Docarpamine

Title: Docarpamine
CAS Registry Number: 74639-40-0
CAS Name: 4-[2-[[(2S)-2-(Acetylamino)-4-(methylthio)-1-oxobutyl]amino]ethyl]-1,2-phenylene diethyl ester
Additional Names: (-)-(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
Manufacturers' Codes: TA-870
Trademarks: Tanadopa (Tanabe Seiyaku)
Molecular Formula: C21H30N2O8S
Molecular Weight: 470.54
Percent Composition: C 53.60%, H 6.43%, N 5.95%, O 27.20%, S 6.81%
Literature 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).
Properties: Crystals form ethyl acetate/n-hexane, mp 85-90°. [a]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).
Melting point: mp 85-90°; mp 105-108° (Nishiyama, 1992)
Optical Rotation: [a]D20 -15.6° (c = 2 in methanol)
Toxicity data: LD50 in male, female rats (mg/kg): 1000-1400, ~1000 s.c.; in rats, dogs (mg/kg): _>2000 orally (Nishiyama, 1992)
Therap-Cat: Cardiotonic.
Keywords: Cardiotonic.
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