View source for Nizatidine

{{short description|Chemical compound}}
{{Drugbox
| Verifiedfields = changed
| verifiedrevid = 457657906
| image = Nizatidine.svg
| width = 260
| alt = 

<!--Clinical data-->
| tradename = Axid, Tazac
| Drugs.com = {{drugs.com|monograph|nizatidine}}
| MedlinePlus = a694030
| DailyMedID = Nizatidine
| pregnancy_AU = B3
| routes_of_administration = [[By mouth]]
| ATC_prefix = A02
| ATC_suffix = BA04
| ATC_supplemental =

| legal_AU = S4
| legal_CA = Rx-only
| legal_CA_comment = /&nbsp;OTC<ref>{{cite web | title=Approved in 2020: Drugs for human use | website=[[Health Canada]] | date=26 July 2021 | url=https://www.canada.ca/en/health-canada/services/publications/drugs-health-products/drug-medical-device-highlights-2020/approved-2020-drugs-human-use.html | access-date=27 March 2024}}</ref>
| legal_UK = POM
| legal_US = OTC
| legal_US_comment = /&nbsp;Rx-only

<!--Pharmacokinetic data-->
| bioavailability = >70%
| protein_bound = 35%
| metabolism = [[Liver]]
| elimination_half-life = 1–2 hours
| excretion = [[Kidney]]

<!--Identifiers-->
| IUPHAR_ligand = 7248
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 76963-41-2
| PubChem = 3033637
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = DB00585
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 2298266
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = P41PML4GHR
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00440
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 7601
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 653

<!--Chemical data-->
| IUPAC_name = (''E'')-1-''N{{'}}''-[2-[<nowiki />[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-1-''N''-methyl-2-nitroethene-1,1-diamine
| C=12 | H=21 | N=5 | O=2 | S=2
| smiles = [O-][N+](=O)\C=C(/NC)NCCSCc1nc(sc1)CN(C)C
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C12H21N5O2S2/c1-13-11(6-17(18)19)14-4-5-20-8-10-9-21-12(15-10)7-16(2)3/h6,9,13-14H,4-5,7-8H2,1-3H3/b11-6+
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = SGXXNSQHWDMGGP-IZZDOVSWSA-N
}}

<!-- Definition and medical uses -->
'''Nizatidine''' is a histamine [[H2 antagonist|H<sub>2</sub> receptor antagonist]] that inhibits [[gastric acid|stomach acid]] production, and is commonly used in the treatment of [[peptic ulcer]] disease and [[gastroesophageal reflux disease]].<ref name="pmid2567957">{{cite journal | vauthors = Romero M, Franzosi MG | title = [Nizatidine] | language = it | journal = Medicina | volume = 9 | issue = 1 | pages = 93–96 | date = 1989 | pmid = 2567957 }}</ref>

<!-- Society and culture -->
It was patented in 1980 and approved for medical use in 1988.<ref name="FDA approval">{{cite web | title=Nizatidine: FDA-Approved Drugs | website=U.S. [[Food and Drug Administration]] (FDA) | url=https://www.accessdata.fda.gov/scripts/cder/daf/index.cfm?event=overview.process&ApplNo=019508 | access-date=20 March 2020}}</ref><ref>{{cite book | vauthors = Fischer J, Ganellin CR |title=Analogue-based Drug Discovery |date=2006 |publisher=John Wiley & Sons |isbn=9783527607495 |page=44 |url=https://books.google.com/books?id=FjKfqkaKkAAC&pg=PA444 |language=en}}</ref> It was developed by [[Eli Lilly and Company|Eli Lilly]].

==Medical use==
{{main|H2 antagonist}}
Nizatidine is used to treat [[duodenal ulcers]], [[gastric ulcers]], and [[gastroesophageal reflux disease]] (GERD/GORD), and to prevent [[stress ulcer]]s.<ref name=LiverTox>{{cite book | title=LiverTox: Clinical and Research Information on Drug-Induced Liver Injury | chapter=Nizatidine | publisher=NCBI Bookshelf | date=25 January 2018 | pmid=31643707 | chapter-url=https://www.ncbi.nlm.nih.gov/books/NBK548387/ | access-date=19 March 2020 | id=NBK548387 }}</ref>

==Adverse effects==
Side effects are uncommon, usually minor, and include diarrhea, constipation, fatigue, drowsiness, headache, and muscle aches.<ref name=LiverTox/>

==History and development==
Nizatidine was developed by [[Eli Lilly and Company|Eli Lilly]], and was first marketed in 1988.<ref name="FDA approval" /> 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]].<ref name="encyclopedia">{{cite encyclopedia | title = Eli Lilly and Company and Reliant Pharmaceuticals Announce Agreement for U.S. Sales and Marketing Rights to Axid(R) | date = 7 September 2000 | url = http://www.encyclopedia.com/doc/1G1-65062714.html?Q=%22axid%22 | archive-url = https://web.archive.org/web/20080526223021/http://www.encyclopedia.com/doc/1G1-65062714.html?Q=%22axid%22 | archive-date=May 26, 2008 | encyclopedia = Encyclopedia.com }}</ref> Subsequently, Reliant developed the oral solution of Axid, marketing this in 2004, after gaining approval from the [[Food and Drug Administration (United States)|U.S. Food and Drug Administration]] (FDA).<ref name="reliant2004">{{cite web | title = Reliant Pharmaceuticals to Launch AxidŽ Oral Solution | url = http://www.reliantrx.com/investor/press_releases/072604.htm | date = 26 July 2004 | publisher = Reliant Pharmaceuticals, LLC }}</ref> However, a year later, they sold rights of the Axid Oral Solution (including the issued patent<ref>{{cite patent | country = US | number = 6930119 | title = Liquid pharmaceutical composition | inventor = Bobotas G, Fawzy AA | assign1 = Reliant Pharmaceuticals, LLC | gdate = 24 June 2005 }}</ref> protecting the product) to [[Braintree Laboratories]].<ref name="reliant2005">{{cite web | title = Reliant Pharmaceuticals Announces the Sale of Axid® Oral Solution to Braintree Laboratories | url = http://www.reliantrx.com/investor/press_releases/063005.htm | archive-url = https://web.archive.org/web/20070814071007/http://www.reliantrx.com/investor/press_releases/063005.htm | archive-date=August 14, 2007 | publisher = Reliant Pharmaceuticals, LLC }}</ref>

== Society and culture ==
=== Brand names ===
{{unreferenced section|date=March 2024}}

Brand names include Tazac and Axid.

== References ==
{{Reflist}}

{{H2-receptor antagonist}}
{{Histaminergics}}
{{Portal bar | Medicine}}

[[Category:Drugs developed by Eli Lilly and Company]]
[[Category:H2 receptor antagonists]]
[[Category:Nitroethenes]]
[[Category:Thiazoles]]
[[Category:Thioethers]]