Nizatidine: Difference between revisions
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{{short description|Chemical compound}} |
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{{Drugbox |
{{Drugbox |
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| Verifiedfields = changed |
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| verifiedrevid = |
| verifiedrevid = 457657906 |
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| image = Nizatidine |
| image = Nizatidine.svg |
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| width = 260 |
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| alt = |
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<!--Clinical data--> |
<!--Clinical data--> |
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| tradename = Axid |
| tradename = Axid, Tazac |
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| Drugs.com = {{drugs.com|monograph|nizatidine}} |
| Drugs.com = {{drugs.com|monograph|nizatidine}} |
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| MedlinePlus = a694030 |
| MedlinePlus = a694030 |
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| |
| DailyMedID = Nizatidine |
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| pregnancy_AU = B3 |
| pregnancy_AU = B3 |
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| legal_AU = S4 |
| legal_AU = S4 |
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| legal_CA = Rx-only |
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| legal_CA_comment = / 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> |
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| legal_UK = POM |
| legal_UK = POM |
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| legal_US = OTC |
| legal_US = OTC |
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| legal_US_comment = / Rx-only |
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<!--Pharmacokinetic data--> |
<!--Pharmacokinetic data--> |
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| bioavailability = >70% |
| bioavailability = >70% |
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| protein_bound = 35% |
| protein_bound = 35% |
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| metabolism = [[Liver |
| metabolism = [[Liver]] |
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| elimination_half-life = |
| elimination_half-life = 1–2 hours |
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| excretion = [[Kidney |
| excretion = [[Kidney]] |
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<!--Identifiers--> |
<!--Identifiers--> |
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| IUPHAR_ligand = 7248 |
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| CASNo_Ref = {{cascite|correct|CAS}} |
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| CAS_number_Ref = {{cascite|correct|??}} |
| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 76963-41-2 |
| CAS_number = 76963-41-2 |
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| PubChem = 3033637 |
| PubChem = 3033637 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| KEGG_Ref = {{keggcite|correct|kegg}} |
| KEGG_Ref = {{keggcite|correct|kegg}} |
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| KEGG = D00440 |
| KEGG = D00440 |
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| ChEBI_Ref = {{ebicite|changed|EBI}} |
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| ChEBI = 7601 |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 653 |
| ChEMBL = 653 |
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<!--Chemical data--> |
<!--Chemical data--> |
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| C=12 | H=21 | N=5 | O=2 | S=2 |
| C=12 | H=21 | N=5 | O=2 | S=2 |
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| molecular_weight = 331.46 g/mol |
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| smiles = [O-][N+](=O)\C=C(/NC)NCCSCc1nc(sc1)CN(C)C |
| smiles = [O-][N+](=O)\C=C(/NC)NCCSCc1nc(sc1)CN(C)C |
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| InChI = 1/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+ |
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| InChIKey = SGXXNSQHWDMGGP-IZZDOVSWBC |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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+ |
| 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+ |
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| StdInChIKey = SGXXNSQHWDMGGP-IZZDOVSWSA-N |
| StdInChIKey = SGXXNSQHWDMGGP-IZZDOVSWSA-N |
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}} |
}} |
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⚫ | '''Nizatidine''' is a histamine [[H2 |
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<!-- Definition and medical uses --> |
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⚫ | '''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> |
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Certain preparations of nizatidine are now available [[Over-the-counter drug|over the counter]] in various countries including the United States. Nizatidine has been used experimentally to control weight gain associated with some antipsychotic medication. <ref name="pmid14716710">{{cite journal |
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<!-- Society and culture --> |
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|author=Atmaca M, Kuloglu M, Tezcan E, Ustundag B, Kilic N |
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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]]. |
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|title=Nizatidine for the treatment of patients with quetiapine-induced weight gain |
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|journal=Hum Psychopharmacol |
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|volume=19 |
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|issue=1 |
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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> |
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|pages=37–40 |
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|year=2004 |
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==Adverse effects== |
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|month=January |
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Side effects are uncommon, usually minor, and include diarrhea, constipation, fatigue, drowsiness, headache, and muscle aches.<ref name=LiverTox/> |
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|pmid=14716710 |
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|doi=10.1002/hup.477 |
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}}</ref> |
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==History and development== |
==History and development== |
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Nizatidine was developed by [[Eli Lilly and Company|Eli Lilly]], and was first marketed in |
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> |
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== Society and culture == |
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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. |
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=== Brand names === |
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{{unreferenced section|date=March 2024}} |
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Brand names include Tazac and Axid. |
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==References== |
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== References == |
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* http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=2929 |
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* [http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=AXID Axid @ FDA] |
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* [http://www.axidos.com/ Axid Oral Solution] |
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{{H2-receptor antagonist}} |
{{H2-receptor antagonist}} |
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{{Portal bar | Medicine}} |
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[[Category:H2 receptor antagonists]] |
[[Category:H2 receptor antagonists]] |
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[[Category:Thiazoles]] |
[[Category:Thiazoles]] |
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[[Category:Thioethers]] |
[[Category:Thioethers]] |
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[[es:Nizatidina]] |
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[[it:Nizatidina]] |
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[[ja:ニザチジン]] |
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[[nl:Nizatidine]] |
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[[th:นิซาทิดีน]] |