Proscillaridin
Title: Proscillaridin
CAS Registry Number: 466-06-8
CAS Name: (3b)-3-[(6-Deoxy-a-L-mannopyranosyl)oxy]-14-hydroxybufa-4,20,22-trienolide
Additional Names: 14-hydroxy-3b-(rhamnosyloxy)bufa-4,20,22-trienolide; 3b-rhamnosido-14b-hydroxy-D4,20,22-bufatrienolide; proscillaridin A; desglucotransvaaline; scillarenin 3b-rhamnoside
Trademarks: Caradrin (AWD); Proscillan (Streuli); Purosin-TC (Tatsumi); Stellarid (GSK); Talusin (Abbott)
Molecular Formula: C30H42O8
Molecular Weight: 530.65
Percent Composition: C 67.90%, H 7.98%, O 24.12%
Literature References: Prepn by acid cleavage of scillaren A: Stoll et al., Helv. Chim. Acta 16, 703 (1933); by enzymic decompn of glucoscillaren A with strophanthobiase: Stoll et al., ibid. 35, 2495 (1952); from Urginea burkei Baker, Liliaceae: Zoller, Tamm, ibid. 36, 1744 (1953); from U. (Scilla) maritima (L.) Baker, Liliaceae: Görlich, Arzneim.-Forsch. 10, 770 (1960). Structure: Stoll et al., Helv. Chim. Acta 35, 1934 (1952). Pharmacology: Lenke, Brock, Arzneim.-Forsch. 20, 1 (1970). Metabolic studies: Davis et al., Arch. Int. Pharmacodyn. 177, 231 (1969); Nakano et al., ibid. 183, 199 (1970). Clinical studies: Several authors, Minerva Med. 58, 4243-4322 (1967). Toxicity study: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). Series of articles on prepn, pharmacology, toxicology, pharmacokinetics, metabolism of 4¢-methyl ether: Arzneim.-Forsch. 28, 493-573 (1978).
Properties: Prisms from methanol, mp 219-222°. [a]D20 -91.5° (CH3OH). LD50 in male, female rats (mg/kg): 56, 76 orally (Goldenthal).
Melting point: mp 219-222°
Optical Rotation: [a]D20 -91.5° (CH3OH)
Toxicity data: LD50 in male, female rats (mg/kg): 56, 76 orally (Goldenthal)
 
Derivative Type: Proscillaridin-4-methyl ether
CAS Registry Number: 33396-37-1
Additional Names: Meproscillarin
Trademarks: Clift (Abbott)
Molecular Formula: C31H44O8
Molecular Weight: 544.68
Percent Composition: C 68.36%, H 8.14%, O 23.50%
Properties: mp 213-217°. [a]D20 -94° (CH3OH). uv max (CH3OH): 297 nm (log e 3.79), (1N KOH/CH3OH): 355 nm (log e 4.65). Sol in methanol, ethanol, THF, dioxane; slightly sol in CHCl3, CH2Cl2, acetone. Practically insol in water, nonpolar organics.
Melting point: mp 213-217°
Optical Rotation: [a]D20 -94° (CH3OH)
Absorption maximum: uv max (CH3OH): 297 nm (log e 3.79)
 
Therap-Cat: Cardiotonic.
Keywords: Cardiotonic.

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