9113. Tegaserod

Nomenclature

CAS number: 145158-71-0
2-[(5-Methoxy-1H-indol-3-yl)methylene]-N-pentylhydrazinecarboximidamide.
C16H23N5O; mol wt 301.39.
C 63.76%, H 7.69%, N 23.24%, O 5.31%.

Description and references

Selective serotonin 5HT4-receptor partial agonist. Prepn: R. K. A. Giger, H. Mattes, EP 505322; eidem, US 5510353 (1992, 1996 both to Sandoz); K.-H. Buchheit et al., J. Med. Chem. 38, 2331 (1995). Clinical pharmacology: S. Appel et al., Clin. Pharmacol. Ther. 62, 546 (1997); and pharmacokinetics: idem et al., J. Clin. Pharmacol. 37, 229 (1997). Clinical trial in irritable bowel syndrome: S. A. Müller-Lissner et al., Aliment. Pharmacol. Ther. 15, 1655 (2001); in female patients: J. Novick et al., ibid. 16, 1877 (2002). Review of clinical efficacy: B. W. Jones et al., J. Clin. Pharm. Ther. 27, 343-352 (2002); of mechanism of action, efficacy and safety: M. Corsetti, J. Tack, Expert Opin. Pharmacother. 3, 1211-1218 (2002).

Chemical structure

Properties

mp 155°.

Derivative

Maleate.

Nomenclature

CAS number: 189188-57-6
SDZ-HTF-919; Zelmac (Novartis); Zelnorm (Novartis).
C16H23N5O.C4H4O4; mol wt 417.46.
C 57.54%, H 6.52%, N 16.78%, O 19.16%.

Properties

White to off-white crystalline powder. Slightly sol in ethanol; very slightly sol in water.

Therapeutic Category

Gastroprokinetic; in treatment of irritable bowel syndrome.

Keywords

Gastroprokinetic; Serotonin Receptor Agonist