2,5-diamino-2-(difluoromethyl)pentanoic acid hydrate hydrochloride

• ChemBase ID: 134042
• Molecular Formular: C6H15ClF2N2O3
• Molecular Mass: 236.6447064
• Monoisotopic Mass: 236.07392647
• SMILES: C(CC(C(F)F)(C(=O)O)N)CN.O.Cl
• Canonical SMILES: NCCCC(C(=O)O)(C(F)F)N.O.Cl
• 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
• InChIKey: FJPAMFNRCFEGSD-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5-diamino-2-(difluoromethyl)pentanoic acid hydrate hydrochloride
• IUPAC Traditional name: vaniqa hydrate hydrochloride
• Synonyms: 2-(Difluoromethyl)ornithine hydrochloride hydrate; DFMO hydrochloride hydrate; Eflornithine hydrochloride hydrate; DL-α-Difluoromethylornithine hydrochloride hydrate; 2,5-diamino-2-(difluoromethyl)pentanoic acid hydrate hydrochloride; 2-(Difluoromethyl)-DL-ornithine Hydrochloride Hydrate; 2-(Difluoromethyl)ornithine; DFMO; DL-2-(Difluoromethyl)ornithine; DL-α-(Difluoromethyl)ornithine; Elfornithine; MDL 71782; MDL 71782A; Ornidyl; RFI 71782; RMI 71782; α,δ-Diamino-α-(difluoromethyl)valeric Acid; α-(Difluoromethyl)-DL-ornithine; α-(Difluoromethyl)ornithine; Eflornithine Hydrochloride Monohydrate

Database IDs

• CAS Number: 70052-12-9(freebase); 96020-91-6
• MDL Number: MFCD00242734
• PubChem SID: 24278809; 162228319
• PubChem CID: 441361

CALCULATED PROPERTIES

• Acid pKa: 2.1902723
• H Acceptors: 4
• H Donor: 3
• LogD (pH = 5.5): -4.6604857
• LogD (pH = 7.4): -3.131913
• Log P: -2.9084373
• Molar Refractivity: 37.7336 cm^3
• Polarizability: 15.039927 Å^3
• Polar Surface Area: 89.34 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: >10 mg/mL; Water
• Apperance: white solid; White Solid
• Melting Point: >210°C (dec.)
• Hydrophobicity(logP): -1.843

Safety Information

• Storage Condition: -20°C Freezer
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Pharmacology Properties

• Gene Information: human ... ODC1(4953)

Product Information

• Purity: ≥97% (NMR); 95%

DETAILS

Sigma Aldrich - D193

Biochem/physiol Actions
Difluoromethylornithine (Eflornithine) inhibits polyamine biosynthesis by the selective, irreversible inhibition of ornithine decarboxylase (ODC). A chemoprotective agent that blocks angiogenesis.

Toronto Research Chemicals - E436000

Irreversible inhibitor of ornithine decarboxylase, an enzyme involved in polyamine biosynthesis. Antineoplastic; antipneumocystic; antiprotozoal (Trypanosoma). Used in the treatment of hirsutism.

REFERENCES

• Bacchi, C.J., et al.: Science, 210, 332 (1980)
• Haegele, K.D., et al.: Clin. Pharmacol. Ther., 30, 210 (1980)
• Meyskens, F.L., et al.: Clin. Cancer Res., 5, 945 (1980)