Warfarin sodium (trade names Coumadin among others) is an anticoagulant normally used in the prevention of thrombosis and thromboembolism, the formation of blood clots in the blood vessels and their migration elsewhere in the body, respectively. It is commonly used to treat blood clots such as deep vein thrombosis and pulmonary embolism and to prevent stroke in people who have atrial fibrillation, valvular heart disease or artificial heart valves. Less commonly it is used following ST-segment elevation myocardial infarction and orthopedic surgery. It is generally taken by mouth but may also be used by injection into a vein. Warfarin was initially introduced in 1948 as a pesticide against rats and mice, and is still used for this purpose, although more potent poisons such as brodifacoum have since been developed. In the early 1950s, warfarin was found to be effective and relatively safe for preventing thrombosis and thromboembolism in many disorders. It was approved for use as a medication in 1954, and has remained popular ever since. Warfarin is the most widely prescribed oral anticoagulant drug in North America.

Physicochemical Properties

Molecular Formula	C19H15NAO4
Molecular Weight	330.31477
Exact Mass	330.086
CAS #	129-06-6
Related CAS #	129-06-6 (sodium);81-81-2 (free acid);2610-86-8 (potassium);
PubChem CID	16204922
Appearance	Solid Powder
Density	1.307g/cm3
Boiling Point	515.2ºC at 760mmHg
Flash Point	188.8ºC
LogP	4.047
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	4
Heavy Atom Count	24
Complexity	508
Defined Atom Stereocenter Count	0
SMILES	CC(=O)CC(C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=O)[O-].[Na+]
InChi Key	KYITYFHKDODNCQ-UHFFFAOYSA-M
InChi Code	InChI=1S/C19H16O4.Na/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/q+1/p-1
Chemical Name	sodium;2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate
Synonyms	Coumadin, Aldocumar, Tedicumar, Warfant, Marevan
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

Toxicity/Toxicokinetics	Effects During Pregnancy and Lactation ◉ Summary of Use during Lactation Because of the very low milk levels with warfarin doses up to at least 12 mg daily, amounts ingested by the infant are small. No adverse reactions in breastfed infants have been reported from maternal warfarin use during lactation, even with a dose of 25 mg daily for 7 days. There is a consensus that maternal warfarin therapy during breastfeeding poses little risk to the breastfed infant. No special precautions are necessary. Women’s postpartum warfarin dosage requirements may be increased by as much as two-fold compared to prepregnancy requirements. Whether breastfeeding contributes to the increased requirement is unclear. ◉ Effects in Breastfed Infants No decreases in vitamin K-dependent clotting factors or bleeding occurred in 2 infants who were breastfed for 56 and 131 days, respectively, during maternal anticoagulation with warfarin. In one telephone follow-up study, mothers taking warfarin reported no adverse effects among 5 breastfed infants. A mother had been taking warfarin 5 mg daily for the first 7 weeks postpartum for a pulmonary embolism. At this time, she began taking 25 mg daily by mistake and took this dose for 7 days. Upon presentation to the emergency room, her INR was greater than 10 (usual therapeutic maximum 3.5), her prothrombin time was greater than 100 seconds (normal up to 11.2 seconds), and her aPTT was 62.5 seconds (normal up to 32.7 seconds). She had been nearly exclusively breastfeeding her infant since birth. Her 8-week-old infant was healthy with an INR of 1.0, prothrombin time of 10.3 seconds, and a slightly elevated aPTT 33.8 seconds. However, 3 weeks previously, the infant's aPTT was 38.9 seconds, so the elevated aPTT was judged not to be caused by warfarin. ◉ Effects on Lactation and Breastmilk Relevant published information was not found as of the revision date.
References	http://en.wikipedia.org/wiki/Warfarin
Additional Infomation	Warfarin sodium is a slightly bitter crystalline powder. An anticoagulant used as a rodenticide. (EPA, 1998) Warfarin Sodium is the sodium salt form of warfarin, a coumarin and a vitamin K antagonist, with anticoagulant activity. Warfarin sodium inhibits both vitamin K and vitamin K epoxide reductases, thereby interfering with the cyclic interconversion of vitamin K epoxide to its reduced form, vitamin KH2. Vitamin KH2 is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins. As a result, maturation of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Without these coagulation factors, thrombogenesis and blood clot formation are prevented. An anticoagulant that acts by inhibiting the synthesis of vitamin K-dependent coagulation factors. Warfarin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, pulmonary embolism, and atrial fibrillation with embolization. It is also used as an adjunct in the prophylaxis of systemic embolism after myocardial infarction. Warfarin is also used as a rodenticide. See also: Warfarin (has active moiety).

Solubility Data

Solubility (In Vitro)

May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples

Solubility (In Vivo)

Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples. Injection Formulations (e.g. IP/IV/IM/SC) Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] *Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Injection Formulation 5: 2-Hydroxypropyl-β-cyclodextrin : Saline = 50 : 50 (i.e. 500 μL 2-Hydroxypropyl-β-cyclodextrin → 500 μL Saline) Injection Formulation 6: DMSO : PEG300 : castor oil : Saline = 5 : 10 : 20 : 65 (i.e. 50 μL DMSO → 100 μLPEG300 → 200 μL castor oil → 650 μL Saline) Injection Formulation 7: Ethanol : Cremophor : Saline = 10： 10 : 80 (i.e. 100 μL Ethanol → 100 μL Cremophor → 800 μL Saline) Injection Formulation 8: Dissolve in Cremophor/Ethanol (50 : 50), then diluted by Saline Injection Formulation 9: EtOH : Corn oil = 10 : 90 (i.e. 100 μL EtOH → 900 μL Corn oil) Injection Formulation 10: EtOH : PEG300：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL EtOH → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Oral Formulations Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). Oral Formulation 3: Dissolved in PEG400 Oral Formulation 4: Suspend in 0.2% Carboxymethyl cellulose Oral Formulation 5: Dissolve in 0.25% Tween 80 and 0.5% Carboxymethyl cellulose Oral Formulation 6: Mixing with food powders Note: Please be aware that the above formulations are for reference only. InvivoChem strongly recommends customers to read literature methods/protocols carefully before determining which formulation you should use for in vivo studies, as different compounds have different solubility properties and have to be formulated differently.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.0275 mL	15.1373 mL	30.2746 mL
	5 mM	0.6055 mL	3.0275 mL	6.0549 mL
	10 mM	0.3027 mL	1.5137 mL	3.0275 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.