LAFUTIDINE, (±)-

Possibly Marketed Outside US

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

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

Description

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	Antagonist 2,849

Conditions

Condition	Modality	Highest Phase	Product
Gastroesophageal reflux disease 68	Primary	Preclinical	Unknown
Chronic gastritis 4	Primary	Phase I 438	Unknown
Peptic ulcer 72	Primary	Phase I 438	Unknown
Erosive esophagitis 7	Primary	Phase III 665	Unknown

C_max

Value	Dose	Analyte	Population
174 ng/mL	10 mg single, oral	LAFUTIDINE plasma	Homo sapiens
167 ng/mL	10 mg single, oral	LAFUTIDINE plasma	Homo sapiens
231 ng/mL	20 mg single, oral	LAFUTIDINE plasma	Homo sapiens
610 ng/mL	40 mg single, oral	LAFUTIDINE plasma	Homo sapiens
834 ng/mL	80 mg single, oral	LAFUTIDINE plasma	Homo sapiens
1666 ng/mL	160 mg single, oral	LAFUTIDINE plasma	Homo sapiens
178 ng/mL	10 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
203 ng/mL	10 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
251 ng/mL	20 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
339 ng/mL	20 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
344 ng/mL	20 mg 2 times / day steady-state, oral	LAFUTIDINE plasma	Homo sapiens
698 ng/mL	60 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
726 ng/mL	60 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
804 ng/mL	60 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens

AUC

Value	Dose	Analyte	Population
793 ng × h/mL	10 mg single, oral	LAFUTIDINE plasma	Homo sapiens
849 ng × h/mL	10 mg single, oral	LAFUTIDINE plasma	Homo sapiens
1089 ng × h/mL	20 mg single, oral	LAFUTIDINE plasma	Homo sapiens
2295 ng × h/mL	40 mg single, oral	LAFUTIDINE plasma	Homo sapiens
3808 ng × h/mL	80 mg single, oral	LAFUTIDINE plasma	Homo sapiens
6513 ng × h/mL	160 mg single, oral	LAFUTIDINE plasma	Homo sapiens
895 ng × h/mL	10 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
1004 ng × h/mL	10 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
1208 ng × h/mL	20 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
1658 ng × h/mL	20 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
1584 ng × h/mL	20 mg 2 times / day steady-state, oral	LAFUTIDINE plasma	Homo sapiens
3027 ng × h/mL	60 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
3845 ng × h/mL	60 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
3664 ng × h/mL	60 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens

T_1/2

Value	Dose	Analyte	Population
3.3 h	10 mg single, oral	LAFUTIDINE plasma	Homo sapiens
3.79 h	10 mg single, oral	LAFUTIDINE plasma	Homo sapiens
4.37 h	20 mg single, oral	LAFUTIDINE plasma	Homo sapiens
4.14 h	40 mg single, oral	LAFUTIDINE plasma	Homo sapiens
4.28 h	80 mg single, oral	LAFUTIDINE plasma	Homo sapiens
4.03 h	160 mg single, oral	LAFUTIDINE plasma	Homo sapiens
2.99 h	10 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
3.54 h	10 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
3.37 h	20 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
2.4 h	20 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
3.12 h	20 mg 2 times / day steady-state, oral	LAFUTIDINE plasma	Homo sapiens
2.08 h	60 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
2.01 h	60 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens
2.41 h	60 mg 2 times / day multiple, oral	LAFUTIDINE plasma	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
1.4%			LAFUTIDINE plasma	Homo sapiens

Doses

Doses

Show entries

Dose	Population	Adverse events
10 mg 2 times / day multiple, oral Recommended	unhealthy, ADULT

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PubMed

Show entries

Title	Date	PubMed
Effects of vanilloid receptor agonists and antagonists on gastric antral ulcers in rats.	2001 Dec 7	11740957
Lafutidine increases hepatic blood flow via potentiating the action of central thyrotropin-releasing hormone in rats.	2003 Feb	12542603
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 Oct	15573930
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 Jan	16416222
Histamine-induced vasodilation and vasoconstriction in the mesenteric resistance artery of the rat.	2006 Jan 4	16337938

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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

Show entries

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

Showing 1 to 5 of 7 entries

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Show entries

Classification Tree

Code System

Code

Anti-ulcer Agent

NCI_THESAURUS

C29702

H₂-receptor antagonists

WHO-ATC

A02BA08

H₂-receptor antagonists

WHO-VATC

QA02BA08

Showing 1 to 3 of 3 entries

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Show entries

Code System

Code

Type

Description

DRUG BANK

DB12770

PRIMARY

PUBCHEM

5282136

PRIMARY

INN

7173

PRIMARY

DRUG CENTRAL

1537

PRIMARY

ChEMBL

CHEMBL1742461

PRIMARY

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ACTIVE MOIETY


					49S4O7ADLC

LAFUTIDINE, (±)-

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound