ranitidine   Click here for help

GtoPdb Ligand ID: 1234

Synonyms: AH-19065 | Gavilast® | GR-122311X | Zantac®
Approved drug
ranitidine is an approved drug (FDA (1977))
Compound class: Synthetic organic
Comment: There is some ambiguity in the exact stereochemistry of ranitidine as represented in the literature and on other databases. The structure shown here matches that in the PubChem entry above. Other common representations include CID 657345. N.B. The structure shown in the INN document does not have a charge.
Marketed formulations may contain ranitidine hydrochloride (PubChem CID 3033332).
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View more information in the IUPHAR Pharmacology Education Project: ranitidine

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 10
Topological polar surface area 108.88
Molecular weight 314.14
XLogP 1.28
No. Lipinski's rules broken 0
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Canonical SMILES CNC(=C[N+](=O)[O-])NCCSCc1ccc(o1)CN(C)C
Isomeric SMILES CN/C(=C\[N+](=O)[O-])/NCCSCc1ccc(o1)CN(C)C
InChI InChI=1S/C13H22N4O3S/c1-14-13(9-17(18)19)15-6-7-21-10-12-5-4-11(20-12)8-16(2)3/h4-5,9,14-15H,6-8,10H2,1-3H3/b13-9+
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Summary of Clinical Use Click here for help
Ranitidine is used in the treatment of gastic ulcers, where blocking of H2 receptors reduces gastric acid secretion and ameliorates disease symptoms. At the beginning of April 2020 the FDA withdrew marketing authorisation for all ranitidine products, after excess levels of the hepatotoxic and carcinogenic chemical N-nitrosodimethylamine (NDMA) were detected in ranitidine medications. Mylan had voluntarily recalled prescription nizatidine capsules for the same reason in January 2020.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Competitive inhibition of H2 receptors on parietal cells leads to supression of gastric acid secretion.
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