3396. Docarpamine

Nomenclature

CAS number: 74639-40-0
4-[2-[[(2S)-2-(Acetylamino)-4-(methylthio)-1-oxobutyl]amino]ethyl]-1,2-phenylene diethyl ester; (-)-(S)-2-acetamido-N-(3,4-dihydroxyphenethyl)-4-(methylthio)butyramide bis(ethylcarbonate) (ester); N-(N-acetyl-l-methionyl)-O,O-bis(ethoxycarbonyl)dopamine; N-(N-acetyl-l-methionyl)-3,4-diethoxycarboxyphenethylamine; TA-870; Tanadopa (Tanabe Seiyaku).
C21H30N2O8S; mol wt 470.54.
C 53.60%, H 6.43%, N 5.95%, O 27.20%, S 6.81%.

Description and references

Dopamine prodrug. Prepn: T. Kiguchi et al., EP 7441; eidem, US 4228183 (both 1980 to Tanabe Seiyaku). Pharmacology: I. Yamaguchi et al., J. Cardiovasc. Pharmacol. 13, 879 (1989). Mechanism of action: S. Nishiyama et al., ibid. 14, 175 (1989). Pharmacokinetics: M. Yoshikawa et al., Drug Metab. Dispos. 16, 754 (1988). Metabolism in humans: eidem, ibid. 18, 212 (1990). HPLC determn in biological fluids: eidem, Biomed. Chromatogr. 4, 181 (1990). Review: S. Nishiyama et al., Cardiovasc. Drug Rev. 10, 101-116 (1992).

Chemical structure

Properties

Crystals form ethyl acetate/n-hexane, mp 85-90°. [α]D20 -15.6° (c = 2 in methanol). Also reported as crystalline powder, mp 105-108° (Nishiyama, 1992). Slightly sol in water, readily sol in ethanol. LD50 in male, female rats (mg/kg): 1000-1400, ≈1000 s.c.; in rats, dogs (mg/kg): _>2000 orally (Nishiyama, 1992).

Therapeutic Category

Cardiotonic.

Keywords

Cardiotonic