A new series of highly potent growth hormone-releasing peptides derived from ipamorelin

J Med Chem. 1998 Sep 10;41(19):3699-704. doi: 10.1021/jm9801962.

Abstract

A new series of GH secretagogues derived from ipamorelin is described. In an attempt to obtain oral bioavailability, by reducing the size and the number of potential hydrogen-bonding sites of the compounds, a strategy using the peptidomimetic fragment 3-(aminomethyl)benzoic acid and sequential backbone N-methylations was applied. Several compounds from this series release GH with high in vitro potency and efficacy in a rat pituitary cell assay and high in vivo potency and efficacy in anesthetized rats. The tetrapeptide NNC 26-0235 (3-(aminomethyl)benzoyl-D-2Nal-N-Me-D-Phe-Lys-NH2) shows, following iv administration, comparable in vivo potency to ipamorelin, GHRP-2, and GHRP-6 with an ED50 in swine at 2 nmol/kg. NNC 26-0235 demonstrated a 10% oral bioavailability in dogs, and NNC 26-0235 and ipamorelin were able to increase basal GH level by more than 10-fold after oral administration of a dose of 1.8 and 2.7 mg/kg, respectively. The tripeptide NNC 26-0323 (3-(aminomethyl)benzoic acid-N-Me-D-2Nal-N-Me-D-Phe-ol) which showed moderate in vitro potency but lacked in vivo potency demonstrated a 20% oral bioavailability in rats.

MeSH terms

  • Administration, Oral
  • Animals
  • Biological Availability
  • Dogs
  • Female
  • Growth Hormone / metabolism*
  • Hormones / chemical synthesis*
  • Hormones / chemistry
  • Hormones / pharmacokinetics
  • Hormones / pharmacology
  • In Vitro Techniques
  • Injections, Intravenous
  • Magnetic Resonance Spectroscopy
  • Male
  • Molecular Mimicry
  • Oligopeptides / chemical synthesis*
  • Oligopeptides / chemistry
  • Oligopeptides / pharmacokinetics
  • Oligopeptides / pharmacology
  • Pituitary Gland / cytology
  • Pituitary Gland / drug effects
  • Pituitary Gland / metabolism
  • Rats
  • Rats, Sprague-Dawley
  • Structure-Activity Relationship
  • Swine

Substances

  • Hormones
  • NNC 26-0235
  • NNC 26-0323
  • Oligopeptides
  • growth hormone releasing hexapeptide
  • Growth Hormone
  • growth hormone-releasing peptide-2
  • ipamorelin