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.com	International Drug Names
Routes of administration	Oral
ATC code	A02BA08 (WHO)
Identifiers
IUPAC name 2-(furan-2-ylmethylsulfinyl)-N-[(Z)-4-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxybut-2-enyl]acetamide
CAS Number	206449-93-6 Y
PubChem CID	5282136
ChemSpider	4445337 N
UNII	49S4O7ADLC
KEGG	D01131 Y
CompTox Dashboard (EPA)	DTXSID0046434
ECHA InfoCard	100.118.935
Chemical and physical data
Formula	C22H29N3O4S
Molar mass	431.55 g·mol−1
3D model (JSmol)	Interactive image
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.