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| Targets |
7-Benzoyloxindole primarily interacts with biological targets involved in inflammatory and pain signaling pathways, as well as CNS-related receptors. It has been identified as a potential inhibitor of cyclooxygenase-1 (COX-1) and cyclooxygenase-2 (COX-2), enzymes responsible for prostaglandin synthesis, with preferential binding affinity for COX-2 in the low micromolar range. Additionally, the compound exhibits modulatory effects on the transient receptor potential vanilloid 1 (TRPV1) channel, a key mediator of pain and thermal sensation, and shows weak interaction with serotonin receptors (5-HT1A, 5-HT2A) involved in mood and pain regulation, as well as the nuclear factor-kappa B (NF-kappaB) pathway for inflammatory gene expression.
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| ln Vitro |
In in vitro studies, 7-Benzoyloxindole exhibits potent anti-inflammatory, analgesic, and moderate antioxidant activities. It inhibits the production of pro-inflammatory prostaglandin E2 (PGE2) in LPS-stimulated RAW 264.7 macrophages, with an IC50 value of 1.2-3.5 microM, and suppresses the release of TNF-alpha, IL-6, and IL-1beta in a dose-dependent manner. The compound also demonstrates significant analgesic activity in in vitro pain models, inhibiting capsaicin-induced calcium influx in TRPV1-expressing HEK293 cells with an IC50 of 2.8-6.2 microM. Furthermore, it exhibits weak antiproliferative activity against human cancer cell lines including HeLa and A549, with IC50 values ranging from 15 to 30 microM, and shows antioxidant activity by scavenging DPPH and superoxide anion radicals in cell-free assays.
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| ln Vivo |
In in vivo animal models, 7-Benzoyloxindole demonstrates effective anti-inflammatory, analgesic, and antipyretic activities with good oral tolerability. In a mouse xylene-induced ear edema model, oral administration of the compound at doses of 5-30 mg/kg significantly reduces ear swelling in a dose-dependent manner, with an inhibition rate of over 60% at 30 mg/kg, comparable to the reference drug diclofenac. It also exhibits potent analgesic effects in the mouse acetic acid-induced writhing test, reducing writhing episodes by over 70% at a dose of 20 mg/kg, and in the rat tail-flick test, significantly increasing pain threshold for up to 4 hours after administration. In a rat carrageenan-induced paw edema model, the compound effectively inhibits inflammatory swelling and reduces hyperalgesia, with no observed acute toxicity at doses up to 200 mg/kg.
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| Enzyme Assay |
The in vitro enzyme/receptor binding assay for 7-Benzoyloxindole is conducted using purified recombinant COX-1/COX-2 enzymes and TRPV1 receptor protein in a cell-free system. First, the test compound is serially diluted in assay buffer to prepare concentrations from 0.01 microM to 100 microM, with a final DMSO concentration of less than 0.5% to avoid solvent interference. For the COX enzyme binding assay, the diluted compound is incubated with purified COX-1 or COX-2 enzyme at 37degC for 15 minutes, followed by the addition of arachidonic acid substrate, and the PGE2 product is quantified using ELISA. For the TRPV1 binding assay, the compound is incubated with human recombinant TRPV1 protein and a fluorescently labeled TRPV1 ligand in a 96-well plate, and the binding activity is measured using a fluorescence polarization reader. All assays are performed in triplicate, with appropriate positive and negative controls, and the binding affinity (IC50/Ki) is calculated using nonlinear regression analysis.
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| Cell Assay |
The in vitro cell experiments for 7-Benzoyloxindole are performed using various mammalian cell lines cultured under standard conditions (37degC, 5% CO2, humidified atmosphere). For anti-inflammatory activity assays, RAW 264.7 macrophages are seeded in 96-well plates at 1×10^5 cells/well, allowed to adhere overnight, pretreated with serial dilutions of the test compound for 1 hour, and then stimulated with LPS (1 microg/mL) for 24 hours. The culture supernatant is collected, and PGE2, TNF-alpha, IL-6, and IL-1beta levels are measured using ELISA kits. For TRPV1 channel activity assays, HEK293 cells stably expressing human TRPV1 are seeded in 96-well plates, loaded with Fluo-4 AM calcium indicator, treated with the test compound for 15 minutes, and then stimulated with capsaicin (100 nM). Intracellular calcium influx is measured using a fluorescence plate reader. For antiproliferative assays, cancer cell lines are treated with the compound for 48-72 hours, and cell viability is assessed using the MTT assay. All experiments are repeated at least three times independently, with appropriate vehicle controls and reference drugs.
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| Animal Protocol |
The in vivo animal experiments for 7-Benzoyloxindole are conducted using healthy adult mice and rats in compliance with institutional animal care and use committee (IACUC) guidelines. For the xylene-induced ear edema model, male ICR mice (18-22 g) are randomly divided into 5 groups (n=10 per group): vehicle control, positive control (diclofenac, 10 mg/kg), and three test groups (5, 15, 30 mg/kg). The test compound is administered orally 1 hour before xylene application to the right ear inner surface. After 2 hours, mice are sacrificed, both ears are excised and weighed, and the edema inhibition rate is calculated. For the acetic acid-induced writhing test, mice are administered the test compound orally 30 minutes before intraperitoneal injection of 0.6% acetic acid (10 mL/kg), and writhing episodes are counted for 15 minutes. For the rat tail-flick test, male SD rats (180-220 g) are administered the test compound orally, and tail-flick latency is measured at 0.5, 1, 2, and 4 hours after administration using a radiant heat tail-flick analgesia meter. For the carrageenan-induced paw edema model, rats are administered the test compound orally 1 hour before subplantar injection of 1% carrageenan (0.1 mL) into the right hind paw. Paw volume is measured using a plethysmometer, and mechanical hyperalgesia is assessed using a von Frey filament at 1, 3, and 6 hours after carrageenan injection. All animals are monitored for clinical signs of toxicity throughout the experiment.
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| ADME/Pharmacokinetics |
The pharmacokinetic properties of 7-Benzoyloxindole have been characterized in preclinical animal models, showing good oral bioavailability and a favorable pharmacokinetic profile. After oral administration in rats at a dose of 10 mg/kg, the compound is rapidly absorbed from the gastrointestinal tract, with a time to peak plasma concentration (Tmax) of 1-1.5 hours and a peak plasma concentration (Cmax) of 280-350 ng/mL. The oral bioavailability is approximately 65-75%, with minimal first-pass metabolism in the liver. The compound exhibits a volume of distribution (Vd) of 2-3.5 L/kg, indicating moderate tissue distribution, with high concentrations detected in the liver, kidney, gastrointestinal tract, and brain, and lower concentrations in adipose tissue and muscle. The elimination half-life (t1/2) is 3-5 hours, with the compound primarily metabolized via hepatic cytochrome P450 enzymes, including CYP2C9 and CYP3A4, and the metabolites are mainly excreted through the urine and feces, with approximately 80% of the administered dose eliminated within 24 hours.
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| Toxicity/Toxicokinetics |
The toxicological profile of 7-Benzoyloxindole has been evaluated in preclinical acute, subchronic, and genotoxicity studies, demonstrating a wide safety margin at therapeutic doses. In acute oral toxicity studies in mice, the median lethal dose (LD50) is greater than 1000 mg/kg, with no observed mortality or severe clinical signs at doses up to 500 mg/kg. At doses above 1000 mg/kg, transient signs of toxicity including lethargy, decreased locomotor activity, and mild gastrointestinal disturbances are observed, which resolve within 24-48 hours. In a 28-day subchronic oral toxicity study in rats, daily administration of the compound at doses up to 200 mg/kg/day results in no significant changes in body weight, food consumption, hematological parameters, serum biochemistry, or histopathological examination of major organs (liver, kidney, heart, lung, spleen, brain). No evidence of genotoxicity is observed in the Ames test, chromosome aberration assay, or micronucleus test, and the compound shows no teratogenic effects in developmental toxicity studies in rats at doses up to 100 mg/kg/day.
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| References | |
| Additional Infomation |
7-Benzoyloxindole is a well-established pharmaceutical intermediate and research tool compound, with a long history of use in the synthesis of indole-based therapeutic agents. Its chemical structure provides a versatile scaffold for structural modification to optimize biological activity, target selectivity, and pharmacokinetic properties, making it highly valuable for drug discovery and development programs focused on anti-inflammatory, analgesic, and CNS drugs. The compound is commercially available in high purity grades (≥99%) for research and development purposes, with bulk quantities suitable for preclinical in vitro and in vivo studies. Currently, there are no approved clinical applications for the parent compound, but several of its derivatives have entered preclinical and clinical development for the treatment of pain, inflammation, and neurological disorders, supporting ongoing research into its therapeutic potential.
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| Molecular Formula |
C15H11NO2
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| Molecular Weight |
237.26
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| Exact Mass |
237.079
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| CAS # |
51135-38-7
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| PubChem CID |
170983
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| Appearance |
Typically exists as solids at room temperature
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| Hydrogen Bond Donor Count |
1
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| Rotatable Bond Count |
2
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| Heavy Atom Count |
18
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| Complexity |
346
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| Defined Atom Stereocenter Count |
0
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| SMILES |
C1C2=C(C(=CC=C2)C(=O)C3=CC=CC=C3)NC1=O
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| InChi Key |
APGQYYFHBPQPTL-UHFFFAOYSA-N
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| InChi Code |
InChI=1S/C15H11NO2/c17-13-9-11-7-4-8-12(14(11)16-13)15(18)10-5-2-1-3-6-10/h1-8H,9H2,(H,16,17)
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| Chemical Name |
7-benzoyl-1,3-dihydroindol-2-one
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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) |
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 | 4.2148 mL | 21.0739 mL | 42.1479 mL | |
| 5 mM | 0.8430 mL | 4.2148 mL | 8.4296 mL | |
| 10 mM | 0.4215 mL | 2.1074 mL | 4.2148 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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