Nizatidine
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Routes of administration | Oral |
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Pharmacokinetic data | |
Bioavailability | >70% |
Protein binding | 35% |
Metabolism | Hepatic |
Elimination half-life | 1-2 hours |
Excretion | Renal |
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ECHA InfoCard | 100.155.683 |
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Formula | C12H21N5O2S2 |
Molar mass | 331.46 g/mol g·mol−1 |
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Nizatidine is a histamine H2-receptor antagonist that inhibits stomach acid production, and commonly used in the treatment of peptic ulcer disease (PUD) and gastroesophageal reflux disease (GERD). It was developed by Eli Lilly and is marketed under the trade names Tazac and Axid.
Clinical use
Certain preparations of nizatidine are now available over the counter in various countries including the United States. Nizatadine has been used experimentally to control weight gain associated with some antipsychotic medication. [1]
History and development
Nizatidine was developed by Eli Lilly, and was first marketed in 1987. It is considered to be equipotent with ranitidine and differs by the substitution of a thiazole-ring in place of the furan-ring in ranitidine. In September 2000 Eli Lilly announced they would sell the sales and marketing rights for Axid to Reliant Pharmaceuticals. [2] Subsequently, Reliant developed the oral solution of Axid, marketing this in 2004, after gaining approval from the U.S. Food and Drug Administration (FDA). [3] However, a year later they sold rights of the Axid Oral Solution (including the issued patent US6,930,119 protecting the product) to Braintree Laboratories.[4]
Nizatidine proved to be the last new histamine H2-receptor antagonists introduced prior to the advent of proton pump inhibitors.
Chemistry
The starting thiazole is prepared by the standard route of condensation of thioamide with ethyl bromoacetate. Reduction of the ester group in by means of lithium aluminum hydride leads to the corresponding methyl carbinol; this is then converted to the bromide. The displacement of bromine by cysteamine incorporates the required side chain. A reagent can be prepared by a reaction of the ranitidine bis-methylthio nitrovinyl intermediate with methylamine. Treatment of the primary amine with leads to an addition of the nitrovinyl group and the formation of nizatidine.
References
- ^ Atmaca M, Kuloglu M, Tezcan E, Ustundag B, Kilic N (2004). "Nizatidine for the treatment of patients with quetiapine-induced weight gain". Hum Psychopharmacol. 19 (1): 37–40. doi:10.1002/hup.477. PMID 14716710.
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ignored (help)CS1 maint: multiple names: authors list (link) - ^ Eli Lilly and Company and Reliant Pharmaceuticals Announce
- ^ Reliant Pharmaceuticals : Press Releases
- ^ Reliant Pharmaceuticals : Press Releases