(4R)-3-[(2S)-5-oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic acid

• ChemBase ID: 119547
• Molecular Formular: C9H12N2O4S
• Molecular Mass: 244.26758
• Monoisotopic Mass: 244.05177787
• SMILES: N1(C(=O)[C@H]2NC(=O)CC2)[C@H](C(=O)O)CSC1
• Canonical SMILES: O=C1CC[C@H](N1)C(=O)N1CSC[C@H]1C(=O)O
• InChI: InChI=1S/C9H12N2O4S/c12-7-2-1-5(10-7)8(13)11-4-16-3-6(11)9(14)15/h5-6H,1-4H2,(H,10,12)(H,14,15)/t5-,6-/m0/s1
• InChIKey: UUTKICFRNVKFRG-WDSKDSINSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (4R)-3-[(2S)-5-oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic acid
• IUPAC Traditional name: pidotimod; (4R)-3-[(2S)-5-oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic acid
• Synonyms: Pidotimod; (R)-3-((S)-5-oxopyrrolidine-2-carbonyl)thiazolidine-4-carboxylic acid; Polimod; Pidotimod; Axil; Onaka; Pigitil

Database IDs

• CAS Number: 121808-62-6
• PubChem SID: 162108072
• PubChem CID: 65944

CALCULATED PROPERTIES

• Acid pKa: 3.5657098
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -3.221541
• LogD (pH = 7.4): -4.647885
• Log P: -1.2931193
• Molar Refractivity: 55.8341 cm^3
• Polarizability: 22.043678 Å^3
• Polar Surface Area: 86.71 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Pharmacology Properties

• Target: Others
• Mechanism of Action: Activator of T-lymphocyctes and stimulator of granulocytes and macrophages

Product Information

• Purity: 95+%
• Salt Data: Free Base
• Description: Isomers
• Application(s): Immunomodulator; Used for treatment of recurrent respiratory infections

REFERENCES

• Eur. Pat., 1988, Poli Ind Chim, 276 752; CA, 109, 190876e, (synth, pharmacol)
• Coppi, G. et al., J. Chromatogr., 1991, 563, 385, (hplc)
• Migliorati, G. et al., Immunopharmacol. Immunotoxicol., 1992, 14, 737, (pharmacol)
• Pugliese, A. et al., Int. J. Immunother., 1992, 8, 212
• Dal Bo, L. et al., Boll. Chim. Farm., 1993, 132, 126, (hplc)
• Arzneim.-Forsch., 1994, 44, 1399, (numerous papers)
• Chiarenza, A. et al., Pharmacol. Toxicol., 1994, 74, 262, (pharmacol)
• Ayala, D.J. et al., Acta Cryst. C, 1995, 51, 473, (cryst struct)