7419. Pidotimod

Nomenclature

CAS number: 121808-62-6
(4R)-3-[[(2S)-5-Oxo-2-pyrrolidinyl]carbonyl]-4-thiazolidinecarboxylic acid; 3-l-pyroglutamyl-l-thiazolidine-4-carboxylic acid; (R)-3-[(S)-5-oxoprolyl]-4-thiazolidinecarboxylic acid; PGT/1A; Axil (Boehringer, Mann.); Onaka (Max Pharma); Pigitil (Fidia); Polimod (Poli).
C9H12N2O4S; mol wt 244.27.
C 44.25%, H 4.95%, N 11.47%, O 26.20%, S 13.13%.

Description and references

Peptide-like biological response modifier. Prepn: S. Poli, EP 276752; idem, US 4839387 (1988, 1989 both to Poli). Immunostimulant effect in nude mice: A. Vacca et al., Int. J. Immunother. 9, 85 (1993); on human peripheral blood monocytes: M. O. Borghi et al., ibid. 10, 35 (1994). HPLC determn in plasma and urine: G. Coppi, M. Barchielli, J. Chromatogr. 563, 385 (1991). Clinical trial in recurrent acute tonsillitis: P. Careddu et al., Adv. Otorhinolaryngol. 47, 328 (1992). Toxicity study: G. Coppi et al., Arzneim.-Forsch. 44, 1448 (1994). Series of articles on chemistry, pharmacology, toxicology and clinical experience: ibid. 1399-1530.

Chemical structure

Properties

White or slightly ivory, odorless microcrystalline powder, mp 194-198° (dec). Also reported as white crystals from water, mp 192-194° (Poli). [α]D25 -150° (c = 2 in 5N HCl). pKa 3.03. Soly (g/l): water 37.8; methanol 13.8; ethanol 4.4; DMF 72.4. Practically insol in chloroform, hexane. LD50 in mice and rats (mg/kg): >4000 i.v.; >4000 i.m.; >8000 i.p.; >8000 orally (Coppi).

Therapeutic Category

Immunomodulator.

Keywords

Immunomodulator