118288-08-7 Usage
Description
Lafutidine is a second-generation histamine H2 receptor antagonist with potent and longer-acting properties compared to other marketed compounds of its class, such as cimetidine and famotidine. It strongly inhibits gastric acid secretion and has gastroprotective activity independent of its acid antisecretory efficacy. Lafutidine is effective in inhibiting gastric acid secretion during both daytime and nighttime, and it also protects against experimentally induced reflux esophagitis, indomethacin-induced intestinal, and dextran sulfate sodium-induced colonic inflammation.
Uses
Used in Pharmaceutical Industry:
Lafutidine is used as an antiulcerative agent for its ability to inhibit gastric acid secretion and provide gastroprotective activity, making it effective in the treatment of gastritis, reflux esophagitis, and peptic ulcers.
Used in Primary Care Practice:
Lafutidine is used as an empiric treatment for patients with dyspepsia, offering superior efficacy in managing their symptoms.
Used in Research:
Lafutidine is used as a model compound to investigate the binding mechanism between antiulcer drugs and human serum albumin (HSA), contributing to the understanding of drug interactions and development of new therapeutic strategies.
Used in Treatment of NSAID-induced Ulcer:
Lafutidine is used as a treatment for nonsteroidal anti-inflammatory drug-induced ulcer in patients who are refractory to existing antiulcer agents, due to its potent H2 antagonist action and gastroprotective properties.
Brand Names:
Lafutidine is available under the brand names Stogar and Protecadin.
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
Originator
Fujirebio (Japan)
Check Digit Verification of cas no
The CAS Registry Mumber 118288-08-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 1,1,8,2,8 and 8 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 118288-08:
(8*1)+(7*1)+(6*8)+(5*2)+(4*8)+(3*8)+(2*0)+(1*8)=137
137 % 10 = 7
So 118288-08-7 is a valid CAS Registry Number.
InChI:InChI=1/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-
118288-08-7Relevant articles and documents
Increasing the Purity of Lafutidine Using a suicide Substrate
Wu, Chengjun,Li, Zhen,Wang, Chunchao,Zhou, Yanan,Sun, Tiemin
, p. 1081 - 1085 (2018)
When preparing lafutidine, we found that the main impurity was dihydrolafutidine. On the basis of the chemical structure of dihydrolafutidine and the mechanism of its production, we decided to use a suicide substrate in the drug preparation to increase the purity of lafutidine. By calculating the energy barrier of the reduction reaction with a quantum-chemical method and evaluating the appropriate physicochemical properties of the terminal olefins, we chose 1-hexene as the suicide substrate to effectively control the formation of dihydrolafutidine in the synthesis of lafutidine. The experimental results showed that the content of the impurity, dihydrolafutidine, decreased from 1.5% to less than 0.05%, proving that using a suicide substrate is an effective method to reduce the formation of the relevant byproduct in drug production. In addition, this method is operationally simple and is suitable for industrial applications.
Method for manufacturing lafutidine crystal with high purity
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Paragraph 0084; 0094-0104; 0118-0126, (2020/09/30)
The present invention relates to a method for manufacturing a lafutidine crystal form with high purity. The method for manufacturing a novel lafutidine crystal form of the present invention produces a desired crystal form according to temperature control after dissolution, thereby being able to be easily applied to production (scale-up) and stably manufacture the lafutidine crystal form with high purity.
Lafutidine hydroxylamine hydrochloride method of preparation
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Paragraph 0043-0044, (2016/10/08)
The invention relates to a novel chemical synthetic method for lafutidine, and in particular relates to a method for preparing the lafutidine from hydroxylamine hydrochloride serving as aminolysis reagent. The method comprises the following steps of: (1) reacting a compound in a formula 4 with the hydroxylamine hydrochloride and sodium hydroxide so as to obtain a compound in a formula 2; (2) carrying out condensation on the compound in the formula 2 and a compound in a formula 3 so as to obtain the lafutidine in a formula 1. The whole preparation process is as shown in the specification. When in preparation of the key intermediate the compound in the formula 2, the hydroxylamine hydrochloride is chosen for substituting other reagents for aminolysis reaction, and the prepared lafutidine product has higher purity and can reach 99.88%; compared with the condition that the aminolysis reagent is removed from the intermediate, the hydroxylamine is easier to remove; and furthermore, the hydroxylamine hydrochloride is a solid reagent, has high purity and high stability, and industrial production is more easily realized.