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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'--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
3D model (JSmol)	Interactive image
SMILES (=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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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 patented in 1980 and approved for medical use in 1988. 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.

Adverse effects

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

History and development

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

Society and culture

Brand names

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Brand names include Tazac and Axid.

References

1. "Approved in 2020: Drugs for human use". Health Canada. 26 July 2021. Retrieved 27 March 2024.
2. Romero M, Franzosi MG (1989). "". Medicina (in Italian). 9 (1): 93–96. PMID 2567957.
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.
5. ^ "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.

• Medicine

• Drugs developed by Eli Lilly and Company
• H2 receptor antagonists
• Nitroethenes
• Thiazoles
• Thioethers