5588. Loxiglumide

Nomenclature

CAS number: 107097-80-3
4-[(3,4-Dichlorobenzoyl)amino]-5-[(3-methoxypropyl)pentylamino]-5-oxopentanoic acid; (±)-4-(3,4-dichlorobenzamido)-N-(3-methoxypropyl)-N-pentylglutaramic acid; CR-1505.
C21H30Cl2N2O5; mol wt 461.38.
C 54.67%, H 6.55%, Cl 15.37%, N 6.07%, O 17.34%.

Description and references

Cholecystokinin type-1 (CCK-1) antagonist. Prepn: F. Makovec et al., WO 8703869; eidem, US 4769389 (1987, 1988 both to Rotta). Pharmacology and receptor binding: I. Setnikar et al., Arzneim.-Forsch. 37, 703 (1987). Pharmacokinetics: idem et al., ibid. 38, 716 (1988). Effect on bilio-pancreatic secretion: W. E. Schmidt et al., Digestion 46, Suppl. 2, 232 (1990). Clinical evaluation in irritable bowel syndrome: P. A. Cann et al., Ann. N.Y. Acad. Sci. 713, 449 (1994); in nonulcer dyspepsia: A. S. B. Chua et al. ibid. 451; in pancreatitis: K. Shiratori et al., Pancreas 25, e1 (2002).

Chemical structure

Properties

Crystals from acetone, mp 113-115°. pKa ≈5. Soly in water: 0.01%.

Derivative

(R)-Form.

Nomenclature

CAS number: 119817-90-2
Dexloxiglumide; CR-2017.

Description and references

HPLC determn in plasma: R. Brodie et al., J. Chromatogr. B 784, 91 (2003). In vitro biopharmaceutical properties: S. Tolle-Sander et al., J. Pharm. Sci. 92, 1968 (2003). Clinical pharmacokinetics: C. Webber et al., Xenobiotica 33, 625 (2003). Clinical evaluation in irritable bowel syndrome: F. Cremonini et al., Am. J. Gastroenterol. 100, 652 (2005).

Properties

Soly (μg/ml): 33 (pH 3.4), 533 (pH 7.5). pKa 4.48.

Therapeutic Category

Gastroprokinetic.

Keywords

CCK Antagonist; Gastroprokinetic