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Substance Name: Dicumarol [USAN:USP]
RN: 66-76-2
UNII: 7QID3E7BG7
InChIKey: DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Note

  • An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.

Molecular Formula

  • C19-H12-O6

Molecular Weight

  • 336.298
 

Classification Codes

  • Agricultural Chemical
  • Anticoagulant
  • Anticoagulants
  • Drug / Therapeutic Agent
  • Enzyme Inhibitors
  • Hematologic Agents
  • Human Data
  • Out-Dated Pesticide
  • Reproductive Effect
  • Rodenticide
  • Uncoupling Agents
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Names and Synonyms

Name of Substance

  • Dicoumarol [INN]
  • Dicumarol
  • Dicumarol [USAN:USP]

MeSH Heading

  • Dicumarol

Synonyms

  • 2H-1-Benzopyran-2-one), 3,3'-methylenebis(4-hydroxy-
  • 3,3'-Methyleen-bis(4-hydroxy-cumarine)
  • 3,3'-Methyleen-bis(4-hydroxy-cumarine) [Dutch]
  • 3,3'-Methylen-bis(4-hydroxy-cumarin)
  • 3,3'-Methylen-bis(4-hydroxy-cumarin) [German]
  • 3,3'-Methylene-bis(4-hydroxycoumarine)
  • 3,3'-Methylene-bis(4-hydroxycoumarine) [French]
  • 3,3'-Methylenebis(4-hydroxy-1,2-benzopyrone)
  • 3,3'-Methylenebis(4-hydroxy-2H-1-benzopyran-2-one)
  • 3,3'-Methylenebis(4-hydroxycoumarin)
  • 3,3'-Metilen-bis(4-idrossi-cumarina)
  • 3,3'-Metilen-bis(4-idrossi-cumarina) [Italian]
  • 4,4'-Dihydroxy-3,3'-methylene bis coumarin
  • 5-19-06-00682 (Beilstein Handbook Reference)
  • Acadyl
  • Acavyl
  • AI3-14546
  • Anathrombase
  • Antitrombosin
  • Apekumarol
  • Baracoumin
  • BHC
  • Bis(4-hydroxycoumarin-3-yl)methane
  • Bis-3,3'-(4-hydroxycoumarinyl)methane
  • Bis-3,3'-(4-oxycoumarinyl)ethylacetate
  • Bishydroxycoumarin
  • BRN 0335444
  • CCRIS 3713
  • Coumarin, 3,3'-methylenebis(4-hydroxy-
  • Cuma
  • Cumid
  • Di-(4-hydroxy-3-coumarinyl)methane
  • Di-4-hydroxy-3,3'-methylenedicoumarin
  • Dicoumal
  • Dicoumarin
  • Dicoumarol
  • Dicoumarolum
  • Dicoumarolum [INN-Latin]
  • Dicoumerol
  • Dicuman
  • Dicumaol R
  • Dicumarine
  • Dicumarinum
  • Dicumarol
  • Dicumarol [INN-Spanish]
  • Dicumarolo
  • Dicumarolo [DCIT]
  • Dicumarolum
  • Dicumol
  • Dufalone
  • Dwukumarol
  • Dwukumarol [Polish]
  • EINECS 200-632-9
  • HSDB 3223
  • Kumoran
  • Melitoxin
  • NC 034
  • NSC 17860
  • NSC 221570
  • NSC 41834
  • Temparin
  • Trombosan
  • UNII-7QID3E7BG7

Systematic Names

  • 2H-1-Benzopyran-2-one, 3,3'-methylenebis(4-hydroxy-
  • Coumarin, 3,3'-methylenebis(4-hydroxy-
  • Dicoumarol
  • Dicumarol

Superlist Name

  • Dicumarol

Registry Numbers

CAS Registry Number

  • 66-76-2

FDA UNII

  • 7QID3E7BG7

System Generated Number

  • 0000066762

Structure Descriptors

InChI

1S/C19H12O6/c20-16-10-5-1-3-7-14(10)24-18(22)12(16)9-13-17(21)11-6-2-4-8-15(11)25-19(13)23/h1-8,20-21H,9H2

InChIKey

DOBMPNYZJYQDGZ-UHFFFAOYSA-N

Smiles

c12c(oc(=O)c(c1O)Cc1c(c3c(cccc3)oc1=O)O)cccc2

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
dog LDLo intravenous 40mg/kg (40mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 57, 1973.
guinea pig LD50 intravenous 59mg/kg (59mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE

SENSE ORGANS AND SPECIAL SENSES: ULCERATED NASAL SEPTUM: OLFACTION
Proceedings of the Society for Experimental Biology and Medicine. Vol. 50, Pg. 228, 1942.
mouse LD50 intraperitoneal 91mg/kg (91mg/kg) CARDIAC: OTHER CHANGES

VASCULAR: PULSE PRESSURE INCREASE
Dissertationes Pharmaceuticae. Vol. 17, Pg. 163, 1965.
mouse LD50 intravenous 42mg/kg (42mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 222, Pg. 107, 1954.
mouse LD50 oral 233mg/kg (233mg/kg) SENSE ORGANS AND SPECIAL SENSES: ULCERATED NASAL SEPTUM: OLFACTION

GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE
Proceedings of the Society for Experimental Biology and Medicine. Vol. 50, Pg. 228, 1942.
mouse LD50 subcutaneous 50mg/kg (50mg/kg)   "CRC Handbook of Antibiotic Compounds," Vols.1- , Berdy, J., Boca Raton, FL, CRC Press, 1980Vol. 8(1), Pg. 360, 1982.
rabbit LD50 intravenous 22mg/kg (22mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 222, Pg. 107, 1954.
rabbit LD50 oral 75mg/kg (75mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 222, Pg. 107, 1954.
rat LD50 intravenous 52mg/kg (52mg/kg) GASTROINTESTINAL: ULCERATION OR BLEEDING FROM LARGE INTESTINE

SENSE ORGANS AND SPECIAL SENSES: ULCERATED NASAL SEPTUM: OLFACTION
Proceedings of the Society for Experimental Biology and Medicine. Vol. 50, Pg. 228, 1942.
rat LD50 oral 250mg/kg (250mg/kg)   Schweizerische Medizinische Wochenschrift. Vol. 83, Pg. 471, 1953.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 290 deg C   EXP
log P (octanol-water) 2.07 (none)   EXP
Water Solubility 128 mg/L 25 EST
Vapor Pressure 6.02E-17 mm Hg 25 EST
Henry's Law Constant 1.36E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 8.20E-11 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.