1.0 2009-07-05 03:18:12 UTC 2026-05-14 16:45:57 UTC T3D2567 Warfarin SmallMolecule 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. Drug Pesticide Food Toxin Synthetic Toxin Organic Compound Pesticide Ester Drug Food Toxin Anticoagulant Coumarin and Indandione Rodenticide Metabolite Synthetic Compound Rodenticide Human Neurotoxin PMT (phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarin (phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarine (S)-4-hydroxy-3-(3-oxo-1-phenylbutyl)-2-benzopyrone 1-(4'-Hydroxy-3'-coumarinyl)-1-phenyl-3-butanone 200 Coumarin 2H-1-Benzopyran-2-one, 4-hydroxy-3-(3-oxo-1-phenylbutyl)- 3-(1'-Phenyl-2'-acetylethyl)-4-hydroxycoumarin 3-(Acetonylbenzyl)-4-hydroxycoumarin 3-(alpha-Acetonylbenzyl)-4-hydroxycoumarin 3-(alpha-Phenyl-beta-acetylaethyl)-4-hydroxycumarin 3-(alpha-Phenyl-beta-acetylethyl)-4-hydroxycoumarin 4-Hydroxy-3- (3-oxo-1-fenyl-butyl) cumarine 4-Hydroxy-3- (3-oxo-1-phenyl-butyl)-cumarin 4-Hydroxy-3-(3-oxo-1-fenyl-butyl) cumarine 4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-cumarin 4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one 4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one 4-Hydroxy-3-(3-oxo-1-phenylbutyl)coumarin 4-Idrossi-3- (3-oxo-)-fenil-butil)-cumarine 4-Idrossi-3-(3-oxo-)-fenil-butil)-cumarine 4-Idrossi-3-(3-oxo-1-fenil-butil)-cumarine 4oh-coumarin deriv. Arab rat death Arab rat deth Athrombin-k Athrombine-k Brumolin Co-rax Compound 42 Coumadin Coumafen Coumafene Coumaphen Coumaphene Coumarins Coumefene Cov-R-tox D-Con delta-Con Dethmor Dethnel Dicusat e DL-3-(alpha-acetonylbenzyl)-4-hydroxycoumarin Eastern states duocide Fasco fascrat powder Frass-ratron Jantoven Killgerm sewarin p Kumader Kumadu Kumatox Kypfarin Latka 42 Lawarin Liqua-tox Maag rattentod cum Mar-frin Marevan Martin'S mar-frin Maveran Mouse pak Place-pax Prothromadin Rat & mice bait Rat and mice bait Rat-a-way Rat-alpha-way Rat-b-gon Rat-beta-gon Rat-gard Rat-kill Rat-mix Rat-O-cide #2 Rat-O-cide no. 2 Rat-ola Rat-trol Ratorex Ratox Ratoxin Ratron Ratron g Rats-no-more Ratten-koederrohr Rattenstreupulver neu schacht Rattenstreupulver new schacht Rattentraenke Rattunal RAX RCR grey squirrel killer concentrate Ro-deth Rodafarin Rodafarin c Rodex Rodex blox Rosex Rough & ready mouse mix Rough and ready mouse mix Sakarat Sewarin Solfarin Sorexa plus Spray-trol brand roden-trol Temus w Tox-hid Twin light rat away Vampirinip II Vampirinip III Waran Warfant Warfarin sodium Warfarin, & salts, conc.>0.3% Zoocoumarin C19H16O4 308.3279 308.104859 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one warfarin 81-81-2 CC(=O)CC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2 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 PJVWKTKQMONHTI-UHFFFAOYSA-N Organic compounds Phenylpropanoids and polyketides Coumarins and derivatives Hydroxycoumarins 4-hydroxycoumarins 1-benzopyrans Benzene and substituted derivatives Heteroaromatic compounds Hydrocarbon derivatives Ketones Lactones Organic oxides Oxacyclic compounds Pyranones and derivatives Vinylogous acids 1-benzopyran 4-hydroxycoumarin Aromatic heteropolycyclic compound Benzenoid Benzopyran Carbonyl group Heteroaromatic compound Hydrocarbon derivative Ketone Lactone Monocyclic benzene moiety Organic oxide Organic oxygen compound Organoheterocyclic compound Organooxygen compound Oxacycle Pyran Pyranone Vinylogous acid Aromatic heteropolycyclic compounds Coumarin rodenticides hydroxycoumarin methyl ketone Detected and Not Quantified Exogenous Membrane Warfarin Action Pathway SMP0000268 Warfarin Action Pathway (New) SMP0124982 Warfarin Metabolism SMP0125601 Warfarin Drug Metabolism Action Pathway SMP0143126 Solid Solid (MSDS, A308). melting_point 161°C solubility 17 mg/L (at 20°C) logp 2.7 logp 2.41 ALOGPS logs -3.82 ALOGPS solubility 4.72e-02 g/l ALOGPS logp 2.74 ChemAxon pka_strongest_acidic 5.56 ChemAxon pka_strongest_basic -6.9 ChemAxon iupac 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one ChemAxon average_mass 308.3279 ChemAxon mono_mass 308.104859 ChemAxon smiles CC(=O)CC(C1=CC=CC=C1)C1=C(O)C2=C(OC1=O)C=CC=C2 ChemAxon formula C19H16O4 ChemAxon inchi 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 ChemAxon inchikey PJVWKTKQMONHTI-UHFFFAOYSA-N ChemAxon polar_surface_area 63.6 ChemAxon refractivity 86.86 ChemAxon polarizability 31.9 ChemAxon rotatable_bond_count 4 ChemAxon acceptor_count 3 ChemAxon donor_count 1 ChemAxon physiological_charge -1 ChemAxon formal_charge 0 ChemAxon Oral ; Inhalation ; Dermal Rapidly absorbed following oral administration with considerable interindividual variations. Also absorbed percutaneously. 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. Metabolized stereo- and regio-selectively by hepatic microsomal enzymes. S-warfarin is predominantly metabolized by cytochrome P450 (CYP) 2C9 to yield the 6- and 7-hydroxylated metabolites. R-warfarin is metabolized by CYP1A1, 1A2, and 3A4 to yield 6-, 8-, and 10-hydroxylated metabolites. Hydroxylated metabolites may be further conjugated prior to excretion into bile and urine. UGT1A1 appears to be responsible for producing the 6-O-glucuronide of warfarin, with a possibly contribution from UGT1A10. Five UGT1As may be involved in the formation of 7-O-glucuronide warfarin. S-warfarin has higher potency than R-warfarin and genetic polymorphisms in CYP2C9 may dramatically decrease clearance of and increase toxicity of the medication. In man, the dextrowarfarin enantiomorph is metabolized by side chain reduction to a secondary alcohol, whereas levowarfarin is metabolized by oxidation of the ring, primarily to 7-hydroxywarfarin. These inactive metabolic products are to some extent conjugated with glucuronic acid, undergo an enterohepatic circulation, & are ultimately excreted in urine & stool. (A613) Route of Elimination: The elimination of warfarin is almost entirely by metabolism. Very little warfarin is excreted unchanged in urine. The metabolites are principally excreted into the urine; and to a lesser extent into the bile. Half Life: R-warfarin t_1/2=37-89 hours; S-warfarin t_1/2=21-43 hours. LD50: 374 mg/kg (Oral, Mouse) (A308) The lowest reported lethal dose in humans is 6667 ug/kg. (A684) No indication of carcinogenicity (not listed by IARC). (L135) Warfarin is an anticoagulant drug and rodenticide derived from coumarin. As a drug it is used for the treatment of retinal vascular occlusion, pulmonary embolism, cardiomyopathy, atrial fibrillation and flutter, cerebral embolism, transient cerebral ischaemia, arterial embolism and thrombosis. (A308) #<HealthEffect::ActiveRecord_Associations_CollectionProxy:0x00007f72248b5f18> LD₅₀=374 (orally in mice) 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. (L1257) DB00682 HMDB01935 54678486 CHEMBL1464 10442445 C01541 10033 D014859 Warfarin 3232 Warfarin 18048412 15383473 646989 14765195 14765194 12742309 8759764 11673765 15911722 18574265 1564123 Lewis RJ (1996). Sax's Dangerous Properties of Industrial Materials. 9th ed. Volumes 1-3. New York, NY: Van Nostrand Reinhold. Gilman AG, Goodman LS, and Gilman A (eds) (1980). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York, NY: Macmillan Publishing Co., Inc. Sax NI, Lewis RJ (1989). Dangerous properties of industrial materials. 7th edition. New York, NY: Van Nostrand Reinhold Company. Macina, Orest T.; Schardein, James L. (2007). &#8220;Warfarin&#8221;. Human Developmental Toxicants. Boca Raton: CRC Taylor &amp; Francis. pp. 193–4 Loftus, Christopher M. (1995). &#8220;Fetal toxicity of common neurosurgical drugs&#8221;. Neurosurgical Aspects of Pregnancy. Park Ridge, Ill: American Association of Neurological Surgeons. pp. 11–3. Loftus, Christopher M. (1995). Fetal toxicity of common neurosurgical drugs. Neurosurgical Aspects of Pregnancy. Park Ridge, Ill: American Association of Neurological Surgeons. pp. 11-3. Macina, Orest T.; Schardein, James L. (2007). Warfarin. Human Developmental Toxicants. Boca Raton: CRC Taylor & Francis. pp. 193-4 International Agency for Research on Cancer (2014). IARC Monographs on the Evaluation of Carcinogenic Risks to Humans. : http://monographs.iarc.fr/index.php Wikipedia. Dinitrotoluene. Last Updated 10 June 2009. : http://en.wikipedia.org/wiki/Dinitrotoluene Hacco (2008). Material Safety Data Sheet for Warfarin Concentrate. : http://www.hacco.com/Hacco_MSDS/Warfarin%20Concentrate%20(not%20registered)%2009-08.pdf Wikipedia. Coumarin. Last Updated 21 July 2009. : http://en.wikipedia.org/wiki/Coumarin Wikipedia. Brodifacoum. Last Updated 22 June 2009. : http://en.wikipedia.org/wiki/Brodifacoum Drugs.com: http://www.drugs.com/cons/Warfarin.html BE0000713 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. BE0000530 Dissociation 2 uM BindingDB 50343352 Dissociation 4.677 uM BindingDB 50343352 Dissociation 5.4 uM BindingDB 50343352 Dissociation 12 uM BindingDB 50343352 Dissociation 510 uM BindingDB 50343352 BE0002329 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. BE0000925 BE0002793 Inhibitory 20 uM BindingDB 50343352 BE0005805 BE0000956 BE0005786 IC50 24.59 uM BindingDB 50343352 BE0000048 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. BE0000215 AC50 6.79 uM Tox21_PPARg_BLA_Agonist_ratio Tox21/NCGC