and NK2 receptors in allergen-induced early and late asthmatic reactions, airway hyperresponsiveness, and airway inflammation in conscious, unrestrained guinea pigs. Schuiling, M., Zuidhof, A.B., Zaagsma, J., Meurs, H. Clin. Exp. Allergy (1999) [Pubmed]
  17. Pharmacological characterization of tachykinin receptors controlling acetylcholine release from rat striatum: an in vivo microdialysis study. Steinberg, R., Rodier, D., Souiclhac, J., Bougault, I., Emonds-Alt, X., Soubrié, P., Le Fur, G. J. Neurochem. (1995) [Pubmed]
  18. Pharmacological analysis of the tachykinin receptors that mediate activation of nonadrenergic, noncholinergic relaxant nerves that innervate guinea pig trachealis. Canning, B.J., Fischer, A., Undem, B.J. J. Pharmacol. Exp. Ther. (1998) [Pubmed]
  19. Potent NK1 antagonism by SR-140333 reduces rat colonic secretory response to immunocyte activation. Moriarty, D., Selve, N., Baird, A.W., Goldhill, J. Am. J. Physiol., Cell Physiol. (2001) [Pubmed]
  20. Tachykinin effects on bladder activity in conscious normal rats. Ishizuka, O., Mattiasson, A., Andersson, K.E. J. Urol. (1995) [Pubmed]
  21. Mechanism of mustard oil-induced skin inflammation in mice. Inoue, H., Asaka, T., Nagata, N., Koshihara, Y. Eur. J. Pharmacol. (1997) [Pubmed]
  22. Effect of substance P on cytokine production by human astrocytic cells and blood mononuclear cells: characterization of novel tachykinin receptor antagonists. Derocq, J.M., Ségui, M., Blazy, C., Emonds-Alt, X., Le Fur, G., Brelire, J.C., Casellas, P. FEBS Lett. (1996) [Pubmed]
  23. Involvement of tachykinin receptors in oedema formation and plasma extravasation induced by substance P, neurokinin A, and neurokinin B in mouse ear. Inoue, H., Nagata, N., Koshihara, Y. Inflamm. Res. (1996) [Pubmed]
  24. Postexercise hypotension in conscious SHR is attenuated by blockade of substance P receptors in NTS. Chen, C.Y., Munch, P.A., Quail, A.W., Bonham, A.C. Am. J. Physiol. Heart Circ. Physiol. (2002) [Pubmed]
  25. Tachykinin inhibition of acid-induced gastric hyperaemia in the rat. Heinemann, A., Jocic, M., Herzeg, G., Holzer, P. Br. J. Pharmacol. (1996) [Pubmed]
  26. Effect of the tachykinin receptor antagonists, SR 140333, FK 888, and SR 142801, on capsaicin-induced mouse ear oedema. Inoue, H., Nagata, N., Koshihara, Y. Inflamm. Res. (1996) [Pubmed]
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