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| CAS No.: | 118288-08-7 |
|---|---|
| Name: | Lafutidine |
| Molecular Structure: | |
|
|
|
| Formula: | C22H29N3O4S |
| Molecular Weight: | 431.556 |
| 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; |
| EINECS: | 601-513-8 |
| Density: | 1.252 g/cm3 |
| Melting Point: | 92.7-94.9° |
| Boiling Point: | 704.2 °C at 760 mmHg |
| Flash Point: | 379.7 °C |
| Solubility: | Insoluble in water |
| Appearance: | Yellowish white crystalline powder |
| Hazard Symbols: |
 Xi
|
| Risk Codes: | R36/37/38 |
| Safety: | 24/25 |
| PSA: | 103.88000 |
| LogP: | 3.85510 |
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- 118288-08-7
lafutidine
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| With sodium tetrahydroborate 1.) EtOH, 3 h, 2.) EtOH, 16 h; Yield given. Multistep reaction; |
- 118288-08-7
lafutidine
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 |
- 118288-08-7
lafutidine
| Conditions | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 | Yield |
|---|---|
| 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 |
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Chemistry
Molecular structure of Lafutidine (CAS NO.118288-08-7) is:
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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
Uses
Lafutidine (CAS NO.118288-08-7) is a second generation histamine H2-receptor antagonist.
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. |
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)- .