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4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzo-pyran-2-on,Natrium-Salz

Warfarin Sodium

HCID 16204922
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Grundinformationen

CAS
129-06-6
Standard-SMILES
CC(=O)CC(c1ccccc1)c1c([O-])c2ccccc2oc1=O.[Na+]
InChIKey
KYITYFHKDODNCQ-UHFFFAOYSA-M
Summenformel
C19H15O4.Na
Durchschnittliche Molmasse
330,3 g/mol
Monoisotopische Masse
330,08680324

Überblick

Warfarin sodium is a slightly bitter crystalline powder. An anticoagulant used as a rodenticide. (EPA, 1998)

Namen und Bezeichner

Bevorzugter Name
Warfarin Sodium
IUPAC
sodium 2-oxo-3-(3-oxo-1-phenylbutyl)chromen-4-olate
Lokaler Name
4-Hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzo-pyran-2-on,Natrium-Salz
Englischer Name
Warfarin sodium
Summenformel
C19H15O4.Na
Molmasse
331.32

Namen und Synonyme

Warfarin sodiumSodium warfarinAldocumarJantovenMarevanAthrombinProthromadinZoocoumarin sodium saltTintoraneWarcouminWarfiloneVarfine
Weitere Namen anzeigen
VITAMIN K2panwarfin3-(ALPHA-ACETONYLBENZYL)-4-HYDROXYCOUMARINSODIUM 4-OXO-3-(3-OXO-1-PHENYL-BUTYL)-CHROMEN-2-OLATE
Warfarin sodium saltCoumadin sodiumRatsul solubleSodium coumadinCoumafene sodiumWaranWarfarin, sodium saltApo-Warfarin

Datenbank-Bezeichner

CAS
129-06-6、5543-79-3、67430-45-9
PubChem CID
16204922
DTXSID
DTXSID7035010
ChEMBL
CHEMBL1200879
UNII
6153CWM0CL
EC Number
204-929-4、226-909-4、614-062-7
Nikkaji
J5.420H

Eigenschaften

Berechnete StruktureigenschaftenWird ergänzt

Polarare Oberfläche (TPSA)
66,4 Ų
H-Brücken-Donoren
0
H-Brücken-Akzeptoren
4
Frei drehbare Bindungen
4
Schwere Atome
24
Formalladung
0
Komplexität
507

Experimentelle und physikochemische Eigenschaften

Human Drugs · 3 Einträge

Breast Feeding; Lactation; Milk, Human; Anticoagulants

FDA approved drugs -> Active ingredient

FDA approved drugs -> Active ingredient

Vapor Pressure0.00001 [mm Hg] @25 °C
Physical DescriptionWarfarin sodium is a slightly bitter crystalline powder. An anticoagulant used as a rodenticide. (EPA, 1998)

Physikochemische Eigenschaften

Schmelzpunkt
161 ℃ · approximate 161℃
Dichte
1.3128 g/cm³ · 1.3128 g/cm³ (solid)
storage temp.
2 · 2-8°C
Löslichkeit
Very soluble in water and in ethanol (96 per cent), soluble in acetone, very slightly soluble in methylene chloride.
Aggregatzustand
powder
Farbe
White to Almost white
PH
pH (10g/l, 25℃) : 7.2~8.3
Merck
14 · 14,10038

Sicherheit und Regulatorisches

Sicherheitsangaben dienen nur zur Orientierung und ersetzen weder das Sicherheitsdatenblatt (SDB) des Lieferanten noch geltende Vorschriften oder eine fachliche Bewertung.

GHS-Klassifizierung

GHS Classification · 4 Einträge

Danger

H300 (99.1%): Fatal if swallowed [Danger Acute toxicity, oral]

P203, P260, P262, P264, P270, P271, P280, P284, P301+P316, P302+P352, P304+P340, P316, P318, P319, P320, P321, P330, P361+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 106 reports by companies from 14 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Gefahrenhinweise

Regulatory Information · 2 Einträge

Warfarin sodium: HSNO Approval: HSR006995 Approved with controls

The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)

Other Safety InformationIMAP assessments - 2H-1-Benzopyran-2-one, 4-hydroxy-3-(3-oxo-1-phenylbutyl)-, sodium salt: Environment tier I assessment
DOT LabelPoison
Fire HazardsWhen heated to decomposition, it emits toxic fumes of sodium oxide. (EPA, 1998)
Health HazardsThis material is highly toxic orally in humans. (EPA, 1998)
Reactive GroupAlcohols and Polyols
Reactivity ProfileA coumarin derivative, a lactone. Lactones are similar to esters reactive chemistries.
Air and Water Reactions

Chemie und Industrie

Pharmakologische Informationen

Metabolism/Metabolites · 1 Eintrag

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<sub>1/2</sub>=37-89 hours; S-warfarin t<sub>1/2</sub>=21-43 hours.

FDA Pharmacological Classification · 2 Einträge

WARFARIN SODIUM

Vitamin K Antagonist [EPC]; Vitamin K Inhibitors [MoA]

MeSH Pharmacological Classification · 2 Einträge

Agents that prevent BLOOD CLOTTING.

Substances used to destroy or inhibit the action of rats, mice, or other rodents.

Verwendung und Herstellung

Uses · 1 Eintrag

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)

Zugehörige Reaktionen

2
Reaktionsaufzeichnung erstellen
Reaktionsgleichung von HRID 1636002
HRID 1636002als Produktuspto-grants-2003_01
Reaktionsgleichung von HRID 2248553
HRID 2248553als Eduktuspto-grants-1991_08

Notizen zur Verbindung

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BCS Class
1 · 1,2
InChI
1S/C19H16O4.Na/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;/q;+1/p-1
InChIKey
KYITYFHKDODNCQ-UHFFFAOYSA-M
SMILES
[Na].CC(=O)CC(c1ccccc1)C2=C(O)c3ccccc3OC2=O
CAS Datenbank
129 · 129-06-6(CAS DataBase Reference)
EPA chemische Informationen
Sodium warfarin (129-06-6)
No rapid reaction with air. No rapid reaction with water.
Hazard Classes and CategoriesAcute Tox. 2 (99.1%)

Sicherheit und Schutzausrüstung

Fire Fighting · 1 Eintrag

(Non-Specific -- Coumarin Derivative Pesticide, Solid, n.o.s.) Keep unnecessary people away; isolate hazard area and deny entry. Stay upwind; keep out of low areas. Ventilate closed spaces before entering them. Wear positive pressure breathing apparatus and special protective clothing. Remove and isolate contaminated clothing at the site. Move container from fire area if you can do it without risk. Fight fire from maximum distance. Dike fire control water for later disposal; do not scatter the material.

First Aid · 1 Eintrag

Signs and Symptoms of Acute Warfarin Sodium Exposure: Warfarin sodium is an anticoagulant. Hemorrhage is the most common sign and may be manifested by hemorrhagic skin rashes and lip, nose, and upper airway bleeding. Upper airway pain, difficulty in speaking and swallowing, and dyspnea (shortness of breath) may occur. Vomiting, abdominal pain, and bloody stools are common. Back pain may be noted.

Nonfire Spill Response · 1 Eintrag

(Non-Specific -- Coumarin Derivative Pesticide, Solid, n.o.s.) Do not touch spilled material; stop leak if you can do it without risk. Use water spray to reduce vapors. For small spills, take up with sand or other noncombustible absorbent material and place into containers for later disposal. For small dry spills, with clean shovel place material into clean, dry container and cover; move containers from spill area. For large spills, dike far ahead of spill for later disposal. (EPA, 1998)

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Protective Action Criteria (PAC) · 3 Einträge

0.16 [mg/m3]

9.0 [mg/m3]

83 [mg/m3]

Personal Protective Equipment (PPE) · 1 Eintrag

For emergency situations, wear a positive pressure, pressure-demand, full facepiece self-contained breathing apparatus (SCBA) or pressure- demand supplied air respirator with escape SCBA and a fully-encapsulating, chemical resistant suit. (EPA, 1998)

Toxikologische Informationen

Treatment · 1 Eintrag

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)

Health EffectsHemorrhage is the most prevalent adverse effect of oral anticoagulant therapy. The incidence of bleeding complications is related to the duration and range of therapy. (L1151)
Exposure RoutesOral ; Inhalation ; Dermal Rapidly absorbed following oral administration with considerable interindividual variations. Also absorbed percutaneously.
Toxicity Summary · 1 Eintrag

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.

Signs and SymptomsLD<sub>50</sub>=374 (orally in mice)
Carcinogen ClassificationNo indication of carcinogenicity (not listed by IARC). (L135)
Drug Induced Liver Injury · 6 Einträge

Drug Induced Liver Injury Rank (DILIrank 2.0)

Warfarin sodium

vLess-DILI-concern

5

Adverse reactions

DOI:10.1016/j.drudis.2016.02.015

Effects During Pregnancy and Lactation◉ Summary of Use during Lactation
Toxicity DataLD50: 374 mg/kg (Oral, Mouse) (A308)

Sicherheitsdaten

wgk
1
tsca
TSCA listed
ridadr
UN 1544 6.1/PG 2
hs_code
29322090
RTECS-Nr.
GN4725000
risk_code
61-28
Toxizität
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_code
T+
safety_code
53-36/37/39-45-36/37-28
hazard_class
6.1(a)
packing_group
II
Speicherklasse
6.1A - Combustible acute toxic Cat. 1 and 2very toxic hazardous materials
Hazard Classifications
Acute Tox. 2 OralAquatic Chronic 3Repr. 1B
General Manufacturing Information2H-1-Benzopyran-2-one, 4-hydroxy-3-(3-oxo-1-phenylbutyl)-, sodium salt (1:1): ACTIVE

Anwendungen

VerwendenWarfarin Sodium (Crystalline Clathrate) is used for pharmaceutical care for patients with chronic heart failure and renal dysfunction.

Vor- und nachgelagerte Produkte

Vorgelagerte Rohstoffe

Natriumhydroxid4-Phenylbutenon4-Hydroxycumarin