Nizatidine: Difference between revisions

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| Verifiedfields = changed
| Verifiedfields = changed
| verifiedrevid = 457657906
| verifiedrevid = 457657906
| IUPAC_name = ''N''-(2-[(2-[(dimethylamino)methyl]thiazol-4-yl)methylthio]ethyl)-''N''-methyl-2-nitroethene-1,1-diamine
| IUPAC_name = (''E'')-1-''N<nowiki>'</nowiki>''-[2-<nowiki>[[</nowiki>2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-1-''N''-methyl-2-nitroethene-1,1-diamine
| image = Nizatidine structure.png
| image = Nizatidine.svg
| width = 260

<!--Clinical data-->
<!--Clinical data-->
| tradename = Axid
| tradename = Axid
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| legal_US_comment = and OTC<ref name=LiverTox/>
| legal_US_comment = and OTC<ref name=LiverTox/>
| routes_of_administration = Oral
| routes_of_administration = Oral

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

<!--Identifiers-->
<!--Identifiers-->
| IUPHAR_ligand = 7248
| IUPHAR_ligand = 7248
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| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 653
| ChEMBL = 653

<!--Chemical data-->
<!--Chemical data-->
| C=12 | H=21 | N=5 | O=2 | S=2
| C=12 | H=21 | N=5 | O=2 | S=2
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| 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.
'''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]]. It was developed by [[Eli Lilly and Company|Eli Lilly]] and is marketed under the brand names '''Tazac''' and '''Axid'''.


==Clinical use==
==Clinical use==
{{main|H2-receptor antagonist}}
{{main|H2 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>
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 web|url=http://livertox.nih.gov/Nizatidine.htm |title=Nizatidine |publisher=Livertox.nih.gov |date= |accessdate=2015-10-11}}</ref>


==Adverse effects==
==Adverse effects==
Line 62: Line 68:


==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 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 proved to be the last new histamine H<sub>2</sub>-receptor antagonist introduced prior to the advent of [[proton pump inhibitor]]s.{{cn}}


⚫
Nizatidine proved to be the last new histamine H<sub>2</sub>-receptor antagonist introduced prior to the advent of [[proton pump inhibitor]]s.
==See also==
==See also==
*[[Famotidine]], Pepcid AC, Pepcidine: another popular H<sub>2</sub>-receptor antagonist
* [[Famotidine]] (Pepcid) — another popular H<sub>2</sub> receptor antagonist


==References==
==References==
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* [http://www.axidos.com/ Axid Oral Solution]
* [http://www.axidos.com/ Axid Oral Solution]


⚫
{{Histaminergics}}
{{H2-receptor antagonist}}
{{H2-receptor antagonist}}
⚫
{{Histaminergics}}


⚫
[[Category:Eli Lilly and Company]]
[[Category:H2 receptor antagonists]]
[[Category:H2 receptor antagonists]]
⚫
[[Category:Nitroethenes]]
[[Category:Thiazoles]]
[[Category:Thiazoles]]
⚫
[[Category:Eli Lilly and Company]]
[[Category:Thioethers]]
[[Category:Thioethers]]
⚫
[[Category:Nitroethenes]]

Revision as of 10:09, 8 January 2016

Nizatidine
Clinical data
Trade namesAxid
AHFS/Drugs.comMonograph
MedlinePlusa694030
License data
Pregnancy
category
  • AU: B3
Routes of
administration		Oral
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability>70%
Protein binding35%
MetabolismHepatic
Elimination half-life1–2 hours
ExcretionRenal
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 mass331.46 g/mol 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. It was developed by Eli Lilly and is marketed under the brand names Tazac and Axid.

Clinical 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.[1]

Adverse effects

Side effects are uncommon, usually minor, and include diarrhea, constipation, fatigue, drowsiness, headache, and muscle aches.[1]

History and development

Nizatidine was developed by 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.[2] Subsequently, Reliant developed the oral solution of Axid, marketing this in 2004, after gaining approval from the U.S. Food and Drug Administration (FDA).[3] However, a year later, they sold rights of the Axid Oral Solution (including the issued patent[4] protecting the product) to Braintree Laboratories.[5]

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

See also

  • Famotidine (Pepcid) — another popular H2 receptor antagonist

References

  1. ^ a b c "Nizatidine". Livertox.nih.gov. Retrieved 2015-10-11.
  2. ^ [1][dead link]
  3. ^ [2][dead link]
  4. ^ "United States Patent: 6930119". Patft.uspto.gov. Retrieved 2015-10-11.
  5. ^ [3][dead link]

External links

Retrieved from "https://en.wikipedia.org/w/index.php?title=Nizatidine&oldid=698804775"