29. Acenocoumarol

Nomenclature

CAS number: 152-72-7
4-Hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-1-benzopyran-2-one; 3-(α-acetonyl-p-nitrobenzyl)-4-hydroxycoumarin; 3-(α-p-nitrophenyl-β-acetylethyl)-4-hydroxycoumarin; acenocoumarin; nicoumalone; G-23350; Mini-Sintrom (Novartis); Sinthrome (Novartis); Sintrom (Novartis).
C19H15NO6; mol wt 353.33.
C 64.59%, H 4.28%, N 3.96%, O 27.17%.

Description and references

Vitamin K antagonist; structurally similar to warfarin, q.v. Prepn: W. Stoll, F. Litvan, US 2648682 (1953 to Geigy); I. C. Ivanov et al., Arch. Pharm. 323, 521 (1990). Resolution and abs config of enantiomers: C. R. Wheeler, W. F. Trager, J. Med. Chem. 22, 1122 (1979). Pharmacology and toxicity: M. Leroux, B. Jamain, Therapie 11, 85 (1956). GC-MS determn in plasma: F. Pommier et al., J. Chromatogr. B 654, 35 (1994). Clinical trial: D. P. M. Brandjes et al., N. Engl. J. Med. 327, 1485 (1992).

Chemical structure

Properties

Crystals, mp 196-199°. Sparingly sol in water and most organic solvents. Forms water-sol salt with alkalies. LD50 orally in mice, rats: 1470, 1000 mg/kg (Leroux, Jamain).

Therapeutic Category

Anticoagulant.

Keywords

Anticoagulant