| Size | Price | Stock | Qty |
|---|---|---|---|
| 5mg |
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| Other Sizes |
| Targets |
L-Ornithine:2-oxoacid aminotransferase (OAT) is the primary molecular target. 5-FMOrn acts as a specific irreversible inactivator of this mitochondrial enzyme, which catalyzes the conversion of ornithine to glutamate-5-semialdehyde, a key step in ornithine metabolism, proline biosynthesis, and the urea cycle.
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| ln Vitro |
In cell-free assays, 5-Fluoromethylornithine irreversibly inactivates purified L-ornithine:2-oxoacid aminotransferase in a time- and concentration-dependent manner. The compound binds to the active site of OAT, leading to covalent modification and permanent loss of enzymatic activity. The residual OAT-like activity can be reduced to near-zero with single doses.
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| ln Vivo |
In vivo, single doses of 5-Fluoromethylornithine (>10 mg/kg) inactivate OAT to a residual OAT-like activity in animal models, leading to elevated ornithine levels and metabolic changes. This compound has been used to study the functional role of OAT in neuroprotection, retinal health, and metabolic regulation in rodents.
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| Enzyme Assay |
For enzyme activity assays, OAT is incubated with varying concentrations of 5-Fluoromethylornithine (0.1-100 uM) in assay buffer (50 mM potassium phosphate, pH 7.5, containing 0.1 mM pyridoxal phosphate, 10 mM ornithine, and 10 mM alpha-ketoglutarate) at 37degC. Residual OAT activity is measured by monitoring the formation of pyrroline-5-carboxylate (P5C) at 440 nm after derivatization.
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| Cell Assay |
For cellular studies, cells (e.g., hepatocytes, neuronal cells) are treated with 5-Fluoromethylornithine dihydrochloride (10-500 uM) for 24-72 hours. OAT activity is measured in cell lysates by the same spectrophotometric assay. Cell viability, ornithine accumulation, and downstream metabolic effects (e.g., proline, glutamate levels) can be assessed by HPLC or LC-MS.
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| Animal Protocol |
A typical in vivo protocol: Rodents are administered 5-Fluoromethylornithine dihydrochloride via intraperitoneal injection (10-100 mg/kg in sterile saline) or intravenously. After 2-24 hours, tissues (liver, kidney, retina) are harvested, and OAT activity is measured in tissue homogenates. Long-term studies may involve repeated daily dosing for 7-14 days to assess chronic OAT inhibition effects.
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| ADME/Pharmacokinetics |
PK properties of 5-Fluoromethylornithine: The compound is highly water-soluble due to the dihydrochloride salt. In rodents, after IV administration, it has a relatively short half-life (1-2 hours) and is rapidly cleared via renal excretion. Oral bioavailability is low (<20%). Formulation is typically in sterile water or saline for injection.
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| Toxicity/Toxicokinetics |
General toxicity of 5-Fluoromethylornithine is relatively low at therapeutic doses (10-50 mg/kg). At higher doses (>200 mg/kg), neurotoxicity and retinal degeneration have been observed in animal models due to dysregulated ornithine metabolism. Standard safety precautions for handling enzyme inhibitors should be followed. The compound is not for human use.
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| References |
[1]. Daune G, et al. 5-Fluoromethylornithine, an irreversible and specific inhibitor of L-ornithine:2-oxo-acid aminotransferase. Biochem J. 1988 Jul 15;253(2):481-8.
[2]. Nakauchi T, et al. Prevention of ornithine cytotoxicity by nonpolar side chain amino acids in retinal pigment epithelial cells. Invest Ophthalmol Vis Sci. 2003 Nov;44(11):5023-8. |
| Additional Infomation |
5-Fluoromethylornithine dihydrochloride is a first-in-class specific irreversible inhibitor of OAT. It is used as a chemical probe to elucidate the physiological and pathological roles of OAT in conditions such as gyrate atrophy (a retinal degenerative disease), hyperammonemia, and neurological disorders. It is also employed in metabolic disease research to manipulate the urea cycle.
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| Molecular Formula |
C6H15CL2FN2O2
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|---|---|
| Molecular Weight |
237.099903345108
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| Exact Mass |
236.049
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| CAS # |
124796-41-4
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| PubChem CID |
14499632
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| Appearance |
Typically exists as solid at room temperature
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| Hydrogen Bond Donor Count |
5
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| Hydrogen Bond Acceptor Count |
5
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| Rotatable Bond Count |
5
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| Heavy Atom Count |
13
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| Complexity |
132
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C(CC(C(=O)O)N)C(CF)N.Cl.Cl
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| InChi Key |
ZOZPMKYVFZNAHT-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C6H13FN2O2.2ClH/c7-3-4(8)1-2-5(9)6(10)11;;/h4-5H,1-3,8-9H2,(H,10,11);2*1H
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| Chemical Name |
2,5-diamino-6-fluorohexanoic acid;dihydrochloride
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture. |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
May dissolve in DMSO (in most cases), if not, try other solvents such as H2O, Ethanol, or DMF with a minute amount of products to avoid loss of samples
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| Solubility (In Vivo) |
Note: Listed below are some common formulations that may be used to formulate products with low water solubility (e.g. < 1 mg/mL), you may test these formulations using a minute amount of products to avoid loss of samples.
Injection Formulations
Injection Formulation 1: DMSO : Tween 80： Saline = 10 : 5 : 85 (i.e. 100 μL DMSO stock solution → 50 μL Tween 80 → 850 μL Saline)(e.g. IP/IV/IM/SC) *Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH ₂ O to obtain a clear solution. Injection Formulation 2: DMSO : PEG300 ：Tween 80 : Saline = 10 : 40 : 5 : 45 (i.e. 100 μL DMSO → 400 μLPEG300 → 50 μL Tween 80 → 450 μL Saline) Injection Formulation 3: DMSO : Corn oil = 10 : 90 (i.e. 100 μL DMSO → 900 μL Corn oil) Example: Take the Injection Formulation 3 (DMSO : Corn oil = 10 : 90) as an example, if 1 mL of 2.5 mg/mL working solution is to be prepared, you can take 100 μL 25 mg/mL DMSO stock solution and add to 900 μL corn oil, mix well to obtain a clear or suspension solution (2.5 mg/mL, ready for use in animals). View More
Injection Formulation 4: DMSO : 20% SBE-β-CD in saline = 10 : 90 [i.e. 100 μL DMSO → 900 μL (20% SBE-β-CD in saline)] Oral Formulations
Oral Formulation 1: Suspend in 0.5% CMC Na (carboxymethylcellulose sodium) Oral Formulation 2: Suspend in 0.5% Carboxymethyl cellulose Example: Take the Oral Formulation 1 (Suspend in 0.5% CMC Na) as an example, if 100 mL of 2.5 mg/mL working solution is to be prepared, you can first prepare 0.5% CMC Na solution by measuring 0.5 g CMC Na and dissolve it in 100 mL ddH2O to obtain a clear solution; then add 250 mg of the product to 100 mL 0.5% CMC Na solution, to make the suspension solution (2.5 mg/mL, ready for use in animals). View More
Oral Formulation 3: Dissolved in PEG400 (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 4.2176 mL | 21.0881 mL | 42.1763 mL | |
| 5 mM | 0.8435 mL | 4.2176 mL | 8.4353 mL | |
| 10 mM | 0.4218 mL | 2.1088 mL | 4.2176 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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