CAS 118288-08-7|Lafutidine

Introduction：Basic information about CAS 118288-08-7|Lafutidine, including its chemical name, molecular formula, synonyms, physicochemical properties, and safety information, etc.

Table of Contents

1. Names
2. Lafutidine BiologicalActivity
3. Chemical & Physical Properties
4. Toxicological Information
CHEMICAL IDENTIFICATION
HEALTH HAZARD DATA
ACUTE TOXICITY DATA
5. Safety Information
6. Customs
7. Synonyms

Common Name	Lafutidine
CAS Number	118288-08-7	Molecular Weight	431.548
Density	1.3±0.1 g/cm3	Boiling Point	704.2±60.0 °C at 760 mmHg
Molecular Formula	C₂₂H₂₉N₃O₄S	Melting Point	99 °C
MSDS	/	Flash Point	379.7±32.9 °C

Names

Name	Lafutidine
Synonym	More Synonyms

Lafutidine BiologicalActivity

Description	Lafutidine, a newly developed histamine H(2)-receptor antagonist, inhibits gastric acid secretion.Target: histamine H(2)-receptorLafutidine, a newly developed histamine H(2)-receptor antagonist, inhibits gastric acid secretion.It is currently marketed in Japan (Stogar) China (Lemeiting) and India (Lafaxid). It not only suppresses gastric acid secretion, but also has cytoprotective properties by the virtue of its property to induce the collagen synthesis in the gastric mucosa. It has a novel mechanism of action in addition to blocking the H2 receptors, it decreases inflammation by modulating calcitonin gene-related peptide (CGRP) and vanilloid receptors. It is also found to stimulate mucin biosynthesis and promote the restitution of damaged mucosa.Lafutidine is absorbed in the small intestine, reaches gastric cells via the systemic circulation, and then directly and rapidly binds to gastric cell histamine H2 receptors, thereby inhibiting the stimulation of cAMP and a resultant decrease in acid production (antisecretory action). It causes a sustained increase in intracellular Ca2+ ion concentration in endothelial cells resulting in the release of Calcitonin Gene Related Peptide (CGRP), which causes acid suppression by decreasing the vagal tone. Lafutidine also increases plasma somatostatin levels which decreases secretion of gastrin from G cells. This decrease in gastrin causes inhibition of parietal cells, resulting in decrease in gastric acid secretion.
Related Catalog	Signaling Pathways >>GPCR/G Protein >>Histamine ReceptorSignaling Pathways >>Immunology/Inflammation >>Histamine ReceptorResearch Areas >>Metabolic Disease
References	[1]. Tanaka M, et al. Pharmacological and therapeutic properties of lafutidine (stogar and protecadin), a novel histamine H2 receptor antagonist with gastroprotective activity. Nihon Yakurigaku Zasshi. 2001 Jun;117(6):377-86.

Chemical & Physical Properties

Density	1.3±0.1 g/cm3
Boiling Point	704.2±60.0 °C at 760 mmHg
Melting Point	99 °C
Molecular Formula	C₂₂H₂₉N₃O₄S
Molecular Weight	431.548
Flash Point	379.7±32.9 °C
Exact Mass	431.187866
PSA	103.88000
LogP	1.10
Vapour Pressure	0.0±2.2 mmHg at 25°C
Index of Refraction	1.599
InChIKey	KMZQAVXSMUKBPD-UHFFFAOYSA-N
SMILES	O=C(CS(=O)Cc1ccco1)NCC=CCOc1cc(CN2CCCCC2)ccn1

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: AC2957000

CHEMICAL NAME :: Acetamide, 2-((2-furanylmethyl)sulfinyl)-N-(4-((4-(1-piperidinyl methyl)-2-pyridinyl)o xy)- 2-butenyl)-, (Z)-

CAS REGISTRY NUMBER :: 118288-08-7

LAST UPDATED :: 199607

DATA ITEMS CITED :: 10

MOLECULAR FORMULA :: C22-H29-N3-O4-S

MOLECULAR WEIGHT :: 431.60

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 1248 mg/kg

TOXIC EFFECTS :: Behavioral - altered sleep time (including change in righting reflex) Behavioral - convulsions or effect on seizure threshold Gastrointestinal - changes in structure or function of salivary glands

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 50,143,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 84 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 50,143,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 1034 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity) Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 50,143,1995

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 47900 ug/kg

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - respiratory depression

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 50,143,1995

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: >400 mg/kg

TOXIC EFFECTS :: Behavioral - tremor Behavioral - convulsions or effect on seizure threshold Gastrointestinal - nausea or vomiting

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 50,417,1995 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 36400 mg/kg/52W-I

TOXIC EFFECTS :: Liver - changes in liver weight Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - other transferases

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 50,167,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 9100 mg/kg/13W-I

TOXIC EFFECTS :: Kidney, Ureter, Bladder - proteinuria Kidney, Ureter, Bladder - changes in bladder weight

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 50,149,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 14 gm/kg/2W-I

TOXIC EFFECTS :: Liver - changes in liver weight Kidney, Ureter, Bladder - changes in bladder weight

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 50,149,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 9100 mg/kg/13W-I

TOXIC EFFECTS :: Behavioral - convulsions or effect on seizure threshold Blood - other changes Related to Chronic Data - death

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 50,421,1995

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Mammal - dog

DOSE/DURATION :: 10920 mg/kg/52W-I

TOXIC EFFECTS :: Gastrointestinal - hypermotility, diarrhea Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - transaminases

REFERENCE :: OYYAA2 Oyo Yakuri. Pharmacometrics. (Oyo Yakuri Kenkyukai, CPO Box 180, Sendai 980-91, Japan) V.1- 1967- Volume(issue)/page/year: 50,439,1995

Safety Information

Hazard Codes	Xi
Risk Phrases	R36/37/38:Irritating to eyes, respiratory system and skin .
Safety Phrases	S26-S36/37/39
HS Code	2929909090

Customs

HS Code	2934999090
Summary	2934999090. other heterocyclic compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Synonyms

(Z)-2-((2-Furanylmethyl)sulfinyl)-N-(4-((4-(1-piperidinylmethyl)-2-pyridinyl)oxy)-2-butenyl)acetamide

rac-2-(furfurylsulfinyl)-N-[(Z)-4-{[4-(piperidinomethyl)-2-pyridyl]oxy}but-2-enyl]acetamide

2-[(Furan-2-ylmethyl)sulfinyl]-N-[(2Z)-4-{[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxy}but-2-en-1-yl]acetamid

(+/-)-2-(furfurylsulfinyl)-N-[4-[4-(piperidinomethyl)-2-pyridyl]oxy-(Z)-2-butenyl]acetamide

(z)-inyl)oxy)-2-butenyl)

Acetamide, 2-[(2-furanylmethyl)sulfinyl]-N-[(2Z)-4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-buten-1-yl]-

LAFUTIDINE(SUBJECTTOPATENTFREE)

Protecadin

Stogar

Laflutidine

2-[(2-Furylmethyl)sulfinyl]-N-[(2Z)-4-{[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxy}but-2-en-1-yl]acetamide

2-[(furan-2-ylmethyl)sulfinyl]-N-[(2Z)-4-{[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxy}but-2-en-1-yl]acetamide

lafutidine

2-[(2-Furylmethyl)sulfinyl]-N-[(2Z)-4-{[4-(1-piperidinylmethyl)-2-pyridinyl]oxy}-2-buten-1-yl]acetamide

enyl)acetamide

MFCD00867520

(±)-2-(Furfurylsulfinyl)-N-(4-(4-(piperidinomethyl)-2-pyridyl)oxy-(Z)-2-butenyl)acetamide

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