Eflornithine

Title: Eflornithine
CAS Registry Number: 67037-37-0
CAS Name: 2-(Difluoromethyl)-DL-ornithine
Additional Names: a-difluoromethylornithine; DFMO
Manufacturers' Codes: RMI-71782
Molecular Formula: C6H12F2N2O2
Molecular Weight: 182.17
Percent Composition: C 39.56%, H 6.64%, F 20.86%, N 15.38%, O 17.57%
Literature 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).
Derivative Type: Hydrochloride monohydrate
CAS Registry Number: 96020-91-6
Trademarks: Ornidyl (Aventis); Vaniqa (SkinMedica)
Molecular Formula: C6H12F2N2O2.HCl.H2O
Molecular Weight: 236.64
Percent Composition: 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.
Melting point: mp 183°
Therap-Cat: Antineoplastic; antipneumocystic; antiprotozoal (Trypanosoma). In treatment of hirsutism.
Keywords: Antineoplastic; Antipneumocystic; Antiprotozoal (Trypanosoma).
Efloxate Efonidipine Efrotomycin EGCG EGF-Urogastrone

Eflornithine
Enantiomer R of eflornithin (top) and S-eflornithin (middle)
Systematic (IUPAC) name
(RS)-2,5-diamino-2-(difluoromethyl)pentanoic acid
Clinical data
AHFS/Drugs.com monograph
Licence data EMA:Link, US FDA:link
Pregnancy cat. Category C for dermal cream
Legal status Prescription only
Routes Intravenous (discontinued)
Dermal
Pharmacokinetic data
Bioavailability 100% (Intravenous)
Negligible (Dermal)
Metabolism Not metabolised
Half-life 8 hours
Excretion Renal
Identifiers
CAS number 70052-12-9 N
ATC code D11AX16 P01CX03
PubChem CID 3009
ChemSpider 2902 YesY
UNII ZQN1G5V6SR YesY
KEGG D07883 YesY
ChEBI CHEBI:41948 YesY
ChEMBL CHEMBL830 N
Chemical data
Formula C6H12F2N2O2 
Mol. mass 182.2 g/mol
 N (what is this?)  (verify)

Eflornithine (α-difluoromethylornithine or DFMO) is a drug found to be effective in the treatment of facial hirsutism [1] (excessive hair growth) as well as in African trypanosomiasis (sleeping sickness).[2] Eflornithine hydrochloride cream for topical application is meant for women suffering from facial hirsutism. Eflornithine for injection against sleeping sickness is manufactured by Sanofi Aventis and sold under the brand name Ornidyl in the USA.[3] Both are prescription drugs.