Structural Formula Vector Image
Title: Omeprazole
CAS Registry Number: 73590-58-6
CAS Name: 5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole
Manufacturers' Codes: H-168/68
Trademarks: Gastrogard (Merial); Losec (AstraZeneca); Mopral (AstraZeneca); OmeLich (Winthrop); Omelind (Lindopharm); Omepral (AstraZeneca); Omeprazen (Malesci); Osiren (Probiomed); Parizac (Lacer); Pepticum (Grñenthal); Prilosec (AstraZeneca); Zegerid (Santarus); Zoltum (AstraZeneca)
Molecular Formula: C17H19N3O3S
Molecular Weight: 345.42
Percent Composition: C 59.11%, H 5.54%, N 12.16%, O 13.90%, S 9.28%
Literature References: Gastric proton-pump inhibitor. Prepn: U. K. Junggren, S. E. Sjostrand, EP 5129; eidem, US 4255431 (1979, 1981 both to AB Hässle). Resolution and activity of enantiomers: P. Erlandsson et al., J. Chromatogr. 532, 305 (1990). Manuf process for optically pure salts: S. Von Unge, US 5693818 (1997 to Astra). Pharmacology: P. Muller et al., Arzneim.-Forsch. 33, 1685 (1983). Mechanism of action study: B. Wallmark et al., Biochim. Biophys. Acta 778, 549 (1984). LC determn in plasma and urine: P. Lagerstrom, B. Persson, J. Chromatogr. 309, 347 (1984). Survey of preclinical data: Scand. J. Gastroenterol. 20, Suppl 108, 1-120 (1985). Toxicological studies: L. Ekman et al., ibid. 53. Clinical trial in Zollinger-Ellison syndrome: C. B. H. W. Lamers et al., N. Engl. J. Med. 310, 758 (1984); in duodenal ulcer: K. Lauritsen et al., ibid. 312, 958 (1985). Veterinary trial in race horses: M. J. Murray et al., Equine Vet. J. 29, 425 (1997). Review of pharmacology and clinical efficacy: H. D. Langtry, M. I. Wilde, Drugs 56, 447-486 (1998).
Properties: Crystals from acetonitrile, mp 156°. Freely sol in ethanol, methanol; slightly sol in acetone, isopropanol; very slightly sol in water. LD50 in mice, rats (g/kg): 0.08, >0.05 i.v.; >4, >4 orally (Ekman).
Melting point: mp 156°
Toxicity data: LD50 in mice, rats (g/kg): 0.08, >0.05 i.v.; >4, >4 orally (Ekman)
Derivative Type: Magnesium salt
CAS Registry Number: 95382-33-5
Trademarks: Antra (AstraZeneca); Gastracid (AWD); Gastroloc (AstraZeneca); Omebeta (Betapharm); Omep (Hexal); Ome-Puren (Alpharma)
Molecular Formula: C34H36MgN6O6S2
Molecular Weight: 713.12
Percent Composition: C 57.26%, H 5.09%, Mg 3.41%, N 11.78%, O 13.46%, S 8.99%
Derivative Type: S-Form
CAS Registry Number: 119141-88-7
Additional Names: Esomeprazole; perprazole
Manufacturers' Codes: H-199/18
Literature References: LC-MS determn in plasma: H. Stenhoff et al., J. Chromatogr. B 734, 191 (1999).
Properties: Colorless syrup. [a]D20 -155° (c = 0.5 in chloroform).
Optical Rotation: [a]D20 -155° (c = 0.5 in chloroform)
Derivative Type: S-Form magnesium salt
CAS Registry Number: 161973-10-0
CAS Name: (T-4)-Bis[5-methoxy-2-[(S)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazolato]magnesium
Additional Names: esomeprazole magnesium
Trademarks: Nexium (AstraZeneca)
Literature References: Review of clinical experience in acid disorders: D. A. Johnson, Expert Opin. Pharmacother. 4, 253-264 (2003).
Properties: White powder. [a]D20 -128.2° (c = 1 in methanol).
Optical Rotation: [a]D20 -128.2° (c = 1 in methanol)
Therap-Cat: Antiulcerative; in treatment of Zollinger-Ellison syndrome.
Therap-Cat-Vet: Antiulcerative.
Keywords: Antiulcerative; Gastric Proton Pump Inhibitor.

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