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MedKoo Cat#: 598231 | Name: Lafutidine HCl

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lafutidine is a second generation histamine H2 receptor antagonist having multimodal mechanism of action and used to treat gastrointestinal disorders. It is marketed in Japan and India. Like other H2 receptor antagonists it prevents the secretion of gastric acid. 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 H. pylori to gastric cells.

Chemical Structure

Lafutidine HCl
Lafutidine HCl
CAS#Unknown (HCl)

Theoretical Analysis

MedKoo Cat#: 598231

Name: Lafutidine HCl

CAS#: Unknown (HCl)

Chemical Formula: C22H30ClN3O4S

Exact Mass: 431.1879

Molecular Weight: 468.01

Elemental Analysis: C, 56.46; H, 6.46; Cl, 7.57; N, 8.98; O, 13.67; S, 6.85

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Related CAS #
118288-08-7 (free base) 169899-19-8 206449-93-6
Synonym
FRG-8813; FRG8813; FRG 8813; Lafutidine HCl; Lafutidine hydrochloride
IUPAC/Chemical Name
(Z)-2-((furan-2-ylmethyl)sulfinyl)-N-(4-((4-(piperidin-1-ylmethyl)pyridin-2-yl)oxy)but-2-en-1-yl)acetamide hydrochloride
InChi Key
KSIJVCSWGMQWNM-PVOKDAACSA-N
InChi Code
InChI=1S/C22H29N3O4S.ClH/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);1H/b5-2-;
SMILES Code
O=C(NC/C=C\COC1=NC=CC(CN2CCCCC2)=C1)CS(CC3=CC=CO3)=O.[H]Cl
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Lafutidine is a second generation histamine H2 receptor antagonist having multimodal mechanism of action and used to treat gastrointestinal disorders.
In vitro activity:
Lafutidine at pharmacological concentrations greater than 1 mM induced a sustained increase in [Ca(2+)](i) in the presence of extracellular CaCl(2) in PC12 cells, while capsaicin showed dual effects on [Ca(2+)](i) in PC12 cells, where it activated TRPV1 and inhibited store-operated Ca(2+) entry. These results suggest that lafutidine stimulates Ca(2+) entry via the capsaicin-sensitive pathway but not the SKF96365-sensitive pathway. Reference: J Pharmacol Sci. 2005 Jan;97(1):67-74. https://pubmed.ncbi.nlm.nih.gov/15655292/
In vivo activity:
Daily administration of lafutidine reduced the severity of intestinal mucositis, diarrhea and body weight loss in a dose-dependent manner, while famotidine had no effect on intestinal mucositis. The preventive effects of lafutidine were completely abolished in sensory deafferented and TRPV1-KO mice. Lafutidine significantly suppressed 5-FU-increased MPO activity and inflammatory cytokine expression on day 6, but not apoptosis induction in intestinal crypts on day 1. Reference: J Physiol Pharmacol. 2017 Feb;68(1):79-90. https://pubmed.ncbi.nlm.nih.gov/28456772/

Preparing Stock Solutions

The following data is based on the product molecular weight 468.01 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Kunieda K, Someya A, Horie S, Ajioka H, Murayama T. Lafutidine-induced increase in intracellular ca(2+) concentrations in PC12 and endothelial cells. J Pharmacol Sci. 2005 Jan;97(1):67-74. doi: 10.1254/jphs.fpj04042x. Epub 2005 Jan 15. PMID: 15655292. 2. Nozawa Y, Nishihara K, Akizawa Y, Orimoto N, Nakano M, Uji T, Ajioka H, Kanda A, Matsuura N, Kiniwa M. Lafutidine inhibits Helicobacter pylori-induced interleukin-8 production in human gastric epithelial cells. J Gastroenterol Hepatol. 2004 May;19(5):506-11. doi: 10.1111/j.1440-1746.2003.03330.x. PMID: 15086593. 3. Sano T, Utsumi D, Amagase K, Matsumoto K, Tominaga M, Higuchi K, Takeuchi T, Kato S. 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 Physiol Pharmacol. 2017 Feb;68(1):79-90. PMID: 28456772. 4. Nakano M, Kitano S, Nanri M, Kiniwa M. Lafutidine, a unique histamine H2-receptor antagonist, inhibits distention-induced gastric acid secretion through an H2 receptor-independent mechanism. Eur J Pharmacol. 2011 May 11;658(2-3):236-41. doi: 10.1016/j.ejphar.2011.02.007. Epub 2011 Feb 22. PMID: 21349265.
In vitro protocol:
1. Kunieda K, Someya A, Horie S, Ajioka H, Murayama T. Lafutidine-induced increase in intracellular ca(2+) concentrations in PC12 and endothelial cells. J Pharmacol Sci. 2005 Jan;97(1):67-74. doi: 10.1254/jphs.fpj04042x. Epub 2005 Jan 15. PMID: 15655292. 2. Nozawa Y, Nishihara K, Akizawa Y, Orimoto N, Nakano M, Uji T, Ajioka H, Kanda A, Matsuura N, Kiniwa M. Lafutidine inhibits Helicobacter pylori-induced interleukin-8 production in human gastric epithelial cells. J Gastroenterol Hepatol. 2004 May;19(5):506-11. doi: 10.1111/j.1440-1746.2003.03330.x. PMID: 15086593.
In vivo protocol:
1. Sano T, Utsumi D, Amagase K, Matsumoto K, Tominaga M, Higuchi K, Takeuchi T, Kato S. 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 Physiol Pharmacol. 2017 Feb;68(1):79-90. PMID: 28456772. 2. Nakano M, Kitano S, Nanri M, Kiniwa M. Lafutidine, a unique histamine H2-receptor antagonist, inhibits distention-induced gastric acid secretion through an H2 receptor-independent mechanism. Eur J Pharmacol. 2011 May 11;658(2-3):236-41. doi: 10.1016/j.ejphar.2011.02.007. Epub 2011 Feb 22. PMID: 21349265.
1: Maity S, Choudhury S, Hazra A, Das AK. Randomized controlled trial of effectiveness of lafutidine versus pantoprazole in uninvestigated dyspepsia. Indian J Pharmacol. 2014 Sep-Oct;46(5):498-502. doi: 10.4103/0253-7613.140580. PubMed PMID: 25298578; PubMed Central PMCID: PMC4175885. 2: Kim EH, Lee YC, Chang YW, Park JJ, Chun HJ, Jung HY, Kim HS, Jeong HY, Seol SY, Han SW, Choi MG, Park SH, Lee OJ, Jung JT, Lee DH, Jung HC, Lee ST, Kim JG, Youn SJ, Kim HY, Lee SW. Efficacy of Lafutidine Versus Famotidine in Patients with Reflux Esophagitis: A Multi-Center, Randomized, Double-Blind, Non-inferiority Phase III Trial. Dig Dis Sci. 2015 Jun;60(6):1724-32. doi: 10.1007/s10620-014-3489-4. Epub 2014 Dec 23. PubMed PMID: 25532503. 3: Takenaka R, Okada H, Kawano S, Komazawa Y, Yoshinaga F, Nagata S, Inoue M, Komatsu H, Onogawa S, Kushiyama Y, Mukai S, Todo H, Okanobu H, Manabe N, Tanaka S, Haruma K, Kinoshita Y. Randomized study of lafutidine vs lansoprazole in patients with mild gastroesophageal reflux disease. World J Gastroenterol. 2016 Jun 21;22(23):5430-5. doi: 10.3748/wjg.v22.i23.5430. PubMed PMID: 27340360; PubMed Central PMCID: PMC4910664. 4: Namikawa T, Munekage E, Maeda H, Kitagawa H, Kobayashi M, Hanazaki K. Feasibility study of supportive care using lafutidine, a histamine H2 receptor antagonist, to prevent gastrointestinal toxicity during chemotherapy for gastric cancer. Anticancer Res. 2014 Dec;34(12):7297-301. PubMed PMID: 25503163. 5: Li S, Xu M, Li H, Du J, Li W. Pharmacokinetic Properties of Oral Lafutidine Tablets and the Effect of Food on its Pharmacokinetics in Healthy Chinese Subjects. Adv Ther. 2016 Oct;33(10):1704-1714. Epub 2016 Jul 21. PubMed PMID: 27444313. 6: Patil S, Talele GS. Gastroretentive mucoadhesive tablet of lafutidine for controlled release and enhanced bioavailability. Drug Deliv. 2015 May;22(3):312-9. doi: 10.3109/10717544.2013.877099. Epub 2014 Jan 29. PubMed PMID: 24471787. 7: Tsukaguchi M, Shibano M, Matsuura A, Mukai S. The protective effects of lafutidine for bortezomib induced peripheral neuropathy. J Blood Med. 2013 Jul 11;4:81-5. doi: 10.2147/JBM.S44127. Print 2013. PubMed PMID: 23874126; PubMed Central PMCID: PMC3712744. 8: Ogawa Y, Ichinokawa Y, Hiruma M, Machida Y, Funakushi N, Sadamasa H, Hiruma M. Retrospective cohort study on combination therapy with the histamine H2-receptor antagonist lafutidine for antihistamine-resistant chronic urticaria. J Dermatolog Treat. 2013 Dec;24(6):463-5. doi: 10.3109/09546634.2013.800183. Epub 2013 May 21. PubMed PMID: 23639034. 9: Nagano H, Sanai H, Muraoka M, Takagi K. Efficacy of lafutidine, a histamine H2-receptor antagonist, for taxane-induced peripheral neuropathy in patients with gynecological malignancies. Gynecol Oncol. 2012 Oct;127(1):172-4. doi: 10.1016/j.ygyno.2012.06.029. Epub 2012 Jun 26. PubMed PMID: 22750259. 10: Kudo T, Fujinami H, Ando T, Nishikawa J, Ogawa K, Hosokawa A, Orihara T, Murakami J, Takahara T, Sugiyama T. Comparison of lafutidine and rabeprazole in 7-day second-line amoxicillin- and metronidazole-containing triple therapy for Helicobacter pylori: a pilot study. Helicobacter. 2012 Aug;17(4):277-81. doi: 10.1111/j.1523-5378.2012.00943.x. Epub 2012 Mar 20. PubMed PMID: 22759327. 11: Nakano M, Ajioka H, Abe M, Kiniwa M. Possible involvement of host defense mechanism in the suppression of rat acute reflux esophagitis by the particular histamine H2 receptor antagonist lafutidine. Pharmacology. 2012;90(3-4):205-11. doi: 10.1159/000342386. Epub 2012 Sep 13. PubMed PMID: 23038658. 12: Nakano M, Kitano S, Nanri M, Kiniwa M. Lafutidine, a unique histamine H2-receptor antagonist, inhibits distention-induced gastric acid secretion through an H2 receptor-independent mechanism. Eur J Pharmacol. 2011 May 11;658(2-3):236-41. doi: 10.1016/j.ejphar.2011.02.007. Epub 2011 Feb 22. PubMed PMID: 21349265. 13: Hatakeyama M, Fukunaga A, Washio K, Ogura K, Yamada Y, Horikawa T, Nishigori C. Addition of lafutidine can improve disease activity and lead to better quality of life in refractory cholinergic urticaria unresponsive to histamine H1 antagonists. J Dermatol Sci. 2016 May;82(2):137-9. doi: 10.1016/j.jdermsci.2016.02.001. Epub 2016 Feb 8. PubMed PMID: 26896422. 14: Iida H, Inamori M, Uchiyama T, Endo H, Hosono K, Akiyama T, Sakamoto Y, Fujita K, Takahashi H, Yoneda M, Koide T, Tokoro C, Goto A, Abe Y, Kobayashi N, Kirikoshi H, Kubota K, Saito S, Nakajima A. Early effects of oral administration of lafutidine with peppermint oil, compared with lafutidine alone, on intragastric pH values. Hepatogastroenterology. 2011 Jan-Feb;58(105):235-8. PubMed PMID: 21510321. 15: Kato M, Kamada G, Yamamoto K, Nishida U, Imai A, Yoshida T, Ono S, Nakagawa M, Nakagawa S, Shimizu Y, Asaka M. Lafutidine prevents low-dose aspirin and loxoprofen induced gastric injury: a randomized, double-blinded, placebo controlled study. J Gastroenterol Hepatol. 2010 Oct;25(10):1631-5. doi: 10.1111/j.1440-1746.2010.06375.x. PubMed PMID: 20880171. 16: Yang H, Huang Y, He J, Li S, Tang B, Li H. Interaction of lafutidine in binding to human serum albumin in gastric ulcer therapy: STD-NMR, WaterLOGSY-NMR, NMR relaxation times, Tr-NOESY, molecule docking, and spectroscopic studies. Arch Biochem Biophys. 2016 Sep 15;606:81-9. doi: 10.1016/j.abb.2016.07.016. Epub 2016 Jul 22. PubMed PMID: 27457418. 17: Amagase K, Ochi A, Sugihara T, Kato S, Takeuchi K. Protective effect of lafutidine, a histamine H2 receptor antagonist, against loxoprofen-induced small intestinal lesions in rats. J Gastroenterol Hepatol. 2010 May;25 Suppl 1:S111-8. doi: 10.1111/j.1440-1746.2010.06223.x. PubMed PMID: 20586851. 18: Ohara S, Haruma K, Kinoshita Y, Kusano M. A double-blind, controlled study comparing lafutidine with placebo and famotidine in Japanese patients with mild reflux esophagitis. J Gastroenterol. 2010 Dec;45(12):1219-27. doi: 10.1007/s00535-010-0283-8. Epub 2010 Jul 15. PubMed PMID: 20632193. 19: Ren Q, Ma B, Yang K, Yan X. Lafutidine-based triple therapy for Helicobacter pylori eradication. Hepatogastroenterology. 2010 Sep-Oct;57(102-103):1074-81. PubMed PMID: 21410034. 20: Dewan B, Philipose N. Lafutidine 10 mg versus Rabeprazole 20 mg in the Treatment of Patients with Heartburn-Dominant Uninvestigated Dyspepsia: A Randomized, Multicentric Trial. Gastroenterol Res Pract. 2011;2011:640685. doi: 10.1155/2011/640685. Epub 2011 May 5. PubMed PMID: 21687618; PubMed Central PMCID: PMC3113257.