Nizatidine: Difference between revisions

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{{short description|Chemical compound}}
{{Drugbox
{{Drugbox
| Verifiedfields = changed
| Verifiedfields = changed
| verifiedrevid = 457657906
| verifiedrevid = 457657906
⚫
| image = Nizatidine.svg
⚫
| IUPAC_name = ''N''-(2-[(2-[(dimethylamino)methyl]thiazol-4-yl)methylthio]ethyl)-''N''-methyl-2-nitroethene-1,1-diamine
| width = 260
⚫
| image = Nizatidine structure.png
| alt =

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

| legal_AU = S4
| 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_UK = POM
| legal_US = Rx
| legal_US = OTC
| legal_US_comment = and OTC<ref name=LiverTox/>
| legal_US_comment = /&nbsp;Rx-only

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

<!--Identifiers-->
<!--Identifiers-->
| IUPHAR_ligand = 7248
| IUPHAR_ligand = 7248
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 76963-41-2
| CAS_number = 76963-41-2
⚫
| ATC_prefix = A02
⚫
| ATC_suffix = BA04
⚫
| ATC_supplemental =
| PubChem = 3033637
| PubChem = 3033637
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
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| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D00440
| KEGG = D00440
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI_Ref = {{ebicite|changed|EBI}}
| ChEBI = 7601
| ChEBI = 7601
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 653
| ChEMBL = 653

<!--Chemical data-->
<!--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
| C=12 | H=21 | N=5 | O=2 | S=2
⚫
| smiles = [O-] [N+](=O)\C=C(/NC)NCCSCc1nc(sc1)CN(C)C
| molecular_weight = 331.46 g/mol
⚫
| smiles = [O-][N+](=O)\C=C(/NC)NCCSCc1nc(sc1)CN(C)C
| 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+
| InChIKey = SGXXNSQHWDMGGP-IZZDOVSWBC
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| 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+
| 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+
Line 52: Line 59:
| StdInChIKey = SGXXNSQHWDMGGP-IZZDOVSWSA-N
| StdInChIKey = SGXXNSQHWDMGGP-IZZDOVSWSA-N
}}
}}
⚫
'''Nizatidine''' is a histamine [[H2-receptor 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. It was developed by [[Eli Lilly and Company|Eli Lilly]] and is marketed under the brand names Tazac and Axid.


<!-- Definition and medical uses -->
⚫
==Clinical use==
⚫
'''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>
⚫
{{main|H2-receptor antagonist}}

⚫
Nizatidine is used to treat [[duodenal ulcers]], [[gastric ulcers]], and [[gastroesophageal reflux disease]] (GERD), and to prevent [[stress ulcer]]s.<ref name=LiverTox>{{cite web|url=http://livertox.nih.gov/Nizatidine.htm |title=Nizatidine |publisher=Livertox.nih.gov |date= |accessdate=2015-10-11}}</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==
==Adverse effects==
Line 62: Line 74:


==History and development==
==History and development==
Nizatidine was developed by [[Eli Lilly and Company|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]].<ref name="encyclopedia">[http://www.encyclopedia.com/doc/1G1-65062714.html?Q=%22axid%22 ]{{dead link|date=October 2015}}</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">[http://www.reliantrx.com/investor/press_releases/072604.htm]{{dead link|date=October 2015}}</ref> However, a year later, they sold rights of the Axid Oral Solution (including the issued patent<ref>{{cite web|url=http://patft.uspto.gov/netacgi/nph-Parser?Sect1=PTO1&Sect2=HITOFF&d=PALL&p=1&u=%2Fnetahtml%2FPTO%2Fsrchnum.htm&r=1&f=G&l=50&s1=6930119.PN.&OS=PN/6930119&RS=PN/6930119 |title=United States Patent: 6930119 |publisher=Patft.uspto.gov |date= |accessdate=2015-10-11}}</ref> protecting the product) to Braintree Laboratories.<ref name="reliant2005">[http://www.reliantrx.com/investor/press_releases/063005.htm]{{dead link|date=October 2015}}</ref>
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 ==
Nizatidine proved to be the last new histamine H<sub>2</sub>-receptor antagonist introduced prior to the advent of [[proton pump inhibitor]]s.
==Synthesis==
=== Brand names ===
{{unreferenced section|date=March 2024}}
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]].
[[File:Nizatidine synthesis.svg|thumb|center|700px|Nizatidine synthesis: R.P. Pioch; [[Eli Lilly]] And Company; {{US patent|4,375,547}} (1983).]]
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''').


Brand names include Tazac and Axid.
==See also==
*[[Famotidine]], Pepcid AC, Pepcidine: another popular H<sub>2</sub>-receptor antagonist


==References==
== References ==
{{Reflist}}
{{Reflist}}


==External links==
* [http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=2929 Dailymed.nlm.nih.gov]
* [http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=AXID Axid @ FDA]
* [http://www.axidos.com/ Axid Oral Solution]

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


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

Latest revision as of 05:29, 27 March 2024

Nizatidine
Clinical data
Trade namesAxid, Tazac
AHFS/Drugs.comMonograph
MedlinePlusa694030
License data
Pregnancy
category
  • AU: B3
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability>70%
Protein binding35%
MetabolismLiver
Elimination half-life1–2 hours
ExcretionKidney
Identifiers
  • (E)-1-N'-[2-[[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-1-N-methyl-2-nitroethene-1,1-diamine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.155.683 Edit this at Wikidata
Chemical and physical data
FormulaC12H21N5O2S2
Molar mass331.45 g·mol−1
3D model (JSmol)
  • [O-] [N+](=O)\C=C(/NC)NCCSCc1nc(sc1)CN(C)C
  • InChI=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+ checkY
  • Key:SGXXNSQHWDMGGP-IZZDOVSWSA-N checkY
 ☒NcheckY (what is this?)  (verify)

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.[2]

It was patented in 1980 and approved for medical use in 1988.[3][4] It was developed by Eli Lilly.

Medical use[edit]

Main article: H2 antagonist

Nizatidine is used to treat duodenal ulcers, gastric ulcers, and gastroesophageal reflux disease (GERD/GORD), and to prevent stress ulcers.[5]

Adverse effects[edit]

Side effects are uncommon, usually minor, and include diarrhea, constipation, fatigue, drowsiness, headache, and muscle aches.[5]

History and development[edit]

Nizatidine was developed by Eli Lilly, and was first marketed in 1988.[3] 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.[6] Subsequently, Reliant developed the oral solution of Axid, marketing this in 2004, after gaining approval from the U.S. Food and Drug Administration (FDA).[7] However, a year later, they sold rights of the Axid Oral Solution (including the issued patent[8] protecting the product) to Braintree Laboratories.[9]

Society and culture[edit]

Brand names[edit]

Brand names include Tazac and Axid.

References[edit]

  1. ^ "Approved in 2020: Drugs for human use". Health Canada. 26 July 2021. Retrieved 27 March 2024.
  2. ^ Romero M, Franzosi MG (1989). "[Nizatidine]". Medicina (in Italian). 9 (1): 93–96. PMID 2567957.
  3. ^ a b "Nizatidine: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 20 March 2020.
  4. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 44. ISBN 9783527607495.
  5. ^ a b "Nizatidine". LiverTox: Clinical and Research Information on Drug-Induced Liver Injury. NCBI Bookshelf. 25 January 2018. PMID 31643707. NBK548387. Retrieved 19 March 2020.
  6. ^ "Eli Lilly and Company and Reliant Pharmaceuticals Announce Agreement for U.S. Sales and Marketing Rights to Axid(R)". Encyclopedia.com. 7 September 2000. Archived from the original on May 26, 2008.
  7. ^ "Reliant Pharmaceuticals to Launch AxidŽ Oral Solution". Reliant Pharmaceuticals, LLC. 26 July 2004.
  8. ^ US 6930119, Bobotas G, Fawzy AA, "Liquid pharmaceutical composition", issued 24 June 2005, assigned to Reliant Pharmaceuticals, LLC 
  9. ^ "Reliant Pharmaceuticals Announces the Sale of Axid® Oral Solution to Braintree Laboratories". Reliant Pharmaceuticals, LLC. Archived from the original on August 14, 2007.
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