Eflornithine hydrochlorideProduct ingredient for Eflornithine
- Name
- Eflornithine hydrochloride
- Drug Entry
- Eflornithine
Eflornithine is an irreversible ornithine decarboxylase inhibitor originally developed as a treatment for human African trypanosomiasis.6 Further research has also implicated ornithine decarboxylase in other conditions like facial hirsutism and cancer, especially when ornithine decarboxylase is highly upregulated in tumor cells.3,7 Additionally, ornithine decarboxylase is activated by c-myc or interacts with ras, both very well-known oncogenes, thus increasing the interest in targeting ornithine carboxylase as a potential cancer treatment.8
In 1960 and 2000, the FDA approved eflornithine under the brand names ORNIDYL and VANIQUA for the treatment of African trypanosomiasis and hirsutism, respectively, but has since been discontinued.5,13 Subsequently, on December 14, 2023, the FDA approved eflornithine again but under the brand name IWILFIN as an oral maintenance therapy to reduce the risk of relapse in adult and pediatric patients with high-risk neuroblastoma who have demonstrated at least a partial response to prior multiagent, multimodality therapy, including anti-GD2 immunotherapy. This approval is based on positive results obtained from a multi-site, single-arm, externally controlled study of children with high-risk neuroblastoma, where a 52% reduction in the risk of relapse and a 68% reduction in the risk of death were observed.12
- Accession Number
- DBSALT001150
- Structure
- Synonyms
- Eflornithine HCl / Eflornithine hydrochloride hydrate / Eflornithine hydrochloride monohydrate
- UNII
- 4NH22NDW9H
- CAS Number
- 96020-91-6
- Weight
- Average: 236.64
Monoisotopic: 236.0739264 - Chemical Formula
- C6H15ClF2N2O3
- InChI Key
- FJPAMFNRCFEGSD-UHFFFAOYSA-N
- InChI
- InChI=1S/C6H12F2N2O2.ClH.H2O/c7-4(8)6(10,5(11)12)2-1-3-9;;/h4H,1-3,9-10H2,(H,11,12);1H;1H2
- IUPAC Name
- 2,5-diamino-2-(difluoromethyl)pentanoic acid hydrate hydrochloride
- SMILES
- O.Cl.NCCCC(N)(C(F)F)C(O)=O
- External Links
- ChemSpider
- 390110
- ChEBI
- 4762
- ChEMBL
- CHEMBL1201037
- Wikipedia
- Eflornithine
- Predicted Properties
Property Value Source Water Solubility 50.0 mg/mL ALOGPS logP -2 ALOGPS logP -2.9 Chemaxon logS -0.56 ALOGPS pKa (Strongest Acidic) 2.19 Chemaxon pKa (Strongest Basic) 10.2 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 89.34 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 37.73 m3·mol-1 Chemaxon Polarizability 15.77 Å3 Chemaxon Number of Rings 0 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon