Nizatidine

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Nizatidine
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Systematic (IUPAC) name
(E)-1-N'-[2-[[2-[(dimethylamino)methyl]-1,3-thiazol-4-yl]methylsulfanyl]ethyl]-1-N-methyl-2-nitroethene-1,1-diamine
Clinical data
Trade names Axid
AHFS/Drugs.com monograph
MedlinePlus a694030
Licence data US FDA:link
Pregnancy
category
Legal status
  • AU: S4 (Prescription only)
  • UK: POM (Prescription only)
  • US: ℞-only and OTC[1]
Routes of
administration
Oral
Pharmacokinetic data
Bioavailability >70%
Protein binding 35%
Metabolism Hepatic
Biological half-life 1–2 hours
Excretion Renal
Identifiers
CAS Number 76963-41-2 YesY
ATC code A02BA04 (WHO)
PubChem CID: 3033637
IUPHAR/BPS 7248
DrugBank DB00585 YesY
ChemSpider 2298266 YesY
UNII P41PML4GHR YesY
KEGG D00440 YesY
ChEBI CHEBI:7601 N
ChEMBL CHEMBL653 YesY
Chemical data
Formula C12H21N5O2S2
Molecular mass 331.46 g/mol
  • [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+ YesY
  • Key:SGXXNSQHWDMGGP-IZZDOVSWSA-N YesY
 NYesY (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

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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

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External links

  1. 1.0 1.1 1.2 Lua error in package.lua at line 80: module 'strict' not found.
  2. [1] Archived May 26, 2008 at the Wayback Machine
  3. [2] Archived December 26, 2013 at the Wayback Machine
  4. Lua error in package.lua at line 80: module 'strict' not found.
  5. [3] Archived August 14, 2007 at the Wayback Machine