Warfarin sodium

Iupac Name：sodium;4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one

Molecular Weight：331.3

Modify Date.: 2022-11-10 19:55

Introduction: Warfarin sodium, 3-( -acetonylbenzyl)-4-hydroxycoumarin sodium salt (Coumadin,Panwarfin), is a white, odorless, crystalline powder, with aslightly bitter taste; it is slightly soluble in chloroform and solublein alcohol or water. A 1% solution has a pH of 7.2 to 8.5. View more+

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1. Names and Identifiers

1.1 Name: Warfarin sodium
1.2 Synonyms: 2H-1-Benzopyran-2-one, 4-hydroxy-3-(3-oxo-1-phenylbutyl)-, sodium salt (1:1) 3-(A-ACETONYLBENZYL)-4-HYDROXYCOUMARIN 3-(A-ACETONYLBENZYL)-4-HYDROXYCOUMARIN SODIUM 3-(A-ACETONYLBENZYL)-4-HYDROXYCOUMARIN SODIUM SALT 3-(ALPHA-ACETONYLBENZYL)-4-HYDROXYCOUMARIN 3-(Alpha-Acetonylbenzyl)-4-Hydroxycoumarin Sodiuim Salt 3-(ALPHA-ACETONYLBENZYL)-4-HYDROXYCOUMARIN SODIUM 3-(ALPHA-ACETONYLBENZYL)-4-HYDROXYCOUMARIN SODIUM CLATHRATE 3-(α-Acetonylbenzyl)-4-hydroxycoumarin Sodiuim Salt (contains Isopropyl Alcohol) 3-(α-ACETONYLBENZYL)-4-HYDROXYCOUMARIN SODIUM SALT 4-hydroxy-3-(3-oxo-1-phenylbutyl)-2H-1-benzopyran-2-one sodium salt 4-Hydroxy-3-(3-oxo-1-phenylbutyl)coumarin Sodium Salt (contains Isopropyl Alcohol) coumadin EINECS 204-929-4 marevan MFCD00083223 panwarfin rac-sodium 2-oxo-3-[(1R)-3-oxo-1-phenylbutyl]-2H-1-benzopyran-4-olate Sodium 2-oxo-3-(3-oxo-1-phenylbutyl)-2H-chromen-4-olate sodium 2-oxo-3-[(RS)-3-oxo-1-phenylbutyl]-2H-chromen-4-olate sodiumcoumadin sodiumwarfarin UNII:6153CWM0CL waran Warfarin SodiuM (contains Isopropyl Alcohol) warfarin sodium salt WARFARIN SODIUM, (CONTAINS ISOPROPYL ALCOHOL) WARFARIN SODIUM, EP STANDARD WARFARIN SODIUMLINE Warfarinsodium zoocoumarin-sodium

1.3 CAS No.: 129-06-6

1.4 CID: 54710741

1.5 EINECS(EC#): 204-929-4

1.6 Molecular Formula: C19H16NaO4+ (isomer)

1.7 Inchi: 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

1.8 InChkey: KYITYFHKDODNCQ-UHFFFAOYSA-N

1.9 Canonical Smiles: CC(=O)CC(C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=O)O.[Na+]

1.10 Isomers Smiles: CC(=O)CC(C1=CC=CC=C1)C2=C(C3=CC=CC=C3OC2=O)O.[Na+]

2. Properties

2.1 Density: 1.307

2.1 Melting point: approximate 161℃

2.1 Boiling point: 515.2°Cat760mmHg

2.1 Flash Point: 188.8°C

2.1 Precise Quality: 331.09462827

2.1 PSA: 70.34000

2.1 logP: 4.04780

2.1 Appearance: white or yellowish powder

2.2 Chemical Properties: Colorless solid

2.3 PH: pH (10g/l, 25℃) : 7.2～8.3

2.4 Water Solubility: Very soluble in water and in ethanol (96 per cent), soluble in acetone, very slightly soluble in methylene chloride.

2.5 Stability: Contact with strong oxidizers may cause fires and explosions.

2.6 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 General Description: Warfarin sodium, 3-( -acetonylbenzyl)-4-hydroxycoumarin sodium salt (Coumadin,Panwarfin), is a white, odorless, crystalline powder, with aslightly bitter taste; it is slightly soluble in chloroform and solublein alcohol or water. A 1% solution has a pH of 7.2 to 8.5.

3.2 Usage: central stimulant

4. Safety and Handling

4.1 Symbol: GHS06, GHS08

4.1 Hazard Codes: T+

4.1 Signal Word: Danger

4.1 Risk Statements: R61;R28

4.1 Safety Statements: S53;S36/37/39;S45

4.1 Packing Group: II

4.1 Fire Hazard: When heated to decomposition, Warfarin sodium emits toxic fumes of sodium oxide.

4.2 Hazard Class: 6.1(a)

4.2 Hazard Declaration: H300-H360

4.2 RIDADR: UN 1544

4.2 Safety Profile: Poison to humans byingestion. Experimental poison by ingestionand intravenous routes. Human systemiceffects by ingestion: dermatitis. Humanreproductive effects by ingestion:fetotoxicity, abnormal condition of newbornat birth, other newborn physical effects, andteratogenic effects includmg developmentalabnormalities of the eye and ear, craniofacialarea, skin and appendages, musculoskeletalsystem, cardiovascular system, andgastrointestinal system of the fetus. ,4nexperimental teratogen. Other experimentalreproductive effects. Mutation datareported. An anticoagulant drug. Whenheated to decomposition it emits toxicfumes of Na2O.

4.3 Caution Statement: Missing Phrase - N15.00950417-P201-P280-P308 + P313

4.3 WGK Germany: 1

4.3 RTECS: GN4725000

4.3 Report: Reported in EPA TSCA Inventory. EPA Extremely Hazardous Substances List.

4.4 Safety: Safety Information of?Warfarin sodium (CAS NO.129-06-6):
Hazard Codes:T+
Risk Statements:61-28
Safety Statements:53-36/37/39-45
RIDADR:UN 1544 6.1/PG 2
WGK Germany:1
RTECS:GN4725000
HazardClass:6.1(a)
PackingGroup:II
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 including developmental abnormalities of the eye and ear, craniofacial area, skin and appendages, musculoskeletal system, cardiovascular system, and gastrointestinal system of the fetus. An experimental teratogen. Other experimental reproductive effects. Mutation data reported. An anticoagulant drug. When heated to decomposition it emits toxic fumes of Na₂O.

4.5 Specification: First Aid Measures of?Warfarin sodium (CAS NO.129-06-6):
Ingestion:Give water and induce vomiting. Never give anthing to an unconscious person. Obtain medical attention.
Inhalation:Remove to fresh air. Give CPR and/or oxygen if required.
Skin:Wash with soap and water.
Eyes:Flush with water for 15 minutes.
Storage of Warfarin sodium (CAS NO.129-06-6):
Store at away from heat and open flame. Do not store near feeds and foodstuffs and keep away from children, domestic animals, pets, or wildlife.

4.6 Toxicity

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
chicken	LD50	intravenous	200mg/kg (200mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BLOOD: HEMORRHAGE SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 42, Pg. 379, 1953.
child	TDLo	oral	4mg/kg (4mg/kg)	BLOOD: CHANGES IN CELL COUNT (UNSPECIFIED)	American Journal of Diseases of Children. Vol. 147, Pg. 609, 1993.
dog	LD50	intravenous	200mg/kg (200mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BLOOD: HEMORRHAGE SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 42, Pg. 379, 1953.
dog	LD50	oral	200mg/kg (200mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 42, Pg. 379, 1953.
guinea pig	LD50	oral	182mg/kg (182mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 42, Pg. 379, 1953.
guinea pig	LDLo	intravenous	543mg/kg (543mg/kg)	?	Therapie. Vol. 18, Pg. 921, 1963.
mouse	LD50	intravenous	160mg/kg (160mg/kg)	?	"Handbook of Analytical Toxicology," Sunshine, I., ed., Cleveland, OH, Chemical Rubber Co., 1969Vol. -, Pg. 123, 1969.
mouse	LD50	oral	374mg/kg (374mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 42, Pg. 379, 1953.
rabbit	LD50	intravenous	100mg/kg (100mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BLOOD: HEMORRHAGE SKIN AND APPENDAGES (SKIN): HAIR: OTHER	Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 42, Pg. 379, 1953.
rabbit	LD50	oral	800mg/kg (800mg/kg)	BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Journal of the American Pharmaceutical Association, Scientific Edition. Vol. 42, Pg. 379, 1953.
rat	LD50	intravenous	25mg/kg (25mg/kg)	?	"Handbook of Analytical Toxicology," Sunshine, I., ed., Cleveland, OH, Chemical Rubber Co., 1969Vol. -, Pg. 123, 1969.
rat	LD50	oral	8700ug/kg (8.7mg/kg)	BLOOD: HEMORRHAGE	Pharmacological Research Communications. Vol. 10, Pg. 445, 1978.
women	TDLo	oral	300ug/kg/2D (0.3mg/kg)	SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"	Archives of Dermatology. Vol. 116, Pg. 444, 1980.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 2

Acute toxicity - Dermal, Category 1

Acute toxicity - Inhalation, Category 2

Reproductive toxicity, Category 1A

Specific target organ toxicity \u2013 repeated exposure, Category 1

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Danger
Hazard statement(s)	H300 Fatal if swallowed H310 Fatal in contact with skin H330 Fatal if inhaled H372 Causes damage to organs through prolonged or repeated exposure
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product. P262 Do not get in eyes, on skin, or on clothing. P280 Wear protective gloves/protective clothing/eye protection/face protection. P260 Do not breathe dust/fume/gas/mist/vapours/spray. P271 Use only outdoors or in a well-ventilated area. P284 [In case of inadequate ventilation] wear respiratory protection. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood.
Response	P301+P310 IF SWALLOWED: Immediately call a POISON CENTER/doctor/\u2026 P321 Specific treatment (see ... on this label). P330 Rinse mouth. P302+P352 IF ON SKIN: Wash with plenty of water/... P310 Immediately call a POISON CENTER/doctor/\u2026 P361+P364 Take off immediately all contaminated clothing and wash it before reuse. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P320 Specific treatment is urgent (see ... on this label). P308+P313 IF exposed or concerned: Get medical advice/ attention. P314 Get medical advice/attention if you feel unwell.
Storage	P405 Store locked up. P403+P233 Store in a well-ventilated place. Keep container tightly closed.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

6. Synthesis Route

129-06-6Total: 1 Synthesis Route

81-81-2

129-06-6 175 Suppliers

Literatures:
WO2008/44246 A2, ; Page/Page column 6-8 ;
Yield: null

7. Precursor and Product

product :

24579-14-4

8. Other Information

8.0 Merck: 14,10038

8.1 Chemical Properties: Colorless solid

8.2 Originator: Coumadin ,Endo,US,1954

8.3 Uses: Warfarin Sodium (Crystalline Clathrate) is used for pharmaceutical care for patients with chronic heart failure and renal dysfunction.

8.4 Uses: central stimulant

8.5 Uses: Rodenticide.

8.6 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.

8.7 Brand name: Athrombin (Purdue Frederick); Coumadin (Bristol-Myers Squibb); Jantoven (USl); Panwarfin (Abbott).

8.8 Therapeutic Function: Anticoagulant

8.9 General Description: Warfarin sodium, 3-( -acetonylbenzyl)-4-hydroxycoumarin sodium salt (Coumadin,Panwarfin), is a white, odorless, crystalline powder, with aslightly bitter taste; it is slightly soluble in chloroform and solublein alcohol or water. A 1% solution has a pH of 7.2 to 8.5.

8.10 General Description: Slightly bitter crystalline powder. An anticoagulant used as a rodenticide.

8.11 Reactivity Profile: A coumarin derivative, a lactone. Lactones are similar to esters reactive chemistries.

8.12 Health Hazard: Warfarin sodium is highly toxic orally in humans.

8.13 Fire Hazard: When heated to decomposition, Warfarin sodium emits toxic fumes of sodium oxide.

8.14 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.

8.15 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.

8.16 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.

9. Computational chemical data

Molecular Weight: 331.3g/mol
Molecular Formula: C₁₉H₁₆NaO₄+
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 331.09462827
Monoisotopic Mass: 331.09462827
Complexity: 502
Rotatable Bond Count: 4
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 63.6
Heavy Atom Count: 24
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 1
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceB4OCAAAAAAAAAAAAAAAAAAAAAAAAAwYIAAAAAAAACBQAAAGgAACAAADQSAmAAyDoAABgCIAqDSCAACCAAgIAAIiAEGCMgMJzKEMRqCeiClwBEIuQeIzuCugAAAAAAIAAAAAAAAABAAAAAAAAAAAA==

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Warfarin Sodium