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| Targets |
Indoprofen is a non-selective COX inhibitor. It activates the AKT-AMPK signaling pathway and inhibits the NF-kB/MAPK signaling pathway. It exhibits anti-inflammatory and immunomodulatory activities.
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|---|---|
| ln Vitro |
In vitro, indoprofen is a non-steroidal anti-inflammatory compound. It activates AKT-AMPK signaling and inhibits NF-kB/MAPK signaling. It exhibits anti-inflammatory and immunomodulatory activities.
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| ln Vivo |
In vivo, indoprofen is orally active. It exhibits anti-inflammatory and immunomodulatory activities. It provides insight into treatments for spinal muscular atrophies.
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| Enzyme Assay |
In vitro enzyme assays for indoprofen typically measure its ability to inhibit COX-1 and COX-2 activity. The enzyme is incubated with arachidonic acid in the presence of increasing concentrations of the compound. Prostaglandin formation is measured by ELISA. IC50 values are calculated.
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| Cell Assay |
Cell-based assays for indoprofen involve treating various cell lines with the compound and measuring prostaglandin production, cell viability, and signaling pathway activation. The compound's effects on COX activity, AKT-AMPK, and NF-kB/MAPK signaling are assessed.
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| Animal Protocol |
In vivo animal studies for indoprofen typically involve administration to animal models of pain and inflammation. Analgesic and anti-inflammatory effects are assessed using standard tests such as the carrageenan-induced paw edema. The compound's effects on spinal muscular atrophy are also studied.
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| ADME/Pharmacokinetics |
Absorption, Distribution and Excretion
Kidneys. Metabolism/Metabolites Glucuronization. Biological Half-Life 2.3 hours. Pharmacokinetic properties of indoprofen are characteristic of orally active NSAIDs. The compound is absorbed following oral administration. It is distributed to tissues. Metabolism occurs in the liver. Excretion occurs through renal pathways. |
| Toxicity/Toxicokinetics |
Indoprofen can cause gastrointestinal side effects, similar to other NSAIDs. It should be used with caution. The compound has been withdrawn from the market in some countries due to safety concerns.
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| Additional Infomation |
Indoprofen is a monocarboxylic acid with the structure propionic acid, wherein a hydrogen atom at the 2-position is replaced by a 4-(1-oxo-1,3-dihydroisoindole-2-yl)phenyl group. Initially used as an anti-inflammatory analgesic, it was withdrawn from the market due to causing severe gastrointestinal bleeding. It was subsequently found to increase the production of motor neuron survival protein. It is a nonsteroidal anti-inflammatory drug, a non-narcotic analgesic, and an EC 1.14.99.1 (prostaglandin endoperoxidase) inhibitor. It is a monocarboxylic acid belonging to the isoindole class and γ-lactam class of compounds. Its function is related to propionic acid.
A drug with analgesic and anti-inflammatory properties. Due to adverse reactions reported in animal studies, including carcinogenicity, this drug has been withdrawn from the market globally. A drug with analgesic and anti-inflammatory effects. Due to adverse reactions reported in animal studies, including carcinogenicity, this drug has been withdrawn from the market globally. (Excerpt from Martindale Pharmacopoeia, 30th edition, page 21) Indoprofen is a non-steroidal anti-inflammatory drug (NSAID). It is a non-selective COX inhibitor. It is not widely used clinically but is a valuable research tool for studying COX inhibition, inflammation, and spinal muscular atrophy. |
| Molecular Formula |
C17H15NO3
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|---|---|
| Molecular Weight |
281.31
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| Exact Mass |
281.105
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| CAS # |
31842-01-0
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| PubChem CID |
3718
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| Appearance |
White to off-white solid powder
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| Density |
1.308g/cm3
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| Boiling Point |
511.3ºC at 760mmHg
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| Melting Point |
213-214°
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| Flash Point |
263ºC
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| Index of Refraction |
1.642
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| LogP |
3.1
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
3
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| Rotatable Bond Count |
3
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| Heavy Atom Count |
21
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| Complexity |
414
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| Defined Atom Stereocenter Count |
0
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| SMILES |
O=C(O)C(C)C1=CC=C(N(CC2=C3C=CC=C2)C3=O)C=C1
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| InChi Key |
RJMIEHBSYVWVIN-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C17H15NO3/c1-11(17(20)21)12-6-8-14(9-7-12)18-10-13-4-2-3-5-15(13)16(18)19/h2-9,11H,10H2,1H3,(H,20,21)
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| Chemical Name |
2-[4-(3-oxo-1H-isoindol-2-yl)phenyl]propanoic acid
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| Synonyms |
Isindone; Flosint; Indoprofen
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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)
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| Solubility (In Vitro) |
DMSO : ~100 mg/mL (~355.48 mM)
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|---|---|
| Solubility (In Vivo) |
Solubility in Formulation 1: 2.08 mg/mL (7.39 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with sonication.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: 2.08 mg/mL (7.39 mM) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 20.8 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. View More
Solubility in Formulation 3: ≥ 2.08 mg/mL (7.39 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.5548 mL | 17.7740 mL | 35.5480 mL | |
| 5 mM | 0.7110 mL | 3.5548 mL | 7.1096 mL | |
| 10 mM | 0.3555 mL | 1.7774 mL | 3.5548 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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