CHEBI:41948 - eflornithine

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ChEBI Name eflornithine
ChEBI ID CHEBI:41948
Definition A fluoroamino acid that is ornithine substituted by a difluoromethyl group at position 2.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:41946, CHEBI:4761
Supplier Information eMolecules:31591966, Selleckchem:AEE788, ZINC000022453679
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AEE788 is a multitargeted human epidermal receptor (HER) 1/2 and vascular endothelial growth factor receptor (VEGFR) 1/2 receptor family tyrosine kinases inhibitor with IC50 of 2, 6, 77, 59 nM for EGFR, ErbB2, KDR, and Flt-1. In cells, growth factor-induced EGFR and ErbB2 phosphorylation was also efficiently inhibited with IC50s of 11 and 220 nM, respectively. It efficiently inhibited growth factor-induced EGFR and ErbB2 phosphorylation in tumors for >72 h, a phenomenon correlating with the antitumor efficacy of intermittent treatment schedules. It also inhibits VEGF-induced angiogenesis in a murine implant model. It has potential as an anticancer agent targeting deregulated tumor cell proliferation as well as angiogenic parameters.
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Formula C6H12F2N2O2
Net Charge 0
Average Mass 182.16850
Monoisotopic Mass 182.08668
InChI InChI=1S/C6H12F2N2O2/c7-4(8)6(10,5(11)12)2-1-3-9/h4H,1-3,9-10H2,(H,11,12)
InChIKey VLCYCQAOQCDTCN-UHFFFAOYSA-N
SMILES NCCCC(N)(C(F)F)C(O)=O
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Bronsted acid
A molecular entity capable of donating a hydron to an acceptor (Bronsted base).
(via oxoacid )
Biological Role(s): trypanocidal drug
A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
Application(s): trypanocidal drug
A drug used to treat or prevent infections caused by protozoal organisms belonging to the suborder Trypanosomatida.
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ChEBI Ontology
Outgoing eflornithine (CHEBI:41948) has functional parent ornithine (CHEBI:18257)
eflornithine (CHEBI:41948) has role trypanocidal drug (CHEBI:36335)
eflornithine (CHEBI:41948) is a α-amino acid (CHEBI:33704)
eflornithine (CHEBI:41948) is a fluoroamino acid (CHEBI:24068)
Incoming eflornithine hydrochloride monohydrate (CHEBI:4762) has part eflornithine (CHEBI:41948)
IUPAC Names
2,5-diamino-2-(difluoromethyl)pentanoic acid
2-(difluoromethyl)ornithine
Synonyms Sources
alpha-(Difluoromethyl)-DL-ornithine DrugCentral
α-difluoromethylornithine ChemIDplus
ALPHA-DIFLUOROMETHYLORNITHINE PDBeChem
DFMO ChemIDplus
DL-Ornithine, 2-(difluoromethyl)- KEGG COMPOUND
Eflornithine KEGG COMPOUND
Manual Xrefs Databases
990 DrugCentral
C07997 KEGG COMPOUND
D07883 KEGG DRUG
DB03856 DrugBank
DMO PDBeChem
Eflornithine Wikipedia
View more database links
Registry Numbers Types Sources
2250529 Beilstein Registry Number ChemIDplus
2250529 Reaxys Registry Number Reaxys
67037-37-0 CAS Registry Number ChemIDplus
70052-12-9 CAS Registry Number ChemIDplus
Citations Types Sources
16541214 PubMed citation Europe PMC
23771434 PubMed citation Europe PMC
24144414 PubMed citation Europe PMC
Last Modified
25 May 2018