Eflornithine HCl hydrate | CAS#96020-91-6 | 70052-12-9

MedKoo Cat#: 329826 | Name: Eflornithine HCl hydrate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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.

Chemical Structure

Eflornithine HCl hydrate

CAS#96020-91-6 (HCl hydrate)

Theoretical Analysis

MedKoo Cat#: 329826

Name: Eflornithine HCl hydrate

CAS#: 96020-91-6 (HCl hydrate)

Chemical Formula: C6H15ClF2N2O3

Exact Mass: 0.0000

Molecular Weight: 236.64

Elemental Analysis: C, 30.45; H, 6.39; Cl, 14.98; F, 16.06; N, 11.84; O, 20.28

Price and Availability

Size	Price	Availability
1g	USD 150.00	Ready to ship
2g	USD 250.00	Ready to ship
5g	USD 550.00	Ready to ship
10g	USD 1,050.00	Ready to ship

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Related CAS #

70052-12-9 (free base) 96020-91-6 (HCl hydrate) 68278-23-9 (HCl) 69955-42-6 (S-isomer) 70050-55-4 (R-isomer) 66640-93-5 (L-isomer)

Synonym

Eflornithine HCl hydrate; Eflornithine HCl; Eflornithine hydrochloride; Ornidyl.CPP-1X; RMI71782; RMI-71782; RMI 71782; DL-Ornithine hydrochloride;

IUPAC/Chemical Name

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

InChi Key

FJPAMFNRCFEGSD-UHFFFAOYSA-N

InChi Code

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

SMILES Code

NC(CCCN)(C(F)F)C(O)=O.[H]Cl.[H]O[H]

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

Shelf Life

>2 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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T7K09C14

QC Data

View QC data: current batch, Lot#T7K09C14

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Eflornithine hydrochloride hydrate (DFMO hydrochloride hydrate) is a specific, irreversible inhibitor of the enzyme ornithine decarboxylase.

In vitro activity:

In these studies, exposure to TMZ (temozolomide) caused a significant increase in frequency of cancer-related mutations in U87MG glioblastoma cells as measured by quantifying known nucleotide polymorphisms using Exon-Seq analysis. Subsequent treatment with DFMO caused a statistically significant decrease in the mutation frequency compared to TMZ-treated cells. The effects were shown for three different TMZ and DFMO concentrations as well as for the combined data set. While the TMZ-induced mutagenesis has been extensively explored in recent research, the inhibitory action of DFMO leading to decrease in mutation frequency has not been reported before. Reference: Oncotarget. 2020 Nov 3; 11(44): 3933–3942. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7646829/

In vivo activity:

The DFMO treatment led to a significant decrease in expression of ODC, Arg1, Sms, Srm and increased Oaz expression (Fig. 4). DFMO caused a significant decrease in tumor progression, with a large amount of the pancreas still appearing normal (Fig 3). The significant reduction in pancreatic ODC mRNA most likely was due to the reduction in the overall tumor area (PanINs and PDAC) in the pancreata of mice exposed to DFMO. The pancreas tissue of untreated mice consists of greater numbers of tumor and stromal cells in comparison with the DFMO treatment groups (Fig. 2, 3). Reference: Cancer Prev Res (Phila). 2014 Dec; 7(12): 1198–1209. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4310684/

	Solvent	mg/mL	mM
Solubility
	Water	48.5	204.95
	PBS (pH 7.2)	10.0	42.26

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 236.64 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

Formulation protocol:

1. Yam N, Levin J, Bao Z, Qian W, Levin VA. Effect of eflornithine on mutation frequency in temozolomide-treated U87MG cells. Oncotarget. 2020 Nov 3;11(44):3933-3942. doi: 10.18632/oncotarget.27782. PMID: 33216820; PMCID: PMC7646829. 2. Koomoa DL, Geerts D, Lange I, Koster J, Pegg AE, Feith DJ, Bachmann AS. DFMO/eflornithine inhibits migration and invasion downstream of MYCN and involves p27Kip1 activity in neuroblastoma. Int J Oncol. 2013 Apr;42(4):1219-28. doi: 10.3892/ijo.2013.1835. Epub 2013 Feb 21. PMID: 23440295; PMCID: PMC3622674. 3. Mohammed A, Janakiram NB, Madka V, Ritchie RL, Brewer M, Biddick L, Patlolla JM, Sadeghi M, Lightfoot S, Steele VE, Rao CV. Eflornithine (DFMO) prevents progression of pancreatic cancer by modulating ornithine decarboxylase signaling. Cancer Prev Res (Phila). 2014 Dec;7(12):1198-209. doi: 10.1158/1940-6207.CAPR-14-0176. Epub 2014 Sep 23. PMID: 25248858; PMCID: PMC4310684. 4. 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. doi: 10.1111/j.1471-4159.2008.05706.x. Epub 2008 Sep 24. PMID: 18823367; PMCID: PMC2695853.

In vitro protocol:

In vivo protocol:

1. Mohammed A, Janakiram NB, Madka V, Ritchie RL, Brewer M, Biddick L, Patlolla JM, Sadeghi M, Lightfoot S, Steele VE, Rao CV. Eflornithine (DFMO) prevents progression of pancreatic cancer by modulating ornithine decarboxylase signaling. Cancer Prev Res (Phila). 2014 Dec;7(12):1198-209. doi: 10.1158/1940-6207.CAPR-14-0176. Epub 2014 Sep 23. PMID: 25248858; PMCID: PMC4310684. 2. 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. doi: 10.1111/j.1471-4159.2008.05706.x. Epub 2008 Sep 24. PMID: 18823367; PMCID: PMC2695853.

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.