Rivaroxaban
Athanor · official
C19H18ClN3O5S · 435.9 g/mol
IUPAC name: 5-chloro-N-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide
Also called Xarelto, factor Xa inhibitor, DOAC
HazardsToxic to aquatic life with long lasting effectsNames and identifiers
- IUPAC name
- 5-chloro-N-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide
- Synonyms
- Xarelto, factor Xa inhibitor, DOAC
+ 36 more
BAY 59-7939, BAY59-7939, 9NDF7JZ4M3, BAY-59-7939, 5-Chloro-N-({(5s)-2-Oxo-3-[4-(3-Oxomorpholin-4-Yl)phenyl]-1,3-Oxazolidin-5-Yl}methyl)thiophene-2-Carboxamide, JNJ39039039, JNJ-39039039, CHEBI:68579, B01AF01, 2-Thiophenecarboxamide, 5-chloro-N-[[(5S)-2-oxo-3-[4-(3-oxo-4-morpholinyl)phenyl]-5-oxazolidinyl]methyl]-, 5-chloro-N-{[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide, 2-Thiophenecarboxamide, 5-chloro-N-(((5S)-2-oxo-3-(4-(3-oxo-4-morpholinyl)phenyl)-5-oxazolidinyl)methyl)-, 5-Chloro-N-(((5S)-2-oxo-3-(4-(3-oxomorpholin-4-yl)phenyl)-1,3-oxazolidin-5-yl)methyl)thiophene-2-carboxamide, 5-chloro-N-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]-1,3-oxazolidin-5-yl]methyl]thiophene-2-carboxamide, DTXSID3057723, rivaroxabanum, BAY 597939, BAY 59 7939, RefChem:6203, DTXCID601508635, (S)-5-Chloro-N-((2-oxo-3-(4-(3-oxomorpholino)phenyl)oxazolidin-5-yl)methyl)thiophene-2-carboxamide, MFCD11974010, 5-CHLORO-N-[[(S)-3-(4-(3-OXOMORPHOLIN-4-YL)PHENYL)-2-OXO-1,3-OXAZOLIDIN-5-YL]METHYL]-THIOPHENE-2-CARBOXAMIDE, RIVAROXABAN [ORANGE BOOK], 2w26, C19H18ClN3O5S, Q420262, 5-CHLORO-N-[[(5S)-2-OXO-3-[4-(3-OXO-4-MORPHOLINYL)PHENYL]-5-OXAZOLIDINYL]METHYL]-2-THIOPHENECARBOXAMIDE, (S)-Rivaroxaban, (S)-5-chloro-N-{[2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl]methyl} thiophene-2-carboxamide, 5-chloro-N-[[(5S)-2-oxo-3-[4-(3-oxomorpholin-4-yl)phenyl]oxazolidin-5-yl]methyl]thiophene-2-carboxamide, Xarelto (TN), Rivaroxaban [INN], UNII-9NDF7JZ4M3, BAY 59-7939 (Rivaroxaban), Rivaroxaban CRS
- Molecular formula
- C19H18ClN3O5S
- Empirical formula
- C19H18ClN3O5S
- Molecular weight
- 435.9 g/mol
- Exact mass
- 435.06557
- CAS number
- 366789-02-8
- PubChem CID
- 9875401
- Canonical SMILES
- C1COCC(=O)N1C2=CC=C(C=C2)N3CC(OC3=O)CNC(=O)C4=CC=C(S4)Cl
- Isomeric SMILES
- C1COCC(=O)N1C2=CC=C(C=C2)N3C[C@@H](OC3=O)CNC(=O)C4=CC=C(S4)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
- InChIKey
- KGFYHTZWPPHNLQ-AWEZNQCLSA-N
- Molfile
Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.
Physical properties
- Appearance
- White to yellowish powder[1]
- Odor
- Odorless[1]
- Solubility in water
- Slightly soluble in organic solvents (e.g. acetone, polyethylene glycol 400) and is pratically insoluble in water and aqueous media[1]
Each value as its source reports it, with the source's number after it (listed under References). Where several sources report a property, the row shows the value most of them agree on, the rule the app uses; open the values to see every one.
Calculated
- Heavy atoms
- 29
- Rings
- 4
- Aromatic rings
- 2
- Fraction sp³ carbons (Fsp3)
- 0.32
- H-bond donors
- 1
- H-bond acceptors
- 6
- Rotatable bonds
- 5
- TPSA (Ų)
- 88.2 computed here · PubChem 116
- Formal charge
- 0
- XLogP3
- 2.5 PubChem
- Complexity
- 645 PubChem
- Stereocenters
- 1 definedCIP: C5: S
- Double-bond geometry
- None specified
- Point group
- C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)
Elemental analysis
- C52.35%
- H4.16%
- Cl8.13%
- N9.64%
- O18.35%
- S7.36%
Isotope pattern
Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.
Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.
Predicted
- log P
- 2.52 Crippen (Wildman and Crippen 1999)
- log S (water solubility)
- -4.08 ESOL (Delaney 2004), log mol/L
- Synthetic accessibility
- 2.99 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)
Drug-likeness: Lipinski’s rule of five
- Molecular weight ≤ 500: 435.89
- log P ≤ 5 (Crippen): 2.52
- H-bond donors ≤ 5: 1
- H-bond acceptors ≤ 10: 6
Passes all four rules.
¹³C NMR shifts, predicted
Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.
Safety
Most widely reported: 85 company reports to ECHA. Source [2].
- Environmental hazard
- H411Toxic to aquatic life with long lasting effects (89.4% of reports)
Precautionary statements: P273, P391, P501
View all classifications (2)
- [2] European Chemicals Agency (ECHA)This chemical does not meet GHS hazard criteria for 1.2% (1 of 85) of reports.
- [2] European Chemicals Agency (ECHA) · 85 reportsH411
Storage
- Store at 25 °C (77 °F) or room temperature; excursions permitted to 15 deg - 30 °C (59 deg - 86 °F)[1]
Safety data sheets on the supplier’s page: LKT Laboratories, Inc. , AbMole Bioscience, Xianglong Pharmaceutical Standards (XL Standards).
Always read the supplier’s safety data sheet before working with it.
Spectra
- Other MSMassBank Europe (Xevo G2 XS QTOF, waters · ESI-QTOF · POSITIVE) · MassBank of North America (MoNA) (Xevo G2 XS QTOF, waters · ESI-QTOF · ESI)
Experimental spectra held by these sources; each link opens the source's own record.
Literature
Reading PubChem, OpenAlex and GSRS…
Bioactivity
Reading ChEMBL…
References
- [1]Hazardous Substances Data Bank (HSDB) · Public domain (US NLM) · via PubChem · retrieved 2026-10-14
- [2]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
- [3]MassBank Europe · Linked only · via PubChem · retrieved 2026-10-14
- [4]MassBank of North America (MoNA) · CC BY 4.0 · via PubChem · retrieved 2026-10-14
- ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
- ·Literature on PubChem
Data last updated 2026-10-14.