Compound: warfarin
SMILES: O=c1oc2c(cccc2)c(c1C(c3ccccc3)CC(=O)C)O
InChIKey: PJVWKTKQMONHTI-UHFFFAOYSA-N
Synonyms: warfarin, 81-81-2, Coumafene, Zoocoumarin, Coumafen, Brumolin, Coumefene, Dethmor, Kumader, Warfarine, Kumadu, Vampirinip II, Coumarins, Kypfarin, Rodafarin, Solfarin, Dethnel, Kumatox, Maveran, Ratron, Rosex, Temus W, Vampirinip iii, Athrombine-K, Frass-Ratron, Mar-Frin, Rattentraenke, Ratorex, Rattunal, Warfarat, CO-Rax, Rats-no-more, Tox-hid, Rat-Gard, Rat-Kill, Rat-Trol, Ratron G, Ratten-Koederrohr, Coumaphene, Rat-Mix, Rat-Ola, Ro-Deth, Rat-a-way, Ratoxin, Martin's mar-frin, Rat & mice bait, Warfarin plus, Compound 42, Rat-B-gon, Maag Rattentod Cum, Rodex blox, Liqua-tox, Mouse pak, Place-pax, Rodafarin C, 4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one, Warfarin Q, Dicusat E, Fasco fascrat powder, Twin light rat away, WARF compound 42, Coumaphen, Eastern states duocide, Ratox, rac-Warfarin, Arab Rat Death, Rough & ready mouse mix, Latka 42, Warf 42, Warfarina, 200 coumarin, Spray-trol brand roden-trol, Rattenstreupulver Neu Schacht, Arab rat deth, Warfarinum, 4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one, 4-Hydroxy-3-(3-oxo-1-phenylbutyl)coumarin, Rattenstreupulver new schacht, W.A.R.F. 42, Rcra waste number P001, 2H-1-Benzopyran-2-one, 4-hydroxy-3-(3-oxo-1-phenylbutyl)-, Choice, 3-(1'-Phenyl-2'-acetylethyl)-4-hydroxycoumarin, 3-(alpha-Acetonylbenzyl)-4-hydroxycoumarin, NSC-59813, 4-Hydroxy-3-(3-oxo-1-fenyl-butyl) cumarine, 4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-cumarin, 1-(4'-Hydroxy-3'-coumarinyl)-1-phenyl-3-butanone, Zoocoumarin [Netherlands and USSR], 5Q7ZVV76EI, Rat and mice bait, 4-Idrossi-3-(3-oxo-1-fenil-butil)-cumarine, (RS)-Warfarin, DL-3-(alpha-Acetonylbenzyl)-4-hydroxycoumarin, (Phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarine, 4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one, DTXSID5023742, 3-(alpha-Phenyl-beta-acetylethyl)-4-hydroxycoumarin, NSC59813, Coumarin, 3-(alpha-acetonylbenzyl)-4-hydroxy-, Rough and ready mouse mix, 3-(Acetonylbenzyl)-4-hydroxycoumarin, 3-(alpha-Phenyl-beta-acetylaethyl)-4-hydroxycumarin, DTXCID703742, 4-Idrossi-3-(3-oxo-)-fenil-butil)-cumarine, Zoocoumarin (Netherlands and USSR), Coumarines, Sodium, Warfarin, Benzopyran 2 ones, Benzopyran-2-ones, 1,2 Benzopyrones, 1,2-Benzopyrones, Potassium, Warfarin, Derivative, Coumarin, (+-)-Warfarin, 1,2 Benzo Pyrones, 1,2-Benzo-Pyrones, RefChem:6354, Warf-12, CHEBI:10033, CHEBI:23403, B01AA03, 3-(alpha-Acetonyl)-benzyl-4-hydroxycoumarin, 3-alpha-phenyl-beta-acetylethyl-4-hydroxycoumarin, 4-hydroxy-3-(3-oxo-1-phenyl butyl)-2h-1-benzopyran-2-one, 201-377-6, Coumarin Derivative, Warf, Coumadin, D-Con, Cov-R-Tox, Rat-o-cide #2, Warficide, Rodex, 2-hydroxy-3-(3-oxo-1-phenylbutyl)-4h-chromen-4-one, Sorexa plus, Sakarat, Sewarin, 951658-59-6, Warfarin (INN), 4OH-Coumarin deriv., RAX, Rat-o-cide No. 2, CHEMBL1464, 3-(.alpha.-Acetonylbenzyl)-4-hydroxycoumarin, Coumafene [French], NCGC00094810-01, WARFARIN [INN], Zoocoumarin [Russian], Latka 42 [Czech], Warfarin [INN:BAN], Warfarine [INN-French], Warfarine [ISO-French], Warfarinum [INN-Latin], (Phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarin, Coumarin, 3-(.alpha.-acetonylbenzyl)-4-hydroxy-, Warfarina [INN-Spanish], Warfarin, analytical standard, 4-hydroxy-3-(3-oxo-1-phenyl-butyl)chromen-2-one, Warfarin plus [discontinued], Caswell No. 903, 3-(.alpha.-Phenyl-.beta.-acetylethyl)-4-hydroxycoumarin, Warfarin [BSI:ISO], Athrombine K, MFCD00006854, CAS-81-81-2, Warfarin [ISO], Choice (TN), HSDB 1786, SR-01000195154, NCGC00094810-04, EINECS 201-377-6, NSC 59813, RCRA waste no. P001, CBKinase1_000192, CBKinase1_012592, UNII-5Q7ZVV76EI, EPA Pesticide Chemical Code 086002, BRN 1293536, wafarin, delta-con, Vampirinip;, Aldocumar;, Coumafene;, Panwarfin;, Coumadin;, Kumatox;, Marevan;, Rat-alpha-way, Rat-beta-gon, Ratron;, Warfarin RS, Waran;, Killgerm sewarin p, 2-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-4-one, 4-Hydroxy-3-(3-oxo-1-fenyl-butyl) cumarine [Dutch], 4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-cumarin [German], 4-Idrossi-3-(3-oxo-1-fenil-butil)-cumarine [Italian], Warfarin - 90%, Rattentraenke (German), Spectrum_000194, (Phenyl-1 acetyl-2 ethyl) 3-hydroxy-4 coumarine [French], 3-(alpha-Phenyl-beta-acetylaethyl)-4-hydroxycumarin [German], WARFARIN [HSDB], WARFARIN [MI], WARF-42;Athrombine-K, WARFARIN [VANDF], (.+/-.)-Warfarin, Spectrum2_000935, Spectrum3_000583, Spectrum4_000381, Spectrum5_001751, WARFARIN [USP-RS], WARFARIN [WHO-DD], EC 201-377-6, Ratten-Koederrohr (German), SCHEMBL3689, CHEMBL7252, BSPBio_002026, CBDivE_002127, CBDivE_013236, KBioGR_000901, KBioSS_000674, 5-18-04-00162 (Beilstein Handbook Reference), MLS001304042, orb342013, DivK1c_000444, SCHEMBL136434, SPECTRUM1500613, SPBio_000870, GTPL6853, orb3027230, SCHEMBL29400364, CHEBI:87732, HMS501G06, KBio1_000444, KBio2_000674, KBio2_003242, KBio2_005810, KBio3_001526, NINDS_000444, QTXVAVXCBMYBJW-UHFFFAOYSA-N, Warfarin, 1mg/ml in Acetonitrile, HMS1921K07, HMS2092C20, HMS2233L10, HMS3372L19, HMS3648B15, HMS3714G21, Pharmakon1600-01500613, HY-B0687, MSK23011, Tox21_113185, Tox21_202182, Tox21_300531, Warfarin 1.0 mg/ml in Acetonitrile, BBL027615, BDBM50343352, CCG-39672, EBC-02047, NSC757385, s4545, SBB058124, STK364490, WLN: T66 BOVJ DYR&1V1 EQ, AKOS005430103, AKOS026749956, DB00682, FW01354, NSC-757385, Rattenstreupulver Neu Schacht (German), SB48255, SB48256, IDI1_000444, SMP1_000316, Warfarin 100 microg/mL in Acetonitrile, NCGC00094810-02, NCGC00094810-03, NCGC00094810-05, NCGC00094810-06, NCGC00159398-03, NCGC00178855-01, NCGC00188986-01, NCGC00188986-02, NCGC00254457-01, NCGC00259731-01, AC-15978, SMR000718754, (3-(a-Acetonylbenzyl)-4-hydroxycoumarin), SBI-0051556.P002, DB-052729, DB-052730, DB-330360, DL-3-(a-Acetonylbenzyl)-4-hydroxycoumarin, S-(-)-3-Acetonybenzyl)-4-hydroxycoumarin, NS00010884, ST50308693, Warfarin, PESTANAL(R), analytical standard, EN300-51918, 4-Hydroxy-3- (3-oxo-1-fenyl-butyl) cumarine, 4-Hydroxy-3- (3-oxo-1-phenyl-butyl)-cumarin, 4-Idrossi-3- (3-oxo-)-fenil-butil)-cumarine, C01541, D08682, H10432, AB00052125_02, AB00876255-06, Q407431, 4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-chromen-2-one, SR-01000195154-3, SR-01000195154-4, BRD-A24514565-001-02-2, BRD-A24514565-001-09-7, BRD-A24514565-236-01-6, SR-01000195154-10, 3-(.alpha.-Phenyl-.beta.-acetylaethyl)-4-hydroxycumarin, 4-hydroxy-3-(3-oxo-1-phenylbutyl)-1-benzopyran-2-one, Warfarin, British Pharmacopoeia (BP) Reference Standard, Z732250592, 4-(4-hydroxy-2-oxo-2H-3-chromenyl)-4-phenyl-2-butanone, 4-HYDROXY-3-((1RS)-3-OXO-1-PHENYLBUTYL)COUMARIN, 4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-chromen-2-one #, Warfarin4-Hydroxy-3-(3-oxo-1-phenyl-butyl)-chromen-2-one, Warfarin, United States Pharmacopeia (USP) Reference Standard, (+/-)-4-HYDROXY-3-(3-OXO-1-PHENYLBUTYL)-2H-1-BENZOPYRAN-2-ONE
Theoretical properties:
molecular_formula: C19H16O4
molecular_weight: 308.3 g/mol
exact_mass: 308.10485899 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 4
heavy_atom_count: 23
topological_polar_surface_area: 63.6 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Crystals from alcohol
color: Crystals from alcohol
odor: Odorless
boiling_point: Decomposes (NIOSH, 2024)
melting_point: 322 °F (EPA, 1998)
density: Relative density (water = 1): 1.4
solubility: 0.002 % (NIOSH, 2024)
vapor_pressure: 0.09 mmHg at 71 °F (NIOSH, 2024)
Descriptions:
{"pubchem": "Warfarin can cause developmental toxicity according to an independent committee of scientific and health experts.", "chebi": "A member of the class of coumarins that is 4-hydroxycoumarin which is substituted at position 3 by a 1-phenyl-3-oxo-1-butyl group.", "chembl": "WARFARIN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Warfarin, sold under the brand name Coumadin among others, is used as an anticoagulant medication. It is commonly used to prevent deep vein thrombosis and pulmonary embolism, and to protect against stroke in people who have atrial fibrillation, valvular heart disease, or artificial heart valves. Warfarin may sometimes be prescribed following a ST-segment elevation myocardial infarction and orthopedic surgery. It is usually taken by mouth, but may also be administered intravenously.\nThe common side effect, a natural consequence of reduced clotting, is bleeding. Less common side effects may include areas of tissue damage, and purple toes syndrome. Use is not recommended during pregnancy. The effects of warfarin are typically monitored by checking prothrombin time (INR) every one to four weeks. Many other medications and dietary factors can interact with warfarin, either increasing or decreasing its effectiveness. The effects of warfarin may be reversed with phytomenadione (vitamin K1), fresh frozen plasma, or prothrombin complex concentrate.\nWarfarin decreases blood clotting by blocking vitamin K epoxide reductase, an enzyme that reactivates vitamin K1. Without sufficient active vitamin K1, the plasma concentrations of clotting factors II, VII, IX, and X are reduced and thus have decreased clotting ability. The anticlotting protein C and protein S are also inhibited, but to a lesser degree. \nIt is wrongly described as a \"vitamin K antagonist\". This term is incorrect. Warfarin does not antagonize the action of vitamin K1, but rather antagonizes vitamin K1 recycling, depleting active vitamin K1.\nA few days are required for full effect to occur, and these effects can last for up to five days. Because the mechanism involves enzymes such as VKORC1, patients on warfarin with polymorphisms of the enzymes may require adjustments in therapy if the genetic variant that they have is more readily inhibited by warfarin, thus requiring lower doses.\nWarfarin first came into large-scale commercial use in 1948 as a rat poison. It was formally approved as a medication to treat blood clots in humans by the U.S. Food and Drug Administration in 1954. In 1955, warfarin's reputation as a safe and acceptable treatment for coronary artery disease, arterial plaques, and ischemic strokes was bolstered when President Dwight D. Eisenhower was treated with warfarin following a highly publicized heart attack. It is on the World Health Organization's List of Essential Medicines. Warfarin is available as a generic medication and is sold under many brand names. In 2023, it was the 116th most commonly prescribed medication in the United States, with more than 5 million prescriptions."}