7014. Pantoprazole

Nomenclature

CAS number: 102625-70-7
5-(Difluoromethoxy)-2-[[(3,4-dimethoxy-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole; SKF-96022; BY-1023.
C16H15F2N3O4S; mol wt 383.37.
C 50.13%, H 3.94%, F 9.91%, N 10.96%, O 16.69%, S 8.36%.

Description and references

Gastric proton pump inhibitor. Prepn: B. Kohl et al., EP 166287; eidem, US 4758579 (1986, 1988 both to Byk Gulden); eidem, J. Med. Chem. 35, 1049 (1992). Mechanism of action: W. A. Simon et al., Biochem. Pharmacol. 39, 1799 (1990). HPLC determn in plasma and serum: R. Huber et al., J. Chromatogr. 529, 389 (1990). Clinical pharmacokinetics: B. Simon et al., Z. Gastroenterol. 28, 443 (1990). Clinical trial in duodenal ulcer: P. Müller et al., ibid. 30, 771 (1992); in Zollinger-Ellison syndrome: E. A. Lew et al., Gastroenterology 118, 696 (2000). Review of pharmacology and clinical experience: P. Poole, Am. J. Health Syst. Pharm. 58, 999-1008 (2001).

Chemical structure

Properties

Off-white solid, mp 139-140° (dec). pKa1 3.92; pKa2 8.19.

Derivative

Sodium salt.

Nomenclature

CAS number: 138786-67-1
Eupantol (Altana); Pantecta (Pfizer); Pantozol (Altana); Pantopan (Pharmacia); Pantorc (Altana); Peptazol (Recordati); Protium (Altana); Protonix (Wyeth); Somac (Pfizer).
C16H14F2N3NaO4S; mol wt 405.35.
C 47.41%, H 3.48%, F 9.37%, N 10.37%, Na 5.67%, O 15.79%, S 7.91%.

Properties

Prepd as the sesquihydrate. White to off-white crystalline powder, dec >130°. uv max (methanol): 289 (ε 1.64 × 104). Freely sol in water; very slightly sol in phosphate buffer (pH 7.4). Practically insol in n-hexane.

Therapeutic Category

Antiulcerative; in treatment of Zollinger-Ellison syndrome.

Keywords

Antiulcerative; Gastric Proton Pump Inhibitor