| Size | Price | Stock | Qty |
|---|---|---|---|
| 1mg |
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| 5mg |
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| 10mg |
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| Other Sizes |
| Targets |
Targets NAAA, but with much lower affinity (IC50=3.53 microM for rat NAAA) compared to the active (S)-enantiomer (IC50=7 nM for human NAAA).
|
|---|---|
| ln Vitro |
Weakly inhibits rat NAAA with IC50=3.53 microM; serves as a low-activity control to confirm the stereospecificity of NAAA inhibition.
|
| ln Vivo |
No significant in vivo activity; the active enantiomer (ARN 077) increases palmitoylethanolamine (PEA) levels in the CNS and produces antinociceptive effects; this enantiomer is inactive.
|
| Enzyme Assay |
In vitro NAAA inhibition assay: incubate rat NAAA enzyme with varying inhibitor concentrations and the substrate, measure product formation (e.g., by LC-MS) to calculate IC50 values.
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| Cell Assay |
Cellular NAAA activity assay: treat cells expressing NAAA with compound, measure the accumulation of endogenous PEA or breakdown of exogenous substrate by LC-MS/MS.
|
| Animal Protocol |
In vivo pain model: administer compound (e.g., IP or oral) to rats, assess antinociceptive effect in formalin or carrageenan-induced hyperalgesia models; inactive enantiomer will show no effect.
|
| ADME/Pharmacokinetics |
No specific PK data for this enantiomer; likely similar to the active ARN 077 but with no pharmacodynamic effect.
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| Toxicity/Toxicokinetics |
No specific toxicity data; expected to be well-tolerated as an inactive stereoisomer, with a safety profile similar to the active compound.
|
| References |
[1]. Stefano Ponzano, et al. Synthesis and structure-activity relationship (SAR) of 2-methyl-4-oxo-3-oxetanylcarbamic acid esters, a class of potent N-acylethanolamine acid amidase (NAAA) inhibitors. J Med Chem. 2013 Sep 12;56(17):6917-34.
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| Additional Infomation |
This compound is a research tool for studying NAAA biology and verifying stereospecificity of ARN 077's effects. It is not for therapeutic use and has no clinical status.
|
| Molecular Formula |
C16H21NO4
|
|---|---|
| Molecular Weight |
291.34
|
| Exact Mass |
291.147
|
| CAS # |
1439366-88-7
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| Related CAS # |
ARN 077;1373625-34-3
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| PubChem CID |
73294306
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| Appearance |
White to off-white solid powder
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| LogP |
3.3
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| Hydrogen Bond Donor Count |
1
|
| Hydrogen Bond Acceptor Count |
4
|
| Rotatable Bond Count |
8
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| Heavy Atom Count |
21
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| Complexity |
352
|
| Defined Atom Stereocenter Count |
2
|
| SMILES |
C[C@@H]1[C@@H](C(=O)O1)NC(=O)OCCCCCC2=CC=CC=C2
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| InChi Key |
PTVDTLVLQXSSEC-OCCSQVGLSA-N
|
| InChi Code |
InChI=1S/C16H21NO4/c1-12-14(15(18)21-12)17-16(19)20-11-7-3-6-10-13-8-4-2-5-9-13/h2,4-5,8-9,12,14H,3,6-7,10-11H2,1H3,(H,17,19)/t12-,14+/m1/s1
|
| Chemical Name |
5-phenylpentyl N-[(2R,3S)-2-methyl-4-oxooxetan-3-yl]carbamate
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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 |
| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
|
| Solubility (In Vitro) |
DMSO: 100 mg/mL (343.24 mM)
|
|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (8.58 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.58 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. (Please use freshly prepared in vivo formulations for optimal results.) |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.4324 mL | 17.1621 mL | 34.3242 mL | |
| 5 mM | 0.6865 mL | 3.4324 mL | 6.8648 mL | |
| 10 mM | 0.3432 mL | 1.7162 mL | 3.4324 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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