Eflornithine
Eflornithine is a difluoromethylated ornithine compound with antineoplastic activity. Eflornithine irreversibly inhibits ornithine decarboxylase, an enzyme required for polyamine biosynthesis, thereby inhibiting the formation and proliferation of tumor cells. Polyamines are involved in nucleosome oligomerization and DNA conformation, creating a chromatin environment that stimulates neoplastic transformation of cells. This agent has been shown to induce apoptosis in leiomyoma cells.
1: Cloete TT, Johansson CC, N'Da DD, Vodnala SK, Rottenberg ME, Breytenbach JC, Ashton M. Mono-, di- and trisubstituted derivatives of eflornithine: synthesis for in vivo delivery of DL-alpha-difluoromethylornithine in plasma. Arzneimittelforschung. 2011;61(5):317-25. PubMed PMID: 21755816.
2: Helena KJ, N'Da DD, Johansson CC, Breytenbach JC, Ashton M. Effects of oral administration of synthesized delta-amides of eflornithine in the rat. Arzneimittelforschung. 2010;60(11):682-8. PubMed PMID: 21175041.
3: Vincent IM, Creek D, Watson DG, Kamleh MA, Woods DJ, Wong PE, Burchmore RJ, Barrett MP. A molecular mechanism for eflornithine resistance in African trypanosomes. PLoS Pathog. 2010 Nov 24;6(11):e1001204. PubMed PMID: 21124824; PubMed Central PMCID: PMC2991269.
4: Baker N, Alsford S, Horn D. Genome-wide RNAi screens in African trypanosomes identify the nifurtimox activator NTR and the eflornithine transporter AAT6. Mol Biochem Parasitol. 2011 Mar;176(1):55-7. Epub 2010 Nov 18. PubMed PMID: 21093499; PubMed Central PMCID: PMC3032052.
5: Zell JA, McLaren CE, Chen WP, Thompson PA, Gerner EW, Meyskens FL. Ornithine decarboxylase-1 polymorphism, chemoprevention with eflornithine and sulindac, and outcomes among colorectal adenoma patients. J Natl Cancer Inst. 2010 Oct 6;102(19):1513-6. Epub 2010 Aug 26. PubMed PMID: 20798393; PubMed Central PMCID: PMC2950167.
6: Jansson-Löfmark R, Römsing S, Albers E, Ashton M. Determination of eflornithine enantiomers in plasma by precolumn derivatization with o-phthalaldehyde-N-acetyl-L-cysteine and liquid chromatography with UV detection. Biomed Chromatogr. 2010 Jul;24(7):768-73. PubMed PMID: 20020417.
7: Priotto G, Kasparian S, Mutombo W, Ngouama D, Ghorashian S, Arnold U, Ghabri S, Baudin E, Buard V, Kazadi-Kyanza S, Ilunga M, Mutangala W, Pohlig G, Schmid C, Karunakara U, Torreele E, Kande V. Nifurtimox-eflornithine combination therapy for second-stage African Trypanosoma brucei gambiense trypanosomiasis: a multicentre, randomised, phase III, non-inferiority trial. Lancet. 2009 Jul 4;374(9683):56-64. Epub 2009 Jun 24. PubMed PMID: 19559476.
8: Balasegaram M, Young H, Chappuis F, Priotto G, Raguenaud ME, Checchi F. Effectiveness of melarsoprol and eflornithine as first-line regimens for gambiense sleeping sickness in nine Médecins Sans Frontières programmes. Trans R Soc Trop Med Hyg. 2009 Mar;103(3):280-90. Epub 2008 Oct 22. PubMed PMID: 18947846.
9: Sanderson L, Dogruel M, Rodgers J, Bradley B, Thomas SA. The blood-brain barrier significantly limits eflornithine entry into Trypanosoma brucei brucei infected mouse brain. J Neurochem. 2008 Nov;107(4):1136-46. Epub 2008 Sep 24. PubMed PMID: 18823367; PubMed Central PMCID: PMC2695853.
10: Jansson R, Malm M, Roth C, Ashton M. Enantioselective and nonlinear intestinal absorption of eflornithine in the rat. Antimicrob Agents Chemother. 2008 Aug;52(8):2842-8. Epub 2008 Jun 2. PubMed PMID: 18519728; PubMed Central PMCID: PMC2493103.
2: Helena KJ, N'Da DD, Johansson CC, Breytenbach JC, Ashton M. Effects of oral administration of synthesized delta-amides of eflornithine in the rat. Arzneimittelforschung. 2010;60(11):682-8. PubMed PMID: 21175041.
3: Vincent IM, Creek D, Watson DG, Kamleh MA, Woods DJ, Wong PE, Burchmore RJ, Barrett MP. A molecular mechanism for eflornithine resistance in African trypanosomes. PLoS Pathog. 2010 Nov 24;6(11):e1001204. PubMed PMID: 21124824; PubMed Central PMCID: PMC2991269.
4: Baker N, Alsford S, Horn D. Genome-wide RNAi screens in African trypanosomes identify the nifurtimox activator NTR and the eflornithine transporter AAT6. Mol Biochem Parasitol. 2011 Mar;176(1):55-7. Epub 2010 Nov 18. PubMed PMID: 21093499; PubMed Central PMCID: PMC3032052.
5: Zell JA, McLaren CE, Chen WP, Thompson PA, Gerner EW, Meyskens FL. Ornithine decarboxylase-1 polymorphism, chemoprevention with eflornithine and sulindac, and outcomes among colorectal adenoma patients. J Natl Cancer Inst. 2010 Oct 6;102(19):1513-6. Epub 2010 Aug 26. PubMed PMID: 20798393; PubMed Central PMCID: PMC2950167.
6: Jansson-Löfmark R, Römsing S, Albers E, Ashton M. Determination of eflornithine enantiomers in plasma by precolumn derivatization with o-phthalaldehyde-N-acetyl-L-cysteine and liquid chromatography with UV detection. Biomed Chromatogr. 2010 Jul;24(7):768-73. PubMed PMID: 20020417.
7: Priotto G, Kasparian S, Mutombo W, Ngouama D, Ghorashian S, Arnold U, Ghabri S, Baudin E, Buard V, Kazadi-Kyanza S, Ilunga M, Mutangala W, Pohlig G, Schmid C, Karunakara U, Torreele E, Kande V. Nifurtimox-eflornithine combination therapy for second-stage African Trypanosoma brucei gambiense trypanosomiasis: a multicentre, randomised, phase III, non-inferiority trial. Lancet. 2009 Jul 4;374(9683):56-64. Epub 2009 Jun 24. PubMed PMID: 19559476.
8: Balasegaram M, Young H, Chappuis F, Priotto G, Raguenaud ME, Checchi F. Effectiveness of melarsoprol and eflornithine as first-line regimens for gambiense sleeping sickness in nine Médecins Sans Frontières programmes. Trans R Soc Trop Med Hyg. 2009 Mar;103(3):280-90. Epub 2008 Oct 22. PubMed PMID: 18947846.
9: Sanderson L, Dogruel M, Rodgers J, Bradley B, Thomas SA. The blood-brain barrier significantly limits eflornithine entry into Trypanosoma brucei brucei infected mouse brain. J Neurochem. 2008 Nov;107(4):1136-46. Epub 2008 Sep 24. PubMed PMID: 18823367; PubMed Central PMCID: PMC2695853.
10: Jansson R, Malm M, Roth C, Ashton M. Enantioselective and nonlinear intestinal absorption of eflornithine in the rat. Antimicrob Agents Chemother. 2008 Aug;52(8):2842-8. Epub 2008 Jun 2. PubMed PMID: 18519728; PubMed Central PMCID: PMC2493103.
| Chemical | |
|---|---|
| CAS Num | 70052-12-9 |
| Chemical Formula | C6H12F2N2O2 |
| Molecular Weight | 182.16849 |
| IUPAC Chemical Name | 2,5-diamino-2-(difluoromethyl)pentanoic acid. |
| Exact Mass | 182.08668 |
| Elemental Analysis | C, 39.56; H, 6.64; F, 20.86; N, 15.38; O, 17.57 |
| Synonym | CPP-1X; DFMO; MDL 71782; MDL-71782; MDL71782; RMI71782; RMI-71782; RMI 71782. |
| Solubility | Soluble in DMSO, not in water |
| SMILES Code | O=C(O)C(C(F)F)(N)CCCN |
| Biological | |
| Targets and Effects | N/A |
| Pathways | Apoptosis |
| Physical | |
| Appearance | Solid powder |
| Purity | >98% (or refer to the Certificate of Analysis) |
| Shipping Condition | Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs. |
| Storage Condition | Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years). |
| Shelf Life | >5 years if stored properly |
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