66640-93-5

66640-93-5 structure

66640-93-5 structure

Name: L-Eflornithine
Chemical Name: C780YUS9YI
CAS Number: 66640-93-5
Molecular Formula: C₆H₁₂F₂N₂O₂
Molecular Weight: 182.169
Catalog: Research Areas Cancer
Create Date: 2018-07-05 19:51:06
Modify Date: 2024-01-11 18:26:01
L-Eflornithine (L-DFMO) is an enantiomer of Eflornithine. L-Eflornithine is an irreversible ornithine decarboxylase (ODC) inhibitor with a KD of 1.3±0.3 µM, and a Kinact of 0.15±0.03 min-1[1].

Name	C780YUS9YI
Synonyms	C780YUS9YI 2-(Difluoromethyl)-L-ornithine EFLORNITHINE, (S)- MFCD00242734 L-Ornithine, 2-(difluoromethyl)- (2S)-2,5-diamino-2-(difluoromethyl)pentanoic acid (S)-eflornithine

Description	L-Eflornithine (L-DFMO) is an enantiomer of Eflornithine. L-Eflornithine is an irreversible ornithine decarboxylase (ODC) inhibitor with a KD of 1.3±0.3 µM, and a Kinact of 0.15±0.03 min-1[1].
Related Catalog	Signaling Pathways >> Others >> Others Research Areas >> Cancer
Target	KD:1.3±0.3 µM (Ornithine decarboxylase, ODC)[1]
In Vitro	Eflornithine (D/L-DFMO) is an inhibitor of ODC, the first enzyme in eukaryotic polyamine biosynthesis. Both enantiomers of Eflornithine (DFMO) irreversibly inactivate ODC. Both Eflornithine enantiomers (L-Eflornithine and D-Eflornithine) suppress ODC activity in a time- and concentration-dependent manner. The inhibitor dissociation constant (KD) values for the formation of enzyme-inhibitor complexes are 28.3±3.4, 1.3±0.3 and 2.2±0.4 µM respectively for D-Eflornithine, L-Eflornithine and Eflornithine. The inhibitor inactivation constants (Kinact) for the irreversible step were 0.25±0.03, 0.15±0.03 and 0.15±0.03 min-1 respectively for D-Eflornithine, L-Eflornithine and Eflornithine. Treatment of human colon tumour-derived HCT116 cells with either L-Eflornithine or D- Eflornithine decreases the cellular polyamine contents in a concentration-dependent manner[1]. The enantiomers display different potencies in vitro, with the L-enantiomer having up to a 20-fold higher affinity for the target enzyme ornithine decarboxylase[2]. The L-Eflornithine also appears to be more potent in cultured T.brucei gambiense parasites[2].
In Vivo	The more potent L-Eflornithine is present at much lower concentrations in both plasma and cerebrospinal fluid (CSF) than those of the D-Eflornithine. The plasma concentrations of L-Eflornithine are on average 52% of the D-enantiomer concentrations. The typical oral clearances of L-Eflornithine and D-eflornithine are 17.4 and 8.23 liters/h, respectively[2].
References	[1]. Qu N, et al. Inhibition of human ornithine decarboxylase activity by enantiomers of difluoromethylornithine. Biochem J. 2003 Oct 15;375(Pt 2):465-70. [2]. Jansson-Löfmark R, et al. Enantiospecific reassessment of the pharmacokinetics and pharmacodynamics of oral eflornithine against late-stage Trypanosoma brucei gambiense sleeping sickness. Antimicrob Agents Chemother. 2015 Feb;59(2):1299-307.

Density	1.3±0.1 g/cm3
Boiling Point	347.0±42.0 °C at 760 mmHg
Molecular Formula	C₆H₁₂F₂N₂O₂
Molecular Weight	182.169
Flash Point	163.7±27.9 °C
Exact Mass	182.086685
LogP	0.29
Vapour Pressure	0.0±1.6 mmHg at 25°C
Index of Refraction	1.462