Details of the Drug

General Information of Drug (ID: DMFQCB1)

Drug Name
Dicumarol
Synonyms
Acadyl; Acavyl; Anathrombase; Antitrombosin; Apekumarol; Baracoumin; Bishydroxycoumarin; Cuma; Cumid; Dicoumal; Dicoumarin; Dicoumarol; Dicoumarolum; Dicoumerol; Dicuman; Dicumarine; Dicumarinum; Dicumarolo; Dicumarolum; Dicumol; Dikumarol; Dufalone; Dwukumarol; Kumoran; Melitoxin; Temparin; Trombosan; Dicumaol R; Dicumarol [USAN]; Dicumarolo [DCIT]; Dwukumarol [Polish]; Uncoupler of oxidative respiration; M0216; NC 034; Bis-hydroxycoumarin; Dicoumarol (INN); Dicoumarolum [INN-Latin]; Dicumarol (TN); Dicumarol (USAN); Dicumarol [INN-Spanish]; Symmetric dicoumarol analogue, 1; Bis(4-hydroxycoumarin-3-yl)methane; Di-(4-hydroxy-3-coumarinyl)methane; Bis-3,3'-(4-hydroxycoumarinyl)methane; Bis-3,3'-(4-oxycoumarinyl)ethylacetate; Di-4-hydroxy-3,3'-methylenedicoumarin; Coumarin, 3,3'-methylenebis[4-hydroxy-(8CI); 2-hydroxy-3-[(2-hydroxy-4-oxochromen-3-yl)methyl]chromen-4-one; 2H-1-Benzopyran-2-one, 3,3'-methylenebis[4-hydroxy-(9CI); 3,3′-Methylenebis(4-hydroxycoumarin); 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-hydroxycoumarin); 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'-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]; 3,3'-methanediylbis(4-hydroxy-2H-chromen-2-one); 3,3'-methylenebis(2-hydroxy-4h-chromen-4-one); 3,3'-methylenebis(4-hydroxy-2H-chromen-2-one); 3,3-Methylene-bis[4-hydroxycoumarin]; 4,4'-Dihydroxy-3,3'-methylene bis coumarin
Indication
Disease Entry ICD 11 Status REF
Bleeding disorder GA20-GA21 Approved [1]
Myocardial infarction BA41-BA43 Approved [2]
Thrombosis DB61-GB90 Approved [1]
Intracranial embolism 8B22.1 Investigative [2]
Venous thromboembolism BD72 Investigative [2]
Therapeutic Class
Anticoagulants
Affected Organisms
Humans and other mammals
ATC Code
B01AA01: Dicumarol
B01AA: Vitamin K antagonists
B01A: ANTITHROMBOTIC AGENTS
B01: ANTITHROMBOTIC AGENTS
B: BLOOD AND BLOOD FORMING ORGANS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 0 Molecular Weight (mw) 336.3
Logarithm of the Partition Coefficient (xlogp) 2.6
Rotatable Bond Count (rotbonds) 2
Hydrogen Bond Donor Count (hbonddonor) 2
Hydrogen Bond Acceptor Count (hbondacc) 6
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [3]
Elimination
0.5% of drug is excreted from urine in the unchanged form [3]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 8.5 micromolar/kg/day [4]
Water Solubility
The ability of drug to dissolve in water is measured as 0.128 mg/mL [3]
Chemical Identifiers
Formula
C19H12O6
IUPAC Name
4-hydroxy-3-[(4-hydroxy-2-oxochromen-3-yl)methyl]chromen-2-one
Canonical SMILES
C1=CC=C2C(=C1)C(=C(C(=O)O2)CC3=C(C4=CC=CC=C4OC3=O)O)O
InChI
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
Cross-matching ID
PubChem CID
54676038
ChEBI ID
CHEBI:4513
CAS Number
66-76-2
UNII
7QID3E7BG7
DrugBank ID
DB00266
TTD ID
D02TJS
INTEDE ID
DR1746
Repurposed Drugs (RPD) Click to Jump to the Detailed RPD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Vitamin K epoxide reductase complex 1 (VKORC1) TTEUC8H VKOR1_HUMAN Inhibitor [5]

Drug-Metabolizing Enzyme (DME)
DME Name DME ID UniProt ID MOA REF
Cytochrome P450 2C9 (CYP2C9)
Main DME 		DE5IED8 CP2C9_HUMAN Substrate [6]

Drug Off-Target (DOT)
DOT Name DOT ID UniProt ID Interaction REF
Albumin (ALB) OTVMM513 ALBU_HUMAN Protein Interaction/Cellular Processes [7]
Catalase (CAT) OTHEBX9R CATA_HUMAN Drug Response [8]
Cellular tumor antigen p53 (TP53) OTIE1VH3 P53_HUMAN Gene/Protein Processing [9]
Mitogen-activated protein kinase 10 (MAPK10) OTC46VX1 MK10_HUMAN Gene/Protein Processing [10]
NAD(P)H dehydrogenase 1 (NQO1) OTZGGIVK NQO1_HUMAN Gene/Protein Processing [11]
Retinoblastoma-associated protein (RB1) OTQJUJMZ RB_HUMAN Post-Translational Modifications [12]
Superoxide dismutase , mitochondrial (SOD2) OTIWXGZ9 SODM_HUMAN Drug Response [8]
Vitamin K epoxide reductase complex subunit 1 OTOJNJRD VKOR1_HUMAN Gene/Protein Processing [13]
Vitamin K epoxide reductase complex subunit 1-like protein 1 OT7QSEWT VKORL_HUMAN Gene/Protein Processing [13]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Same Disease as Dicumarol
DDI Drug Name DDI Drug ID Severity Mechanism Disease REF
Apixaban DM89JLN Major Increased risk of bleeding by the combination of Dicumarol and Apixaban. Thrombosis [DB61-GB90] [14]
Cangrelor DM8JRH0 Major Increased risk of bleeding by the combination of Dicumarol and Cangrelor. Thrombosis [DB61-GB90] [15]
Brilinta DMBR01X Moderate Increased risk of bleeding by the combination of Dicumarol and Brilinta. Thrombosis [DB61-GB90] [14]
Argatroban DMFI46A Major Increased risk of bleeding by the combination of Dicumarol and Argatroban. Thrombosis [DB61-GB90] [16]
Clopidogrel DMOL54H Major Increased risk of bleeding by the combination of Dicumarol and Clopidogrel. Thrombosis [DB61-GB90] [17]
Coadministration of a Drug Treating the Disease Different from Dicumarol (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Metreleptin DM1NOEK Moderate Decreased metabolism of Dicumarol caused by Metreleptin mediated inhibition of CYP450 enzyme. Acute diabete complication [5A2Y] [18]
Arn-509 DMT81LZ Moderate Increased metabolism of Dicumarol caused by Arn-509 mediated induction of CYP450 enzyme. Acute myeloid leukaemia [2A60] [19]
Emapalumab DMZG5WL Moderate Altered metabolism of Dicumarol due to Emapalumab alters the formation of CYP450 enzymes. Adaptive immunity immunodeficiency [4A01] [20]
Mitotane DMU1GX0 Moderate Increased metabolism of Dicumarol caused by Mitotane mediated induction of CYP450 enzyme. Adrenal cancer [2D11] [15]
Metronidazole DMTIVEN Major Decreased metabolism of Dicumarol caused by Metronidazole mediated inhibition of CYP450 enzyme. Amoebiasis [1A36] [21]
Siltuximab DMGEATB Moderate Altered metabolism of Dicumarol due to Siltuximab alters the formation of CYP450 enzymes. Anemia [3A00-3A9Z] [20]
Methylphenobarbital DMDSWAG Major Increased metabolism of Dicumarol caused by Methylphenobarbital mediated induction of CYP450 enzyme. Anxiety disorder [6B00-6B0Z] [22]
Voriconazole DMAOL2S Major Decreased metabolism of Dicumarol caused by Voriconazole mediated inhibition of CYP450 enzyme. Aspergillosis [1F20] [23]
Posaconazole DMUL5EW Moderate Decreased metabolism of Dicumarol caused by Posaconazole mediated inhibition of CYP450 enzyme. Aspergillosis [1F20] [24]
Zafirlukast DMHNQOG Moderate Decreased metabolism of Dicumarol caused by Zafirlukast mediated inhibition of CYP450 enzyme. Asthma [CA23] [25]
Tindamax DM3OWT4 Moderate Decreased metabolism of Dicumarol caused by Tindamax mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [26]
Clarithromycin DM4M1SG Major Decreased metabolism of Dicumarol caused by Clarithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [14]
Ticarcillin DM4ME02 Moderate Increased risk of bleeding by the combination of Dicumarol and Ticarcillin. Bacterial infection [1A00-1C4Z] [27]
Sulfamethoxazole DMB08GE Major Decreased metabolism of Dicumarol caused by Sulfamethoxazole mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [21]
Aztreonam DMDNJHG Moderate Increased risk of bleeding by the combination of Dicumarol and Aztreonam. Bacterial infection [1A00-1C4Z] [28]
Chloramphenicol DMFXEWT Moderate Decreased metabolism of Dicumarol caused by Chloramphenicol mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [29]
Ampicillin DMHWE7P Moderate Increased risk of bleeding by the combination of Dicumarol and Ampicillin. Bacterial infection [1A00-1C4Z] [27]
Penicillin V DMKVOYF Moderate Increased risk of bleeding by the combination of Dicumarol and Penicillin V. Bacterial infection [1A00-1C4Z] [27]
Rabeprazole DMMZXIW Moderate Decreased metabolism of Dicumarol caused by Rabeprazole mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [30]
Oxacillin DMTAFY4 Moderate Increased risk of bleeding by the combination of Dicumarol and Oxacillin. Bacterial infection [1A00-1C4Z] [27]
Piperacillin DMTBKF3 Moderate Increased risk of bleeding by the combination of Dicumarol and Piperacillin. Bacterial infection [1A00-1C4Z] [27]
Amoxicillin DMUYNEI Moderate Increased risk of bleeding by the combination of Dicumarol and Amoxicillin. Bacterial infection [1A00-1C4Z] [27]
Telithromycin DMZ4P3A Moderate Decreased metabolism of Dicumarol caused by Telithromycin mediated inhibition of CYP450 enzyme. Bacterial infection [1A00-1C4Z] [23]
Phytonadione DM8HDOL Moderate Antagonize the effect of Dicumarol when combined with Phytonadione. Bleeding disorder [GA20-GA21] [31]
Nitazoxanide DMOWLVG Moderate Increased plasma concentration of Dicumarol and Nitazoxanide due to competitive binding of plasma proteins. Bowel habit change [ME05] [23]
Esterified estrogens DM9KZDO Moderate Antagonize the effect of Dicumarol when combined with Esterified estrogens. Breast cancer [2C60-2C6Y] [32]
Toremifene DMQYUWG Moderate Decreased metabolism of Dicumarol caused by Toremifene mediated inhibition of CYP450 enzyme. Breast cancer [2C60-2C6Y] [19]
Estradiol DMUNTE3 Moderate Antagonize the effect of Dicumarol when combined with Estradiol. Breast cancer [2C60-2C6Y] [32]
Atorvastatin DMF28YC Minor Increased risk of bleeding by the combination of Dicumarol and Atorvastatin. Cardiovascular disease [BA00-BE2Z] [33]
Fenofibric acid DMGO2MC Major Increased plasma concentration of Dicumarol and Fenofibric acid due to competitive binding of plasma proteins. Cardiovascular disease [BA00-BE2Z] [34]
Chenodiol DMQ8JIK Moderate Increased risk of bleeding by the combination of Dicumarol and Chenodiol. Cholelithiasis [DC11] [15]
Secobarbital DM14RF5 Major Increased metabolism of Dicumarol caused by Secobarbital mediated induction of CYP450 enzyme. Chronic insomnia [7A00] [22]
Pentosan polysulfate DM2HRKE Moderate Increased risk of bleeding by the combination of Dicumarol and Pentosan polysulfate. Chronic pain [MG30] [35]
Levomilnacipran DMV26S8 Moderate Increased risk of bleeding by the combination of Dicumarol and Levomilnacipran. Chronic pain [MG30] [36]
Regorafenib DMHSY1I Major Increased risk of bleeding by the combination of Dicumarol and Regorafenib. Colorectal cancer [2B91] [14]
Intedanib DMSTA36 Moderate Increased risk of bleeding by the combination of Dicumarol and Intedanib. Colorectal cancer [2B91] [37]
Mestranol DMG3F94 Moderate Antagonize the effect of Dicumarol when combined with Mestranol. Contraceptive management [QA21] [32]
Ardeparin DMYRX8B Major Increased risk of bleeding by the combination of Dicumarol and Ardeparin. Coronary thrombosis [BA43] [38]
Ethanol DMDRQZU Moderate Increased risk of bleeding by the combination of Dicumarol and Ethanol. Cystitis [GC00] [14]
Rivaroxaban DMQMBZ1 Major Increased risk of bleeding by the combination of Dicumarol and Rivaroxaban. Deep vein thrombosis [BD71] [39]
Aprepitant DM053KT Moderate Increased metabolism of Dicumarol caused by Aprepitant mediated induction of CYP450 enzyme. Depression [6A70-6A7Z] [40]
Sertraline DM0FB1J Moderate Increased risk of bleeding by the combination of Dicumarol and Sertraline. Depression [6A70-6A7Z] [36]
Fluoxetine DM3PD2C Moderate Increased plasma concentration of Dicumarol and Fluoxetine due to competitive binding of plasma proteins. Depression [6A70-6A7Z] [41]
Vilazodone DM4LECQ Moderate Increased risk of bleeding by the combination of Dicumarol and Vilazodone. Depression [6A70-6A7Z] [36]
Paroxetine DM5PVQE Moderate Increased risk of bleeding by the combination of Dicumarol and Paroxetine. Depression [6A70-6A7Z] [36]
Vortioxetine DM6F1PU Moderate Increased risk of bleeding by the combination of Dicumarol and Vortioxetine. Depression [6A70-6A7Z] [36]
Milnacipran DMBFE74 Moderate Increased risk of bleeding by the combination of Dicumarol and Milnacipran. Depression [6A70-6A7Z] [36]
Escitalopram DMFK9HG Moderate Increased risk of bleeding by the combination of Dicumarol and Escitalopram. Depression [6A70-6A7Z] [36]
Desvenlafaxine DMHD4PE Moderate Increased risk of bleeding by the combination of Dicumarol and Desvenlafaxine. Depression [6A70-6A7Z] [36]
Clomipramine DMINRKW Moderate Increased risk of bleeding by the combination of Dicumarol and Clomipramine. Depression [6A70-6A7Z] [36]
Venlafaxine DMR6QH0 Moderate Increased risk of bleeding by the combination of Dicumarol and Venlafaxine. Depression [6A70-6A7Z] [36]
Griseofulvin DMK54YG Moderate Increased metabolism of Dicumarol caused by Griseofulvin mediated induction of CYP450 enzyme. Dermatophytosis [1F28] [42]
[3H]estrone-3-sulphate DMGPF0N Moderate Antagonize the effect of Dicumarol when combined with [3H]estrone-3-sulphate. Discovery agent [N.A.] [32]
Apigenin DMI3491 Minor Increased risk of bleeding by the combination of Dicumarol and Apigenin. Discovery agent [N.A.] [43]
Benzylpenicillin DMS9503 Moderate Increased risk of bleeding by the combination of Dicumarol and Benzylpenicillin. Discovery agent [N.A.] [27]
PMID28870136-Compound-49 DMTUC9E Moderate Increased risk of bleeding by the combination of Dicumarol and PMID28870136-Compound-49. Discovery agent [N.A.] [34]
Fenfluramine DM0762O Moderate Increased risk of bleeding by the combination of Dicumarol and Fenfluramine. Epilepsy/seizure [8A61-8A6Z] [36]
Primidone DM0WX6I Major Increased metabolism of Dicumarol caused by Primidone mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [22]
Felbamate DM1V5ZS Moderate Decreased metabolism of Dicumarol caused by Felbamate mediated inhibition of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [44]
Mephenytoin DM5UGDK Moderate Increased risk of bleeding by the combination of Dicumarol and Mephenytoin. Epilepsy/seizure [8A61-8A6Z] [45]
Valproate DMCFE9I Moderate Increased plasma concentration of Dicumarol and Valproate due to competitive binding of plasma proteins. Epilepsy/seizure [8A61-8A6Z] [46]
Fosphenytoin DMOX3LB Moderate Increased risk of bleeding by the combination of Dicumarol and Fosphenytoin. Epilepsy/seizure [8A61-8A6Z] [45]
Ethotoin DMXWOCP Moderate Increased risk of bleeding by the combination of Dicumarol and Ethotoin. Epilepsy/seizure [8A61-8A6Z] [45]
Phenobarbital DMXZOCG Major Increased metabolism of Dicumarol caused by Phenobarbital mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [22]
Carbamazepine DMZOLBI Moderate Increased metabolism of Dicumarol caused by Carbamazepine mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [47]
Eslicarbazepine DMZREFQ Moderate Increased metabolism of Dicumarol caused by Eslicarbazepine mediated induction of CYP450 enzyme. Epilepsy/seizure [8A61-8A6Z] [14]
Suprofen DMKXJZ7 Moderate Increased risk of bleeding by the combination of Dicumarol and Suprofen. Eye anterior segment structural developmental anomaly [LA11] [48]
Itraconazole DMCR1MV Moderate Decreased metabolism of Dicumarol caused by Itraconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [24]
Miconazole DMPMYE8 Major Decreased metabolism of Dicumarol caused by Miconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [49]
Ketoconazole DMPZI3Q Moderate Decreased metabolism of Dicumarol caused by Ketoconazole mediated inhibition of CYP450 enzyme. Fungal infection [1F29-1F2F] [24]
Omeprazole DM471KJ Moderate Decreased metabolism of Dicumarol caused by Omeprazole mediated inhibition of CYP450 enzyme. Gastro-oesophageal reflux disease [DA22] [30]
Cimetidine DMH61ZB Moderate Decreased metabolism of Dicumarol caused by Cimetidine mediated inhibition of CYP450 enzyme. Gastro-oesophageal reflux disease [DA22] [50]
Avapritinib DMK2GZX Major Increased risk of bleeding by the combination of Dicumarol and Avapritinib. Gastrointestinal stromal tumour [2B5B] [14]
PSI-7977 DMLSUWZ Moderate Antagonize the effect of Dicumarol when combined with PSI-7977. Hepatitis virus infection [1E50-1E51] [14]
Simeprevir DMLUA9D Moderate Antagonize the effect of Dicumarol when combined with Simeprevir. Hepatitis virus infection [1E50-1E51] [14]
Daclatasvir DMSFK9V Moderate Antagonize the effect of Dicumarol when combined with Daclatasvir. Hepatitis virus infection [1E50-1E51] [14]
GS-5885 DMSL3DX Moderate Antagonize the effect of Dicumarol when combined with GS-5885. Hepatitis virus infection [1E50-1E51] [14]
Isoniazid DM5JVS3 Moderate Decreased metabolism of Dicumarol caused by Isoniazid mediated inhibition of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [51]
Rifampin DMA8J1G Major Increased metabolism of Dicumarol caused by Rifampin mediated induction of CYP450 enzyme. HIV-infected patients with tuberculosis [1B10-1B14] [52]
Delavirdine DM3NF5G Moderate Decreased metabolism of Dicumarol caused by Delavirdine mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [15]
Tipranavir DM8HJX6 Major Increased risk of bleeding by the combination of Dicumarol and Tipranavir. Human immunodeficiency virus disease [1C60-1C62] [34]
Etravirine DMGV8QU Moderate Decreased metabolism of Dicumarol caused by Etravirine mediated inhibition of CYP450 enzyme. Human immunodeficiency virus disease [1C60-1C62] [15]
Simvastatin DM30SGU Minor Increased plasma concentration of Dicumarol and Simvastatin due to competitive binding of plasma proteins. Hyper-lipoproteinaemia [5C80] [53]
Gemfibrozil DMD8Q3J Major Increased plasma concentration of Dicumarol and Gemfibrozil due to competitive binding of plasma proteins. Hyper-lipoproteinaemia [5C80] [34]
Fenofibrate DMFKXDY Major Increased plasma concentration of Dicumarol and Fenofibrate due to competitive binding of plasma proteins. Hyper-lipoproteinaemia [5C80] [34]
Dipyridamole DMXY30O Moderate Increased risk of bleeding by the combination of Dicumarol and Dipyridamole. Hypertension [BA00-BA04] [54]
Liothyronine DM6IR3P Moderate Increased risk of bleeding by the combination of Dicumarol and Liothyronine. Hypo-thyroidism [5A00] [55]
Levothyroxine DMHN027 Moderate Increased risk of bleeding by the combination of Dicumarol and Levothyroxine. Hypo-thyroidism [5A00] [55]
Allopurinol DMLPAOB Moderate Decreased metabolism of Dicumarol caused by Allopurinol mediated inhibition of CYP450 enzyme. Inborn purine/pyrimidine/nucleotide metabolism error [5C55] [56]
Amobarbital DM0GQ8N Major Increased metabolism of Dicumarol caused by Amobarbital mediated induction of CYP450 enzyme. Insomnia [7A00-7A0Z] [22]
Pentobarbital DMFNH7L Major Increased metabolism of Dicumarol caused by Pentobarbital mediated induction of CYP450 enzyme. Insomnia [7A00-7A0Z] [22]
Erlotinib DMCMBHA Moderate Increased plasma concentration of Dicumarol and Erlotinib due to competitive binding of plasma proteins. Lung cancer [2C25] [23]
Proguanil DMBL79I Moderate Decreased metabolism of Dicumarol caused by Proguanil mediated inhibition of CYP450 enzyme. Malaria [1F40-1F45] [57]
Calaspargase pegol DMQZBXI Moderate Increased risk of bleeding by the combination of Dicumarol and Calaspargase pegol. Malignant haematopoietic neoplasm [2B33] [58]
Acalabrutinib DM7GCVW Major Increased risk of bleeding by the combination of Dicumarol and Acalabrutinib. Mature B-cell lymphoma [2A85] [35]
Blinatumomab DMGECIJ Moderate Decreased metabolism of Dicumarol caused by Blinatumomab mediated inhibition of CYP450 enzyme. Mature B-cell lymphoma [2A85] [15]
Ibrutinib DMHZCPO Major Increased risk of bleeding by the combination of Dicumarol and Ibrutinib. Mature B-cell lymphoma [2A85] [28]
Mercaptopurine DMTM2IK Moderate Antagonize the effect of Dicumarol when combined with Mercaptopurine. Mature B-cell lymphoma [2A85] [59]
Ponatinib DMYGJQO Major Increased risk of bleeding by the combination of Dicumarol and Ponatinib. Mature B-cell lymphoma [2A85] [35]
Conjugated estrogens DMLT0E1 Moderate Antagonize the effect of Dicumarol when combined with Conjugated estrogens. Menopausal disorder [GA30] [32]
Ethinyl estradiol DMODJ40 Moderate Antagonize the effect of Dicumarol when combined with Ethinyl estradiol. Menopausal disorder [GA30] [32]
Lanthanum carbonate DMMJQSH Moderate Decreased absorption of Dicumarol due to formation of complexes caused by Lanthanum carbonate. Mineral absorption/transport disorder [5C64] [34]
Rifabutin DM1YBHK Major Increased metabolism of Dicumarol caused by Rifabutin mediated induction of CYP450 enzyme. Mycobacterium infection [1B10-1B21] [52]
Dasatinib DMJV2EK Major Increased risk of bleeding by the combination of Dicumarol and Dasatinib. Myeloproliferative neoplasm [2A20] [19]
Omacetaxine mepesuccinate DMPU2WX Major Increased risk of bleeding by the combination of Dicumarol and Omacetaxine mepesuccinate. Myeloproliferative neoplasm [2A20] [35]
Prasugrel DM7MT6E Major Increased risk of bleeding by the combination of Dicumarol and Prasugrel. Myocardial infarction [BA41-BA43] [14]
Vorapaxar DMA16BR Major Increased risk of bleeding by the combination of Dicumarol and Vorapaxar. Myocardial infarction [BA41-BA43] [60]
Tirofiban DMQG17S Major Increased risk of bleeding by the combination of Dicumarol and Tirofiban. Myocardial infarction [BA41-BA43] [23]
Econazole DMFSWGH Moderate Decreased metabolism of Dicumarol caused by Econazole mediated inhibition of CYP450 enzyme. Non-dermatophyte superficial dermatomycose [1F2D] [61]
Sibutramine DMFJTDI Moderate Increased risk of bleeding by the combination of Dicumarol and Sibutramine. Obesity [5B80-5B81] [36]
Orlistat DMRJSP8 Moderate Altered absorption of Dicumarol caused by Orlistat. Obesity [5B80-5B81] [23]
Diclofenac DMPIHLS Moderate Increased risk of bleeding by the combination of Dicumarol and Diclofenac. Osteoarthritis [FA00-FA05] [48]
Nepafenac DMYK490 Moderate Increased risk of bleeding by the combination of Dicumarol and Nepafenac. Osteoarthritis [FA00-FA05] [48]
Rucaparib DM9PVX8 Moderate Decreased metabolism of Dicumarol caused by Rucaparib mediated inhibition of CYP450 enzyme. Ovarian cancer [2C73] [15]
Carboplatin DMG281S Moderate Increased plasma concentration of Dicumarol and Carboplatin due to competitive binding of plasma proteins. Ovarian cancer [2C73] [23]
MK-4827 DMLYGH4 Moderate Increased risk of bleeding by the combination of Dicumarol and MK-4827. Ovarian cancer [2C73] [14]
Aspirin DM672AH Major Increased risk of bleeding by the combination of Dicumarol and Aspirin. Pain [MG30-MG3Z] [62]
Acetaminophen DMUIE76 Moderate Increased risk of bleeding by the combination of Dicumarol and Acetaminophen. Pain [MG30-MG3Z] [63]
Tolcapone DM8MNVO Minor Decreased metabolism of Dicumarol caused by Tolcapone mediated inhibition of CYP450 enzyme. Parkinsonism [8A00] [15]
Esomeprazole DM7BN0X Moderate Decreased metabolism of Dicumarol caused by Esomeprazole mediated inhibition of CYP450 enzyme. Peptic ulcer [DA61] [30]
Choline salicylate DM8P137 Moderate Increased risk of bleeding by the combination of Dicumarol and Choline salicylate. Postoperative inflammation [1A00-CA43] [64]
Ketorolac DMI4EL5 Moderate Increased risk of bleeding by the combination of Dicumarol and Ketorolac. Postoperative inflammation [1A00-CA43] [48]
Bromfenac DMKB79O Moderate Increased risk of bleeding by the combination of Dicumarol and Bromfenac. Postoperative inflammation [1A00-CA43] [48]
Enzalutamide DMGL19D Moderate Increased metabolism of Dicumarol caused by Enzalutamide mediated induction of CYP450 enzyme. Prostate cancer [2C82] [19]
Flutamide DMK0O7U Moderate Increased risk of bleeding by the combination of Dicumarol and Flutamide. Prostate cancer [2C82] [15]
Estramustine DMWTAOI Moderate Antagonize the effect of Dicumarol when combined with Estramustine. Prostate cancer [2C82] [32]
Bicalutamide DMZMSPF Minor Increased plasma concentration of Dicumarol and Bicalutamide due to competitive binding of plasma proteins. Prostate cancer [2C82] [15]
Ustekinumab DMHTYK3 Moderate Altered metabolism of Dicumarol due to Ustekinumab alters the formation of CYP450 enzymes. Psoriasis [EA90] [20]
Ixekizumab DMXW92T Moderate Altered metabolism of Dicumarol due to Ixekizumab alters the formation of CYP450 enzymes. Psoriasis [EA90] [20]
Bosentan DMIOGBU Moderate Increased metabolism of Dicumarol caused by Bosentan mediated induction of CYP450 enzyme. Pulmonary hypertension [BB01] [15]
Treprostinil DMTIQF3 Moderate Increased risk of bleeding by the combination of Dicumarol and Treprostinil. Pulmonary hypertension [BB01] [65]
Epoprostenol DMUTYR2 Moderate Increased risk of bleeding by the combination of Dicumarol and Epoprostenol. Pulmonary hypertension [BB01] [65]
Iloprost DMVPZBE Moderate Increased risk of bleeding by the combination of Dicumarol and Iloprost. Pulmonary hypertension [BB01] [65]
Sorafenib DMS8IFC Moderate Decreased metabolism of Dicumarol caused by Sorafenib mediated inhibition of CYP450 enzyme. Renal cell carcinoma [2C90] [66]
Sulfadiazine DMTW3R8 Major Increased plasma concentration of Dicumarol and Sulfadiazine due to competitive binding of plasma proteins. Rheumatic fever [1B40] [21]
Salsalate DM13P4C Moderate Increased risk of bleeding by the combination of Dicumarol and Salsalate. Rheumatoid arthritis [FA20] [64]
Celecoxib DM6LOQU Moderate Increased plasma concentrations of Dicumarol and Celecoxib due to competitive inhibition of the same metabolic pathway. Rheumatoid arthritis [FA20] [67]
Tocilizumab DM7J6OR Moderate Altered metabolism of Dicumarol due to Tocilizumab alters the formation of CYP450 enzymes. Rheumatoid arthritis [FA20] [20]
Canakinumab DM8HLO5 Moderate Altered metabolism of Dicumarol due to Canakinumab alters the formation of CYP450 enzymes. Rheumatoid arthritis [FA20] [20]
Rilonacept DMGLUQS Moderate Altered metabolism of Dicumarol due to Rilonacept alters the formation of CYP450 enzymes. Rheumatoid arthritis [FA20] [20]
Flurbiprofen DMGN4BY Moderate Increased risk of bleeding by the combination of Dicumarol and Flurbiprofen. Rheumatoid arthritis [FA20] [48]
Golimumab DMHZV7X Moderate Altered metabolism of Dicumarol due to Golimumab alters the formation of CYP450 enzymes. Rheumatoid arthritis [FA20] [20]
Sulfasalazine DMICA9H Major Increased plasma concentration of Dicumarol and Sulfasalazine due to competitive binding of plasma proteins. Rheumatoid arthritis [FA20] [21]
Sarilumab DMOGNXY Moderate Altered metabolism of Dicumarol due to Sarilumab alters the formation of CYP450 enzymes. Rheumatoid arthritis [FA20] [20]
Leflunomide DMR8ONJ Moderate Decreased metabolism of Dicumarol caused by Leflunomide mediated inhibition of CYP450 enzyme. Rheumatoid arthritis [FA20] [68]
Clozapine DMFC71L Moderate Increased plasma concentration of Dicumarol and Clozapine due to competitive binding of plasma proteins. Schizophrenia [6A20] [69]
Armodafinil DMGB035 Moderate Decreased metabolism of Dicumarol caused by Armodafinil mediated inhibition of CYP450 enzyme. Solid tumour/cancer [2A00-2F9Z] [70]
Etoposide DMNH3PG Moderate Increased plasma concentration of Dicumarol and Etoposide due to competitive binding of plasma proteins. Solid tumour/cancer [2A00-2F9Z] [23]
Curcumin DMQPH29 Minor Increased risk of bleeding by the combination of Dicumarol and Curcumin. Solid tumour/cancer [2A00-2F9Z] [71]
Caplacizumab DMPUKA7 Major Increased risk of bleeding by the combination of Dicumarol and Caplacizumab. Thrombocytopenia [3B64] [19]
Cabozantinib DMIYDT4 Major Increased risk of bleeding by the combination of Dicumarol and Cabozantinib. Thyroid cancer [2D10] [15]
Azathioprine DMMZSXQ Moderate Antagonize the effect of Dicumarol when combined with Azathioprine. Transplant rejection [NE84] [59]
Tolbutamide DM02AWV Moderate Increased plasma concentration of Dicumarol and Tolbutamide due to competitive binding of plasma proteins. Type 2 diabetes mellitus [5A11] [72]
Lixisenatide DM0QJDC Minor Altered absorption of Dicumarol due to GI dynamics variation caused by Lixisenatide. Type 2 diabetes mellitus [5A11] [19]
Chlorpropamide DMPHZQE Moderate Increased plasma concentration of Dicumarol and Chlorpropamide due to competitive binding of plasma proteins. Type 2 diabetes mellitus [5A11] [72]
Carbenicillin DMLEDNK Moderate Increased risk of bleeding by the combination of Dicumarol and Carbenicillin. Urinary tract infection [GC08] [27]
Trimethoprim DMM7CHK Moderate Increased risk of bleeding by the combination of Dicumarol and Trimethoprim. Urinary tract infection [GC08] [28]
Amiodarone DMUTEX3 Major Decreased metabolism of Dicumarol caused by Amiodarone mediated inhibition of CYP450 enzyme. Ventricular tachyarrhythmia [BC71] [73]
⏷ Show the Full List of 158 DDI Information of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6808).
2 Dicumarol FDA Label
3 BDDCS applied to over 900 drugs
4 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5 Vitamin K antagonism of coumarin intoxication in the rat. Thromb Haemost. 1986 Apr 30;55(2):235-9.
6 Pharmacogenetics aspects of oral anticoagulants therapy. J Med Life. 2015 Apr-Jun;8(2):171-5.
7 Comparison of graphical and computerized methods for calculating binding parameters for two strongly bound drugs to human serum albumin. J Pharm Sci. 1976 Aug;65(8):1182-7. doi: 10.1002/jps.2600650813.
8 Mitochondrial production of reactive oxygen species mediate dicumarol-induced cytotoxicity in cancer cells. J Biol Chem. 2006 Dec 8;281(49):37416-26. doi: 10.1074/jbc.M605063200. Epub 2006 Oct 13.
9 Impairment of antioxidant defenses as a contributor to arsenite-induced cell transformation. Biometals. 2012 Oct;25(5):927-37. doi: 10.1007/s10534-012-9559-1. Epub 2012 Jun 13.
10 Quinone reductase inhibitors block SAPK/JNK and NFkappaB pathways and potentiate apoptosis. J Biol Chem. 1999 Oct 29;274(44):31150-4. doi: 10.1074/jbc.274.44.31150.
11 NRH:quinone oxidoreductase2 (NQO2). Chem Biol Interact. 2000 Dec 1;129(1-2):99-112.
12 Dicoumarol relieves serum withdrawal-induced G0/1 blockade in HL-60 cells through a superoxide-dependent mechanism. Biochem Pharmacol. 2005 Jun 1;69(11):1613-25.
13 VKORC1 and VKORC1L1 have distinctly different oral anticoagulant dose-response characteristics and binding sites. Blood Adv. 2018 Mar 27;2(6):691-702.
14 Cerner Multum, Inc. "UK Summary of Product Characteristics.".
15 Bodiford AB, Kessler FO, Fermo JD, Ragucci KR "Elevated international normalized ratio with the consumption of grapefruit and use of warfarin." SAGE Open Med Case Rep 0 (2013): 1-3. [PMID: 27489634]
16 Bates ER, Mukherjee D, Lau WC "Drug-drug interactions involving antiplatelet agents." Eur Heart J 24 (2003): 1707-9. [PMID: 14522564]
17 Hermosillo AJ, Spinler SA "Aspirin, clopidogrel, and warfarin: is the combination appropriate and effective or inappropriate and too danterous?" Ann Pharmacother 42 (2008): 790-805. [PMID: 18477734]
18 Bailey DG, Arnold JMO, Spence JD "Grapefruit juice and drugs - how significant is the interaction." Clin Pharmacokinet 26 (1994): 91-8. [PMID: 8162660]
19 Cerner Multum, Inc. "Australian Product Information.".
20 Product Information. Cosentyx (secukinumab). Novartis Pharmaceuticals, East Hanover, NJ.
21 Hermida J, Zarza J, Alberca I, et al. "Differential effects of 2C9*3 and 2C9*2 variants of cytochrome P-450 CYP2C9 on sensitivity to acenocoumarol." Blood 99 (2002): 4237-9. [PMID: 12010835]
22 Antlitz AM, Tolentino M, Kosai MF "Effect of butabarbital on orally administered anticoagulants." Curr Ther Res Clin Exp 10 (1968): 70-3. [PMID: 4967727]
23 Guo LQ, Yamazoe Y "Inhibition of cytochrome P450 by furanocoumarins in grapefruit juice and herbal medicines." Acta Pharmacol Sin 25 (2004): 129-36. [PMID: 14769198]
24 Brass C, Galgiani JN, Blaschke TF, et al "Disposition of ketoconazole, an oral antifungal, in humans." Antimicrob Agents Chemother 21 (1982): 151-8. [PMID: 6282204]
25 Dekhuijzen PN, Koopmans PP "Pharmacokinetic profile of zafirlukast." Clin Pharmacokinet 41 (2002): 105-14. [PMID: 11888331]
26 Dean RP, Talbert RL "Bleeding associated with concurrent warfarin and metronidazole therapy." Drug Intell Clin Pharm 14 (1980): 864-6.
27 Alexander DP, Russo ME, Fohrman DE, Rothstein G "Nafcillin-induced platelet dysfunction and bleeding." Antimicrob Agents Chemother 23 (1983): 59-62. [PMID: 6830209]
28 Agencia Espaola de Medicamentos y Productos Sanitarios Healthcare "Centro de informacion online de medicamentos de la AEMPS - CIMA.".
29 Christensen LK, Skovsted L "Inhibition of drug metabolism by chloramphenicol." Lancet 2 (1969): 1397-9. [PMID: 4188280]
30 Product Information. Omeprazole (omeprazole). Mylan Pharmaceuticals Inc, Morgantown, WV.
31 Howard PA, Hannaman KN "Warfarin resistance linked to enteral nutrition products." J Am Diet Assoc 85 (1985): 713-5. [PMID: 3998343]
32 Notelovitz M "Oral contraception and coagulation." Clin Obstet Gynecol 28 (1985): 73-83. [PMID: 3987135]
33 Product Information. Lipitor (atorvastatin). Parke-Davis, Morris Plains, NJ.
34 Canadian Pharmacists Association.
35 Product Information. Brukinsa (zanubrutinib). BeiGene USA, Inc, San Mateo, CA.
36 Bannister SJ, Houser VP, Hulse JD, Kisicki JC, Rasmussen JG "Evaluation of the potential for interactions of paroxetine with diazepam, cimetidine, warfarin, and digoxin." Acta Psychiatr Scand Suppl 350 (1989): 102-6. [PMID: 2530759]
37 Product Information. Ofev (nintedanib). Boehringer Ingelheim, Ridgefield, CT.
38 Product Information. Fragmin (dalteparin). Pharmacia and Upjohn, Kalamazoo, MI.
39 Product Information. Xarelto (rivaroxaban). Bayer Inc, Toronto, IA.
40 Hermans JJ, Thijssen HH "Human liver microsomal metabolism of the enantiomers of warfarin and acenocoumarol: P450 isozyme diversity determines the differences in their pharmacokinetics." Br J Pharmacol 110 (1993): 482-90. [PMID: 8220911]
41 Ciraulo DA, Shader RI "Fluoxetine drug-drug interactions. II." J Clin Psychopharmacol 10 (1990): 213-7. [PMID: 2198298]
42 Koch-Weser J, Sellers EM "Drug interactions with coumarin anticoagulants (second of two parts)." N Engl J Med 285 (1971): 547-58. [PMID: 4397794]
43 Heck AM, DeWitt BA, Lukes AL "Potential interactions between alternative therapies and warfarin." Am J Health Syst Pharm 57 (2000): 1221-7 quiz 1228-30. [PMID: 10902065]
44 Glue P, Banfield CR, Colucci RD, Perhach JL "Warfarin-felbamate interaction." Ann Pharmacother 28 (1994): 1412-3. [PMID: 7696739]
45 Koch-Weser J, Sellers EM "Drug interactions with coumarin anticoagulants (first of two parts)." N Engl J Med 285 (1971): 487-98. [PMID: 4397794]
46 Guthrie SK, Stoysich AM, Bader G, Hilleman DE "Hypothesized interaction between valproic acid and warfarin." J Clin Psychopharmacol 15 (1995): 138-9. [PMID: 7782487]
47 Denbow CE, Frazer HS "Clinically significant hemorrhage due to warfarin-carbamazepine interaction." South Med J 83 (1990): 981. [PMID: 2382161]
48 Product Information. Acular (ketorolac). Allergan Inc, Irvine, CA.
49 Colquhoun MC, Daly M, Stewart P, Beeley L "Interaction between warfarin and miconazole oral gel." Lancet 1 (1987): 695-6. [PMID: 2882124]
50 Flind AC "Cimetidine and oral anticoagulants ." Lancet 2 (1978): 1054. [PMID: 82071]
51 Eade NR, McLeod PJ, MacLeod SM "Potentiation of bishydroxycoumarin in dogs by isoniazid and paminosalicylic acid." Am Rev Respir Dis 103 (1971): 792-9. [PMID: 4103778]
52 Heimark LD, Gilbaldi M, Trager WF, et al "The mechanism of the warfarin-rifampin drug interaction in humans." Clin Pharmacol Ther 42 (1987): 388-94. [PMID: 3665337]
53 Gaw A, Wosornu D "Simvastatin during warfarin therapy in hyperlipoproteinaemia." Lancet 340 (1992): 979-80. [PMID: 1357387]
54 Massel D, Little SH "Risks and benefits of adding anti-platelet therapy to warfarin among patients with prosthetic heart valves: A meta-analysis." J Am Coll Cardiol 37 (2001): 569-78. [PMID: 11216981]
55 Product Information. Synthroid (levothyroxine). Abbott Pharmaceutical, Abbott Park, IL.
56 Rawlins MD, Smith SE "Influence of allopurinol on drug metabolism in man." Br J Clin Pharmacol 48 (1973): 693-8. [PMID: 4788211]
57 Product Information. Malarone (atovaquone-proguanil) Glaxo Wellcome, Research Triangle Pk, NC.
58 Caruso V, Iacoviello L, Di Castelnuovo A, et.al "Thrombotic complications in childhood acute lymphoblastic leukemia: a meta-analysis of 17 prospective studies comprising 1752 pediatric patients." Blood 108 (2006): 2216-22. [PMID: 16804111]
59 Rivier G, Khamashta MA, Hughes GR "Warfarin and azathioprine: a drug interaction does exist." Am J Med 95 (1993): 342. [PMID: 8368235]
60 Product Information. Zontivity (vorapaxar). Merck &amp Company Inc, Whitehouse Station, NJ.
61 Lang PG Jr, Leclercq AH "Increase in anticoagulant effect of warfarin in a patient using econazole cream." J Am Acad Dermatol 55(5 Suppl) (2006): S117-9. [PMID: 17052529]
62 Barrow MV, Quick DT, Cunningham RW "Salicylate hypoprothrombinemia in rheumatoid arthritis with liver disease. Report of two cases." Arch Intern Med 120 (1967): 620-4. [PMID: 6054600]
63 Hylek EM, Heiman H, Skates SJ, Sheehan MA, Singer DE "Acetaminophen and other risk factors for excessive warfarin anticoagulation." JAMA 279 (1998): 657-62. [PMID: 9496982]
64 Fausa O "Salicylate-induced hypoprothrombinemia: a report of four cases." Acta Med Scand 188 (1970): 403-8. [PMID: 5490567]
65 Product Information. Flolan (epoprostenol). Glaxo Wellcome, Research Triangle Park, NC.
66 Laber DA, Mushtaq M "Compassionate use of sorafenib in patients with advanced renal cell cancer." Clin Genitourin Cancer 7 (2009): 34-8. [PMID: 19213666]
67 Mersfelder TL, Stewart LR "Warfarin and celecoxib interaction." Ann Pharmacother 34 (2000): 325-7. [PMID: 10917378]
68 Chonlahan J, Halloran MA, Hammonds A "Leflunomide and warfarin interaction: case report and review of the literature." Pharmacotherapy 26 (2006): 868-71. [PMID: 16716139]
69 Gilman AG, Rall TW, Nies AS, Taylor P, eds. "Goodman and Gilman's the Pharmacological Basis of Therapeutics. 8th ed." New York, NY: Pergamon Press Inc. (1990):.
70 Product Information. Nuvigil (armodafinil). Cephalon Inc, West Chester, PA.
71 Abebe W "Herbal medication: potential for adverse interactions with analgesic drugs." J Clin Pharm Ther 27 (2002): 391-401. [PMID: 12472978]
72 Hansen JM, Christensen LK "Drug interactions with oral sulphonylurea hypoglycaemic drugs." Drugs 13 (1977): 24-34. [PMID: 401727]
73 Cheung B, Lam FM, Kumana CR "Lesson of the week: insidiously evolving, occult drug interaction involving warfarin and amiodarone." BMJ 312 (1996): 107-8. [PMID: 8555895]