Edoxudine, 依度尿苷

2'-Deoxy-5-ethyluridine

2'-Deoxy-5-ethyluridine is a nucleoside analog that is used in cancer gene therapy. It is an analog of the natural pyrimidine base uracil and inhibits RNA synthesis by competing with natural nucleosides for incorporation into the growing RNA chain. 2'-Deoxy-5-ethyluridine is cytotoxic to cervical cancer cells, inhibiting cell growth and proliferation at inhibitory doses of 0.1 μM. This drug has also been shown to have synergistic effects with other drugs such as trifluoroacetic acid, monoclonal antibody, tissue culture, glycosidic bond, biological properties, cancer tissues, and polymerase chain reaction (PCR).

Edoxudine is a deoxythymidine analog with activity against herpes simplex virus. Edoxudine is activated by viral thymidine kinase to the 5'-monophosphate which is further phosphorylated by cellular enzymes to the 5'-triphosphate, a competitive inhibitor of the viral-coded DNA polymerase.

Edoxudine is a pyrimidine 2'-deoxyribonucleoside.

Edoxudine is a deoxythymidine analog with activity against herpes simplex virus. It is a potent and selective inhibitor of herpes simplex virus type 1 and 2. The obtained product is an antiviral ointment. The activity of edoxudine against herpes simplex virus was first recognized in 1967. It was later recognized to be effective in vivo in a preclinical model of keratitis caused by herpes virus. It was developed by McNeil Pharmaceutical and approved by Health Canada on December 31, 1992. This medication was later discontinued from the market in 1998.

Title: Edoxudine

CAS Registry Number: 15176-29-1

CAS Name: 2'-Deoxy-5-ethyluridine

Additional Names: 5-ethyl-2'-deoxyuridine; 5-ethyl-3-(2'-deoxyribosyl)uracil; EDU; EUDR

Manufacturers' Codes: ORF-15817

Trademarks: Aedurid (Robugen); Edurid (Robugen)

Molecular Formula: C11H16N2O5

Molecular Weight: 256.26

Percent Composition: C 51.56%, H 6.29%, N 10.93%, O 31.22%

Literature 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-b, 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).

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

Melting point: mp 152-153°

pKa: pKa: 9.98

Absorption maximum: uv max: 267 nm (e 9610) at pH 2, 267 nm (e 7280) at pH 1

Therap-Cat: Antiviral (herpes simplex).

Keywords: Antiviral; Purines/Pyrimidinones.