Devazepide

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Devazepide
Devazepide.svg
Systematic (IUPAC) name
N-(1-methyl-2-oxo-5-phenyl-3H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide
Identifiers
CAS Number 103420-77-5 YesY
ATC code none
PubChem CID: 443375
IUPHAR/BPS 878
ChemSpider 391607 N
UNII JE6P7QY7NH N
KEGG D02693 YesY
ChEMBL CHEMBL9506 N
Chemical data
Formula C25H20N4O2
Molecular mass 408.452 g/mol
  • O=C(c2cc1ccccc1n2)N[C@H]3/N=C(\c4ccccc4N(C3=O)C)c5ccccc5
  • InChI=1S/C25H20N4O2/c1-29-21-14-8-6-12-18(21)22(16-9-3-2-4-10-16)27-23(25(29)31)28-24(30)20-15-17-11-5-7-13-19(17)26-20/h2-15,23,26H,1H3,(H,28,30)/t23-/m1/s1 N
  • Key:NFHRQQKPEBFUJK-HSZRJFAPSA-N N
 NYesY (what is this?)  (verify)

Devazepide[1] (L-364,718, MK-329) is benzodiazepine drug, but with quite different actions from most benzodiazepines, lacking affinity for GABAA receptors and instead acting as an CCKA receptor antagonist.[2] It increases appetite and accelerates gastric emptying,[3][4] and has been suggested as a potential treatment for a variety of gastrointestinal problems including dyspepsia, gastroparesis and gastric reflux.[5] It is also widely used in scientific research into the CCKA receptor.[6][7]

Synthesis

Devazepide is synthesised in a similar manner to other benzodiazepines.[8][9]

See also

References

  1. ↑ US Patent 4820834
  2. ↑ Hill DR, Woodruff GN. Differentiation of central cholecystokinin receptor binding sites using the non-peptide antagonists MK-329 and L-365,260. Brain Research. 1990 Sep 3;526(2):276-83. PMID 2257485
  3. ↑ Cooper SJ, Dourish CT. Multiple cholecystokinin (CCK) receptors and CCK-monoamine interactions are instrumental in the control of feeding. Physiology and Behaviour. 1990 Dec;48(6):849-57. PMID 1982361
  4. ↑ Cooper SJ, Dourish CT, Clifton PG. CCK antagonists and CCK-monoamine interactions in the control of satiety. American Journal of Clinical Nutrition. 1992 Jan;55(1 Suppl):291S-295S. PMID 1728842
  5. ↑ Scarpignato C, Varga G, Corradi C. Effect of CCK and its antagonists on gastric emptying. Journal of Physiology Paris. 1993;87(5):291-300. PMID 8298606
  6. ↑ Weller A. The ontogeny of postingestive inhibitory stimuli: examining the role of CCK. Developmental Psychobiology. 2006 Jul;48(5):368-79. PMID 16770766
  7. ↑ Savastano DM, Covasa M. Intestinal nutrients elicit satiation through concomitant activation of CCK(1) and 5-HT(3) receptors. Physiology and Behaviour. 2007 Oct 22;92(3):434-42. PMID 17531277
  8. ↑ doi:10.1021/jm00120a002
  9. ↑ EP 1492540 
  1. REDIRECT Template:Peptide receptor modulators
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