Lafutidine Chemical Properties

Melting point:

92.7-94.9°

Boiling point:

704.2±60.0 °C(Predicted)

Density 

1.252±0.06 g/cm3(Predicted)

storage temp. 

Sealed in dry,Store in freezer, under -20°C

Water Solubility 

Insoluble in water

solubility 

DMF:5.0(Max Conc. mg/mL);11.59(Max Conc. mM)
DMSO:48.67(Max Conc. mg/mL);112.77(Max Conc. mM)
DMSO:PBS (pH 7.2) (1:10):0.09(Max Conc. mg/mL);0.21(Max Conc. mM)
Ethanol:9.0(Max Conc. mg/mL);20.86(Max Conc. mM)

form 

powder to crystal

pka

13.13±0.46(Predicted)

color 

White to Orange to Green

InChIKey

KMZQAVXSMUKBPD-DJWKRKHSSA-N

SMILES

C(NC/C=C\COC1=NC=CC(CN2CCCCC2)=C1)(=O)CS(CC1=CC=CO1)=O

CAS DataBase Reference

118288-08-7(CAS DataBase Reference)

Safety Information

Safety Statements 

24/25

HS Code 

29349990

Lafutidine Usage And Synthesis

Description

Lafutidine is a second generation of H2-receptor antagonist. H2-receptor antagonist can strongly inhibit gastric acid secretion compared with conventional drugs such as antacids. Unlike conventional H2-receptor antagonist, lafutidine inhibits gastric acid secretion during daytime as well as nighttime in clinical studies in humans. Lafutidine also has gastroprotective activity independent of its acid antisecretory efficacy, preventing noxious agent-induced gastric mucosal injury and accelerating the repair process following gastric mucosal damage. It also protects experimentally induced reflux esophagitis, indomethacin-induced intestinal, and dextran sulfate sodium-induced colonic inflammation.
Lafutidine is used for gastric and duodenal ulcers. It is also confirmed that lafutidine can be used as an empiric treatment and superior efficacy for primary care practice patients with dyspepsia.

References

[1] Tomohiko Shimatani, Masaki Inoue, Tomoko Kuroiwa, Jing Xu, Masuo Nakamura, Susumu Tazuma, Kazuro Ikawa, Norifumi Morikawa (2006) 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, Digestive Diseases and Sciences, 51, 114-120
[2] Bhupesh Dewan, Nisha Philipose (2011) Lafutidine 10 mg versus Rabeprazole 20 mg in the Treatment of Patients with Heartburn-Dominant Uninvestigated Dyspepsia: A Randomized, Multicentric Trial, Gastroenterology Research and Practice, 2011, Article ID 640685
[3] https://www.drugs.com

Description

Lafutidine was launched in Japan for the treatment of gastritis, reflux oesophagitis and peptic ulcers. It can be prepared in eight steps from 4-(2-tetrahydropyranyloxy)-2(Z)-butenl- ol. Lafutidine is a potent and longer-acting H₂ antagonist compared to other marketed compounds of its class such as cimetidine and famotidine. In contrast to other commercially available H₂ antagonists, lafutidine also exerts a gastroprotective action probably via capsaicin-sensitive afferent nerves. It was clinically effective in the treatment of nonsteroidal antiinflammatory drug-induced ulcer in patients refractory to existing antiulcer agents.

Description

Lafutidine is a histamine H₂ receptor antagonist with gastroprotective activity. It inhibits histamine-induced cAMP production in CHO cells expressing human histamine H₂ receptors when used at a concentration of 10 nM. Intragastric administration of lafutidine (3, 10, and 30 mg/kg) reduces hemorrhagic esophageal lesion size and gastric acid secretion in a rat model of pyloric ligation-induced reflux esophagitis. It prevents 5-fluorouracil-induced intestinal mucositis, diarrhea, and body weight loss in wild-type, but not Trpv1^-/- or sensory deafferented, mice when administered at doses ranging from 3 to 30 mg/kg. Lafutidine (10 mg/kg) also reduces indomethacin-induced antral ulcer size in wild-type, but not chemically-deafferented, rats.

Originator

Fujirebio (Japan)

Uses

(Z)-2-((Furan-2-ylmethyl)sulfinyl)-n-(4-((3-(piperidin-1-ylmethyl)pyridin-2-yl)oxy)but-2-en-1-yl)acetamide is a Histaminic H2 receptor antagonists in ulcer disease. Also, it is a model compound used to investigate the binding mechanism between antiulcer drugs and human serum albumin (HSA).

Uses

Second generation histamine H2-receptor antagonist. Antiulcerative

Uses

Lafutidine, a newly developed histamine H(2)-receptor antagonist, inhibits gastric acid secretion

Definition

ChEBI: Lafutidine is an organic molecular entity.

brand name

Stogar, Protecadin

References

[1] Y. FUKUSHIMA. Potent and Long-Lasting Action of Lafutidine on the Human Histamine H2 Receptor[J]. Digestion, 2001, 64 1: 155-160. DOI: 10.1159/000048856
[2] KENJI NAGAHAMA. Protective effect of lafutidine, a novel H2-receptor antagonist, on reflux esophagitis in rats through capsaicin-sensitive afferent neurons.[J]. Journal of pharmacological sciences, 2003, 93 1: 55-61. DOI: 10.1254/jphs.93.55
[3] T SANO. Lafutidine, a histamine H2 receptor antagonist with mucosal protective properties, attenuates 5-fluorouracil-induced intestinal mucositis in mice through activation of extrinsic primary afferent neurons.[J]. Journal of Physiology and Pharmacology, 2017, 68 1: 79-90.
[4] S ONODERA. Gastroprotective mechanism of lafutidine, a novel anti-ulcer drug with histamine H2-receptor antagonistic activity.[J]. Arzneimittel-Forschung-Drug Research, 1999, 49 6: 519-526. DOI: 10.1055/s-0031-1300454

Lafutidine(118288-08-7)Related Product Information

• Omeprazole
• Famotidine
• Ranitidine
• Lafutidine
• N-{4-[4-(PIPERIDINOMETHYL)PYRIDYL-2-OXY]-CIS-2-BUTENE}PHTHALIMIDE MALEIC ACID(INTERMEDIATE FOR LAFUTIDINE)
• LACTITOL MONOHYDRATE,LACTITOL H2O,D-LACTITOL MONOHYDRATE,LACTITOL MONOHYDRATE 99%
• p-Nitrophenyl 2-(Furfurylsulfinyl)acetate
• 4-[4-(Piperidinomethyl)pyridyl-2-oxy]-cis-2-butenamine
• 2-ALLYLOXYPYRIDINE
• LACTITOL
• (Z)-4-[(TETRAHYDRO-2H-PYRAN-2-YL)OXY]-2-BUTEN-1-OL (PREPARATION FOR LAFUTIDINE)
• Lomerizine
• Furan
• Acetamide
• 2-Butene
• 2(1H)-Pyridinone,4-(aminomethyl)-(9CI)
• 2-((FURAN-2-YL)METHYLSULFINYL)-N-((Z)-4-HYDROXYBUT-2-ENYL)ACETAMIDE
• N-(PYRIDIN-4-YLMETHYL)BUTAN-1-AMINE