3713. Etanidazole

Nomenclature

CAS number: 22668-01-5
N-(2-Hydroxyethyl)-2-nitro-1H-imidazole-1-acetamide; DUP-453; NSC-301467; SR-2508; Radinyl (Roberts).
C7H10N4O4; mol wt 214.18.
C 39.25%, H 4.71%, N 26.16%, O 29.88%.

Description and references

Oxygen-mimetic which renders hypoxic cells sensitive to chemo- and radiotherapy. Prepn: A. G. Beaman et al., Antimicrob. Agents Chemother. 1967, 520. See also: W. W. Lee et al., US 4371540 (1983 to U.S. Sec'y Health Human Serv.). Pharmacology: J. M. Brown et al., Int. J. Radiat. Oncol. Biol. Phys. 7, 695 (1981). HPLC determn in biological materials: R. Ward, P. Workman, J. Chromatogr. 420, 223 (1987). Clinical pharmacokinetics and efficacy in radiation therapy: T. H. Wasserman et al., Radiother. Oncol. 20, Suppl. 1, 129 (1991). Evaluation in combination with alkylating agents: L. N. Shulman et al., Int. J. Radiat. Oncol. Biol. Phys. 29, 545 (1994).

Chemical structure

Properties

Crystals from ethanol, mp 162-163° (Beaman); also reported as white powder from ethyl acetate + methanol, mp 164.5-165° (Lee). Partition coefficient (octanol/water): 0.046. uv max (isopropanol): 313 nm (ε 7800). Soly in isotonic saline: 200 mg/ml.

Therapeutic Category

Antineoplastic adjunct (radiosensitizer).

Keywords

Antineoplastic Adjunct; Radiosensitizer