CAS No 121808-62-6 , (4R)-3-[(2S)-5-oxopyrrolidine-2-carbonyl]-1,3-thiazolidine-4-carboxylic
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Title: Pidotimod
CAS Registry Number: 121808-62-6
CAS Name: (4R)-3-[[(2S)-5-Oxo-2-pyrrolidinyl]carbonyl]-4-thiazolidinecarboxylic acid
Synonyms: 3-L-pyroglutamyl-L-thiazolidine-4-carboxylic acid; (R)-3-[(S)-5-oxoprolyl]-4-thiazolidinecarboxylic acid
Manufacturers' Codes: PGT/1A
Trademarks: Axil (Boehringer, Mann.); Onaka (Max Pharma); Pigitil (Fidia); Polimod (Poli)
Molecular Formula: C9H12N2O4S
Molecular Weight: 244.27
Percent Composition: C 44.25%, H 4.95%, N 11.47%, O 26.20%, S 13.13%
Literature 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.
Properties: White or slightly ivory, odorless microcrystalline powder, mp 194-198° (dec). Also reported as white crystals from water, mp 192-194° (Poli). [a]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).
Melting point: mp 194-198° (dec); mp 192-194° (Poli)
pKa: pKa 3.03
Optical Rotation: [a]D25 -150° (c = 2 in 5N HCl)
Toxicity data: LD50 in mice and rats (mg/kg): >4000 i.v.; >4000 i.m.; >8000 i.p.; >8000 orally (Coppi)
Therap-Cat: Immunomodulator.
Keywords: Immunomodulator.