nizatidine   Click here for help

GtoPdb Ligand ID: 7248

Synonyms: Axid® | LY-139037
Approved drug
nizatidine is an approved drug (FDA (1988))
Compound class: Synthetic organic
Comment: Nizatidine is a histamine H2 receptor antagonist. It is structurally related to ranitidine but has a thiazole ring substitution in place of the furan ring in ranitidine. Nizatidine was the last new histamine H2 receptor antagonist to be approved prior to proton pump inhibitors reaching the clinic.
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
Hydrogen bond acceptors 4
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 139.55
Molecular weight 331.11
XLogP 1.41
No. Lipinski's rules broken 0
Click here for help
Canonical SMILES CNC(=CN(=O)=O)NCCSCc1csc(n1)CN(C)C
Isomeric SMILES CN/C(=C\N(=O)=O)/NCCSCc1csc(n1)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+
No information available.
Summary of Clinical Use Click here for help
Used to treat peptic ulcer disease (PUD) and gastroesophageal reflux disease. in January 2020 Mylan voluntarily recalled prescription nizatidine medications after excess levels of the hepatotoxic and carcinogenic chemical N-nitrosodimethylamine (NDMA) were detected in the capsules. FDA authorisation for all ranitidine medications was withdrawn in April 2020 for the same reason.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Nizatidine is a histamine H2 receptor antagonist which inhibits stomach acid production.
External links Click here for help