6845. Omeprazole

Nomenclature

CAS number: 73590-58-6
5-Methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazole; H-168/68; Gastrogard (Merial); Losec (AstraZeneca); Mopral (AstraZeneca); OmeLich (Winthrop); Omelind (Lindopharm); Omepral (AstraZeneca); Omeprazen (Malesci); Osiren (Probiomed); Parizac (Lacer); Pepticum (Grünenthal); Prilosec (AstraZeneca); UlcerGard (AstraZeneca); Zegerid (Santarus); Zoltum (AstraZeneca).
C17H19N3O3S; mol wt 345.42.
C 59.11%, H 5.54%, N 12.16%, O 13.90%, S 9.28%.

Description and references

Gastric proton-pump inhibitor. Prepn: U. K. Junggren, S. E. Sjostrand, EP 5129; eidem, US 4255431 (1979, 1981 both to AB H"assle). 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).

Chemical structure

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).

Derivative

Magnesium salt.

Nomenclature

CAS number: 95382-33-5
Antra (AstraZeneca); Gastracid (AWD); Gastroloc (AstraZeneca); Omebeta (Betapharm); Omep (Hexal); Ome-Puren (Alpharma).
C34H36MgN6O6S2; mol wt 713.12.
C 57.26%, H 5.09%, Mg 3.41%, N 11.78%, O 13.46%, S 8.99%.

Derivative

S-Form.

Nomenclature

CAS number: 119141-88-7
Esomeprazole; perprazole; H-199/18.

Description and references

LC-MS determn in plasma: H. Stenhoff et al., J. Chromatogr. B 734, 191 (1999).

Properties

Colorless syrup. [α]D20 -155° (c = 0.5 in chloroform).

Derivative

S-Form magnesium salt.

Nomenclature

CAS number: 161973-10-0
(T-4)-Bis[5-methoxy-2-[(S)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1H-benzimidazolato]magnesium; esomeprazole magnesium; Nexium (AstraZeneca).

Description and references

Review of clinical experience in acid disorders: D. A. Johnson, Expert Opin. Pharmacother. 4, 253-264 (2003).

Properties

White powder. [α]D20 -128.2° (c = 1 in methanol).

Therapeutic Category

Antiulcerative; in treatment of Zollinger-Ellison syndrome.

Therapeutic Category (Veterinary)

Antiulcerative.

Keywords

Antiulcerative; Gastric Proton Pump Inhibitor