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Home> Encyclopedia >Cardiovascular Agents>Pharmaceutical Intermediates>Pharmaceutical
Warfarin sodium structure
Warfarin sodium structure

Warfarin sodium

Iupac Name:sodium;4-hydroxy-3-(3-oxo-1-phenylbutyl)chromen-2-one
CAS No.: 129-06-6
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+
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.

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

6. Synthesis Route
129-06-6Total: 1 Synthesis Route
7. Precursor and Product
product :
24579-14-4
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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