5-chloro-N-{[(5S)-3-{4-[2-hydroxy-N-(2-hydroxyethyl)acetamido]phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide

• ChemBase ID: 177576
• Molecular Formular: C19H20ClN3O6S
• Molecular Mass: 453.8966
• Monoisotopic Mass: 453.07613406
• SMILES: c1c(ccc(c1)N(C(=O)CO)CCO)N1C(=O)O[C@H](C1)CNC(=O)c1ccc(s1)Cl
• Canonical SMILES: OCCN(c1ccc(cc1)N1C[C@@H](OC1=O)CNC(=O)c1ccc(s1)Cl)C(=O)CO
• InChI: InChI=1S/C19H20ClN3O6S/c20-16-6-5-15(30-16)18(27)21-9-14-10-23(19(28)29-14)13-3-1-12(2-4-13)22(7-8-24)17(26)11-25/h1-6,14,24-25H,7-11H2,(H,21,27)/t14-/m0/s1
• InChIKey: ZZABLIJBKARJCB-AWEZNQCLSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 5-chloro-N-{[(5S)-3-{4-[2-hydroxy-N-(2-hydroxyethyl)acetamido]phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide
• IUPAC Traditional name: 5-chloro-N-{[(5S)-3-{4-[2-hydroxy-N-(2-hydroxyethyl)acetamido]phenyl}-2-oxo-1,3-oxazolidin-5-yl]methyl}thiophene-2-carboxamide
• Synonyms: 5-Chloro-N-[[(5S)-3-[4-[(2-hydroxyacetyl)(2-hydroxyethyl)amino]phenyl]-2-oxo-5-oxazolidinyl]methyl]-2-thiophenecarboxamide; Rivaroxaban Diol(Mixture of Diastereomers)

Database IDs

• CAS Number: 1160170-00-2
• PubChem SID: 164233486
• PubChem CID: 46782891

CALCULATED PROPERTIES

• Acid pKa: 13.261019
• H Acceptors: 6
• H Donor: 3
• LogD (pH = 5.5): 0.7359411
• LogD (pH = 7.4): 0.7359406
• Log P: 0.7359412
• Molar Refractivity: 108.2538 cm^3
• Polarizability: 41.927586 Å^3
• Polar Surface Area: 119.41 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - R538010

A metabolite of Rivaroxaban (R538000).

REFERENCES

• Kubitza, D., et al.: Clin. Pharmacol. Ther., 78, 412 (2005)
• Roehrig, S., et al.: J. Med. Chem., 48, 5900 (2005)
• Biemond, B., et al.: Thromb. Haemost., 97, 471 (2005)
• Lang, D., et al.: Drug Metab. Dispos., 37, 1046 (2005)