rivaroxaban   

GtoPdb Ligand ID: 6388

Synonyms: BAY 59-7939 | Xarelto®
rivaroxaban is an approved drug (EMA (2008), FDA (2011))
Compound class: Synthetic organic
Comment: First in class orally active direct factor Xa inhibitor.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 8
Hydrogen bond donors 1
Rotatable bonds 6
Topological polar surface area 116.42
Molecular weight 435.07
XLogP 0.61
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C1OC(CN1c1ccc(cc1)N1CCOCC1=O)CNC(=O)c1ccc(s1)Cl
Isomeric SMILES O=C1O[C@H](CN1c1ccc(cc1)N1CCOCC1=O)CNC(=O)c1ccc(s1)Cl
InChI InChI=1S/C19H18ClN3O5S/c20-16-6-5-15(29-16)18(25)21-9-14-10-23(19(26)28-14)13-3-1-12(2-4-13)22-7-8-27-11-17(22)24/h1-6,14H,7-11H2,(H,21,25)/t14-/m0/s1
InChI Key KGFYHTZWPPHNLQ-AWEZNQCLSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (EMA (2008), FDA (2011))
IUPAC Name
5-chloro-N-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide
International Nonproprietary Names
INN number INN
8428 rivaroxaban
Synonyms
BAY 59-7939 | Xarelto®
Database Links
CAS Registry No. 366789-02-8 (source: ChEBI)
ChEBI CHEBI:68579
ChEMBL Ligand CHEMBL198362
DrugCentral Ligand 4182
GtoPdb PubChem SID 178103004
PubChem CID 9875401
RCSB PDB Ligand RIV
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SynPHARM 78509 (in complex with coagulation factor X)
Wikipedia Rivaroxaban