5-HT3 receptor antagonist effects of DAT-582, (R) enantiomer of AS-5370

Eur J Pharmacol. 1992 Jun 17;216(3):435-40. doi: 10.1016/0014-2999(92)90442-7.

Abstract

The serotonin 5-HT3 receptor antagonist effects of DAT-582, the (R) enantiomer of AS-5370 ((+/-)-N-[1-methyl-4-(3-methyl-benzyl)hexahydro-1H-1,4-diazepin-6- yl]-1H- indazole-3-carboxamide dihydrochloride), and its antipode were compared with those of AS-5370 and existing 5-HT3 receptor antagonists. In anesthetized rats, DAT-582 antagonized 2-methyl-5-HT-induced bradycardia with an ED50 value of 0.25 microgram/kg i.v., whereas the (S) enantiomer was without effect even at 1000 micrograms/kg i.v. In antagonizing the bradycardia, DAT-582 was as potent as granisetron, slightly more potent than AS-5370, and 2, 5 and 18 times more potent than ondansetron, ICS 205-903 and renzapride, respectively, although it was less potent than zacopride. DAT-582 inhibited cisplatin (10 mg/kg i.v.)-induced emesis in ferrets with an ED50 value of 3.2 micrograms/kg i.v. twice. The antiemetic activity of DAT-582 was more potent than that of the existing 5-HT3 receptor antagonists examined, except zacopride. In contrast, the (S) enantiomer had little effect at 1000 micrograms/kg i.v. twice. In isolated guinea-pig ileum, DAT-582 inhibited 5-HT-induced contractions with an IC50 value of 91 nM, whereas the (S) enantiomer hardly inhibited them even at 1000 nM. These results suggest that DAT-582, the (R) enantiomer of AS-5370, potently and selectively blocks 5-HT3 receptors.

Publication types

  • Comparative Study

MeSH terms

  • Animals
  • Azepines / pharmacology*
  • Bradycardia / chemically induced
  • Bradycardia / prevention & control
  • Cisplatin / antagonists & inhibitors
  • Ferrets
  • Guinea Pigs
  • Ileum / drug effects
  • In Vitro Techniques
  • Indazoles / pharmacology*
  • Male
  • Muscle Contraction / drug effects
  • Muscle, Smooth / drug effects
  • Rats
  • Serotonin Antagonists*
  • Stereoisomerism
  • Vomiting / chemically induced
  • Vomiting / prevention & control

Substances

  • Azepines
  • Indazoles
  • Serotonin Antagonists
  • DAT 582
  • Cisplatin