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Lafutidine
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Name

Lafutidine

 EINECS 601-513-8
CAS No. 118288-08-7 Density 1.252 g/cm3
PSA 103.88000 LogP 3.85510
Solubility Insoluble in water Melting Point 92.7-94.9°
Formula C22H29N3O4S Boiling Point 704.2 °C at 760 mmHg
Molecular Weight 431.556 Flash Point 379.7 °C
Transport Information N/A Appearance Yellowish white crystalline powder
Safety 24/25 Risk Codes R36/37/38
Molecular Structure Molecular Structure of 118288-08-7 (Lafutidine) Hazard Symbols Xi
Synonyms

Acetamide,2-[(2-furanylmethyl)sulfinyl]-N-[(2Z)-4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-butenyl]-,(+)- (9CI);Acetamide,2-[(2-furanylmethyl)sulfinyl]-N-[4-[[4-(1-piperidinylmethyl)-2-pyridinyl]oxy]-2-butenyl]-,(Z)-(+)-;(+)-2-(Furfurylsulfinyl)-N-[(Z)-4-[[4-(piperidinomethyl)-2-pyridyl]oxy]-2-butenyl]acetamide;(+)-Lafutidine;FRG 8813;Protecadin;Stogar;

Article Data 5

Lafutidine Synthetic route

(2Z)-4-({4-[(piperidin-1-yl)methyl]pyridin-2-yl}oxy)but-2-en-1-amine

p-nitrophenyl 2-(furfurylsulfinyl)acetate

118288-08-7

lafutidine

Conditions
ConditionsYield
In dichloromethane at 25 - 30℃;94.6%
In tetrahydrofuran at 5 - 20℃; for 19h; Large scale;91.3%
In Isopropyl acetate at 35 - 40℃; for 5h; Solvent;87%
In ethyl acetate at 20℃;60%
110-89-4

piperidine

118287-95-9

N-[(Z)-4-(4-Formyl-pyridin-2-yloxy)-but-2-enyl]-2-(furan-2-ylmethanesulfinyl)-acetamide

118288-08-7

lafutidine

Conditions
ConditionsYield
With sodium tetrahydroborate 1.) EtOH, 3 h, 2.) EtOH, 16 h; Yield given. Multistep reaction;

2-Bromo-4-[1,3]dioxolan-2-yl-pyridine

118288-08-7

lafutidine

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: 87 percent / NaOH, K2CO3, n-Bu4NHSO4 / toluene / 18 h / Ambient temperature
2: 90 percent / pyridinium p-toluenesulfonate, ethanol / 18 h / 55 °C
3: SOCl2, Et3N / CH2Cl2 / 1 h / 0 °C
4: n-Bu4NHSO4 / acetonitrile / 18 h / Heating
5: 78 percent / NH2NH2*H2O / methanol / 10 h / Heating
6: 91 percent / tetrahydrofuran / 18 h / Ambient temperature
7: 52 percent / p-TsOH, H2O / acetone / 18 h / Heating
8: 2.) NaBH4 / 1.) EtOH, 3 h, 2.) EtOH, 16 h
View Scheme
118289-22-8

(Z)-4-(4-[1,3]Dioxolan-2-yl-pyridin-2-yloxy)-but-2-enylamine

118288-08-7

lafutidine

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 91 percent / tetrahydrofuran / 18 h / Ambient temperature
2: 52 percent / p-TsOH, H2O / acetone / 18 h / Heating
3: 2.) NaBH4 / 1.) EtOH, 3 h, 2.) EtOH, 16 h
View Scheme
118289-20-6

4-[4-(1,3-dioxolan-2-yl)-2-pyridyloxy]-(Z)-2-buten-1-ol

118288-08-7

lafutidine

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: SOCl2, Et3N / CH2Cl2 / 1 h / 0 °C
2: n-Bu4NHSO4 / acetonitrile / 18 h / Heating
3: 78 percent / NH2NH2*H2O / methanol / 10 h / Heating
4: 91 percent / tetrahydrofuran / 18 h / Ambient temperature
5: 52 percent / p-TsOH, H2O / acetone / 18 h / Heating
6: 2.) NaBH4 / 1.) EtOH, 3 h, 2.) EtOH, 16 h
View Scheme

2-((Z)-4-Chloro-but-2-enyloxy)-4-[1,3]dioxolan-2-yl-pyridine

118288-08-7

lafutidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: n-Bu4NHSO4 / acetonitrile / 18 h / Heating
2: 78 percent / NH2NH2*H2O / methanol / 10 h / Heating
3: 91 percent / tetrahydrofuran / 18 h / Ambient temperature
4: 52 percent / p-TsOH, H2O / acetone / 18 h / Heating
5: 2.) NaBH4 / 1.) EtOH, 3 h, 2.) EtOH, 16 h
View Scheme
118289-19-3

2-[4-(2-tetrahydropyranyloxy)-(Z)-2-buten-1-yloxy]-4-(1,3-dioxolan-2-yl)-pyridine

118288-08-7

lafutidine

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 90 percent / pyridinium p-toluenesulfonate, ethanol / 18 h / 55 °C
2: SOCl2, Et3N / CH2Cl2 / 1 h / 0 °C
3: n-Bu4NHSO4 / acetonitrile / 18 h / Heating
4: 78 percent / NH2NH2*H2O / methanol / 10 h / Heating
5: 91 percent / tetrahydrofuran / 18 h / Ambient temperature
6: 52 percent / p-TsOH, H2O / acetone / 18 h / Heating
7: 2.) NaBH4 / 1.) EtOH, 3 h, 2.) EtOH, 16 h
View Scheme
118289-21-7

2-[(Z)-4-(4-[1,3]Dioxolan-2-yl-pyridin-2-yloxy)-but-2-enyl]-isoindole-1,3-dione

118288-08-7

lafutidine

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 78 percent / NH2NH2*H2O / methanol / 10 h / Heating
2: 91 percent / tetrahydrofuran / 18 h / Ambient temperature
3: 52 percent / p-TsOH, H2O / acetone / 18 h / Heating
4: 2.) NaBH4 / 1.) EtOH, 3 h, 2.) EtOH, 16 h
View Scheme
118289-23-9

N-[(Z)-4-(4-[1,3]Dioxolan-2-yl-pyridin-2-yloxy)-but-2-enyl]-2-(furan-2-ylmethanesulfinyl)-acetamide

118288-08-7

lafutidine

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 52 percent / p-TsOH, H2O / acetone / 18 h / Heating
2: 2.) NaBH4 / 1.) EtOH, 3 h, 2.) EtOH, 16 h
View Scheme
146270-02-2

(Z)-4-(Piperidin-1-ylmethyl)-2-((4-((tetrahydro-2H-pyran2-yl)oxy)but-2-en-1-yl)oxy)pyridine

118288-08-7

lafutidine

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: hydrogenchloride / ethyl acetate; water / 2 h / 25 °C / Large scale
2: potassium carbonate; thionyl chloride / dichloromethane / 2 h / 0 - 25 °C / Large scale
3: tetra(n-butyl)ammonium hydrogensulfate / acetonitrile / 18 h / Reflux; Large scale
4: hydrazine hydrate; 1-hexene / methanol / 4 h / Reflux; Large scale
5: tetrahydrofuran / 19 h / 5 - 20 °C / Large scale
View Scheme

Lafutidine Chemical Properties

Molecular structure of Lafutidine (CAS NO.118288-08-7) is:

Product Name: Lafutidine
CAS Registry Number: 118288-08-7
IUPAC Name: 2-(furan-2-ylmethylsulfinyl)-N-[(Z)-4-[4-(piperidin-1-ylmethyl)pyridin-2-yl]oxybut-2-enyl]acetamide
Molecular Weight: 431.54836 [g/mol]
Molecular Formula: C22H29N3O4S
XLogP3-AA: 1.4
H-Bond Donor: 1
H-Bond Acceptor: 6 
Surface Tension: 59.8 dyne/cm
Density: 1.252 g/cm3
Flash Point: 379.7 °C
Enthalpy of Vaporization: 103.04 kJ/mol
Boiling Point: 704.2 °C at 760 mmHg
Vapour Pressure: 1.12E-19 mmHg at 25°C 
Other Registry Number: 143375-16-0
Product Categories: Active Pharmaceutical Ingredients;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds

Lafutidine Uses

 Lafutidine (CAS NO.118288-08-7) is a second generation histamine H2-receptor antagonist.

Lafutidine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LD oral > 400mg/kg (400mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

GASTROINTESTINAL: NAUSEA OR VOMITING		 Oyo Yakuri. Pharmacometrics. Vol. 50, Pg. 417, 1995.
mouse LD50 intravenous 47900ug/kg (47.9mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Oyo Yakuri. Pharmacometrics. Vol. 50, Pg. 143, 1995.
mouse LD50 oral 1034mg/kg (1034mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Oyo Yakuri. Pharmacometrics. Vol. 50, Pg. 143, 1995.
rat LD50 intravenous 84mg/kg (84mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION		 Oyo Yakuri. Pharmacometrics. Vol. 50, Pg. 143, 1995.
rat LD50 oral 1248mg/kg (1248mg/kg) 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		 Oyo Yakuri. Pharmacometrics. Vol. 50, Pg. 143, 1995.

Lafutidine Specification

 Lafutidine , its cas register number is 118288-08-7. It also can be called Lafutidine [INN] ; (+-)-2-(Furfurylsulfinyl)-N-((Z)-4-((4-(piperidinomethyl)-2-pyridyl)oxy)-2-butenyl) acetamide ; (+-)-2-(Furfurylsulfinyl)-N-(4-(4-(piperidinomethyl)-2-pyridyl)oxy-(Z)-2-butenyl)acetamide ; N-(4-(4-Piperidinylmethyl)pyridyl-2-oxy)butenyl-2-(furfurylsulfinyl)acetamide ; Acetamide, 2-((2-furanylmethyl)sulfinyl)-N-(4-((4-(1-piperidinylmethyl)-2-pyridinyl)oxy)-2-butenyl)-, (Z)- .

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