WARNING: This product is for research use only, not for human or veterinary use.
MedKoo CAT#: 205260
CAS#: 70052-12-9 (free base)
Description: Eflornithine, also known as Difluoromethylornithine, 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.
MedKoo Cat#: 205260
Name: Eflornithine free base
CAS#: 70052-12-9 (free base)
Chemical Formula: C6H12F2N2O2
Exact Mass: 182.08668
Molecular Weight: 182.16849
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; Difluoromethylornithine; Eflornithine
IUPAC/Chemical Name: 2,5-diamino-2-(difluoromethyl)pentanoic acid.
InChi Key: VLCYCQAOQCDTCN-UHFFFAOYSA-N
InChi Code: InChI=1S/C6H12F2N2O2/c7-4(8)6(10,5(11)12)2-1-3-9/h4H,1-3,9-10H2,(H,11,12)
SMILES Code: O=C(O)C(C(F)F)(N)CCCN
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).
Solubility: Soluble in DMSO, not in water
Shelf Life: >5 years if stored properly
Drug Formulation: This drug may be formulated in DMSO
Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code: 2934.99.9001
The following data is based on the product molecular weight 182.16849 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.
|Concentration / Solvent Volume / Mass||1 mg||5 mg||10 mg|
|1 mM||1.15 mL||5.76 mL||11.51 mL|
|5 mM||0.23 mL||1.15 mL||2.3 mL|
|10 mM||0.12 mL||0.58 mL||1.15 mL|
|50 mM||0.02 mL||0.12 mL||0.23 mL|
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-LÃ¶fmark R, RÃ¶msing 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 MÃ©decins Sans FrontiÃ¨res 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.
Eflornithine (α-difluoromethylornithine or DFMO) is a drug found to be effective in the treatment of facial hirsutism (excessive hair growth) as well as in African trypanosomiasis (sleeping sickness). Eflornithine hydrochloride cream, which is for topical administration in women suffering from facial hirsutism, is marketed under the brand name Vaniqa by Almirall in Europe, CSL in Australia, Triton in Canada, Medison in Israel and SkinMedica in the USA. Eflornithine for injection against sleeping sickness is manufactured by Sanofi Aventis and sold under the brand name Ornidyl in the USA. Both are prescription drugs. Eflornithine was initially developed for cancer treatment at Merrell Dow Research Institute in the late 1970s, but, while having little use in treating malignancies, it was found to be highly effective in reducing hair growth, as well as in treatment of African trypanosomiasis (sleeping sickness), especially the West African form (Trypanosoma brucei gambiense). (source: http://en.wikipedia.org/wiki/Eflornithine).