A water-soluble, stable dipeptide NK1 receptor-selective neurokinin receptor antagonist with potent in vivo pharmacological effects: S18523

Eur J Pharmacol. 1996 Aug 22;310(1):37-46. doi: 10.1016/0014-2999(96)00362-7.

Abstract

The potassium salt of a chemically stabilized dipeptide, {1-[4-(1 H-tetrazol-5-yl)butyl]indol-3-yl}carbonyl-Hyp-Nal-N(methyl)-Bzl , (Hyp = (R)-4-hydroxy-L-proline; Nal = 3-L-(beta-naphthyl)-alanine), S18523, is described as a new water-soluble, potent and selective NK1 receptor antagonist. The low molecular weight antagonist (M(r) = 736) displays nanomolar potency (pA2 = 9.6) in the rabbit vena cava (NK1) bioassay and nanomolar affinity (pKi = 9.1) on the human NK1 receptor expressed by lymphoblastoma cells. It is devoid of mu-opiate affinity (Ki > 10(-4) M with respect to tritiated Tyr-DAla-Gly-MePhe-Gly-ol), has negligible calcium-channel affinity (estimated Ki = 2.6 x 10(-5) M, with respect to isradipine) and does not cause peritoneal mast-cell degranulation. S18523 has strong antinociceptive effects in three classical pain tests in vivo both by i.v. and p.o. routes. The dipeptide potently antagonizes bronchoconstriction provoked by exogenous substance P in the guinea-pig and acts longer than the non-peptide antagonist CP99994, when administered as aerosol. Finally, S18523 displays antiinflammatory properties, since it dose-dependently inhibits substance P-induced plasma extravasation both in the bladder (ID50 = 0.18 mg/kg i.v.) and bronchi (ID50 = 0.14 mg/kg i.v.) of the guinea-pig.

MeSH terms

  • Animals
  • Bronchoconstriction / drug effects
  • Cell Line / drug effects
  • Dipeptides / blood
  • Dipeptides / chemical synthesis
  • Dipeptides / metabolism
  • Dipeptides / pharmacology*
  • Dose-Response Relationship, Drug
  • Female
  • Guinea Pigs
  • In Vitro Techniques
  • Male
  • Mice
  • Neurokinin-1 Receptor Antagonists*
  • Pain Measurement / drug effects
  • Piperidines / pharmacology
  • Rabbits
  • Rats
  • Receptors, Neurokinin-1 / blood
  • Receptors, Neurokinin-1 / metabolism
  • Substance P / pharmacology
  • Tetrazoles / blood
  • Tetrazoles / chemical synthesis
  • Tetrazoles / metabolism
  • Tetrazoles / pharmacology*

Substances

  • Dipeptides
  • Neurokinin-1 Receptor Antagonists
  • Piperidines
  • Receptors, Neurokinin-1
  • S 18523
  • Tetrazoles
  • 3-(2-methoxybenzylamino)-2-phenylpiperidine
  • Substance P