Repositioning Candidate Details
| Candidate ID: | R0519 |
| Source ID: | DB01418 |
| Source Type: | approved; investigational |
| Compound Type: | small molecule |
| Compound Name: | Acenocoumarol |
| Synonyms: | 3-(alpha-(4'-Nitrophenyl)-beta-acetylethyl)-4-hydroxycoumarin; 3-(alpha-(p-Nitrophenol)-beta-acetylethyl)-4-hydroxycoumarin; 3-(alpha-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin; 3-(alpha-Acetonyl-p-nitrobenzyl)-4-hydroxycoumarin; 3-(alpha-p-Nitrophenyl-beta-acetylethyl)-4-hydroxycoumarin; 4-Hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2H-1-benzopyran-2-one; 4-Hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one; Acenocoumarin; Acenocoumarol; Acenocumarolo; Acenokumarin; Nicoumalone; Nicumalon; Nitrophenylacetylethyl-4-hydroxycoumarine; Nitrovarfarian; Nitrowarfarin |
| Molecular Formula: | C19H15NO6 |
| SMILES: | CC(=O)CC(C1=CC=C(C=C1)[N+]([O-])=O)C1=C(O)C2=CC=CC=C2OC1=O |
| Structure: |
|
| DrugBank Description: | Acenocoumarol is a coumarin derivative used as an anticoagulant. Coumarin derivatives inhibit the reduction of vitamin K by vitamin K reductase. This prevents carboxylation of vitamin K-dependent clotting factors, II, VII, IX and X, and interferes with coagulation. Hematocrit, hemoglobin, international normalized ratio and liver panel should be monitored. Patients on acenocoumarol are prohibited from giving blood. |
| CAS Number: | 152-72-7 |
| Molecular Weight: | 353.3255 |
| DrugBank Indication: | For the treatment and prevention of thromboembolic diseases. More specifically, it is indicated for the prevention of cerebral embolism, deep vein thrombosis, pulmonary embolism, thromboembolism in infarction and transient ischemic attacks. It is used for the treatment of deep vein thrombosis and myocardial infarction. |
| DrugBank Pharmacology: | Acenocoumarol inhibits the reduction of vitamin K by vitamin K reductase. This prevents carboxylation of certain glutamic acid residues near the N-terminals of clotting factors II, VII, IX and X, the vitamin K-dependent clotting factors. Glutamic acid carboxylation is important for the interaction between these clotting factors and calcium. Without this interaction, clotting cannot occur. Both the extrinsic (via factors VII, X and II) and intrinsic (via factors IX, X and II) are affected by acenocoumarol. |
| DrugBank MoA: | Acenocoumarol inhibits vitamin K reductase, resulting in depletion of the reduced form of vitamin K (vitamin KH2). As vitamin K is a cofactor for the carboxylation of glutamate residues on the N-terminal regions of vitamin K-dependent clotting factors, this limits the gamma-carboxylation and subsequent activation of the vitamin K-dependent coagulant proteins. The synthesis of vitamin K-dependent coagulation factors II, VII, IX, and X and anticoagulant proteins C and S is inhibited resulting in decreased prothrombin levels and a decrease in the amount of thrombin generated and bound to fibrin. This reduces the thrombogenicity of clots. |
| Targets: | Vitamin K epoxide reductase complex subunit 1 inhibitor |
| Inclusion Criteria: | Indication associated |
| Strategy ID | Strategy | Synonyms | Related Targets | Related Drugs |
|---|
| Target ID | Target Name | GENE | Action | Class | UniProtKB ID | Entry Name |
|---|
| Diseases ID | DO ID | Disease Name | Definition | Class | |
|---|---|---|---|---|---|
| I08 | 114 | Cardiovascular system disease | A disease of anatomical entity which occurs in the blood, heart, blood vessels or the lymphatic system that passes nutrients (such as amino acids and electrolytes), gases, hormones, blood cells or lymph to and from cells in the body to help fight diseases and help stabilize body temperature and pH to maintain homeostasis. http://en.wikipedia.org/wiki/Circulatory_system | disease of anatomical entity | Details |