betrixaban

Also known as N-(5-chloropyridin-2-yl)-2-{[4-(N,N-dimethylcarbamimidoyl)benzoyl]amino}-5-methoxybenzamide, N-(5-chloropyridin-2-yl)-2-[4-(N,N-dimethylcarbamimidoyl)benzamido]-5-methoxybenzamide

Betrixaban (trade name Bevyxxa) is an oral anticoagulant drug which acts as a direct factor Xa inhibitor. Betrixaban is FDA approved for venous thrombosis prevention in adults hospitalized for an acute illness who are at risk for thromboembolic complications. Compared to other directly acting oral anticoagulants betrixaban has relatively low renal excretion and is not metabolized by CYP3A4.

Chemical data

Formula: C23H22ClN5O3
Molecular weight: 451.9 g/mol
IUPAC name: N-(5-chloro-2-pyridinyl)-2-[[4-(N,N-dimethylcarbamimidoyl)benzoyl]amino]-5-methoxybenzamide
SMILES: CN(C)C(=N)C1=CC=C(C=C1)C(=O)NC2=C(C=C(C=C2)OC)C(=O)NC3=NC=C(C=C3)Cl
InChIKey: XHOLNRLADUSQLD-UHFFFAOYSA-N
XLogP: 3.6
Polar surface area: 107 Å²
H-bond donors: 3
H-bond acceptors: 5
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 2017
Admin. routes: oral
Indications: atrial fibrillation, venous thromboembolism, liver disease, atrial flutter

via ChEMBL · EBI

Research

245 papers

Betrixaban.2006
Betrixaban.2012
Betrixaban: A Novel Oral Anticoagulant With a New Niche.The Journal of pharmacy technology : jPT : official publication of the Association of Pharmacy Technicians · 2018
Betrixaban for Extended Venous Thromboembolism Prophylaxis in High-Risk Hospitalized Patients: Putting the APEX Results into Practice.Drugs · 2019
Betrixaban for first-line venous thromboembolism prevention in acute medically ill patients with risk factors for venous thromboembolism.Expert review of cardiovascular therapy · 2018

via PubMed

Wikidata facts

Subclass of: chemical compound
Mass: 451.141
Has use: medication

Show 5 more facts

Commons category: Betrixaban
chemical formula: C₂₃H₂₂ClN₅O₃
canonical SMILES: CN(C)C(=N)C1=CC=C(C=C1)C(=O)NC2=C(C=C(C=C2)OC)C(=O)NC3=NC=C(C=C3)Cl
NCI Thesaurus ID: C75154
subject has role: direct Xa inhibitor

Sources (3)

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Encyclopedic overview

3 sections

Contents

History
See also
References

== History == Betrixaban was originally developed by Millennium Pharmaceuticals. Portola Pharmaceuticals acquired rights for betrixaban in 2004 and co-developed it with Merck. In 2011 Merck discontinued joint development.

Excerpted from Wikipedia’s “betrixaban” article, available under the CC BY-SA 4.0 licence.

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