Dexloxiglumide

Dexloxiglumide
Clinical data
ATC code	none;
Identifiers
	IUPAC name (4R)-4-[(3,4-dichlorobenzoyl)amino]-5-(3-methoxypropylpentylamino)-5-oxopentanoic acid;
CAS Number	119817-90-2 ;
PubChem CID	65937;
IUPHAR/BPS	889;
ChemSpider	59342 ;
UNII	69DY40RH9B;
ChEMBL	ChEMBL550781 ;
CompTox Dashboard (EPA)	DTXSID50152604 ;
Chemical and physical data
Formula	C21H30Cl2N2O5
Molar mass	461.38 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCN(CCCOC)C(=O)[C@@H](CCC(=O)O)NC(=O)C1=CC(=C(C=C1)Cl)Cl;
	InChI InChI=1S/C21H30Cl2N2O5/c1-3-4-5-11-25(12-6-13-30-2)21(29)18(9-10-19(26)27)24-20(28)15-7-8-16(22)17(23)14-15/h7-8,14,18H,3-6,9-13H2,1-2H3,(H,24,28)(H,26,27)/t18-/m1/s1 ; Key:QNQZBKQEIFTHFZ-GOSISDBHSA-N ;
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Dexloxiglumide is a drug which acts as a cholecystokinin antagonist, selective for the CCK_A subtype. It inhibits gastrointestinal motility and reduces gastric secretions, and despite older selective CCK_A antagonists such as lorglumide and devazepide having had only limited success in trials and ultimately never making it into clinical use, dexloxiglumide is being investigated as a potential treatment for a variety of gastrointestinal problems including irritable bowel syndrome,^[1] dyspepsia,^[2] constipation^[3] and pancreatitis,^[4]^[5] and has had moderate success so far although trials are still ongoing.

References

^ Cremonini F, Camilleri M, McKinzie S, Carlson P, Camilleri CE, Burton D, et al. (March 2005). "Effect of CCK-1 antagonist, dexloxiglumide, in female patients with irritable bowel syndrome: a pharmacodynamic and pharmacogenomic study". The American Journal of Gastroenterology. 100 (3): 652–63. doi:10.1111/j.1572-0241.2005.41081.x. PMID 15743365. S2CID 34227592.
^ Galligan JJ, Vanner S (October 2005). "Basic and clinical pharmacology of new motility promoting agents". Neurogastroenterology and Motility. 17 (5): 643–53. doi:10.1111/j.1365-2982.2005.00675.x. PMID 16185302. S2CID 7298061.
^ Roberts DJ, Banh HL, Hall RI (August 2006). "Use of novel prokinetic agents to facilitate return of gastrointestinal motility in adult critically ill patients". Current Opinion in Critical Care. 12 (4): 295–302. doi:10.1097/01.ccx.0000235205.54579.5d. PMID 16810038. S2CID 32307333.
^ Maselli MA, Mennuni L (September 2003). "CCK1 receptor antagonist, dexloxiglumide: effects on human isolated gallbladder. Potential clinical applications". Minerva Gastroenterologica e Dietologica. 49 (3): 211–6. PMID 16484960.
^ Barrett TD, Yan W, Freedman JM, Lagaud GJ, Breitenbucher JG, Shankley NP (April 2008). "Role of CCK and potential utility of CCK1 receptor antagonism in the treatment of pancreatitis induced by biliary tract obstruction". British Journal of Pharmacology. 153 (8): 1650–8. doi:10.1038/bjp.2008.44. PMC 2438255. PMID 18297100.

[1] Cremonini F, Camilleri M, McKinzie S, Carlson P, Camilleri CE, Burton D, et al. (March 2005). "Effect of CCK-1 antagonist, dexloxiglumide, in female patients with irritable bowel syndrome: a pharmacodynamic and pharmacogenomic study". The American Journal of Gastroenterology. 100 (3): 652–63. doi:10.1111/j.1572-0241.2005.41081.x. PMID 15743365. S2CID 34227592.

[2] Galligan JJ, Vanner S (October 2005). "Basic and clinical pharmacology of new motility promoting agents". Neurogastroenterology and Motility. 17 (5): 643–53. doi:10.1111/j.1365-2982.2005.00675.x. PMID 16185302. S2CID 7298061.

[3] Roberts DJ, Banh HL, Hall RI (August 2006). "Use of novel prokinetic agents to facilitate return of gastrointestinal motility in adult critically ill patients". Current Opinion in Critical Care. 12 (4): 295–302. doi:10.1097/01.ccx.0000235205.54579.5d. PMID 16810038. S2CID 32307333.

[4] Maselli MA, Mennuni L (September 2003). "CCK1 receptor antagonist, dexloxiglumide: effects on human isolated gallbladder. Potential clinical applications". Minerva Gastroenterologica e Dietologica. 49 (3): 211–6. PMID 16484960.

[5] Barrett TD, Yan W, Freedman JM, Lagaud GJ, Breitenbucher JG, Shankley NP (April 2008). "Role of CCK and potential utility of CCK1 receptor antagonism in the treatment of pancreatitis induced by biliary tract obstruction". British Journal of Pharmacology. 153 (8): 1650–8. doi:10.1038/bjp.2008.44. PMC 2438255. PMID 18297100.

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Clinical data

ATC code	none
Identifiers
IUPAC name (4R)-4-[(3,4-dichlorobenzoyl)amino]-5-(3-methoxypropylpentylamino)-5-oxopentanoic acid
CAS Number	119817-90-2^Y
PubChem CID	65937
IUPHAR/BPS	889
ChemSpider	59342^N
UNII	69DY40RH9B
ChEMBL	ChEMBL550781^N
CompTox Dashboard (EPA)	DTXSID50152604
Chemical and physical data
Formula	C₂₁H₃₀Cl₂N₂O₅
Molar mass	461.38 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCCCCN(CCCOC)C(=O)[C@@H](CCC(=O)O)NC(=O)C1=CC(=C(C=C1)Cl)Cl
InChI InChI=1S/C21H30Cl2N2O5/c1-3-4-5-11-25(12-6-13-30-2)21(29)18(9-10-19(26)27)24-20(28)15-7-8-16(22)17(23)14-15/h7-8,14,18H,3-6,9-13H2,1-2H3,(H,24,28)(H,26,27)/t18-/m1/s1^N Key:QNQZBKQEIFTHFZ-GOSISDBHSA-N^N
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