| Identification | More | [Name]
Warfarin sodium | [CAS]
129-06-6 | [Synonyms]
3-(A-ACETONYLBENZYL)-4-HYDROXYCOUMARIN SODIUM
3-(ALPHA-ACETONYLBENZYL)-4-HYDROXYCOUMARIN
3-(ALPHA-ACETONYLBENZYL)-4-HYDROXYCOUMARIN SODIUM
3-(ALPHA-ACETONYLBENZYL)-4-HYDROXYCOUMARIN SODIUM SALT
SODIUM 4-OXO-3-(3-OXO-1-PHENYL-BUTYL)-CHROMEN-2-OLATE
WARFARIN SODIUM
WARFARIN, SODIUM CLATHRATE
WARFARIN SODIUM SALT
WARFARIN SODIUM SALT CLATHRATE
((3-(alpha-acetonylbenzyl)-2-oxo-2h-1-benzopyran-4-yl)oxy)-sodiu
3-(alpha-acetonylbenzyl)-4-hydroxy-coumarisodiumsalt
4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one(C19H15O4)
4-hydroxy-3-(3-oxo-1-phenylbutyl)-2h-1-benzopyran-2-onsodiumsalt
athrombin
coumadin
coumadinsodium
coumafenesodium
marevan
panwarfin
prothromadin | [EINECS(EC#)]
204-929-4 | [Molecular Formula]
C19H16NaO4 | [MDL Number]
MFCD00083223 | [Molecular Weight]
331.32 | [MOL File]
129-06-6.mol |
| Safety Data | Back Directory | [Hazard Codes ]
T+ | [Risk Statements ]
R61:May cause harm to the unborn child.
R28:Very Toxic if swallowed. | [Safety Statements ]
S53:Avoid exposure-obtain special instruction before use .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) . | [RIDADR ]
UN 1544 6.1/PG 2
| [WGK Germany ]
1
| [RTECS ]
GN4725000
| [HazardClass ]
6.1(a) | [PackingGroup ]
II | [HS Code ]
29322090 | [Safety Profile]
Poison to humans by
ingestion. Experimental poison by ingestion
and intravenous routes. Human systemic
effects by ingestion: dermatitis. Human
reproductive effects by ingestion:
fetotoxicity, abnormal condition of newborn
at birth, other newborn physical effects, and
teratogenic effects includmg developmental
abnormalities of the eye and ear, craniofacial
area, skin and appendages, musculoskeletal
system, cardiovascular system, and
gastrointestinal system of the fetus. ,4n
experimental teratogen. Other experimental
reproductive effects. Mutation data
reported. An anticoagulant drug. When
heated to decomposition it emits toxic
fumes of Na2O. | [Toxicity]
LD50 in male rats, female rats, mice, rabbits (mg/kg): 323, 58, 374, ~800 orally (Hagen); also reported as LD50 in male, female rats (mg/kg): 100.3, 8.7 orally (Back) |
| Hazard Information | Back Directory | [General Description]
Slightly bitter crystalline powder. An anticoagulant used as a rodenticide. | [Reactivity Profile]
A coumarin derivative, a lactone. Lactones are similar to esters reactive chemistries. | [Health Hazard]
This material is highly toxic orally in humans. | [Fire Hazard]
When heated to decomposition, WARFARIN SODIUM emits toxic fumes of sodium oxide. | [Chemical Properties]
Colorless solid | [Originator]
Coumadin ,Endo,US,1954 | [Uses]
central stimulant | [Uses]
Rodenticide. | [Manufacturing Process]
About 0.1 mol each of 4-hydroxycoumarin and benzalacetone are dissolved, in
any desired order, in about three times their combined weight of pyridine. The
solution is refluxed for about 24 hours, and then allowed to cool; after which
it is poured into about 15 volumes of water, and acidified to about pH 2 by the
addition of hydrochloric acid. An oil separates, and on cooling and standing
overnight solidifies. The solid product is recovered, as by filtration, and
recrystallized from ethanol, according to US Patent 2,427,578.
The base melts at about 161°C. It is a white crystalline solid, soluble in hot
ethyl alcohol and substantially insoluble in cold water; it dissolves in alkali
solutions with formation of the salt. The yield is about 40%.
Then, as described in US Patent 2,777,859, warfarin may be reacted with
NaOH to give a sodium salt solution. Crystalline warfarin sodium may be
prepared as described in US Patent 2,765,321. | [Brand name]
Athrombin (Purdue Frederick); Coumadin (Bristol-Myers
Squibb); Jantoven (USl); Panwarfin (Abbott). | [Therapeutic Function]
Anticoagulant | [Clinical Use]
By virtue of its great potency, warfarin sodium at firstwas considered unsafe for use in humans and was used veryeffectively as a rodenticide, especially against rats. At theproper dosage level, however, it can be used in humans, especiallythrough the intravenous route. | [Veterinary Drugs and Treatments]
In veterinary medicine, warfarin is used primarily for the oral,
long-term treatment (or prevention of recurrence) of thrombotic
conditions, primarily in cats, dogs, or horses. Use of warfarin in
veterinary species is somewhat controversial and due to unproven
benefit in reducing mortality, increased expense associated with
monitoring, and potential for serious effects (bleeding), many do
not recommend its use. | [Drug interactions]
Potentially hazardous interactions with other drugs
There are many significant interactions with warfarin.
Prescribe with care with regard to the following:
Anticoagulant effect enhanced by: alcohol,
amiodarone, anabolic steroids, aspirin, aztreonam,
bicalutamide, cephalosporins, chloramphenicol,
cimetidine, ciprofloxacin, clopidogrel, cranberry
juice, danazol, danshen, dipyridamole, dronedarone,
disulfiram, entacapone, esomeprazole, exenatide,
ezetimibe, fibrates, fluconazole, flutamide, fluvastatin,
glucosamine, grapefruit juice, itraconazole,
ketoconazole, levamisole, levofloxacin, macrolides,
methylphenidate, metronidazole, miconazole,
mirtazepine, nalidixic acid, neomycin, norfloxacin,
NSAIDs, ofloxacin, omeprazole, pantoprazole,
paracetamol, penicillins, proguanil, propafenone,
ritonavir, rosuvastatin, saquinavir, SSRIs, simvastatin,
sulfinpyrazone, sulphonamides, tamoxifen, tegafur,
testosterone, tetracyclines, thyroid hormones,
tigecycline, toremifene, tramadol, trimethoprim,
valproate, venlafaxine, vitamin E and voriconazole.
Anticoagulant effect decreased by: acitretin,
atorvastatin, azathioprine, barbiturates,
carbamazepine, enteral feeds, eslicarbazepine,
enzalutamide, fosphenytoin, ginseng, griseofulvin,
oral contraceptives, phenobarbital, phenytoin,
primidone, rifamycins, St John’s wort (avoid
concomitant use), sucralfate, vitamin K.
Anticoagulant effects enhanced / reduced by: anion
exchange resins, atazanavir, corticosteroids, dietary
changes, disopyramide, efavirenz, fosamprenavir,
nevirapine, ritonavir, telaprevir, tricyclics, trazodone.
Analgesics: increased risk of bleeding with IV
diclofenac and ketorolac - avoid concomitant use.
Anticoagulants: increased risk of haemorrhage with
apixaban, dabigatran, edoxaban and rivaroxaban -
avoid concomitant use.
Antidiabetic agents: enhanced hypoglycaemic
effect with sulphonylureas; also possible changes to
anticoagulant effect.
Camomile: enhanced anticoagulation.
Ciclosporin: there have been a few reports of altered
anticoagulant effect; decreased ciclosporin levels have
been seen rarely.
Cytotoxics: increased risk of bleeding with erlotinib,
imatinib and regorafenib; enhanced effect with
capecitabine, etoposide, fluorouracil, ifosfamide,
gefitinib, gemcitabine, sorafenib and vemurafenib;
reduced effect with mercaptopurine and mitotane.
Melatonin: possibly enhanced INR. | [Metabolism]
The R- and S-isomers are both metabolised in the liver. The
S-isomer is metabolised more rapidly than the R-isomer,
mainly by the cytochrome P450 isoenzyme CYP2C9, which
shows genetic polymorphism. Other isoenzymes are also
involved in the metabolism of the R-isomer.
The metabolites, which have negligible or no
anticoagulant activity, are excreted in the urine following
reabsorption from the bile.
Dose in renal impairment G |
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