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=CC(CN2CCCCC2)=CC=N1)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 2849

Conditions

Condition	Modality	Highest Phase	Product
Gastroesophageal reflux disease 68 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 438	Unknown Approved Use Unknown
Peptic ulcer 72 Sources: https://clinicaltrials.gov/ct2/show/NCT02581696	Primary	Phase I 438	Unknown Approved Use Unknown
Erosive esophagitis 7 Sources: https://clinicaltrials.gov/ct2/show/NCT01499368	Primary	Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Analyte	Population
174 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400107_2325006F1036_1_04F_1F.pdf#page=37 \| https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=165	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
167 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400107_2325006F1036_1_04F_1F.pdf#page=37 \| https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=165	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
231 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=164	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
610 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=164	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
834 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=164	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
1666 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=164	160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
178 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400107_2325006F1036_1_04F_1F.pdf#page=38 \| https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=165	10 mg 2 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
203 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400107_2325006F1036_1_04F_1F.pdf#page=38 \| https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=165	10 mg 2 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
251 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
339 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
344 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
698 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	60 mg 2 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
726 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	60 mg 2 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
804 ng/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	60 mg 2 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Analyte	Population
793 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400107_2325006F1036_1_04F_1F.pdf#page=37 \| https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=165	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
849 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400107_2325006F1036_1_04F_1F.pdf#page=37 \| https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=165	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
1089 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=164	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2295 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=164	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3808 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=164	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
6513 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=164	160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
895 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400107_2325006F1036_1_04F_1F.pdf#page=38 \| https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=165	10 mg 2 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1004 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400107_2325006F1036_1_04F_1F.pdf#page=38 \| https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=165	10 mg 2 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1208 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1658 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
1584 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3027 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	60 mg 2 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3845 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	60 mg 2 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3664 ng × h/mL OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	60 mg 2 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
3.3 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400107_2325006F1036_1_04F_1F.pdf#page=37 \| https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=165	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
3.79 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400107_2325006F1036_1_04F_1F.pdf#page=37 \| https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=165	10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FED
4.37 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=164	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.14 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=164	40 mg single, oral dose: 40 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.28 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=164	80 mg single, oral dose: 80 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
4.03 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=164	160 mg single, oral dose: 160 mg route of administration: Oral experiment type: SINGLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED
2.99 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400107_2325006F1036_1_04F_1F.pdf#page=38 \| https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=165	10 mg 2 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.54 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400107_2325006F1036_1_04F_1F.pdf#page=38 \| https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=165	10 mg 2 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.37 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.4 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	20 mg 2 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.12 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	20 mg 2 times / day steady-state, oral dose: 20 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.08 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	60 mg 2 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.01 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	60 mg 2 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.41 h OTHER GOV'T https://www.pmda.go.jp/drugs/2000/g000103/65ctdp_1-249.pdf#page=166	60 mg 2 times / day multiple, oral dose: 60 mg route of administration: Oral experiment type: MULTIPLE co-administered:	LAFUTIDINE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1.4% OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/400107_2325006F1036_1_04F_1F.pdf#page=42			LAFUTIDINE plasma	Homo sapiens

Doses

Dose	Population	Adverse events
10 mg 2 times / day multiple, oral Recommended Dose: 10 mg, 2 times / day Route: oral Route: multiple Dose: 10 mg, 2 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/25532503/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/25532503/	Sources: https://pubmed.ncbi.nlm.nih.gov/25532503/

PubMed

Title	Date	PubMed
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.	2011-07-14	21599003
Protective effect of lafutidine, a histamine H2 receptor antagonist, against loxoprofen-induced small intestinal lesions in rats.	2010-05	20586851
[A case of paclitaxel-induced peripheral neuropathy successfully treated by H2-blocker, lafutidine].	2009-09	19755835
Stronger inhibition of gastric acid secretion by lafutidine, a novel H2 receptor antagonist, than by the proton pump inhibitor lansoprazole.	2008-04-21	18416470
Lafutidine facilitates calcitonin gene-related peptide (CGRP) nerve-mediated vasodilation via vanilloid-1 receptors in rat mesenteric resistance arteries.	2008-03	18344609
Histamine-induced vasodilation and vasoconstriction in the mesenteric resistance artery of the rat.	2006-01-04	16337938
Lafutidine, a newly developed antiulcer drug, elevates postprandial intragastric pH and increases plasma calcitonin gene-related peptide and somatostatin concentrations in humans: comparisons with famotidine.	2006-01	16416222
Protective effect of lafutidine, a novel histamine H2-receptor antagonist, on dextran sulfate sodium-induced colonic inflammation through capsaicin-sensitive afferent neurons in rats.	2004-10	15573930
Lafutidine increases hepatic blood flow via potentiating the action of central thyrotropin-releasing hormone in rats.	2003-02	12542603
Effects of vanilloid receptor agonists and antagonists on gastric antral ulcers in rats.	2001-12-07	11740957
Intestinal protection by lafutidine, a histamine H(2)-receptor antagonist, against indomethacin-induced damage in rats--role of endogenous nitric oxide.	2001-09-06	11535926
Protective effect of lafutidine against indomethacin-induced intestinal ulceration in rats: relation to capsaicin-sensitive sensory neurons.	2000	10671773

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 `Mon Mar 31 18:16:54 GMT 2025` Edited by `admin` on `Mon Mar 31 18:16:54 GMT 2025`
Record UNII	49S4O7ADLC
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

LAFUTIDINE

Preferred Name

English

LAFUTIDINE, (±)-

Common Name

English

LAFUTIDINE [JAN]

Common Name

English

Lafutidine [WHO-DD]

Common Name

English

LAFUTIDINE [MART.]

Common 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