WARFARIN

First approved in 1954

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H16O4
Molecular Weight	308.3279
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)CC(C1=CC=CC=C1)C2=C(O)C3=C(OC2=O)C=CC=C3

InChI

InChIKey=PJVWKTKQMONHTI-UHFFFAOYSA-N

InChI=1S/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

HIDE SMILES / InChI

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/009218s108lbl.pdf | https://www.drugbank.ca/drugs/DB00682 | https://www.ncbi.nlm.nih.gov/pubmed/23618698

Warfarin is an anticoagulant drug normally used to prevent blood clot formation as well as migration. Warfarin is marketed under the brand name Coumadin among others. Coumadin (crystalline warfarin sodium) is an anticoagulant which acts by inhibiting vitamin K-dependent coagulation factors. Chemically, it is 3-(α-acetonylbenzyl)-4-hydroxycoumarin and is a racemic mixture of the R- and S-enantiomers. Coumadin is indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, and pulmonary embolism. It is also indicated for the prophylaxis and/or treatment of the thromboembolic complications associated with atrial fibrillation and/or cardiac valve replacement. Warfarin is thought to interfere with clotting factor synthesis by inhibition of the C1 subunit of the vitamin K epoxide reductase (VKORC1) enzyme complex, thereby reducing the regeneration of vitamin K1 epoxide. The degree of depression is dependent upon the dosage administered and, in part, by the patient’s VKORC1 genotype. Therapeutic doses of warfarin decrease the total amount of the active form of each vitamin K dependent clotting factor made by the liver by approximately 30% to 50%.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Vitamin k epoxide reductase complex subunit 1 isoform 1 22 Target ID: CHEMBL1930 Sources: https://www.ncbi.nlm.nih.gov/pubmed/6712738 \| https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/009218s108lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/23618698	Inhibitor 8297		24.7 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Venous thrombosis 9 Sources: https://www.drugs.com/dosage/warfarin.html	Primary	Approved 8429	COUMADIN Approved Use Warfarin sodium tablets are indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, and pulmonary embolism. Warfarin sodium tablets are indicated for the prophylaxis and/or treatment of the thromboembolic complications associated with atrial fibrillation and/or cardiac valve replacement. Warfarin sodium tablets are indicated to reduce the risk of death, recurrent myocardial infarction, and thromboembolic events such as stroke or systemic embolization after myocardial infarction. Launch Date 1954
Myocardial infarction 121 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/009218s108lbl.pdf https://www.drugs.com/pro/warfarin.html	Preventing	Approved 8429	COUMADIN Approved Use Warfarin sodium tablets are indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, and pulmonary embolism. Warfarin sodium tablets are indicated for the prophylaxis and/or treatment of the thromboembolic complications associated with atrial fibrillation and/or cardiac valve replacement. Warfarin sodium tablets are indicated to reduce the risk of death, recurrent myocardial infarction, and thromboembolic events such as stroke or systemic embolization after myocardial infarction. Launch Date 1954
Thromboembolic complications associated with atrial fibrillation 7 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/009218s108lbl.pdf	Preventing	Approved 8429	COUMADIN Approved Use Warfarin sodium tablets are indicated for the prophylaxis and/or treatment of venous thrombosis and its extension, and pulmonary embolism. Warfarin sodium tablets are indicated for the prophylaxis and/or treatment of the thromboembolic complications associated with atrial fibrillation and/or cardiac valve replacement. Warfarin sodium tablets are indicated to reduce the risk of death, recurrent myocardial infarction, and thromboembolic events such as stroke or systemic embolization after myocardial infarction. Launch Date 1954

C_max

Value	Dose	Co-administered	Analyte	Population
2186 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19552747	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		WARFARIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
52278 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19552747	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		WARFARIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
32.4 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/19552747	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		WARFARIN plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
7 day DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf	single, oral		WARFARIN unknown	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Co-administered	Analyte	Population
1% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf	single, oral		WARFARIN unknown	Homo sapiens population: UNHEALTHY age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
125 mg single, oral Overdose Dose: 125 mg Route: oral Route: single Dose: 125 mg Co-administed with:: oxycodone, p.o(200 mg, single) Sources: https://pubmed.ncbi.nlm.nih.gov/14639058 Page: p.718	unhealthy, 43 n = 1 Health Status: unhealthy Condition: Deep venous thromboses Age Group: 43 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14639058 Page: p.718	Disc. AE: Vomiting, Loss of consciousness... AEs leading to discontinuation/dose reduction: Vomiting Loss of consciousness Sources: https://pubmed.ncbi.nlm.nih.gov/14639058 Page: p.718
150 mg single, oral Overdose Dose: 150 mg Route: oral Route: single Dose: 150 mg Co-administed with:: chlorpromazine, p.o(3 g, single) Sources: https://pubmed.ncbi.nlm.nih.gov/14639058 Page: p.718	unhealthy, 44 n = 1 Health Status: unhealthy Condition: Aortic valve replacement Age Group: 44 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14639058 Page: p.718	Disc. AE: Drowsiness... AEs leading to discontinuation/dose reduction: Drowsiness Sources: https://pubmed.ncbi.nlm.nih.gov/14639058 Page: p.718
540 mg single, oral Overdose Dose: 540 mg Route: oral Route: single Dose: 540 mg Co-administed with:: clonazepam, p.o(4 mg, single) Sources: https://pubmed.ncbi.nlm.nih.gov/24674108 Page: p.1	healthy, 59 n = 1 Health Status: healthy Age Group: 59 Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/24674108 Page: p.1	Sources: https://pubmed.ncbi.nlm.nih.gov/24674108 Page: p.1
5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26658807 Page: p.1	unhealthy, 64 n = 1 Health Status: unhealthy Condition: Cardiomyopathy \|Atrial fibrillation Age Group: 64 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/26658807 Page: p.1	Disc. AE: Hemoptysis, Hematuria... AEs leading to discontinuation/dose reduction: Hemoptysis Hematuria Dyspnea Cough Sources: https://pubmed.ncbi.nlm.nih.gov/26658807 Page: p.1
10 mg 1 times / day multiple, oral (max) Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Venous thrombosis\|Atrial fibrillation\|Myocardial infarction Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf Page: p.1	Disc. AE: Bleeding... AEs leading to discontinuation/dose reduction: Bleeding (grade 5) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf Page: p.1

AEs

AE	Significance	Dose	Population
Loss of consciousness	Disc. AE	125 mg single, oral Overdose Dose: 125 mg Route: oral Route: single Dose: 125 mg Co-administed with:: oxycodone, p.o(200 mg, single) Sources: https://pubmed.ncbi.nlm.nih.gov/14639058 Page: p.718	unhealthy, 43 n = 1 Health Status: unhealthy Condition: Deep venous thromboses Age Group: 43 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14639058 Page: p.718
Vomiting	Disc. AE	125 mg single, oral Overdose Dose: 125 mg Route: oral Route: single Dose: 125 mg Co-administed with:: oxycodone, p.o(200 mg, single) Sources: https://pubmed.ncbi.nlm.nih.gov/14639058 Page: p.718	unhealthy, 43 n = 1 Health Status: unhealthy Condition: Deep venous thromboses Age Group: 43 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14639058 Page: p.718
Drowsiness	Disc. AE	150 mg single, oral Overdose Dose: 150 mg Route: oral Route: single Dose: 150 mg Co-administed with:: chlorpromazine, p.o(3 g, single) Sources: https://pubmed.ncbi.nlm.nih.gov/14639058 Page: p.718	unhealthy, 44 n = 1 Health Status: unhealthy Condition: Aortic valve replacement Age Group: 44 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14639058 Page: p.718
Cough	Disc. AE	5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26658807 Page: p.1	unhealthy, 64 n = 1 Health Status: unhealthy Condition: Cardiomyopathy \|Atrial fibrillation Age Group: 64 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/26658807 Page: p.1
Dyspnea	Disc. AE	5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26658807 Page: p.1	unhealthy, 64 n = 1 Health Status: unhealthy Condition: Cardiomyopathy \|Atrial fibrillation Age Group: 64 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/26658807 Page: p.1
Hematuria	Disc. AE	5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26658807 Page: p.1	unhealthy, 64 n = 1 Health Status: unhealthy Condition: Cardiomyopathy \|Atrial fibrillation Age Group: 64 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/26658807 Page: p.1
Hemoptysis	Disc. AE	5 mg 1 times / day multiple, oral Recommended Dose: 5 mg, 1 times / day Route: oral Route: multiple Dose: 5 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/26658807 Page: p.1	unhealthy, 64 n = 1 Health Status: unhealthy Condition: Cardiomyopathy \|Atrial fibrillation Age Group: 64 Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/26658807 Page: p.1
Bleeding	grade 5 Disc. AE	10 mg 1 times / day multiple, oral (max) Recommended Dose: 10 mg, 1 times / day Route: oral Route: multiple Dose: 10 mg, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf Page: p.1	unhealthy Health Status: unhealthy Condition: Venous thrombosis\|Atrial fibrillation\|Myocardial infarction Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf Page: p.1

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1737	substrate 1037 inhibitor 1767

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
	CYP2C19 991 CYP2C8 693 CYP2C18 138 CYP1A2 1054

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2C9 1819	inhibitor 3277 Sources: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5406237/	yes [Ki 8 uM]

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2C18 138	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf#page=14 Page: 14.0	yes
CYP2C19 991	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf#page=14 Page: 14.0	yes
CYP2C8 693	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf#page=14 Page: 14.0	yes
CYP1A2 1054	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf#page=14 Page: 14.0	yes	likely (co-administration study) Comment: Inhibitors of CYP2C9, 1A2, and/or 3A4 have the potential to increase the effect (increase INR) of warfarin by increasing the exposure of warfarin; Inducers of CYP2C9, 1A2, and/or 3A4 have the potential to decrease the effect (decrease INR) of warfarin by decreasing the exposure of warfarin Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf#page=14 Page: 14.0
CYP3A4 1737	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf#page=14 Page: 14.0	yes	likely (co-administration study) Comment: Inhibitors of CYP2C9, 1A2, and/or 3A4 have the potential to increase the effect (increase INR) of warfarin by increasing the exposure of warfarin; Inducers of CYP2C9, 1A2, and/or 3A4 have the potential to decrease the effect (decrease INR) of warfarin by decreasing the exposure of warfarin Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf#page=14 Page: 14.0
CYP2C9 1037	substrate 3367 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf#page=14 Page: 14.0	yes	yes (pharmacogenomic study) Comment: If the patient’s CYP2C9 and/or VKORC1 genotype are known, consider these ranges in choosing the initial dose. Patients with CYP2C9 1/3, 2/2, 2/3, and 3/3 may require more prolonged time (>2 to 4 weeks) to achieve maximum INR effect for a given dosage regimen than patients without these CYP variants; Inhibitors of CYP2C9, 1A2, and/or 3A4 have the potential to increase the effect (increase INR) of warfarin by increasing the exposure of warfarin; Inducers of CYP2C9, 1A2, and/or 3A4 have the potential to decrease the effect (decrease INR) of warfarin by decreasing the exposure of warfarin Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2011/009218s107lbl.pdf#page=14 Page: 14.0

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY560195	https://www.001chemical.com/chem/5543-57-7
001 Chemical	DY560196	https://www.001chemical.com/chem/5543-58-8
3B Scientific (Wuhan) Corp	3B3-029941	http://www.3bsc.com/index/pro_info.php?id=51198
AA Blocks	AA003248	https://www.aablocks.com/goods/Goods/detail?id=AA003248
AHH Chemical co.,ltd	MT-60432	http://www.ahhchemical.com/product/MT-60432.html
AK Scientific, Inc. (AKSCI)	N022	http://www.aksci.com/item_detail.php?cat=N022
AbMole Bioscience	M6059	http://www.abmole.com/products/warfarin.html
Acadechem	ACDS-030017	http://www.acadechemical.com/product/104716
Achemtek	0104-006074	http://www.achemtek.com/81-81-2
Acros Organics	AC454680100	https://www.fishersci.com/shop/products/4-hydroxy-3-3-oxo-1-phenylbutyl-coumarin-97-acros-organics/AC454680100
Alfa Chemistry	AP5543588	https://reagents.alfa-chemistry.com/product/r-warfarin-cas-5543-58-8-13054.html
Alsachim	1632	http://www.alsachim.com/product-C2641-glo.bal-view.html
Ambinter	Amb19134261	http://www.ambinter.com/reference/19134261
Ambinter	Amb1967203	http://www.ambinter.com/reference/1967203
Ambinter	Amb22269258	http://www.ambinter.com/reference/22269258
Aurora Fine Chemicals LLC	K00.332.840	http://online.aurorafinechemicals.com/info?ID=K00.332.840
Avantor Inc	101096-426	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101096-426
Avantor Inc	101096-428	https://us.vwr.com/store/catalog/product.jsp?catalog_number=101096-428
BLD Pharm	BD634785	http://www.bldpharm.com/products/951658-59-6.html
BOC Sciences	773005-79-1	https://www.bocsci.com/r-warfarin-d5-cas-773005-79-1-item-485323.html
BOC Sciences	791013-22-4	https://www.bocsci.com/s-warfarin-d5-cas-791013-22-4-item-485322.html
BOC Sciences	75472-93-4	https://www.bocsci.com/warfarin-d5-cas-75472-93-4-item-418144.html
Boerchem	BC209814	http://www.boerchem.com/?product_35612.html
Chem Scene	CS-2926	http://www.chemscene.com/81-81-2.html
ChemBridge	5103031	http://www.hit2lead.com/comp.asp?db=SC&id=5103031
ChemMol	30105039	http://www.chemmol.com/chemmol/30105039.html
ChemMol	44026663	http://www.chemmol.com/chemmol/44026663.html
ChemMol	49416852	http://www.chemmol.com/chemmol/49416852.html
ChemMol	96700285	http://www.chemmol.com/chemmol/96700285.html
ChemMol	96701916	http://www.chemmol.com/chemmol/96701916.html
Chemchart	cc-warfarin	http://chemchart.com/warfarin-detail.html
Chemenu	CM110351	http://www.chemenu.com/products/CM110351
Chemspace	CSSB00000064351	https://chem-space.com/CSSB00000064351
Clearsynth	CS-O-10379	https://www.clearsynth.com/en/CSO10379.html
DC Chemicals	DC9053	http://www.dcchemicals.com/product_show-Warfarin.html
Debye Scientific	DB-052729	http://www.debyesci.com/cas_5543-57-7.html
Debye Scientific	DB-052730	http://www.debyesci.com/cas_5543-58-8.html
Enamine	Z1692482575	https://www.enaminestore.com/catalog/Z1692482575
Finetech	FT-0635767	http://www.finetechnology-ind.com/prod/detail/pub/5543-57-7.html
Finetech	FT-0635768	http://www.finetechnology-ind.com/prod/detail/pub/5543-58-8.html
Glentham Life Sciences	GL2208	http://www.glentham.com/products/product/GL2208/
Glentham Life Sciences	GP7659	http://www.glentham.com/products/product/GP7659/
Huateng Pharma	F80010283	http://en.huatengsci.com/product/Warfarin.html
LGC Standards	DRE-C17940000	https://www.lgcstandards.com/US/en/p/DRE-C17940000
LGC Standards	DRE-XA17940000AL	https://www.lgcstandards.com/US/en/p/DRE-XA17940000AL
LGC Standards	LGCAMP0638.00-11	https://www.lgcstandards.com/US/en/p/LGCAMP0638.00-11
LGC Standards	LGCFOR0638.00	https://www.lgcstandards.com/US/en/p/LGCFOR0638.00
LGC Standards	MM0638.00	https://www.lgcstandards.com/US/en/p/MM0638.00
MedChem Express	HY-B0687	https://www.medchemexpress.com/Warfarin.html
Molcore	MC560195	https://www.molcore.com/product/5543-57-7
Molcore	MC560196	https://www.molcore.com/product/5543-58-8
MuseChem	A000086	https://www.musechem.com/product/A000086.html
OChem	4139	http://www.ocheminc.com/index.php?act=psearch&pid=006W854
Oakwood	245858	http://www.oakwoodchemical.com/ProductsList.aspx?CategoryID=-2&txtSearch=167707&ExtHyperLink=1
Parchem	30305	http://www.parchem.com/chemical-supplier-distributor/Warfarin-020305.aspx
Selleck Chemicals	S4545	http://www.selleckchem.com/products/warfarin.html
Sigma-Aldrich	45706_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/45706?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	A2250_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/a2250?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	BP672_SIAL	https://www.sigmaaldrich.com/catalog/product/sial/bp672?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	N13750_SUPELCO	https://www.sigmaaldrich.com/catalog/product/supelco/n13750?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sigma-Aldrich	1719000_USP	https://www.sigmaaldrich.com/catalog/product/usp/1719000?utm_source=pubchem&utm_campaign=pubchem_2017&utm_medium=referral
Sinfoo Biotech	S014360	http://www.sinfoobiotech.com/product/1017758
Smolecule	S547079	http://www.smolecule.com/products/s547079
Smolecule	S919271	https://www.smolecule.com/products/s919271
THE BioTek	bt-285232	https://www.thebiotek.com/product/inhibitors/bt-285232
Vesino Industrial Co Ltd	VC30411	http://www.vsnchem.com/goto/product/22479/
Yuhao Chemical	RT6489	http://www.chemyuhao.com/81-81-2.html
abcr GmbH	AB463721	http://www.abcr.de/shop/en/AB463721
mcule	MCULE-1618253893	https://mcule.com/MCULE-1618253893/

PubMed

Title	Date	PubMed
Prosthetic heart valve thrombosis during dicloxacillin therapy.	1999	10622550
Unexplained thrombosis in HIV-infected patients receiving protease inhibitors: report of seven cases.	1999 Dec	10625032
Rhabdomyolysis and acute renal failure due to combination therapy with simvastatin and warfarin.	1999 Dec	10620105
Potentiation of anticoagulant effect of warfarin caused by enantioselective metabolic inhibition by the uricosuric agent benzbromarone.	1999 Dec	10613612
[Treatment of cardiac insufficiency: does treatment depend on whether its cause is ischemic or idiopathic?].	1999 Jun	10410811
Use of factor IX complex in warfarin-related intracranial hemorrhage.	1999 Nov	10549927
Multicentric warfarin-induced skin necrosis complicating heparin-induced thrombocytopenia.	1999 Sep	10467275
Analysis of risk factors involved in oral-anticoagulant-related intracranial haemorrhages.	2000 Aug	10924533
Long-term treatment with warfarin in Chinese population.	2000 Dec	11144695
Warfarin-induced artery calcification is accelerated by growth and vitamin D.	2000 Feb	10669626
Anticoagulant induced submucosal hemorrhage mimicking a renal pelvic tumor.	2000 Jan	10604355
Intraspinal hemorrhage complicating oral anticoagulant therapy: an unusual case of cervical hematomyelia and a review of the literature.	2000 Jan 24	10647763
Coumarin derivatives and breast-feeding.	2000 Jun	10831996
Genetic modulation of oral anticoagulation with warfarin.	2000 Nov	11127854
Warfarin-associated hemorrhage and cerebral amyloid angiopathy: a genetic and pathologic study.	2000 Oct 10	11061249
[Marked creatine-phosphokinase elevation in myopathy after treatment with bezafibrate].	2000 Sep	11062950
Management of intracranial bleeding associated with anticoagulation: balancing the risk of further bleeding against thromboembolism from prosthetic heart valves.	2000 Sep	10945818
Spontaneous subcapsular renal hematoma secondary to anticoagulant therapy.	2001 Apr	11257671
Behçet's disease with a large intracardiac thrombus: a case report.	2001 Apr	11250984
Perioperative management and reversal of antithrombotic therapy.	2001 Feb	11270131
Thrombolysis and antithrombotic therapy for coronary artery disease.	2001 Feb	11270130
Antithrombotic therapy in valvular heart disease.	2001 Feb	11270129
Oral anticoagulants. Pharmacologic issues for use in the elderly.	2001 Feb	11270124
Anticoagulation and cataract surgery: a review of the current literature.	2001 Feb	11261903
Current trends in the management of deep venous thrombosis and postthrombotic syndrome.	2001 Feb	11214388
Implications of cytochrome P450 2C9 polymorphism on warfarin metabolism and dosing.	2001 Feb	11213860
Stroke prophylaxis in nonvalvular atrial fibrillation.	2001 Feb	11176219
Endovascular caval interruption in pregnant patients with deep vein thrombosis of the lower extremity.	2001 Feb	11174792
Heparin and coumadin: delayed postpolypectomy bleeding.	2001 Feb	11174318
Images in clinical medicine. Retroperitoneal hemorrhage.	2001 Feb 1	11172166
Thrombus formation on atherosclerotic plaques: pathogenesis and clinical consequences.	2001 Feb 6	11177336
[Old adrenal hematoma: a case report].	2001 Jan	11235216
Catastrophic antiphospholipid antibody syndrome.	2001 Jan	11227622
Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors.	2001 Jan	11225565
Hypertension due to renal artery occlusion in a patient with antiphospholipid syndrome.	2001 Jan	11206681
Effect of regimen complexity on patient satisfaction and compliance with warfarin therapy.	2001 Jan	11190902
HIV and thrombosis: a review.	2001 Jan	11177584
Antithrombotic therapy in patients with mechanical and biological prosthetic heart valves.	2001 Jan	11157651
Congenital heart disease: current indications for antithrombotic therapy in pediatric patients.	2001 Jan	11139805
Antithrombotic therapy for prosthetic valves: routine treatment and special considerations.	2001 Jan	11139804
Anticoagulation and heart failure.	2001 Jan	11139802
Is optimal antithrombotic therapy after myocardial infarction well defined?	2001 Jan	11139799
Clinical problem-solving. High time for action.	2001 Jan 4	11136960
Sneddon's syndrome: a case report.	2001 Mar	11270293
Prevention, diagnosis, and treatment of venous thromboembolic complications of gynecologic surgery.	2001 Mar	11262484
The association of vitamin K status with warfarin sensitivity at the onset of treatment.	2001 Mar	11260056
Treatment of the patient with deep vein thrombosis.	2001 Mar	11252215
Adverse reactions to fluoroquinolones. an overview on mechanistic aspects.	2001 Mar	11172695
Warfarin therapy for an octogenarian who has atrial fibrillation.	2001 Mar 20	11255522
Clinical trials that have influenced the treatment of venous thromboembolism: a historical perspective.	2001 Mar 6	11242501

Patents

Sample Use Guides

In Vivo Use Guide

Usual Adult Dose for Prevention of Thromboembolism in Atrial Fibrillation Initial dose: 2 to 5 mg orally once a day Maintenance dose: 2 to 10 mg orally once a day Usual Adult Dose for Myocardial Infarction Initial dose: 2 to 5 mg orally once a day Maintenance dose: 2 to 10 mg orally once a day Usual Adult Dose for Deep Vein Thrombosis - Prophylaxis Initial dose: 2 to 5 mg orally once a day Maintenance dose: 2 to 10 mg orally once a day

Route of Administration: Oral

In Vitro Use Guide

Vitamin K-reductase activity was inhibited by approximately 13 and 8% respectively when microsomal preparations from TAS and HW animals were incubated with 50 uM vitamin K1 and 10 uM warfarin.

Name

Type

Language

WARFARIN

Official Name

English

NSC-59813

Code

English

(±)-4-HYDROXY-3-(3-OXO-1-PHENYLBUTYL)-2H-1-BENZOPYRAN-2-ONE

Systematic Name

English

warfarin [INN]

Common Name

English

WARFARIN [MI]

Common Name

English

WARFARIN [USP-RS]

Common Name

English

WARFARIN [VANDF]

Common Name

English

WARFARIN [ISO]

Common Name

English

WARFARIN [HSDB]

Common Name

English

Warfarin [WHO-DD]

Common Name

English

CHOICE

Brand Name

English

4-HYDROXY-3-(3-OXO-1-PHENYLBUTYL)-2H-1-BENZOPYRAN-2-ONE

Systematic Name

English

4-HYDROXY-3-((1RS)-3-OXO-1-PHENYLBUTYL)COUMARIN

Systematic Name

English

Classification Tree Code System Code

NDF-RT

N0000175964

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

WHO-ATC

B01AA03

Created by admin on Fri Dec 15 16:11:54 GMT 2023 , Edited by admin on Fri Dec 15 16:11:54 GMT 2023

WHO-VATC

QB01AA03

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

NCI_THESAURUS

C263

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

LIVERTOX

NBK548837

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

NCI_THESAURUS

C45597

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

WHO-ESSENTIAL MEDICINES LIST

10.2

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

NDF-RT

N0000175476

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

EPA PESTICIDE CODE

86002

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

Code System Code Type Description

RS_ITEM_NUM

1719000

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

NCI_THESAURUS

C945

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

IUPHAR

6853

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

INN

341

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

RXCUI

11289

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

RxNorm

WIKIPEDIA

WARFARIN

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

CAS

81-81-2

Created by admin on Fri Dec 15 16:11:54 GMT 2023 , Edited by admin on Fri Dec 15 16:11:54 GMT 2023

PRIMARY

LACTMED

Warfarin

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

EPA CompTox

DTXSID5023742

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

EVMPD

SUB00090MIG

Created by admin on Fri Dec 15 16:11:54 GMT 2023 , Edited by admin on Fri Dec 15 16:11:54 GMT 2023

PRIMARY

ALANWOOD

warfarin

Created by admin on Fri Dec 15 16:11:54 GMT 2023 , Edited by admin on Fri Dec 15 16:11:54 GMT 2023

PRIMARY

NSC

59813

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

CHEBI

10033

Created by admin on Fri Dec 15 16:11:54 GMT 2023 , Edited by admin on Fri Dec 15 16:11:54 GMT 2023

PRIMARY

PUBCHEM

54678486

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

FDA UNII

5Q7ZVV76EI

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

CHEBI

87732

Created by admin on Fri Dec 15 16:11:54 GMT 2023 , Edited by admin on Fri Dec 15 16:11:54 GMT 2023

PRIMARY

DAILYMED

5Q7ZVV76EI

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

ECHA (EC/EINECS)

201-377-6

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

ChEMBL

CHEMBL1464

Created by admin on Fri Dec 15 16:11:54 GMT 2023 , Edited by admin on Fri Dec 15 16:11:54 GMT 2023

PRIMARY

SMS_ID

100000079328

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

DRUG BANK

DB00682

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

HSDB

1786

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

MERCK INDEX

m11506

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

Merck Index

DRUG CENTRAL

2847

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

MESH

D014859

Created by admin on Fri Dec 15 16:11:55 GMT 2023 , Edited by admin on Fri Dec 15 16:11:55 GMT 2023

PRIMARY

ACTIVE MOIETY


					5Q7ZVV76EI

WARFARIN

METABOLITE INACTIVE (PARENT)


					T1CK4E3S36

8-HYDROXYWARFARIN

METABOLITE INACTIVE (PARENT)


					3D8G6747YQ

4'-HYDROXYWARFARIN

METABOLITE INACTIVE (PARENT)


					P25D26M0HK

6-HYDROXYWARFARIN

METABOLITE INACTIVE (PARENT)


					B92SFW09LJ

7-HYDROXYWARFARIN

METABOLITE LESS ACTIVE (PARENT)


					ASZ12CF9OS

WARFARIN ALCOHOL

SALT/SOLVATE (PARENT)


					I47IU4FOCO

WARFARIN POTASSIUM

SALT/SOLVATE (PARENT)


					4V2UBU7H8W

WARFARIN SODIUM ISOPROPANOL COMPLEX

SALT/SOLVATE (PARENT)


					6153CWM0CL

WARFARIN SODIUM

Details

SMILES

InChI

DescriptionSources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/009218s108lbl.pdf | https://www.drugbank.ca/drugs/DB00682 | https://www.ncbi.nlm.nih.gov/pubmed/23618698

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Launch Date

Approved Use

Launch Date

Approved Use

Launch Date

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Sourcing

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2010/009218s108lbl.pdf | https://www.drugbank.ca/drugs/DB00682 | https://www.ncbi.nlm.nih.gov/pubmed/23618698

C_max

T_1/2

F_unbound

Drug as perpetrator