Warfarin (CED0001066)

Record Information

Version

1.0

Creation Date

2009-07-05 03:18:12 UTC

Update Date

2026-05-14 16:45:57 UTC

Accession Number

CHEM002093

Identification

Common Name

Warfarin

Class

Small Molecule

Description

Warfarin belongs to the hydroxycoumarins, a subclass of coumarins and derivatives within the organic compounds. This exogenous solid has the formula C19H16O4 and an average molecular weight of 308.33 g/mol. It is classified within the superclass of phenylpropanoids and polyketides. Warfarin acts as a drug (PMC7382647), biological anticoagulant (PMC8708529), biological vitamin K antagonist (PMC6521271), biological antioxidant (PMC10896161, PMC8124610), and biological analgesic (PMC8720699). It inhibits vitamin K reductase, which depletes the reduced form of vitamin K (vitamin KH2). Because vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this action limits gamma-carboxylation and the subsequent activation of vitamin K-dependent coagulant proteins, inhibiting the synthesis of anticoagulant proteins C and S as well as coagulation factors II, VII, IX, and X. Its recorded protein targets include Prothrombin (F2), Albumin (ALB), Cytochrome P450 2C9 (CYP2C9), Nuclear receptor subfamily 1 group I member 2 (NR1I2), Peroxisome proliferator-activated receptor gamma (PPARG), Vitamin K epoxide reductase complex subunit 1 (VKORC1), and Vitamin K epoxide reductase complex subunit 1-like protein 1 (VKORC1L1). Therapeutically, warfarin is used as a treatment for thrombosis (PMC13028019, PMC6223128, PMC9313999, PMC9387011), stroke (PMC4398952, PMC8084398), and atrial fibrillation (PMC1492602). It has therapeutic effects on inflammation (PMC8398118), cancer (PMC7913302), and ischemic stroke (PMC4398952, PMC8520343). It is associated with stroke (PMC9399375) and malaria (PMC4876981). Warfarin is found in 29 recorded sources, including pesticides, drinking water, aquatic systems, wastewater, and electrical equipment. Exposure routes include oral, intravenous, inhalation, and touch.

Contaminant Type

Anticoagulant
Coumarin and Indandione Rodenticide
Drug
Ester
Food Toxin
Human Neurotoxin
Metabolite
Organic Compound
PMT
Pesticide
Rodenticide
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Warfarine	Kegg
Choice	Kegg
(Phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarin	HMDB
(Phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarine	HMDB
(S)-4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2-benzopyrone	HMDB
1-(4'-Hydroxy-3'-coumarinyl)-1-phenyl-3-butanone	HMDB
200 Coumarin	HMDB
3-(1'-Phenyl-2'-acetylethyl)-4-hydroxycoumarin	HMDB
3-(Acetonylbenzyl)-4-hydroxycoumarin	HMDB
3-(alpha-Acetonylbenzyl)-4-hydroxycoumarin	HMDB
3-(alpha-Phenyl-beta-acetylaethyl)-4-hydroxycumarin	HMDB
3-(alpha-Phenyl-beta-acetylethyl)-4-hydroxycoumarin	HMDB
4-Hydroxy-3- (3-oxo-1-fenyl-butyl) cumarine	HMDB
4-Hydroxy-3- (3-oxo-1-phenyl-butyl)-cumarin	HMDB
4-Hydroxy-3-(3-oxo-1-fenyl-butyl) cumarine	HMDB
4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-cumarin	HMDB
4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one	HMDB, MeSH
4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one	HMDB
4-Hydroxy-3-(3-oxo-1-phenylbutyl)coumarin	HMDB
4-Idrossi-3- (3-oxo-)-fenil-butil)-cumarine	HMDB
4-Idrossi-3-(3-oxo-)-fenil-butil)-cumarine	HMDB
4-Idrossi-3-(3-oxo-1-fenil-butil)-cumarine	HMDB
4oh-Coumarin deriv.	HMDB
Arab rat death	HMDB
Arab rat deth	HMDB
Athrombin-K	HMDB
Athrombine-K	HMDB
Brumolin	HMDB
CO-Rax	HMDB
Compound 42	HMDB
Coumadin	HMDB, MeSH
Coumafen	HMDB
Coumafene	HMDB
Coumaphen	HMDB
Coumaphene	HMDB
Coumarins	HMDB
Coumefene	HMDB
Cov-R-tox	HMDB
D-CON	HMDB
delta-CON	HMDB
Dethmor	HMDB
Dethnel	HMDB
Dicusat e	HMDB
DL-3-(alpha-Acetonylbenzyl)-4-hydroxycoumarin	HMDB
Eastern states duocide	HMDB
fasco Fascrat powder	HMDB
Frass-ratron	HMDB
Killgerm sewarin P	HMDB
Kumader	HMDB
Kumadu	HMDB
Kumatox	HMDB
Kypfarin	HMDB
Latka 42	HMDB
Liqua-tox	HMDB
Maag rattentod cum	HMDB
Mar-frin	HMDB
Martin'S mar-frin	HMDB
Maveran	HMDB
Mouse pak	HMDB
Place-pax	HMDB
Prothromadin	HMDB
Rat & mice bait	HMDB
Rat and mice bait	HMDB
Rat-a-way	HMDB
Rat-alpha-way	HMDB
Rat-b-gon	HMDB
Rat-beta-gon	HMDB
Rat-gard	HMDB
Rat-kill	HMDB
Rat-mix	HMDB
Rat-O-cide #2	HMDB
Rat-O-cide no. 2	HMDB
Rat-ola	HMDB
Rat-trol	HMDB
Ratorex	HMDB
Ratox	HMDB
Ratoxin	HMDB
Ratron	HMDB
Ratron g	HMDB
Rats-NO-more	HMDB
Ratten-koederrohr	HMDB
Rattenstreupulver neu schacht	HMDB
Rattenstreupulver new schacht	HMDB
Rattentraenke	HMDB
Rattunal	HMDB
RAX	HMDB
RCR Grey squirrel killer concentrate	HMDB
ro-Deth	HMDB
Rodafarin	HMDB
Rodafarin c	HMDB
Rodex	HMDB
Rodex blox	HMDB
Rosex	HMDB
Rough & ready mouse mix	HMDB
Rough and ready mouse mix	HMDB
Sakarat	HMDB
Sewarin	HMDB
Solfarin	HMDB
Sorexa plus	HMDB
Spray-trol brand roden-trol	HMDB
Temus W	HMDB
Tox-hid	HMDB
Twin light rat away	HMDB
Vampirinip II	HMDB
Vampirinip III	HMDB
Waran	HMDB
Warfarin sodium	HMDB, MeSH
Zoocoumarin	HMDB
aldo Brand OF warfarin sodium	MeSH, HMDB
apo-Warfarin	MeSH, HMDB
Apotex brand OF warfarin sodium	MeSH, HMDB
Bailly brand OF warfarin sodium	MeSH, HMDB
Boots brand OF warfarin sodium	MeSH, HMDB
Marevan	MeSH, HMDB
Aldocumar	MeSH, HMDB
Coumadine	MeSH, HMDB
Warfant	MeSH, HMDB
Bristol-myers squibb brand OF warfarin sodium	MeSH, HMDB
Genpharm brand OF warfarin sodium	MeSH, HMDB
Goldshield brand OF warfarin sodium	MeSH, HMDB
Sodium, warfarin	MeSH, HMDB
Tedicumar	MeSH, HMDB
Warfarin potassium	MeSH, HMDB
Antigen brand OF warfarin sodium	MeSH, HMDB
Estedi brand OF warfarin sodium	MeSH, HMDB
Gen-warfarin	MeSH, HMDB
Potassium, warfarin	MeSH, HMDB

Chemical Formula

C₁₉H₁₆O₄

Average Molecular Mass

308.328 g/mol

Monoisotopic Mass

308.105 g/mol

CAS Registry Number

81-81-2

IUPAC Name

4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one

Traditional Name

warfarin

SMILES

CC(=O)CC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2

InChI Identifier

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

InChI Key

PJVWKTKQMONHTI-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as 4-hydroxycoumarins. These are coumarins that contain one or more hydroxyl groups attached to C4-position the coumarin skeleton.

Kingdom

Organic compounds

Super Class

Phenylpropanoids and polyketides

Class

Coumarins and derivatives

Sub Class

Hydroxycoumarins

Direct Parent

4-hydroxycoumarins

Alternative Parents

Substituents

4-hydroxycoumarin
Benzopyran
1-benzopyran
Pyranone
Monocyclic benzene moiety
Benzenoid
Pyran
Heteroaromatic compound
Vinylogous acid
Ketone
Lactone
Oxacycle
Organoheterocyclic compound
Organic oxygen compound
Carbonyl group
Hydrocarbon derivative
Organic oxide
Organooxygen compound
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

methyl ketone (CHEBI:87732 )
hydroxycoumarin (CHEBI:87732 )
Coumarin rodenticides (C01541 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Applications

Not Available

Biological Roles

Chemical Roles

Not Available

Organoleptic Effects

Not Available

Physical Properties

State

Solid

Appearance

Solid (MSDS, A308).

Experimental Properties

Property	Value
Melting Point	161°C
Boiling Point	Not Available
Solubility	17 mg/L (at 20°C)

Predicted Properties

Property	Value	Source
Water Solubility	0.047 g/L	ALOGPS
logP	2.41	ALOGPS
logP	2.74	ChemAxon
logS	-3.8	ALOGPS
pKa (Strongest Acidic)	5.56	ChemAxon
pKa (Strongest Basic)	-6.9	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	63.6 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	86.86 m³·mol⁻¹	ChemAxon
Polarizability	31.9 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	Deposition Date	View
GC-MS	GC-MS Spectrum	splash10-014i-0293000000-848341bcbd6a3f0a2c6b	Not Available	View Spectrum
GC-MS	GC-MS Spectrum	splash10-014i-0293000000-848341bcbd6a3f0a2c6b	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-0udl-3190000000-b963cb54bb6abedefbe3	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	splash10-00xr-7195000000-ca3a892fd51e0eac1242	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum	Not Available	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0429000000-1e818b579dc7a0fade2d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-f568338c06cd9b4762ac	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-acdd0ed19e403aa73c77	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0bt9-0539000000-5b1c7c6c812ba72325e3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-e461e1aca7977a2838ad	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0w29-0960000000-9fa099190280529cd891	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0910000000-d7dbaf6e7b34ee85e1f7	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0920000000-4fb886a5c160afa86df9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0920000000-ad608fe7680a2adf9d90	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ik9-0942000000-5864f2d15892753d6a8b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-acdd0ed19e403aa73c77	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0w29-0960000000-b5bc3614bc1379df068c	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0bt9-0539000000-3554db4e3651d4691cbb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0229-2900000000-022920b191a958c73833	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-07vi-5920000000-0506f7adccf44b63822a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-e461e1aca7977a2838ad	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0429000000-1e818b579dc7a0fade2d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0229-2900000000-6909a3446398afc7d421	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03kc-0910000000-b4521bf9a45fcfff36ac	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0900000000-f568338c06cd9b4762ac	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ik9-0942000000-c6a39cbb951c352769e1	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0920000000-ef46ede8101d55bbd39f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0109000000-b8e4bb0d0b9463565b69	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0udi-0690000000-106a5e6e146debe97e84	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0w29-0590000000-f854101d99efcf69faea	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-066r-6900000000-22289729b41b48885cec	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ik9-3970000000-3e76b9c10e2ce7b3d978	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-066r-5900000000-4f0b3a64e01cc8b84bac	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0nmi-1944000000-6a51eba9506c87238693	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-07vi-4920000000-afe593d82f29ab2a7f90	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-07vi-5920000000-784a5beba9e42bedd8cf	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-114i-0797000000-ad7374c49037a362f4fd	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ir3-0930000000-781e69b8f1fa43fe0811	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0j4i-0970000000-2c75cacce7c41d3cabc3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0w29-0890000000-dabf6e6775376bba4c39	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-066r-7900000000-70f07d43dd1c92114668	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-066r-7900000000-04b3cfe3c25b09fc3260	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0109000000-6e2b921fd23f2c14f995	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0bt9-0309000000-fc71f74941a91a3b814a	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0229-0910000000-473f884ad18890ccc00f	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-08fr-0925000000-3359d14794e9d992116e	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ik9-0950000000-2366e5c1c2cffe093e7d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ik9-0960000000-43d4d9d4f1b4f3712824	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0nmi-1945000000-a63b9404788713f576f9	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ik9-0950000000-29aeaa13fa4c069c9e60	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-4900000000-5c4ad857d39cbfa7c2fb	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-4900000000-99b29b3cbf7046f84d9b	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03kc-0910000000-4dc8cd5116df0ba13b31	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0a4i-0009000000-19faa5b2808260378571	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0229-2900000000-7f1bc7ade9fc387fc470	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ik9-3970000000-5ebdf52405161af90bca	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-0ik9-0960000000-0cefff6ef63a09e8a26d	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-08fr-0925000000-d5eeb86fb9c5c12f77a8	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03kc-0910000000-282342df977f94bd97b3	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-00di-0910000000-37414c883b940743dfb6	Not Available	View Spectrum
LC-MS/MS	LC-MS/MS Spectrum	splash10-03di-0920000000-71509140096456701bde	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4l-0197000000-a98e039dbdc8da6c3b7c	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-0292000000-d9a969b41fe312282de6	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00di-2690000000-f20b105406ab790d37f0	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-1149000000-4072cf2742b0e6164f82	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0bt9-5988000000-eb075587f79ddb4af966	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-052f-9350000000-47075e4967528dede6f3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0bt9-0759000000-294235076cec6ed7f530	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0ik9-0980000000-d49fb8ac419eb20ff44e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-00dj-3920000000-8fade8f1e9ed3376f7f3	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0a4i-0009000000-f7e77fb1a377e56b8e6d	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0bt9-4956000000-6f4c317e211f8733083e	Not Available	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum	splash10-0006-9510000000-f6214185f509174c3867	Not Available	View Spectrum
MS	MS Spectrum	splash10-014i-7692000000-6e3993fee62d7eb7438e	Not Available	View Spectrum

Toxicity Profile

Mechanism of Toxicity

Warfarin inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decreased prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.

Carcinogenicity (IARC Classification)

No indication of carcinogenicity (not listed by IARC). (12)

Minimum Risk Level

Not Available

Symptoms

LD₅₀=374 (orally in mice)

Treatment

The primary antidote to warfarin poisoning is immediate administration of vitamin K1 (initially slow intravenous injections of 10-25 mg repeated all 3-6 hours until normalisation of the prothrombin time; then 10 mg orally four times daily as a "maintenance dose"). It is an extremely effective antidote, provided the poisoning is caught before too much damage has been done to the victim's circulatory system. At high doses warfarin can affect the body for many months, and the antidote must be administered regularly for a long period of time. (16)

Toxicity Values

Toxicity Value	Unit	Value Range	Organism	Dose Descriptor	Route of Exposure	Predicted or Experimental	Reference
374.0	mg/kg	Not Available	Mouse	LD50	Oral	experimental	A308
118.0	Log mg/kg	[70:210]	Rat	LD50	oral	predicted	Not Available

Health Effects

Health Effect	Relationship	Direction	Reference
inflammation	has_therapeutic_effect_on	Not Available	PMC8398118
cancer	has_therapeutic_effect_on	Not Available	PMC7913302
malaria	associated_with	Not Available	PMC4876981
ischemic stroke	has_therapeutic_effect_on	Not Available	PMC4398952 , PMC8520343
stroke	is_treatment_for	Not Available	PMC4398952 , PMC8084398
stroke	associated_with	Not Available	PMC9399375
thrombosis	is_treatment_for	Not Available	PMC13028019 , PMC6223128 , PMC9313999 , PMC9387011
atrial fibrillation	is_treatment_for	Not Available	PMC1492602
migraine	has_therapeutic_effect_on	Not Available	PMC12255647
antiphospholipid syndrome	is_treatment_for	Not Available	PMC12221332
hemarthrosis	associated_with	Not Available	PMC9399375
Primary pulmonary hypertension	has_therapeutic_effect_on	Not Available	PMC1492602

Exposure Sources

Source ID	Source	Sector	Reference
3	Irrigation water	Agriculture & land management	Not Available
7	Pesticides	Agriculture & land management	Not Available
27	Water Coolers	Appliances, HVAC & refrigerants	Not Available
43	Water heaters	Appliances, HVAC & refrigerants	Not Available
50	Groundwater	Aquatic systems & sediments	Not Available
51	Surface water	Aquatic systems & sediments	Not Available
52	Seawater	Aquatic systems & sediments	Not Available
53	Freshwater	Aquatic systems & sediments	Not Available
70	Stormwater runoff	Automotive & urban infrastructure	Not Available
88	Waterproofing sprays	Building & Construction	Not Available
115	Drinking water	Drinking water & water supply	Not Available
116	Tap water	Drinking water & water supply	Not Available
117	Bottled water	Drinking water & water supply	Not Available
118	Desalinated water	Drinking water & water supply	Not Available
181	Ballast water	Marine, shipping & aquaculture	Not Available
182	Bilge water	Marine, shipping & aquaculture	Not Available
273	Antithrombotic agents	Healthcare, pharmaceuticals & veterinary products	Not Available
468	Industrial wastewater	Wastewater, sanitation & biosolids	Not Available
470	Wastewater treatment effluent	Wastewater, sanitation & biosolids	Not Available
475	Mine wastewater	Wastewater, sanitation & biosolids	Not Available
477	Wastewater, unspecified	Wastewater, sanitation & biosolids	Not Available
497	Floors	Building & Construction	Not Available
505	Amplifiers	Electrical & Electronic Equipment	Not Available
506	Antennas	Electrical & Electronic Equipment	Not Available
516	Electric Hearing Aids	Electrical & Electronic Equipment	Not Available
523	Gas Filled Discharge Tubes With Solid Cathode	Electrical & Electronic Equipment	Not Available
526	Loudspeakers	Electrical & Electronic Equipment	Not Available
539	Video Games	Electrical & Electronic Equipment	Not Available
540	X Ray Tubes	Electrical & Electronic Equipment	Not Available
597	Chemosterilants	Agriculture & land management	Not Available
620	Card Games	Recreation & sports surfaces	Not Available
641	Foam Dyeing	Textiles, leather & furnishings	Not Available
653	Sewing	Textiles, leather & furnishings	Not Available

Pathways

4 pathways

Warfarin Action Pathway

Warfarin Action Pathway (New)

Warfarin Metabolism

Warfarin Drug Metabolism Action Pathway

Targets

Structure	Protein	UniProt ID	Organism	Relationship	Details
Click to view 3D structure	Vitamin K epoxide reductase complex subunit 1	Q9BQB6	Humans	Predicted (SEA)	0.0778492
Click to view 3D structure	Vitamin K epoxide reductase complex subunit 1	Q6TEK4	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	NAD(P)H dehydrogenase [quinone] 1	P05982	Rattus norvegicus	Predicted (SEA)	0.155698
Click to view 3D structure	Albumin	P02768	Humans	Predicted (SEA)	2.95827
Click to view 3D structure	NAD(P)H dehydrogenase [quinone] 1	P15559	Humans	Predicted (SEA)	0.389246
Click to view 3D structure	Pol polyprotein	Q72874	Human immunodeficiency virus 1	Predicted (SEA)	27.9479
Click to view 3D structure	Protein phosphatase EYA3	Q99504	Humans	Predicted (SEA)	0.856341
Click to view 3D structure	Carbonic anhydrase 9	Q16790	Humans	Predicted (SEA)	129.619
Click to view 3D structure	Vitamin K epoxide reductase complex subunit 1	Q6B4J2	Bos taurus	Predicted (SEA)	0.467095
Click to view 3D structure	Carbonic anhydrase 12	O43570	Humans	Predicted (SEA)	128.218
Click to view 3D structure	Carbonic anhydrase 1	P00915	Humans	Predicted (SEA)	156.555
Click to view 3D structure	Carbonic anhydrase 2	P00918	Humans	Predicted (SEA)	218.211
Click to view 3D structure	Long-chain-fatty-acid--CoA ligase 6	Q9UKU0	Humans	Predicted (SEA)	6.07224
Click to view 3D structure	Albumin	P02770	Rattus norvegicus	Predicted (SEA)	0.0778492
Click to view 3D structure	Poly [ADP-ribose] polymerase tankyrase-1	O95271	Humans	Predicted (SEA)	39.5474
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Predicted (SEA)	670.749
Click to view 3D structure	Mitogen-activated protein kinase 1	P28482	Humans	Predicted (SEA)	544.322
Click to view 3D structure	Gag-Pol polyprotein	Q7ZJM1	Human immunodeficiency virus 1	Predicted (SEA)	42.9728
Click to view 3D structure	Cytochrome P450 2C19	P33261	Humans	Predicted (SEA)	529.997
Click to view 3D structure	G-protein coupled receptor 35	Q9HC97	Humans	Predicted (SEA)	26.858
Click to view 3D structure	Cytochrome P450 1B1	Q16678	Humans	Predicted (SEA)	67.2617
Click to view 3D structure	Induced myeloid leukemia cell differentiation protein Mcl-1	Q07820	Humans	Predicted (SEA)	188.317
Click to view 3D structure	Aldo-keto reductase family 1 member B1	P07943	Rattus norvegicus	Predicted (SEA)	45.1525
Click to view 3D structure	Pyruvate kinase PKM	P14618	Humans	Predicted (SEA)	15.0249
Click to view 3D structure	Amine oxidase [flavin-containing] B	P27338	Humans	Predicted (SEA)	353.435
Click to view 3D structure	Vitamin K epoxide reductase complex subunit 1	Q9BQB6	Humans	Known	Warfarin inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decresed prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.
Click to view 3D structure	Albumin	P02768	Humans	Known	Not Available
Click to view 3D structure	Vitamin K epoxide reductase complex subunit 1-like protein 1	Q8N0U8	Humans	Known	Warfarin inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decresed prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.
Click to view 3D structure	Alpha-1-acid glycoprotein 1	P02763	Humans	Known	Not Available
Click to view 3D structure	Cytochrome P450 2C9	P11712	Humans	Known	Not Available
Click to view 3D structure	Nuclear receptor subfamily 1 group I member 2	O75469	Humans	Known	Not Available
Click to view 3D structure	Prothrombin	P00734	Humans	Known	Warfarin inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent proteins, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited. Depression of three of the four vitamin K-dependent coagulation factors (factors II, VII, and X) results in decresed prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots.
Click to view 3D structure	Peroxisome proliferator-activated receptor gamma	P37231	Humans	Known	Not Available

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Not Available

Chemspider ID

10442445

ChEBI ID

87732

PubChem Compound ID

Not Available

Kegg Compound ID

C01541

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Nasri W. Badran, “Microcrystalline 3-(alpha-acetonylbenzyl)-4-hydroxycoumarin (warfarin) and methods of making.” U.S. Patent US4113744, issued April, 1960.

MSDS

Link

General References

Warfarin (CED0001066)

Structure for CHEM002093: Warfarin

Structure