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dicoumarol 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | BioActivity |
| Stem definition | Drug id | CAS RN |
|---|---|---|
| anticoagulants, dicoumarol derivatives | 867 | 66-76-2 |
Description:
| Molecule | Description |
|---|---|
|
Synonyms:
|
An oral anticoagulant that interferes with the metabolism of vitamin K. It is also used in biochemical experiments as an inhibitor of reductases.
Legend: OFP - off patent OFM - off market ONP - on patent |
Drug dosage:
| Dose | Unit | Route |
|---|---|---|
| 0.10 | g | O |
ADMET properties:
| Property | Value | Reference |
|---|---|---|
| BDDCS (Biopharmaceutical Drug Disposition Classification System) | 2 | Benet LZ, Broccatelli F, Oprea TI |
| S (Water solubility) | 0.13 mg/mL | Benet LZ, Broccatelli F, Oprea TI |
| EoM (Fraction excreted unchanged in urine) | 0.50 % | Benet LZ, Broccatelli F, Oprea TI |
| MRTD (Maximum Recommended Therapeutic Daily Dose) | 8.50 µM/kg/day | Contrera JF, Matthews EJ, Kruhlak NL, Benz RD |
Predicted pharmacokinetic/toxicological properties (PK-AZ):
| Property | Description | Value | Unit | Confidence | Similarity |
|---|---|---|---|---|---|
| azlogd74 | LogD at pH 7.4 | 1.823 | High | 1 | |
| caco2-efflux | Caco-2 efflux ratio (BA/AB) | 2.576 | High | 1 | |
| caco2-intrinsic-papp | Caco-2 intrinsic apparent permeability | 112.460 | 10^-6 cm/s | High | 1 |
| dh-clint | Dog hepatocyte intrinsic clearance | 8.933 | uL/min/10^6 cells | High | 1 |
| dppb | Dog plasma protein binding (% unbound) | 0.540 | % | High | 1 |
| fcs-ppb | Fetal calf serum protein binding (% unbound) | 0.970 | % | High | 1 |
| herg | hERG pIC50 | 4.598 | pIC50 | High | 1 |
| hh-clint | Human hepatocyte intrinsic clearance | 8.299 | uL/min/10^6 cells | High | 1 |
| hlm-clint | Human liver microsomal intrinsic clearance | 34.198 | uL/min/mg protein | High | 1 |
| hppb | Human plasma protein binding (% unbound) | 0.160 | % | High | 1 |
| kinase-safety-class | ACVR1B,ACVR2A,ACVR2B,ACVRL1,AKT2,AKT3,ALK,AURKA,AURKB,AURKC,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK1,CDK19,CDK2,CDK4,CDK5,CDK9,CHEK1,CSF1R,DDR1,DYRK1B,EGFR,EIF2AK3,EPHA2,EPHB4,ERBB2,FGFR1,FLT3,GRK2,GRK3,GSK3B,IGF1R,IKBKB,IRAK1,ITK,JAK1,JAK2,JAK3,KDR,KIT,MAP2K6,MAP3K1,MAP3K10,MAP3K14,MAP3K21,MAP3K7,MAP4K1,MAP4K3,MAPK1,MAPK10,MAPK12,MAPK7,MAPK8,MAPK9,MAPKAPK2,MAPKAPK5,MARK4,MELK,MET,MTOR,NTRK2,PAK4,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIK3CD,PIM1,PIM2,PIM3,PLK1,PRKCD,PRKDC,PTK2,SGK1,SIK2,SIK3,STK33,SYK,TEK,TGFBR1,TTK,ULK1,ULK2,ZAP70 | 91 | |||
| kinase-selectivity-class | ACVR2A,ACVR2B,AURKB,AURKC,AXL,BRAF,CAMK2D,CDK9,DDR1,DYRK1B,EIF2AK3,EPHB4,ERBB2,GRK2,GSK3A,JAK2,MAP2K3,MAP2K6,MAPK1,MAPK12,MAPK7,MAPK8,MARK4,PIK3CB,PIK3CD,PRKDC,SGK1,SIK2,STK10,STK33,SYK,TEK,TGFBR1,TTK,TYRO3,ULK1 | 36 | |||
| mdck-mdr1-efflux | MDCK-MDR1 efflux ratio | 7.499 | High | 1 | |
| mh-clint | Mouse hepatocyte intrinsic clearance | 5.794 | High | 1 | |
| mppb | Mouse plasma protein binding (% unbound) | 1.020 | High | 1 | |
| nih-mdck-mdr1-efflux | NIH MDCK-MDR1 efflux ratio | 1.560 | High | 1 | |
| pfas-class | PFAS structural alert (1 = True, 0 = False) | 0 | |||
| pppb | Pig plasma protein binding (% unbound) | 0.300 | % | High | 1 |
| rh-clint | Rat hepatocyte intrinsic clearance | 10.328 | uL/min/10^6 cells | High | 1 |
| rh-fuinc | Rat hepatocyte fraction unbound in incubation | 43.590 | % | High | 1 |
| rppb | Rat plasma protein binding (% unbound) | 0.200 | % | High | 1 |
| solubility-dd | Solubility at pH 7.4 in DMSO | 23.496 | uM | High | 1 |
Approvals:
| Date | Agency | Company | Orphan |
|---|---|---|---|
| July 31, 1944 | FDA | ABBVIE |
FDA Adverse Event Reporting System (Female)
None
FDA Adverse Event Reporting System (Male)
None
FDA Adverse Event Reporting System (Geriatric)
None
FDA Adverse Event Reporting System (Pediatric)
None
Pharmacologic Action:
| Source | Code | Description |
|---|---|---|
| ATC | B01AA01 | BLOOD AND BLOOD FORMING ORGANS ANTITHROMBOTIC AGENTS ANTITHROMBOTIC AGENTS Vitamin K antagonists |
| MeSH PA | D000925 | Anticoagulants |
| MeSH PA | D004791 | Enzyme Inhibitors |
| MeSH PA | D006401 | Hematologic Agents |
| MeSH PA | D014475 | Uncoupling Agents |
| CHEBI has role | CHEBI:50249 | anticoagulant |
| CHEBI has role | CHEBI:50390 | EC 1.6.5.2 [NAD(P)H dehydrogenase (quinone)] inhibitor |
| CHEBI has role | CHEBI:55347 | vitamin K antagonist |
| CHEBI has role | CHEBI:63962 | Hsp90 inhibitor |
Related Drugs by ATC class:
B01AA Vitamin K antagonists 9 drugs
Drug Use | Suggest Off label Use Form| |View source of the data|
| Disease | Relation | SNOMED_ID | DOID |
|---|---|---|---|
| Myocardial infarction | indication | 22298006 | DOID:5844 |
| Cerebral embolism | indication | 75543006 | DOID:4372 |
| Thromboembolic disorder | indication | 371039008 | |
| Thrombosis | indication | 439127006 | |
| Prevention of Cerebral Thrombosis | indication | ||
| Prosthetic replacement of heart valve | off-label use | 307279007 | |
| Nutritional disorder | contraindication | 2492009 | DOID:374 |
| Pericarditis | contraindication | 3238004 | DOID:1787 |
| Necrosis | contraindication | 6574001 | |
| Alcoholism | contraindication | 7200002 | |
| Obstruction of bile duct | contraindication | 30144000 | |
| Vasculitis | contraindication | 31996006 | DOID:865 |
| Hyperthyroidism | contraindication | 34486009 | DOID:7998 |
| Gangrene | contraindication | 36024000 | |
| Hypertensive disorder | contraindication | 38341003 | DOID:10763 |
| Gastrointestinal ulcer | contraindication | 40845000 | |
| Hypothyroidism | contraindication | 40930008 | DOID:1459 |
| Secondary uterine inertia | contraindication | 43715006 | |
| Tropical sprue | contraindication | 47384003 | DOID:10607 |
| Nephrotic syndrome | contraindication | 52254009 | DOID:1184 |
| Vitamin K deficiency | contraindication | 52675005 | DOID:11249 |
| Threatened abortion | contraindication | 54048003 | DOID:9667 |
| Hyperlipidemia | contraindication | 55822004 | DOID:1168 |
| Hepatic failure | contraindication | 59927004 | |
| Cerebrovascular disease | contraindication | 62914000 | DOID:6713 |
| Blood coagulation disorder | contraindication | 64779008 | DOID:1247 |
| Fatty stool | contraindication | 66187002 | |
| Psychotic disorder | contraindication | 69322001 | |
| Heparin-induced thrombocytopenia | contraindication | 73397007 | |
| Gastrointestinal hemorrhage | contraindication | 74474003 | |
| Protein C deficiency disease | contraindication | 76407009 | DOID:3756 |
| Respiratory tract hemorrhage | contraindication | 95431003 | |
| Disorder of connective tissue | contraindication | 105969002 | DOID:65 |
| Polycythemia vera | contraindication | 109992005 | |
| Procedure on central nervous system | contraindication | 118679007 | |
| Intracranial aneurysm | contraindication | 128609009 | DOID:10941 |
| Bleeding | contraindication | 131148009 | |
| Impaired renal function disorder | contraindication | 197663003 | |
| Eclampsia in pregnancy | contraindication | 198992004 | |
| Local anesthetic intrathecal block | contraindication | 231249005 | |
| Disease of liver | contraindication | 235856003 | DOID:409 |
| Chronic diarrhea | contraindication | 236071009 | |
| Edema | contraindication | 267038008 | |
| Anemia | contraindication | 271737000 | DOID:2355 |
| Cerebral hemorrhage | contraindication | 274100004 | |
| Lumbar puncture | contraindication | 277762005 | |
| Pregnancy, function | contraindication | 289908002 | |
| Bacterial endocarditis | contraindication | 301183007 | |
| Dissection of aorta | contraindication | 308546005 | |
| Primary malignant neoplasm | contraindication | 372087000 | |
| Surgical procedure on eye proper | contraindication | 373353005 | |
| Pericardial effusion | contraindication | 373945007 | DOID:118 |
| Fever | contraindication | 386661006 | |
| Surgical procedure | contraindication | 387713003 | |
| Severe diarrhea | contraindication | 409587002 | |
| Traumatic injury | contraindication | 417746004 | |
| Genitourinary tract hemorrhage | contraindication | 417941003 | |
| Poor metabolizer due to cytochrome p450 CYP2C9 variant | contraindication | 424451001 | |
| Hypertensive urgency | contraindication | 443482000 | |
| Severe Diabetes Mellitus | contraindication | ||
| Cholesterol Embolism | contraindication | ||
| Internal Hemorrhage | contraindication | ||
| Indwelling Vascular Catheter | contraindication | ||
| Bleeding Risk Associated with Vitamin-K-Epoxide Reductase (Warfarin-Sensitive) Gene | contraindication |
🐶 Veterinary Drug Use
None
🐶 Veterinary products
None
Acid dissociation constants calculated using MoKa v3.0.0
| Dissociation level | Dissociation constant | Type (acidic/basic) |
|---|---|---|
| pKa1 | 4.26 | acidic |
| pKa2 | 8.21 | acidic |
Orange Book patent data (new drug applications)
None
Orange Book exclusivity data (new drug applications)
None
Bioactivity Summary:
| Target | Class | Pharos | UniProt | Action | Type | Activity value (-log[M]) | Mechanism action | Bioact source | MoA source |
|---|---|---|---|---|---|---|---|---|---|
| Vitamin K epoxide reductase complex subunit 1 | Enzyme | INHIBITOR | IC50 | 5.51 | SCIENTIFIC LITERATURE | CHEMBL | |||
| NAD(P)H dehydrogenase [quinone] 1 | Enzyme | Ki | 8 | WOMBAT-PK | |||||
| Mitogen-activated protein kinase 1 | Kinase | IC50 | 5.35 | DRUG MATRIX | |||||
| Proprotein convertase subtilisin/kexin type 7 | Enzyme | IC50 | 5.89 | CHEMBL | |||||
| Cytochrome P450 2C9 | Enzyme | Ki | 5.97 | WOMBAT-PK | |||||
| G-protein coupled receptor 35 | GPCR | Ki | 7.41 | CHEMBL | |||||
| Aldose reductase | Enzyme | IC50 | 5.39 | DRUG MATRIX | |||||
| Enoyl-[acyl-carrier-protein] reductase [NADH] | Enzyme | IC50 | 4.33 | CHEMBL | |||||
| Urease | Enzyme | IC50 | 4.82 | CHEMBL | |||||
| ATP phosphoribosyltransferase | Enzyme | Ki | 4.22 | CHEMBL | |||||
| NAD(P)H dehydrogenase [quinone] 1 | Enzyme | Ki | 9 | CHEMBL |
External reference:
| ID | Source |
|---|---|
| 4018715 | VUID |
| N0000147021 | NUI |
| D03798 | KEGG_DRUG |
| 1598 | RXNORM |
| 4018715 | VANDF |
| C0005640 | UMLSCUI |
| CHEBI:4513 | CHEBI |
| DTC | PDB_CHEM_ID |
| CHEMBL1466 | ChEMBL_ID |
| DB00266 | DRUGBANK_ID |
| 54676038 | PUBCHEM_CID |
| 1065 | MMSL |
| 4586 | MMSL |
| d03889 | MMSL |
| 002082 | NDDF |
| 423414002 | SNOMEDCT_US |
| 79209008 | SNOMEDCT_US |
| D001728 | MESH_DESCRIPTOR_UI |
| 6808 | IUPHAR_LIGAND_ID |
| 2897 | INN_ID |
| 7QID3E7BG7 | UNII |
| 7QID3E7BG7 | INXIGHT DRUGS |
Pharmaceutical products:
None