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.
Click here for help
2D Structure
Click here for help
Click here for structure editor
Physico-chemical Properties
Click here for help
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
Click here for help
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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2000), EMA (2001))
WHO Essential Medicine WHO Model List of Essential Medicines (21st List, 2019). Access PDF version.
IUPAC Name Click here for help
2,5-diamino-2-(difluoromethyl)pentanoic acid
International Nonproprietary Names Click here for help
INN number INN
5551 eflornithine
Synonyms Click here for help
2-(difluoromethyl)ornithine (DMFO) | difluoromethylornithine | Ornidyl® | Vaniqa®
Database Links Click here for help
CAS Registry No. 70052-12-9
ChEBI CHEBI:41948
ChEMBL Ligand CHEMBL830
DrugCentral Ligand 990
GtoPdb PubChem SID 178101866
PubChem CID 3009
Search Google for chemical match using the InChIKey VLCYCQAOQCDTCN-UHFFFAOYSA-N
Search Google for chemicals with the same backbone VLCYCQAOQCDTCN
Search PubMed clinical trials eflornithine
Search PubMed titles eflornithine
Search PubMed titles/abstracts eflornithine
Search UniChem for chemical match using the InChIKey VLCYCQAOQCDTCN-UHFFFAOYSA-N
Search UniChem for chemicals with the same backbone VLCYCQAOQCDTCN
Wikipedia Eflornithine