Nizatidine: Difference between revisions

Nizatidine
Clinical data
Trade names	Axid, Tazac
AHFS/Drugs.com	Monograph
MedlinePlus	a694030
License data	US DailyMed: Nizatidine;
Pregnancy; category	AU: B3; ;
Routes of; administration	By mouth
ATC code	A02BA04 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); CA: ℞-only / OTC; UK: POM (Prescription only); US: OTC / Rx-only;
Pharmacokinetic data
Bioavailability	>70%
Protein binding	35%
Metabolism	Liver
Elimination half-life	1–2 hours
Excretion	Kidney
Identifiers
	IUPAC name (E)-1-N'-[2-[[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-1-N-methyl-2-nitroethene-1,1-diamine;
CAS Number	76963-41-2 ;
PubChem CID	3033637;
IUPHAR/BPS	7248;
DrugBank	DB00585 ;
ChemSpider	2298266 ;
UNII	P41PML4GHR;
KEGG	D00440 ;
ChEBI	CHEBI:7601 ;
ChEMBL	ChEMBL653 ;
CompTox Dashboard (EPA)	DTXSID5023376 ;
ECHA InfoCard	100.155.683
Chemical and physical data
Formula	C12H21N5O2S2
Molar mass	331.45 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES [O-] [N+](=O)\C=C(/NC)NCCSCc1nc(sc1)CN(C)C;
	InChI 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+ ; Key:SGXXNSQHWDMGGP-IZZDOVSWSA-N ;
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Revision as of 05:29, 27 March 2024

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

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

Adverse effects

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

History and development

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

Brand names

Brand names include Tazac and Axid.

References

^ "Approved in 2020: Drugs for human use". Health Canada. 26 July 2021. Retrieved 27 March 2024.
^ Romero M, Franzosi MG (1989). "[Nizatidine]". Medicina (in Italian). 9 (1): 93–96. PMID 2567957.
^ ^a ^b "Nizatidine: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 20 March 2020.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 44. ISBN 9783527607495.
^ ^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.
^ "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.
^ "Reliant Pharmaceuticals to Launch AxidŽ Oral Solution". Reliant Pharmaceuticals, LLC. 26 July 2004.
^ US 6930119, Bobotas G, Fawzy AA, "Liquid pharmaceutical composition", issued 24 June 2005, assigned to Reliant Pharmaceuticals, LLC
^ "Reliant Pharmaceuticals Announces the Sale of Axid® Oral Solution to Braintree Laboratories". Reliant Pharmaceuticals, LLC. Archived from the original on August 14, 2007.

[1] "Approved in 2020: Drugs for human use". Health Canada. 26 July 2021. Retrieved 27 March 2024.

[pmid2567957-2] Romero M, Franzosi MG (1989). "[Nizatidine]". Medicina (in Italian). 9 (1): 93–96. PMID 2567957.

[FDA_approval-3] "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.

[LiverTox-5] "Nizatidine". LiverTox: Clinical and Research Information on Drug-Induced Liver Injury. NCBI Bookshelf. 25 January 2018. PMID 31643707. NBK548387. Retrieved 19 March 2020.

[encyclopedia-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.

[reliant2004-7] "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

[reliant2005-9] "Reliant Pharmaceuticals Announces the Sale of Axid® Oral Solution to Braintree Laboratories". Reliant Pharmaceuticals, LLC. Archived from the original on August 14, 2007.

[1]

[2]

[3]

[4]

[5]

[6]

[7]

[8]

[9]

@@ Line 1: / Line 1: @@
+{{short description|Chemical compound}}
 {{Drugbox
+| Verifiedfields = changed
 | 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-->
-| tradename = Axid
+| tradename = Axid, Tazac
 | Drugs.com = {{drugs.com|monograph|nizatidine}}
 | MedlinePlus = a694030
-| licence_US = Nizatidine
+| 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 = Rx and OTC<ref>[http://livertox.nih.gov/Nizatidine.htm Nizatidine]</ref>
+| legal_US_comment = /&nbsp;Rx-only
-| routes_of_administration = Oral
 <!--Pharmacokinetic data-->
 | bioavailability = >70%
 | 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-->
+| IUPHAR_ligand = 7248
-| CASNo_Ref = {{cascite|correct|CAS}}
 | CAS_number_Ref = {{cascite|correct|??}}
 | CAS_number = 76963-41-2
-| ATC_prefix = A02
-| ATC_suffix = BA04
-| ATC_supplemental =
 | PubChem = 3033637
 | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
- | DrugBank = DB00585
+| DrugBank = DB00585
 | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 2298266
@@ Line 38: / Line 45: @@
 | KEGG_Ref = {{keggcite|correct|kegg}}
 | KEGG = D00440
-| ChEBI_Ref = {{ebicite|correct|EBI}}
+| ChEBI_Ref = {{ebicite|changed|EBI}}
 | ChEBI = 7601
 | ChEMBL_Ref = {{ebicite|correct|EBI}}
@@ Line 44: / Line 51: @@
 <!--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
-| molecular_weight = 331.46 g/mol
-| smiles = [O-][N+](=O)\C=C(/NC)NCCSCc1nc(sc1)CN(C)C
+| 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 = 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 54: / Line 59: @@
 | 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 commonly used in the treatment of  [[peptic ulcer]] disease (PUD) and [[gastroesophageal reflux]] disease (GERD). 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}}
-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
+<!-- Society and culture -->
-|author=Atmaca M, Kuloglu M, Tezcan E, Ustundag B, Kilic N
+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]].
-|title=Nizatidine for the treatment of patients with quetiapine-induced weight gain
-|journal=Hum Psychopharmacol
+==Medical use==
-|volume=19
+{{main|H2 antagonist}}
-|issue=1
+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>
-|pages=37–40
-|date=January 2004
-|pmid=14716710
-|doi=10.1002/hup.477
-}}</ref>
 ==Adverse effects==
+Side effects are uncommon, usually minor, and include diarrhea, constipation, fatigue, drowsiness, headache, and muscle aches.<ref name=LiverTox/>
-Antacid preparations such as nizatidine work by suppressing acid mediated break down of proteins, leads to an elevated risk of developing food or drug allergies. This happens due to undigested proteins then passing into the gastrointestinal tract where sensitisation occurs. It is unclear whether this risk occurs with only long-term use or with short-term use as well.<ref name="pmid21121928">{{cite journal |author=Pali-Schöll I, Jensen-Jarolim E |title=Anti-acid medication as a risk factor for food allergy |journal=Allergy |volume=66 |issue=4 |pages=469–77 |date=April 2011 |pmid=21121928 |doi=10.1111/j.1398-9995.2010.02511.x |url=}}</ref>
 ==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 Eli Lilly and Company and Reliant Pharmaceuticals Announce<!-- Bot generated title -->]</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 Reliant Pharmaceuticals : Press Releases<!-- Bot generated title -->]</ref> However, a year later they sold rights of the Axid Oral Solution (including the issued patent [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 US6,930,119] protecting the product) to [[Braintree Laboratories]].<ref name="reliant2005">[http://www.reliantrx.com/investor/press_releases/063005.htm Reliant Pharmaceuticals : Press Releases<!-- Bot generated title -->]</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.
+=== Brand names ===
+{{unreferenced section|date=March 2024}}
+Brand names include Tazac and Axid.
-==See also==
-*[[Famotidine]], aka Pepcid AC, Pepcidine: another popular H2-receptor antagonist
-==References==
+== References ==
-{{Reflist|2}}
+{{Reflist}}
-==External links==
-* http://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?id=2929
-* [http://www.accessdata.fda.gov/scripts/cder/drugsatfda/index.cfm?fuseaction=Search.Overview&DrugName=AXID Axid @ FDA]
-* [http://www.axidos.com/ Axid Oral Solution]
-{{Histaminergics}}
 {{H2-receptor antagonist}}
+{{Histaminergics}}
+{{Portal bar | Medicine}}
+[[Category:Drugs developed by Eli Lilly and Company]]
 [[Category:H2 receptor antagonists]]
+[[Category:Nitroethenes]]
 [[Category:Thiazoles]]
-[[Category:Eli Lilly and Company]]
 [[Category:Thioethers]]
-[[Category:Nitroethenes]]

v t e Drugs for peptic ulcer and GERD/GORD (A02B)
H₂ antagonists ("-tidine")	Cimetidine Famotidine Lafutidine Lavoltidine (loxtidine) Nizatidine Ranitidine^#‡ Roxatidine
Prostaglandins (E)/ analogues ("-prost-")	Misoprostol Enprostil
Proton-pump inhibitors ("-prazole")	Azeloprazole Dexlansoprazole Esomeprazole Ilaprazole Lansoprazole Omeprazole^# Pantoprazole Picoprazole Rabeprazole Tenatoprazole Timoprazole
Potassium-competitive acid blockers ("-prazan")	Linaprazan Revaprazan Soraprazan Vonoprazan
Others	Aceglutamide aluminum Acetoxolone Alginic acid Arbaclofen placarbil Bismuth subcitrate Carbenoxolone Cetraxate Gefarnate Irsogladine Lesogaberan Pirenzepine Proglumide Rebamipide Sucralfate Sulglicotide Telenzepine Teprenone Troxipide Zinc L-carnosine Zolimidine
Combinations	Bismuth subcitrate/metronidazole/tetracycline Omeprazole/amoxicillin/rifabutin Vonoprazan/amoxicillin Vonoprazan/amoxicillin/clarithromycin
See also: Helicobacter pylori* eradication protocols*
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III