Devazepide

Devazepide^[1] (L-364,718, MK-329) is benzodiazepine drug, but with quite different actions from most benzodiazepines, lacking affinity for GABA_A receptors and instead acting as an CCK_A 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 CCK_A receptor.^[6]^[7]

ATC code

none

CAS Number

103420-77-5^Y

PubChem CID

443375

IUPHAR/BPS

Quick facts Clinical data, ATC code ...

Devazepide
Clinical data

ATC code	none
Identifiers
IUPAC name N-(1-methyl-2-oxo-5-phenyl-3H-1,4-benzodiazepin-3-yl)-1H-indole-2-carboxamide
CAS Number	103420-77-5^Y
PubChem CID	443375
IUPHAR/BPS	878
ChemSpider	391607^N
UNII	JE6P7QY7NH
KEGG	D02693^Y
ChEMBL	ChEMBL9506^N
CompTox Dashboard (EPA)	DTXSID2046092
ECHA InfoCard	100.208.547
Chemical and physical data
Formula	C₂₅H₂₀N₄O₂
Molar mass	408.461 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C(c2cc1ccccc1[nH]2)N[C@H]3/N=C(\c4ccccc4N(C3=O)C)c5ccccc5
InChI 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
^NY (what is this?) (verify)

Synthesis

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

References

[1]
US 4820834, Evans, Ben E.; Freidinger, Roger M. & Bock, Mark G., "Benzodiazepine analogs", published 1989-04-11, assigned to Merck & Co. Inc.
[2]
Hill DR, Woodruff GN (September 1990). "Differentiation of central cholecystokinin receptor binding sites using the non-peptide antagonists MK-329 and L-365,260". Brain Research. 526 (2): 276–83. doi:10.1016/0006-8993(90)91232-6. PMID 2257485. S2CID 23851131.
[3]
Cooper SJ, Dourish CT (December 1990). "Multiple cholecystokinin (CCK) receptors and CCK-monoamine interactions are instrumental in the control of feeding". Physiology & Behavior. 48 (6): 849–57. doi:10.1016/0031-9384(90)90239-z. PMID 1982361. S2CID 24850080.
[4]
Cooper SJ, Dourish CT, Clifton PG (January 1992). "CCK antagonists and CCK-monoamine interactions in the control of satiety". The American Journal of Clinical Nutrition. 55 (1 Suppl): 291S–295S. doi:10.1093/ajcn/55.1.291s. PMID 1728842.
[5]
Scarpignato C, Varga G, Corradi C (1993). "Effect of CCK and its antagonists on gastric emptying". Journal of Physiology, Paris. 87 (5): 291–300. doi:10.1016/0928-4257(93)90035-r. PMID 8298606. S2CID 23725376.
[6]
Weller A (July 2006). "The ontogeny of postingestive inhibitory stimuli: examining the role of CCK". Developmental Psychobiology. 48 (5): 368–79. doi:10.1002/dev.20148. PMID 16770766.
[7]
Savastano DM, Covasa M (October 2007). "Intestinal nutrients elicit satiation through concomitant activation of CCK(1) and 5-HT(3) receptors". Physiology & Behavior. 92 (3): 434–42. doi:10.1016/j.physbeh.2007.04.017. PMID 17531277. S2CID 5566756.
[8]
Evans BE, Rittle KE, Bock MG, DiPardo RM, Freidinger RM, Whitter WL, et al. (December 1988). "Methods for drug discovery: development of potent, selective, orally effective cholecystokinin antagonists". Journal of Medicinal Chemistry. 31 (12): 2235–46. doi:10.1021/jm00120a002. PMID 2848124.
[9]
EP 1492540, Jackson, Karen, "The use of devazepide as analgesic agent", published 2005-01-05, assigned to ML Laboratories plc

Synthesis

See also

References

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