1-carbamoyl-2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}ethane-1-sulfonic acid

• ChemBase ID: 176749
• Molecular Formular: C18H22N2O5S
• Molecular Mass: 378.44268
• Monoisotopic Mass: 378.12494281
• SMILES: n1cc(ccc1CCOc1ccc(cc1)CC(C(=O)N)S(=O)(=O)O)CC
• Canonical SMILES: CCc1ccc(nc1)CCOc1ccc(cc1)CC(S(=O)(=O)O)C(=O)N
• InChI: InChI=1S/C18H22N2O5S/c1-2-13-3-6-15(20-12-13)9-10-25-16-7-4-14(5-8-16)11-17(18(19)21)26(22,23)24/h3-8,12,17H,2,9-11H2,1H3,(H2,19,21)(H,22,23,24)
• InChIKey: GKXIVIFUPLEQLN-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-carbamoyl-2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}ethane-1-sulfonic acid
• IUPAC Traditional name: 1-carbamoyl-2-{4-[2-(5-ethylpyridin-2-yl)ethoxy]phenyl}ethanesulfonic acid
• Synonyms: α-(Aminocarbonyl)-4-[2-(5-ethyl-2-pyridinyl)ethoxy]benzeneethanesulfonic Acid; Pioglitazone Sulfonic Acid Impurity

Database IDs

• CAS Number: 625853-73-8
• PubChem SID: 164232659
• PubChem CID: 71751679

CALCULATED PROPERTIES

• Acid pKa: -1.1789303
• H Acceptors: 6
• H Donor: 2
• LogD (pH = 5.5): -0.4864037
• LogD (pH = 7.4): -0.36175457
• Log P: -0.6055111
• Molar Refractivity: 96.6609 cm^3
• Polarizability: 38.309246 Å^3
• Polar Surface Area: 119.58 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - P471030

Pioglitazone (P471015) impurity or metabolite formed via oxidative cleavage of the thiazolidinedione ring.

REFERENCES

• Krieter, P., et al.: Drug Metab. Dispos., 22, 625 (1994)
• Kiyota, Y., et al.: Arzneim.-Forsch., 47, 22 (1994)