Nizatidine: Difference between revisions
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Nizatidine proved to be the last new histamine H<sub>2</sub>-receptor antagonist introduced prior to the advent of [[proton pump inhibitor]]s. |
Nizatidine proved to be the last new histamine H<sub>2</sub>-receptor antagonist introduced prior to the advent of [[proton pump inhibitor]]s. |
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==Synthesis== |
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The replacement of [[imidazole]] in [[cimetidine]] by [[furan]] to give [[ranitidine]] includes some additional changes in functionality. The furan ring in the latter can, however, be replaced directly by [[thiazole]]. |
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[[File:Nizatidine synthesis.svg|thumb|center|700px|Nizatidine synthesis: R.P. Pioch; [[Eli Lilly]] And Company; {{US patent|4,375,547}} (1983).]] |
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The starting [[thiazole]] ('''3''') is prepared by the standard route of condensation of thioamide '''1''' with [[ethyl bromoacetate]] ('''2'''). Reduction of the ester group in '''3''' by means of [[LiAlH4]] leads to the corresponding methyl carbinol; this is then converted to the bromide ('''4'''). The displacement of bromide by [[cystamine]] incorporates the required side chain ('''5'''). A reagent ('''6''') can be prepared by by a reaction of the ranitidine ''bis''-methylthio nitrovinyl intermediate with [[methylamine]]. Treatment of the primary amine ('''5''') with '''6''' leads to addition of the nitrovinyl group and formation of nizatidine ('''7'''). |
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==See also== |
==See also== |
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*[[Famotidine]], Pepcid AC, Pepcidine: another popular H<sub>2</sub>-receptor antagonist |
*[[Famotidine]], Pepcid AC, Pepcidine: another popular H<sub>2</sub>-receptor antagonist |
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Revision as of 20:16, 2 November 2015
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| Clinical data | |
|---|---|
| Trade names | Axid |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a694030 |
| License data |
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| Pregnancy category |
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| Routes of administration | Oral |
| ATC code | |
| Legal status | |
| Legal status | |
| Pharmacokinetic data | |
| Bioavailability | >70% |
| Protein binding | 35% |
| Metabolism | Hepatic |
| Elimination half-life | 1-2 hours |
| Excretion | Renal |
| Identifiers | |
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| CAS Number | |
| PubChem CID | |
| IUPHAR/BPS | |
| DrugBank | |
| ChemSpider | |
| UNII | |
| KEGG | |
| ChEBI | |
| ChEMBL | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.155.683 |
| Chemical and physical data | |
| Formula | C12H21N5O2S2 |
| Molar mass | 331.46 g/mol g·mol−1 |
| 3D model (JSmol) | |
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Nizatidine is a histamine H2-receptor antagonist that inhibits stomach acid production, and is commonly used in the treatment of peptic ulcer disease and gastroesophageal reflux disease. It was developed by Eli Lilly and is marketed under the brand names Tazac and Axid.
Clinical use
Nizatidine is used to treat duodenal ulcers, gastric ulcers, and gastroesophageal reflux disease (GERD), and to prevent stress ulcers.[1]
Adverse effects
Side effects are uncommon, usually minor, and include diarrhea, constipation, fatigue, drowsiness, headache, and muscle aches.[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[4] protecting the product) to Braintree Laboratories.[5]
Nizatidine proved to be the last new histamine H2-receptor antagonist introduced prior to the advent of proton pump inhibitors.
See also
- Famotidine, Pepcid AC, Pepcidine: another popular H2-receptor antagonist