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Warfarin

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Name

Warfarin

EINECS 201-377-6
CAS No. 81-81-2 Density 1.308 g/cm3
Solubility Practically insoluble Melting Point 162-164 °C(lit.)
Formula C19H16O4 Boiling Point 515.155 °C at 760 mmHg
Molecular Weight 308.33 Flash Point 188.828 °C
Transport Information UN 2811 6.1/PG 1 Appearance crystalline solid
Safety 53-45-61-52 Risk Codes 61-48/25-52/53
Molecular Structure Molecular Structure of 81-81-2 (2H-1-Benzopyran-2-one,4-hydroxy-3-(3-oxo-1-phenylbutyl)-) Hazard Symbols ToxicT
Synonyms

Coumarin,3-(a-acetonylbenzyl)-4-hydroxy- (7CI,8CI);(RS)-Warfarin;1-(4'-Hydroxy-3'-coumarinyl)-1-phenyl-3-butanone;3-(1'-Phenyl-2'-acetylethyl)-4-hydroxycoumarin;3-(a-Acetonylbenzyl)-4-hydroxycoumarin;3-(a-Phenyl-b-acetylethyl)-4-hydroxycoumarin;4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one;Athrombine-K;Brumolin;Co-Rax;Compound 42;Coumafen;Coumaphen;Coumefene;DL-3-(a-Acetonylbenzyl)-4-hydroxycoumarin;Kumader;Kumadu;Ratron;Rodafarin;Rodafarin C;Rodex;Vampirinip II;Vampirinip III;W.A.R.F. 42;WARF compound 42;Warfarin;Zoocoumarin;rac-Warfarin;

 

Warfarin History

1. The early 1920s saw the outbreak of a previously unrecognized disease of cattle in the northern United States and Canada. Cattle would die of uncontrollable bleeding from very minor injuries, or sometimes drop dead of internal hemorrhage with no external signs of injury. In 1921, Frank Schofield, a Canadian veterinarian, determined that the cattle were ingesting moldy silage made from sweet clover that functioned as a potent anticoagulant.In 1929, North Dakota veterinarian Dr L.M. Roderick demonstrated that the condition was due to a lack of functioning prothrombin.
2. After an incident in 1951, where a US Army inductee unsuccessfully attempted suicide with warfarin and recovered fully,studies began in the use of warfarin as a therapeutic anticoagulant
3. A 2003 theory posits that warfarin was used by a conspiracy of Lavrenty Beria, Nikita Khrushchev and others to poison Soviet leader Joseph Stalin.
 

Warfarin Specification

The CAS registry number of Warfarin is 81-81-2. The IUPAC name is 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one. Its EINECS registry number is 201-377-6. In addition, the molecular formula is C19H16O4 and the molecular weight is 308.33. It is a kind of white to off-white crystalline powder and belongs to the classes of Coumarins; Insecticide; Intermediates & Fine Chemicals; Pharmaceuticals; Miscellaneous Compounds. And it is a synthetic derivative of dicoumarol, a 4-hydroxycoumarin-derived mycotoxin anticoagulant originally discovered in spoiled sweet clover-based animal feeds.

Physical properties about this chemical are: (1)ACD/LogP: 3.13 ; (2)ACD/LogD (pH 5.5): 2; (3)ACD/LogD (pH 7.4): 1; (4)ACD/BCF (pH 5.5): 21; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 157; (7)ACD/KOC (pH 7.4): 3; (8)#H bond acceptors: 4; (9)#H bond donors: 1; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 63.6 Å2; (12)Index of Refraction: 1.635; (13)Molar Refractivity: 84.447 cm3; (14)Molar Volume: 235.758 cm3; (15)Polarizability: 33.477 ×10-24cm3; (16)Surface Tension: 58.658 dyne/cm; (17)Density: 1.308 g/cm3; (18)Flash Point: 188.828 °C; (19)Enthalpy of Vaporization: 82.854 kJ/mol; (20)Boiling Point: 515.155 °C at 760 mmHg.

Preparation of Warfarin: it can be prepared by 4-hydroxy-chromen-2-one and 4-phenyl-but-3-en-2-one. This reaction will need catalyst triethylbenzylammonium chloride and solvent H2O. The reaction time is 2 hours by heating. The yield is about 82%.

Warfarin can be prepared by 4-hydroxy-chromen-2-one and 4-phenyl-but-3-en-2-one

Uses of Warfarin: is used to decrease the tendency for thrombosis or as secondary prophylaxis (prevention of further episodes) in those individuals that have already formed a blood clot (thrombus). And is also used in antiphospholipid syndrome. It has been used occasionally after heart attacks (myocardial infarctions), but is far less effective at preventing new thromboses in coronary arteries. In addition, it can be used to get 3-fluoro-3-(3-oxo-1-phenyl-butyl)-chroman-2,4-dione. This reaction will need reagent (CF3SO2)2NF and solvent CHCl3 and H2O. The reaction time is 15 minutes at reaction temperature of 35 °C. The yield is about 92%.

Warfarin can be used to get 3-fluoro-3-(3-oxo-1-phenyl-butyl)-chroman-2,4-dione

When you are using this chemical, please be cautious about it as the following:
It is toxic if swallowed and may cause harm to the unborn child. And it has danger of serious damage to health by prolonged exposure. In addition, it is harmful to aquatic organisms, may cause long-term adverse effects in the aquatic environment. It is refer to special instructions/safety data sheets. Avoid exposure - obtain special instructions before use. During using it, not recommended for interior use on large surface areas. In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.). You should avoid release to the environment.

You can still convert the following datas into molecular structure:
(1)SMILES: CC(=O)CC(C\1=C(/O)c2ccccc2OC/1=O)c3ccccc3
(2)InChI: InChI=1/C19H16O4/c1-12(20)11-15(13-7-3-2-4-8-13)17-18(21)14-9-5-6-10-16(14)23-19(17)22/h2-10,15,21H,11H2,1H3
(3)InChIKey: PJVWKTKQMONHTI-UHFFFAOYAW

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LD50 oral 6mg/kg (6mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 27, 1978.
chicken LD50 oral 942mg/kg (942mg/kg) PERIPHERAL NERVE AND SENSATION: SPASTIC PARALYSIS WITH OR WITHOUT SENSORY CHANGE

LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BLOOD: HEMORRHAGE
Bulletin of Environmental Contamination and Toxicology. Vol. 37, Pg. 544, 1986.
dog LD50 oral 3mg/kg (3mg/kg)   Defense des Vegetaux. Vol. 43(255-256), Pg. 20, 1989.
guinea pig LD50 oral 180mg/kg (180mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 27, 1978.
human LDLo oral 6667ug/kg (6.667mg/kg)   Yakkyoku. Pharmacy. Vol. 28, Pg. 329, 1977.
man TDLo oral 10200ug/kg (10.2mg/kg) BLOOD: HEMORRHAGE "Clinical Memoranda on Economic Poisons," U.S. Dept. HEW, Public Health Service, Communicable Disease Center, Atlanta, GA, 1956Vol. -, Pg. 1, 1956.
mouse LD50 intraperitoneal 750mg/kg (750mg/kg)   European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 30, Pg. 531, 1995.
mouse LD50 intravenous 165mg/kg (165mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 274, 1973.
mouse LD50 oral 3mg/kg (3mg/kg)   Defense des Vegetaux. Vol. 43(255-256), Pg. 20, 1989.
mouse LD50 unreported 60mg/kg (60mg/kg)   Yakkyoku. Pharmacy. Vol. 30, Pg. 397, 1979.
mouse LDLo subcutaneous 800mg/kg (800mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: FOOD INTAKE (ANIMAL)
Trudy, VNIIVS. Transactions of the All-Union Scientific Research Institute of Veterinary Sanitation. Vol. 58, Pg. 122, 1977.
pig LD50 oral 1mg/kg (1mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 27, 1978.
rabbit LD50 oral 800mg/kg (800mg/kg)   Defense des Vegetaux. Vol. 32, Pg. 27, 1978.
rat LC50 inhalation 320mg/m3 (320mg/m3)   Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 22(7), Pg. 49, 1978.
rat LD50 oral 1600ug/kg (1.6mg/kg)   Toxicology and Applied Pharmacology. Vol. 11, Pg. 327, 1967.
rat LD50 skin 1400mg/kg (1400mg/kg) SENSE ORGANS AND SPECIAL SENSES: CHROMODACYRORREA: EYE

KIDNEY, URETER, AND BLADDER: HEMATURIA

BEHAVIORAL: MUSCLE WEAKNESS
Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. Vol. 22(7), Pg. 49, 1978.
rat LD50 unreported 50mg/kg (50mg/kg)   Yakkyoku. Pharmacy. Vol. 30, Pg. 397, 1979.
rat LDLo intraperitoneal 420mg/kg (420mg/kg)   Toxicology and Applied Pharmacology. Vol. 1, Pg. 156, 1959.
women TDLo oral 250ug/kg/2D-I (0.25mg/kg) VASCULAR: STRICTIRA; CJAMGES OM VESSE;S American Journal of Emergency Medicine. Vol. 16, Pg. 541, 1998.
women TDLo oral 15mg/kg/21W-I (15mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM SMALL INTESTINE

BLOOD: CHANGE IN CLOTTING FACTORS
Southern Medical Journal. Vol. 75, Pg. 242, 1982.

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