3514. Edoxudine

Nomenclature

CAS number: 15176-29-1
2′-Deoxy-5-ethyluridine; 5-ethyl-2′-deoxyuridine; 5-ethyl-3-(2′-deoxyribosyl)uracil; EDU; EUDR; ORF-15817; Aedurid (Robugen); Edurid (Robugen).
C11H16N2O5; mol wt 256.26.
C 51.56%, H 6.29%, N 10.93%, O 31.22%.

Description and references

Substituted uracil with anti-herpes activity. Prepn and properties: K. K. Gauri, GB 1170565; eidem, US 3553192 (1968, 1971 both to Robugen). Synthesis via organopalladium intermediates: D. E. Bergstrom, J. L. Ruth, J. Am. Chem. Soc. 98, 1587 (1976); D. E. Bergstrom, M. K. Ogawa, ibid. 100, 8106 (1978). Physical properties: M. Swierkowski, D. Shugar, J. Med. Chem. 12, 533 (1969). Antiviral activity: E. De Clercq, D. Shugar, Biochem. Pharmacol. 24, 1073 (1975). Preferential inhibition of herpes simplex virus type 2: C.-Z. Teh, S. L. Sacks, Antimicrob. Agents Chemother. 23, 637 (1983). Synergistic effect with interferon-β, q.v., on herpes simplex virus: C. Janz, R. Wigand, Arch. Virol. 73, 135 (1982). Inhibitory effect on growth of murine leukemia cells: J. Balzarini et al., Invest. New Drugs 2, 35 (1984).

Chemical structure

Properties

Long clear needles from acetone, mp 152-153°. uv max: 267 nm (ε 9610) at pH 2, 267 nm (ε 7280) at pH 1. pKa: 9.98.

Therapeutic Category

Antiviral (herpes simplex).

Keywords

Antiviral; Nucleosides/Nucleotides