Dicumarol

• Catalog No.: DB00266
• CAS Number: 66-76-2
• M. F.: C19H12O6
• M. W.: 336.29498

SYNONYMS

• IUPAC name: 2-hydroxy-3-[(2-hydroxy-4-oxo-4H-chromen-3-yl)methyl]-4H-chromen-4-one
• IUPAC Traditional name: dicumarol
• Brand Name: Cuma; Acavyl; Antitrombosin; Baracoumin; Cumid; Dicoumal; Dicumarine; Dicumol; Dikumarol; Dufalone; Temparin; Acadyl; Dicuman; Dicumaol R; Kumoran; Melitoxin; Trombosan
• Synonyms: Bishydroxycoumarin; Dicoumarol; BHC; Dicoumarin; Bis-Hydroxycoumarin

DATABASE IDS

• CAS Number: 66-76-2

PROPERTIES

• Hydrophobicity(logP): 3.1
• Solubility: 128 mg/L

DETAILS

Description (English)

• Drug Groups: approved
• Description: An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases. [PubChem]
• Indication: For decreasing blood clotting. Often used along with heparin for treatment of deep vein thrombosis.
• Pharmacology: Dicumarol is an coumarin-like compound found in sweet clover. It is used as an oral anticoagulant and acts by inhibiting the hepatic synthesis of vitamin K-dependent coagulation factors (prothrombin and factors VII, IX, and X). It is also used in biochemical experiments as an inhibitor of reductases.
• Toxicity: LD₅₀=233 mg/kg (orally in mice); LD₅₀=250 mg/kg (orally in rats)
• Affected Organisms: Humans and other mammals
• References: Cullen JJ, Hinkhouse MM, Grady M, Gaut AW, Liu J, Zhang YP, Weydert CJ, Domann FE, Oberley LW: Dicumarol inhibition of NADPH:quinone oxidoreductase induces growth inhibition of pancreatic cancer via a superoxide-mediated mechanism. Cancer Res. 2003 Sep 1;63(17):5513-20. [Pubmed] ; Mironov AA, Colanzi A, Polishchuk RS, Beznoussenko GV, Mironov AA Jr, Fusella A, Di Tullio G, Silletta MG, Corda D, De Matteis MA, Luini A: Dicumarol, an inhibitor of ADP-ribosylation of CtBP3/BARS, fragments golgi non-compact tubular zones and inhibits intra-golgi transport. Eur J Cell Biol. 2004 Jul;83(6):263-79. [Pubmed] ; Abdelmohsen K, Stuhlmann D, Daubrawa F, Klotz LO: Dicumarol is a potent reversible inhibitor of gap junctional intercellular communication. Arch Biochem Biophys. 2005 Feb 15;434(2):241-7. [Pubmed] ; Thanos CG, Liu Z, Reineke J, Edwards E, Mathiowitz E: Improving relative bioavailability of dicumarol by reducing particle size and adding the adhesive poly(fumaric-co-sebacic) anhydride. Pharm Res. 2003 Jul;20(7):1093-100. [Pubmed]
• External Links: Wikipedia

REFERENCES

• Cullen JJ, Hinkhouse MM, Grady M, Gaut AW, Liu J, Zhang YP, Weydert CJ, Domann FE, Oberley LW: Dicumarol inhibition of NADPH:quinone oxidoreductase induces growth inhibition of pancreatic cancer via a superoxide-mediated mechanism. Cancer Res. 2003 Sep 1;63(17):5513-20. Pubmed
• Mironov AA, Colanzi A, Polishchuk RS, Beznoussenko GV, Mironov AA Jr, Fusella A, Di Tullio G, Silletta MG, Corda D, De Matteis MA, Luini A: Dicumarol, an inhibitor of ADP-ribosylation of CtBP3/BARS, fragments golgi non-compact tubular zones and inhibits intra-golgi transport. Eur J Cell Biol. 2004 Jul;83(6):263-79. Pubmed
• Abdelmohsen K, Stuhlmann D, Daubrawa F, Klotz LO: Dicumarol is a potent reversible inhibitor of gap junctional intercellular communication. Arch Biochem Biophys. 2005 Feb 15;434(2):241-7. Pubmed
• Thanos CG, Liu Z, Reineke J, Edwards E, Mathiowitz E: Improving relative bioavailability of dicumarol by reducing particle size and adding the adhesive poly(fumaric-co-sebacic) anhydride. Pharm Res. 2003 Jul;20(7):1093-100. Pubmed