MedKoo Cat#: 317606 | Name: Dicumarol
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dicoumarol (INN) or dicumarol (USAN) is a naturally occurring anticoagulant that functions as a functional vitamin K depleter (similar to warfarin, a drug that dicoumarol inspired). It is also used in biochemical experiments as an inhibitor of reductases. Like all 4-hydroxycoumarin drugs it is a competitive inhibitor of vitamin K epoxide reductase, an enzyme that recycles vitamin K, thus causing depletion of active vitamin K in blood. This prevents the formation of the active form of prothrombin and several other coagulant enzymes. These compounds are not antagonists of Vitamin K directly—as they are in pharmaceutical uses—but rather promote depletion of vitamin K in bodily tissues allowing vitamin K's mechanism of action as a potent medication for dicoumarol toxicity. The mechanism of action of Vitamin K along with the toxicity of dicoumarol are measured with the prothrombin time (PT) blood test. (Source: https://en.wikipedia.org/wiki/Dicoumarol).

Chemical Structure

Dicumarol
CAS#66-76-2

Theoretical Analysis

MedKoo Cat#: 317606

Name: Dicumarol

CAS#: 66-76-2

Chemical Formula: C19H12O6

Exact Mass: 336.0634

Molecular Weight: 336.29

Elemental Analysis: C, 67.86; H, 3.60; O, 28.55

Price and Availability

Size Price Availability Quantity
2g USD 150.00 2 Weeks
5g USD 250.00 2 Weeks
10g USD 350.00 2 Weeks
25g USD 650.00 2 Weeks
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Related CAS #
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Synonym
Dicumarol; Dicoumarol; Bishydroxycoumarin; Dicoumarin; Melitoxin; Antitrombosin; NSC 17860; NSC17860; NSC-17860; NSC 41834; NSC41834; NSC-41834; NSC 221570; NSC221570; NSC-221570;
IUPAC/Chemical Name
4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one
InChi Key
DOBMPNYZJYQDGZ-UHFFFAOYSA-N
InChi Code
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
SMILES Code
C1=CC=C2C(=C1)C(=C(C(=O)O2)CC3=C(C4=CC=CC=C4OC3=O)O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO, not in water
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Biological target:
Dicoumarol is an inhibitor of both NAD(P)H:quinone oxidoreductase 1 (NQO1) and PDK1 with IC50s of 0.37 and 19.42 μM, respectively.
In vitro activity:
Exposure of rat liver epithelial cells or of human skin fibroblasts to dicumarol resulted in a rapid and complete inhibition of connexin-43-dependent gap junctional intercellular communication (GJC). Reference: Arch Biochem Biophys. 2005 Feb 15;434(2):241-7. https://pubmed.ncbi.nlm.nih.gov/15639223/
In vivo activity:
During the 12-day treatment, the body weight from all groups of mice did not significantly change, suggesting that all treatments were safe for the animals (Fig 6A). However, DCA at 100 mg/kg, DIC (dicumarol) at 30 mg/kg, and DIC at 50 mg/kg all significantly reduced tumor volume and decreased tumor weight, when compared to tumors from control or vehicle groups (Fig 6B). Reference: PLoS One. 2017; 12(6): e0179672. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5472302/
Solvent mg/mL mM comments
Solubility
DMSO 3.1 9.10
DMSO:PBS (pH 7.2) (1:1) 0.5 1.49
DMF 1.3 3.72
Water 50.0 148.68
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 336.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. 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. doi: 10.1016/j.abb.2004.11.002. PMID: 15639223. 2. 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. doi: 10.1078/0171-9335-00377. PMID: 15511084. 3. Zhang W, Su J, Xu H, Yu S, Liu Y, Zhang Y, Sun L, Yue Y, Zhou X. Dicumarol inhibits PDK1 and targets multiple malignant behaviors of ovarian cancer cells. PLoS One. 2017 Jun 15;12(6):e0179672. doi: 10.1371/journal.pone.0179672. PMID: 28617852; PMCID: PMC5472302. 4. Díaz-Véliz G, Mora S, Gómez P, Dossi MT, Montiel J, Arriagada C, Aboitiz F, Segura-Aguilar J. Behavioral effects of manganese injected in the rat substantia nigra are potentiated by dicumarol, a DT-diaphorase inhibitor. Pharmacol Biochem Behav. 2004 Feb;77(2):245-51. doi: 10.1016/j.pbb.2003.10.016. PMID: 14751451.
In vitro protocol:
1. 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. doi: 10.1016/j.abb.2004.11.002. PMID: 15639223. 2. 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. doi: 10.1078/0171-9335-00377. PMID: 15511084.
In vivo protocol:
1. Zhang W, Su J, Xu H, Yu S, Liu Y, Zhang Y, Sun L, Yue Y, Zhou X. Dicumarol inhibits PDK1 and targets multiple malignant behaviors of ovarian cancer cells. PLoS One. 2017 Jun 15;12(6):e0179672. doi: 10.1371/journal.pone.0179672. PMID: 28617852; PMCID: PMC5472302. 2. Díaz-Véliz G, Mora S, Gómez P, Dossi MT, Montiel J, Arriagada C, Aboitiz F, Segura-Aguilar J. Behavioral effects of manganese injected in the rat substantia nigra are potentiated by dicumarol, a DT-diaphorase inhibitor. Pharmacol Biochem Behav. 2004 Feb;77(2):245-51. doi: 10.1016/j.pbb.2003.10.016. PMID: 14751451.
1: Salan Ü, Altındal A, Özkaya AR, Salih B, Bekaroğlu Ö. Photovoltaic and electrocatalytic properties of novel ball-type phthalocyanines bridged with four dicumarol. Dalton Trans. 2012 May 7;41(17):5177-87. doi: 10.1039/c2dt12510b. Epub 2012 Mar 19. PubMed PMID: 22430033. 2: Du J, Daniels DH, Asbury C, Venkataraman S, Liu J, Spitz DR, Oberley LW, Cullen JJ. Mitochondrial production of reactive oxygen species mediate dicumarol-induced cytotoxicity in cancer cells. J Biol Chem. 2006 Dec 8;281(49):37416-26. Epub 2006 Oct 13. PubMed PMID: 17040906. 3: 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 PMID: 15639223. 4: 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 PMID: 15511084. 5: Lewis A, Ough M, Li L, Hinkhouse MM, Ritchie JM, Spitz DR, Cullen JJ. Treatment of pancreatic cancer cells with dicumarol induces cytotoxicity and oxidative stress. Clin Cancer Res. 2004 Jul 1;10(13):4550-8. PubMed PMID: 15240547. 6: Bustamante D, Bustamante L, Segura-Aguilar J, Goiny M, Herrera-Marschitz M. Effects of the DT-diaphorase inhibitor dicumarol on striatal monoamine levels in L-DOPA and L-deprenyl pre-treated rats. Neurotox Res. 2004;5(8):569-77. PubMed PMID: 15111234. 7: Díaz-Véliz G, Mora S, Gómez P, Dossi MT, Montiel J, Arriagada C, Aboitiz F, Segura-Aguilar J. Behavioral effects of manganese injected in the rat substantia nigra are potentiated by dicumarol, a DT-diaphorase inhibitor. Pharmacol Biochem Behav. 2004 Feb;77(2):245-51. PubMed PMID: 14751451. 8: 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 PMID: 14500388. 9: Thanos CG, Liu Z, Goddard M, Reineke J, Bailey N, Cross M, Burrill R, Mathiowitz E. Enhancing the oral bioavailability of the poorly soluble drug dicumarol with a bioadhesive polymer. J Pharm Sci. 2003 Aug;92(8):1677-89. PubMed PMID: 12884254. 10: 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 PMID: 12880296.