Nizatidine

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]

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[1] 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 Y
PubChem CID	3033637
IUPHAR/BPS	7248
DrugBank	DB00585 Y
ChemSpider	2298266 Y
UNII	P41PML4GHR
KEGG	D00440 Y
ChEBI	CHEBI:7601 N
ChEMBL	ChEMBL653 Y
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+ Y Key:SGXXNSQHWDMGGP-IZZDOVSWSA-N Y
NY (what is this?)  (verify)

It was patented in 1980 and approved for medical use in 1988.^[3][4] It was developed by Eli Lilly.

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.^[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.