Apixaban

Base Information

• Chemical Name: Apixaban
• CAS No.: 503612-47-3
• Molecular Formula: C25H25N5O4
• Molecular Weight: 459.50
• European Community (EC) Number: 639-684-6
• UNII: 3Z9Y7UWC1J
• DSSTox Substance ID: DTXSID80436500
• Nikkaji Number: J2.566.952E
• Wikipedia: Apixaban
• Wikidata: Q414462
• NCI Thesaurus Code: C61308
• RXCUI: 1364430
• Pharos Ligand ID: K9R389ZL42D1
• Metabolomics Workbench ID: 65917
• ChEMBL ID: CHEMBL231779
• Mol file: 503612-47-3.mol

Synonyms:apixaban;BMS 562247;BMS-562247;BMS-562247-01;BMS562247;Eliquis

Chemical Property of Apixaban

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.705
• Boiling Point: 770.468 °C at 760 mmHg
• PKA: 15.01±0.20(Predicted)
• Flash Point: 419.764 °C
• PSA: 110.76000
• Density: 1.421 g/cm³
• LogP: 3.52990
• Storage Temp.: Refrigerator
• Solubility.: DMSO (Slightly, Heated), Methanol (Slightly)
• XLogP3: 2.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 459.19065430
• Heavy Atom Count: 34
• Complexity: 777

Purity/Quality:

98% ,99% , ^*data from raw suppliers

Apixaban ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antithrombotic Agents
• Canonical SMILES: COC1=CC=C(C=C1)N2C3=C(CCN(C3=O)C4=CC=C(C=C4)N5CCCCC5=O)C(=N2)C(=O)N
• Recent ClinicalTrials: Study to Gather Information About the Safety of Oral Anticoagulation Drugs and How Well These Drugs Work in Real World for Patients With Non-valvular Atrial Fibrillation (Irregularly Heart Beats Which is Not Caused by a Heart Valve Problem)
• Recent EU Clinical Trials: A single dose of apixaban for the prevention of thrombotic events in the context of long-distance flights
• Recent NIPH Clinical Trials: Noac for Desimplanted IHD Patients Complicated with Atrial Fibrillation
• Drug Interactions: 1.A double inhibitor of strong CYP3A4 and P-gp increases apixaban’s blood levels: decrease Eliquis dosage to 2.5mg or avoid simultaneous usage. 2.A inductor of strong CYP3A4 and P-gp can decrease apixaban’s blood levels: avoid simultaneous usage.
• Description: Eliquis (apixaban), a direct inhibitor of factor Xa (FXa), was approved by the European Commission on May 18, 2011 for prevention of venous thromboembolic events (VTE) in adult patients who have undergone elective hip or knee replacement surgery. The discovery of apixaban was the culmination of a succession of novel and innovative medicinal chemistry discoveries starting with the identification of nonpeptide leads, rational drug design using computer-aided and X-ray crystallographic information, and the building of drug-like properties through the systematic replacement of basic groups with neutral moieties. Apixaban arose from modifications to razaxaban by constraining a pyrazole amide to form a bicyclic pyrazolo-pyridinone scaffold. Optimization of the P1 group resulted in the identification of the nonbasic methoxy phenyl group, while a P4 piperidinone improved the balance of potency and pharmacokinetics with low Vdss. The synthesis of apixaban begins with the generation of a hydrazone of 4-methoxyaniline which is then used in a 3+2 cycloaddition with a dihydropiperidinone to form a bicyclic pyrazolo-pyridinone scaffold. The distal piperidinone group is installed using an Ullmann coupling reaction followed by aminolysis of an ethyl ester on the pyrazole ring to complete the synthesis of apixaban. Apixaban is an orally bioavailable, selective inhibitor of both free and prothrombinase-bound factor Xa (Kis = 0.8 nM). In vivo, apixaban has antithrombotic effects in a rabbit model of venous thrombosis. Apixaban (357.5 mg) also prevents thrombus formation without inducing adverse bleeding events in a porcine model of aortic heterotopic valve replacement. Formulations containing apixaban have been used to prevent blood clot formation in patients with atrial fibrillation.
• Uses: Apixaban is a highly selective, reversible inhibitor of Factor Xa with Ki of 0.08 nM and 0.17 nM in human and rabbit, respectively.
• Clinical Use: Apixaban is an oral anticoagulant with highly selective inhibition of factor Xa. It was approved by the European Medicines Agency (EMA) for the treatment of venous thromboembolic events and first marketed in Germany under the brand name Eliquis in June 2011. Apixaban was co-developed by Bristol-Myers Squibb and Pfizer and represents the first approved drug for this indication since warfarin over 50 years ago.
• Drug interactions: Potentially hazardous interactions with other drugs Analgesics: increased risk of haemorrhage with IV diclofenac and ketorolac - avoid. Antibacterials: avoid with clarithromycin and telithromycin; concentration possibly reduced by rifampicin - avoid if treating DVT/PE. Anticoagulants: increased risk of haemorrhage with other anticoagulants - avoid. Antidepressants: concentration possibly reduced by St John’s wort - avoid if treating DVT/PE. Antiepileptics: concentration possibly reduced by carbamazepine, fosphenytoin, phenobarbital, phenytoin and primidone - avoid if treating DVT/ PE with carbamazepine. Antifungals: concentration increased by ketoconazole - avoid; avoid with itraconazole, posaconazole and voriconazole. Antivirals: avoid with atazanavir, boceprevir, darunavir, fosamprenavir, indinavir, lopinavir, ritonavir, saquinavir, telaprevir and tipranavir. Cobicistat: avoid concomitant use.