LAFUTIDINE, (±)-

Details

Stereochemistry	RACEMIC
Molecular Formula	C22H29N3O4S
Molecular Weight	431.548
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[O-][S+](CC(=O)NC\C=C/COC1=NC=CC(CN2CCCCC2)=C1)CC3=CC=CO3

InChI

InChIKey=KMZQAVXSMUKBPD-DJWKRKHSSA-N

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-

HIDE SMILES / InChI

Molecular Formula	C22H29N3O4S
Molecular Weight	431.548
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: http://www.ncbi.nlm.nih.gov/pubmed/11436515
Curator's Comment: description was created based on several sources, including http://www.zuventus.co.in/doctor_wise_products_selected.aspx?Medi_Id=39

Lafutidine is a novel histamine H2 antagonist with gastroprotective activity. Lafutidine exhibited potent and long-lasting H2 antagonism and prolonged antisecretion. In addition, lafutidine showed a gastroprotective effect against noxious agents-induced gastric mucosal damage through capsaicin-sensitive afferent nerves. Lafutidine showed antiulcer activities against acute ulcer models, prevented gastric ulcer relapse of acetic ulcer. Adverse events observed during clinical trials included constipation, diarrhea, drug rash, nausea, vomiting and dizziness.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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Histamine H2 receptor 46 Target ID: CHEMBL1941 Sources: http://www.ncbi.nlm.nih.gov/pubmed/11786663	Antagonist 2778

Conditions

Condition	Modality	Highest Phase	Product
Gastroesophageal reflux disease 59 Sources: http://www.ncbi.nlm.nih.gov/pubmed/27340360	Primary	Preclinical	Unknown Approved Use Unknown
Chronic gastritis 4 Sources: https://clinicaltrials.gov/ct2/show/NCT02658864	Primary	Phase I 428	Unknown Approved Use Unknown
Peptic ulcer 72 Sources: https://clinicaltrials.gov/ct2/show/NCT02581696	Primary	Phase I 428	Unknown Approved Use Unknown
Erosive esophagitis 7 Sources: https://clinicaltrials.gov/ct2/show/NCT01499368	Primary	Phase III 656	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Protective effect of lafutidine against indomethacin-induced intestinal ulceration in rats: relation to capsaicin-sensitive sensory neurons.	2000	10671773
Effects of vanilloid receptor agonists and antagonists on gastric antral ulcers in rats.	2001 Dec 7	11740957
Stronger inhibition of gastric acid secretion by lafutidine, a novel H2 receptor antagonist, than by the proton pump inhibitor lansoprazole.	2008 Apr 21	18416470
Lafutidine facilitates calcitonin gene-related peptide (CGRP) nerve-mediated vasodilation via vanilloid-1 receptors in rat mesenteric resistance arteries.	2008 Mar	18344609
[A case of paclitaxel-induced peripheral neuropathy successfully treated by H2-blocker, lafutidine].	2009 Sep	19755835
Protective effect of lafutidine, a histamine H2 receptor antagonist, against loxoprofen-induced small intestinal lesions in rats.	2010 May	20586851
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011 Jul 14	21599003

Patents

Sample Use Guides

In Vivo Use Guide

20 mg

Route of Administration: Oral

In Vitro Use Guide

lafutidine, 86.64 +/- 9.52 pg/mL pretreatment of gastric mucosal before water-immersion restraint stress caused a significant increase in serum calcitonin gene-related peptide concentration

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:02:04 UTC 2023` Edited by `admin` on `Fri Dec 15 16:02:04 UTC 2023`
Record UNII	49S4O7ADLC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LAFUTIDINE, (±)-

Common Name

English

LAFUTIDINE [JAN]

Common Name

English

Lafutidine [WHO-DD]

Common Name

English

LAFUTIDINE [MART.]

Common Name

English

LAFUTIDINE

Official Name

English

(±)-2-(FURFURYLSULFINYL)-N-((Z)-4-((4-(PIPERIDINOMETHYL)-2-PYRIDYL)OXY)-2-BUTENYL) ACETAMIDE

Common Name

English

lafutidine [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29702