9453. Tiopronin

Nomenclature

CAS number: 1953-02-2
N-(2-Mercapto-1-oxopropyl)glycine; N-(2-mercaptopropionyl)glycine; α-mercaptopropionylglycine; Acadione (Sanofi-Aventis); Captimer (MIT); Thiola (Mission); Thiosol (Coop. Farm.).
C5H9NO3S; mol wt 163.19.
C 36.80%, H 5.56%, N 8.58%, O 29.41%, S 19.65%.

Description and references

Synthetic thiol; undergoes thiol-disulfide exchange to form a water-soluble complex with biological cystine. Prepn: Mita et al., US 3246025 (1966 to Santen). Antidotal effects in mice: H. Fujimura et al., Nippon Yakurigaku Zasshi 60, 278 (1964), C.A. 62, 972h (1965). Anti-inflammatory pharmacology in animals: F. Capasso, Agents Actions 11, 741 (1981). Chemiluminescence determn in pharmaceutical formulations: J. Lu et al., J. Pharm. Biomed. Anal. 33, 1033 (2003). LC/MS determn in plasma: J. Ma et al., J. Chromatogr. A 1113, 55 (2006). Clinical trial in chronic hepatitis: F. Ichida et al., J. Int. Med. Res. 10, 325 (1982). Clinical comparison with d-penicillamine in rheumatoid arthritis: B. Amor et al., Arthritis Rheum. 25, 698 (1982); G. Pasero et al., ibid. 923.

Chemical structure

Properties

Crystals from ethyl acetate, mp 95-97°. Freely sol in water. LD50 i.v. in mice: 2.1 g/kg (Fujimura).

Therapeutic Category

Antidote (heavy metal poisoning); hepatoprotectant; mucolytic.

Therapeutic Category (Veterinary)

In treatment of cystine urolithiasis.

Keywords

Antidote (Heavy Metal Poisoning); Hepatoprotectant; Mucolytic