Lafutidine

Lafutidine (INN) is a second generation histamine H2 receptor antagonist having multimodal mechanism of action and used to treat gastrointestinal disorders.[1] It is marketed in South Korea, Japan and India.

Lafutidine
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration		Oral
ATC code
Identifiers
IUPAC name
  • 2-(furan-2-ylmethylsulfinyl)-N-[(Z)-4-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxybut-2-enyl]acetamide
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
ECHA InfoCard100.118.935
Chemical and physical data
FormulaC22H29N3O4S
Molar mass431.55 g·mol−1
3D model (JSmol)
SMILES
  • C1CCCCN1Cc2ccnc(c2)OC/C=C\CNC(=O)CS(=O)Cc3ccco3
InChI
  • InChI=1S/C22H29N3O4S/c26-21(18-30(27)17-20-7-6-14-28-20)23-9-2-5-13-29-22-15-19(8-10-24-22)16-25-11-3-1-4-12-25/h2,5-8,10,14-15H,1,3-4,9,11-13,16-18H2,(H,23,26)/b5-2- N
  • Key:KMZQAVXSMUKBPD-DJWKRKHSSA-N N
 NY (what is this?)  (verify)

Medical use

Lafutidine is used to treat gastric ulcers, duodenal ulcers, as well as wounds in the lining of the stomach associated with acute gastritis and acute exacerbation of chronic gastritis.[2][3]

Adverse effects

Adverse events observed during clinical trials included constipation, diarrhea, drug rash, nausea, vomiting and dizziness.[3]

Mechanism of action

Like other H2 receptor antagonists, lafutidine acts by preventing the secretion of gastric acid.[3] It also activates calcitonin gene-related peptide, resulting in the stimulation of nitric oxide (NO) and regulation of gastric mucosal blood flow, increases somatostatin levels also resulting in less gastric acid secretion, causes the stomach lining to generate more mucin, inhibits neutrophil activation thus preventing injury from inflammation, and blocks the attachment of Helicobacter pylori to gastric cells.[3]

Trade names

It is marketed in Japan as Stogar by UCB[2] and in India as Lafaxid by Zuventus Healthcare.[3] It is also marketed in South Korea as Ildong Lafutidine by Ildong Pharmaceutical Co Ltd.

References
  1. Tanaka M, Banba M, Joko A, Moriyama Y (June 2001). "[Pharmacological and therapeutic properties of lafutidine (stogar and protecadin), a novel histamine H2 receptor antagonist with gastroprotective activity]". Nihon Yakurigaku Zasshi. Folia Pharmacologica Japonica (in Japanese). 117 (6): 377–86. doi:10.1254/fpj.117.377. PMID 11436515.
  2. UCB Japan Revised: April 2005 Stogar tablets
  3. Zuventus Healthcare Ltd. India Lafaxid tablets
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