Saturday, November 29, 2014

Omeprazole



Common name: Omeprazole, H-168/68, SAN-15, Omez, Nuclosina, Parizac, Omapren, Audazol, Omepradex, Losec, Prilosec, Omeprazon, Omepral, Antra, Mopral, Miol
Trademarks: Antra (AstraZeneca); Gastrogard (Merial); Gastroloc (Pharma-Stern); Losec (AstraZeneca); Mepral (Bracco); Mopral (AstraZeneca); Omepral (Fujisawa); Omeprazen (Malesci); Parizac (Lacer); Pepticum (Andromaco); Prilosec (AstraZeneca); Zoltum (RPR); Nexium;  Esomeprazole RBX; Nexmezol; Raciper
Molecular Formula: C17H19N3O3S
CAS Registry Number: 73590-58-6; 119141-88-7 (esomeprazole)
CAS Name: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole; (S)-5-Methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-3H-benzoimidazole
Molecular Weight: 345.42
Activity: Anti-Helicobacter Pylori Agents, Antiulcer Drugs, Esophageal Diseases, Gastric Antisecretory Drugs, Gastroesophageal Reflux Disease, GASTROINTESTINAL DRUGS, ABCC3 Expression Enhancers, H+/K+-ATPase Inhibitors

Omeprazole synthesis: EP1085019

Omeprazole synthesis: US6191148




Esomeprazole synthesis: Tetrahedron: Asymmetry 200011(18), 3819–3825 (revisited in Ref. 5)


Esomeprazole synthesis (Biooxidation): WO1996017076A1



References:
1. Junggren, U. K.; et. al. Gastric acid secretion inhibiting substituted 2-(2-benzimidazolyl)-pyridines, pharmaceutical preparations containing same, and method for inhibiting gastric acid secretion. US4255431
2. Blancafort, P.; et al. Omeprazole. Drugs Fut 1983, 8(2), 129.
3. Hamied, Y. K.; et. al. Omeprazole synthesis. EP1085019
4. Liu, H.; et. al. Improved omeprazole process and compositions thereof. US6191148
5. Baumann, M.; et. al. An overview of the key routes to the best selling 5-membered ring heterocyclic pharmaceuticals. Beilstein J Org Chem 2011, 7, 442-95.
6. Cotton, H.; et. al. Novel Form of S-Omeprazole. WO1998054171A1
7. Holt, R.; et. al. Enantioselective preparation of pharmaceutically active sulfoxides by biooxidation. WO1996017076A1
8. Cotton, H.; et. al. Asymmetric synthesis of esomeprazole. Tetrahedron: Asymmetry 2000, 11(18), 3819–3825.

For more drugs and their synthesis: Synayurajan database