eflornithine   Click here for help

GtoPdb Ligand ID: 5176

Synonyms: 2-(difluoromethyl)ornithine (DMFO) | difluoromethylornithine | Ornidyl® | Vaniqa®
Approved drug
eflornithine is an approved drug (FDA (2000), EMA (2001))
Compound class: Synthetic organic
Comment: Eflornithine is an irreversible ornithine decarboxylase inhibitor [1,4] and is a partial inhibitor of arginase enzymes [6]. Marketed formulations may contain eflornithine hydrochloride (PubChem CID 57004).

Eflornithine has recently been reported to provide neuroprotective effects in a mouse model of Alzheimer's disease (AD) [3]. The authors identify microglial-induced arginine depletion as a causative factor in AD pathophysiology in their model, focussing on inhibition of arginine catabolising enzymes as a novel mechanism by which to halt the neurodegeneration observed in AD. These findings suggest that eflornithine could be used as a starting point for medicinal chemists to identify novel compounds with anti-arginase activity in humans.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 4
Hydrogen bond donors 3
Rotatable bonds 5
Topological polar surface area 89.34
Molecular weight 182.09
XLogP -2.71
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES NCCCC(C(=O)O)(C(F)F)N
Isomeric SMILES NCCCC(C(=O)O)(C(F)F)N
InChI InChI=1S/C6H12F2N2O2/c7-4(8)6(10,5(11)12)2-1-3-9/h4H,1-3,9-10H2,(H,11,12)
InChI Key VLCYCQAOQCDTCN-UHFFFAOYSA-N
Selectivity at enzymes
Key to terms and symbols Click column headers to sort
Target Sp. Type Action Value Parameter Concentration range (M) Reference
Ornithine decarboxylase Primary target of this compound Hs Inhibitor Inhibition 4.9 pKd - 5
pKd 4.9 (Kd 1.3x10-5 M) [5]