Nizatidine: Difference between revisions

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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}}
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| 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
| 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
| smiles = [O-] [N+](=O)\C=C(/NC)NCCSCc1nc(sc1)CN(C)C
| 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+
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==History and development==
==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 = High Beam Encyclopedia }}</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>
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>


Nizatidine proved to be the last new histamine H<sub>2</sub> receptor antagonist introduced prior to the advent of [[proton pump inhibitor]]s.{{citation needed|date=January 2016}}
Nizatidine proved to be the last new histamine H<sub>2</sub> receptor antagonist introduced prior to the advent of [[proton pump inhibitor]]s.{{citation needed|date=January 2016}}

Revision as of 02:04, 7 October 2023

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
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: OTC / Rx-only
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.[1]

It was patented in 1980 and approved for medical use in 1988.[2][3] It was developed by Eli Lilly. Brand names include Tazac and Axid.

Medical use

Main article: H2 antagonist

Nizatidine is used to treat duodenal ulcers, gastric ulcers, and gastroesophageal reflux disease (GERD/GORD), and to prevent stress ulcers.[4]

Adverse effects

Side effects are uncommon, usually minor, and include diarrhea, constipation, fatigue, drowsiness, headache, and muscle aches.[4]

History and development

Nizatidine was developed by Eli Lilly, and was first marketed in 1988.[2] 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.[5] Subsequently, Reliant developed the oral solution of Axid, marketing this in 2004, after gaining approval from the U.S. Food and Drug Administration (FDA).[6] However, a year later, they sold rights of the Axid Oral Solution (including the issued patent[7] protecting the product) to Braintree Laboratories.[8]

Nizatidine proved to be the last new histamine H2 receptor antagonist introduced prior to the advent of proton pump inhibitors.[citation needed]

Axid (nizatidine) drug recalled due to presence of NDMA.[citation needed]

See also

  • Famotidine (Pepcid) — another popular H2 receptor antagonist

References

  1. ^ Romero M, Franzosi MG (1989). "[Nizatidine]". Medicina (in Italian). 9 (1): 93–96. PMID 2567957.
  2. ^ a b "Nizatidine: FDA-Approved Drugs". U.S. Food and Drug Administration (FDA). Retrieved 20 March 2020.
  3. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 44. ISBN 9783527607495.
  4. ^ 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.
  5. ^ "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.
  6. ^ "Reliant Pharmaceuticals to Launch AxidŽ Oral Solution". Reliant Pharmaceuticals, LLC. 26 July 2004.
  7. ^ US 6930119, Bobotas G, Fawzy AA, "Liquid pharmaceutical composition", issued 24 June 2005, assigned to Reliant Pharmaceuticals, LLC 
  8. ^ "Reliant Pharmaceuticals Announces the Sale of Axid® Oral Solution to Braintree Laboratories". Reliant Pharmaceuticals, LLC. Archived from the original on August 14, 2007.

External links

  • "Nizatidine". Drug Information Portal. U.S. National Library of Medicine.
Retrieved from "https://en.wikipedia.org/w/index.php?title=Nizatidine&oldid=1178976986"