3522. Eflornithine

Nomenclature

CAS number: 67037-37-0
2-(Difluoromethyl)-dl-ornithine; α-difluoromethylornithine; DFMO; RMI-71782.
C6H12F2N2O2; mol wt 182.17.
C 39.56%, H 6.64%, F 20.86%, N 15.38%, O 17.57%.

Description and references

Irreversible inhibitor of ornithine decarboxylase, an enzyme involved in polyamine biosynthesis. Prepn: B. W. Metcalf et al., J. Am. Chem. Soc. 100, 2551 (1978); P. Bey et al., J. Org. Chem. 44, 2732 (1979). Effect on polyamine biosynthesis in trypanosomes: C. J. Bacchi et al., Science 210, 332 (1980). Clinical pharmacokinetics: K. D. Haegele et al., Clin. Pharmacol. Ther. 30, 210 (1981). Reviews of clinical experience in Pneumocystis carinii pneumonia: J. Sahai, A. J. Berry, Pharmacotherapy 9, 29-33 (1989); in cancer chemotherapy: F. L. Meyskens, Jr., E. W. Gerner, Clin. Cancer Res. 5, 945-951 (1999); in trypanosomiasis: C. Burri, R. Brun, Parasitol. Res. 90, S49-S52 (2003). Review of topical use in hirsutism: J. A. Barman Balfour, K. McClellen, Am. J. Clin. Dermatol. 2, 197-201 (2001).

Chemical structure

Derivative

Hydrochloride monohydrate.

Nomenclature

CAS number: 96020-91-6
Ornidyl (Aventis); Vaniqa (SkinMedica).
C6H12F2N2O2.HCl.H2O; mol wt 236.64.
C 30.45%, H 6.39%, F 16.06%, N 11.84%, O 20.28%, Cl 14.98%.

Properties

Crystals from ethanol/water, mp 183°. Freely sol in water; sparingly sol in ethanol.

Therapeutic Category

Antineoplastic; antipneumocystic; antiprotozoal (Trypanosoma). In treatment of hirsutism.

Keywords

Antineoplastic; Antipneumocystic; Antiprotozoal (Trypanosoma)