Racecadotril
Title: Racecadotril
CAS Registry Number: 81110-73-8
CAS Name: N-[2-[(Acetylthio)methyl]-1-oxo-3-phenylpropyl]glycine phenylmethyl ester
Additional Names: N-[(R,S)-3-acetylthio-2-benzylpropanoyl]glycine benzyl ester; acetorphan
Trademarks: Hidrasec (GSK); Tiorfan (Bioprojet)
Molecular Formula: C21H23NO4S
Molecular Weight: 385.48
Percent Composition: C 65.43%, H 6.01%, N 3.63%, O 16.60%, S 8.32%
Literature References: Antisecretory enkephalinase inhibitor. Prepn: B. Roques et al., EP 38758 (1981); eidem, US 4513009 (1985 to Bioprojet). Pharmacology: J.-M. Lecomte et al., J. Pharmacol. Exp. Ther. 237, 937 (1986). Effect on intestinal transit: J. F. Bergmann et al., Aliment. Pharmacol. Ther. 6, 305 (1992). Clinical trial in acute diarrhea: P. Baumer et al., Gut 33, 753 (1992); in children: E. Salazar-Lindo et al., N. Engl. J. Med. 343, 463 (2000). Symposium on pharmacology and clinical experience: Aliment. Pharmacol. Ther. 13, Suppl. 6, 1-32 (1999). Review of clinical development: J.-C. Schwartz, Int. J. Antimicrob. Agents 14, 75-79 (2000); J. M. Lecomte, ibid. 81-87.
Properties: White crystals from ether mp 89°.
Melting point: mp 89°
 
Derivative Type: (S)-Form
CAS Registry Number: 112573-73-6
Additional Names: Ecadotril; sinorphan
Manufacturers' Codes: Bay-y-7432
Molecular Formula: C21H23NO4S
Molecular Weight: 385.48
Percent Composition: C 65.43%, H 6.01%, N 3.63%, O 16.60%, S 8.32%
Literature References: Prepn: P. Duhamel et al., EP 318377; eidem, US 5208255 (1989, 1993 both to Bioprojet); and pharmacology: B. Giros et al., J. Pharmacol. Exp. Ther. 243, 666 (1987). Clinical effect on plasma ANP levels in CHF: J. C. Kahn et al., Lancet 335, 118 (1990); on renal function: F. Schmitt et al., Am. J. Physiol. 267, F20 (1994). Clinical trial in heart failure: C. M. O'Connor et al., Am. Heart J. 138, 1140 (1999); J. G. F. Cleland, K. Swedberg, Lancet 351, 1657 (1998).
Properties: mp 71°. [a]D25 -24.1° (c = 1.3 in methanol). LD50 i.v. in mice: >100 mg/kg (Duhamel, 1993).
Melting point: mp 71°
Optical Rotation: [a]D25 -24.1° (c = 1.3 in methanol)
Toxicity data: LD50 i.v. in mice: >100 mg/kg (Duhamel, 1993)
 
Therap-Cat: Antidiarrheal.
Keywords: Antidiarrheal; Neutral Endopeptidase Inhibitor.

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