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Indomethacin

Cox inhibitor CAS# 53-86-1

Indomethacin

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Chemical structure

Indomethacin

3D structure

Chemical Properties of Indomethacin

Cas No. 53-86-1 SDF Download SDF
PubChem ID 3715 Appearance Powder
Formula C19H16ClNO4 M.Wt 357.79
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Indometacin
Solubility DMSO : 100 mg/mL (279.49 mM; Need ultrasonic)
Ethanol : 12.5 mg/mL (34.94 mM; Need ultrasonic)
H2O : < 0.1 mg/mL (insoluble)
Chemical Name 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid
SMILES CC1=C(C2=C(N1C(=O)C3=CC=C(C=C3)Cl)C=CC(=C2)OC)CC(=O)O
Standard InChIKey CGIGDMFJXJATDK-UHFFFAOYSA-N
Standard InChI InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Indomethacin

DescriptionCyclooxgenase (COX) inhibitor; displays selectivity for COX-1 (IC50 values are 230 and 630 nM for human COX-1 and COX-2 respectively). Widely used anti-inflammatory agent.

Indomethacin Dilution Calculator

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Indomethacin Molarity Calculator

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Preparing Stock Solutions of Indomethacin

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 2.7949 mL 13.9747 mL 27.9494 mL 55.8987 mL 69.8734 mL
5 mM 0.559 mL 2.7949 mL 5.5899 mL 11.1797 mL 13.9747 mL
10 mM 0.2795 mL 1.3975 mL 2.7949 mL 5.5899 mL 6.9873 mL
50 mM 0.0559 mL 0.2795 mL 0.559 mL 1.118 mL 1.3975 mL
100 mM 0.0279 mL 0.1397 mL 0.2795 mL 0.559 mL 0.6987 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Indomethacin

Indomethacin, an anti-inflammatory agent, inhibits Cox-1 and Cox-2 (cyclooxygenases) with selectivity for Cox-1 (IC50 of 230 nM) over Cox-2 (IC50 of 630 nM). Additionally, Indomethacin displays adipogenic actions via binding and activation of PPARγ (peroxisome proliferator-activated receptor γ), a ligand-activated transcription factor known to play an important role in adipogenesis. Other studies show Indomethacin to stabilize cholesterol-dependent nanoclusters and enhance phase separation in biological membranes, which could consequentially effect plasma membrane assembled cell signaling cascades. Indomethacin is an activator of PPAR α.

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References on Indomethacin

Combined effects off indomethacin and oxaliplatin on lymph node metastasis related factors in human lung cancerxenografts in nude mice.[Pubmed:28375128]

Pak J Pharm Sci. 2016 Nov;29(6):2083-2088.

To investigate the combined effects of Indomethacin and oxaliplatin on expressions of epidermal growth factor receptor (EGFR), E-cadherin (E-cad), intercellular adhesion molecule-1 (ICAM-1) and CD44v6 related to lymph node metastasis of human lung cancer cell lines. Human lung adenocarcinoma A549 cells were inoculated subcutaneously into the left armpit of nude mice to establish human lung cancer xenografts. The mice were randomly divided into control group, Indomethacin group, oxaliplatin group and combination therapy group, which were treated with sterile distilled water, Indomethacin, oxaliplatin and Indomethacin combined with oxaliplatin, respectively. After 42 days, the mice were sacrificed. The immunohistochemistry and reverse transcription polymerase chain reaction were used to detect the expressions of EGFR, E-cad, ICAM-1 and CD44v6 in tumor tissues. Compared to control group, the protein and mRNA expressions of EGFR, ICAM-1 and CD44v6 in the Indomethacin, oxaliplatin, and combination therapy groups were significantly reduced (P<0.05) and the protein and mRNA expressions of E-cad expression were significantly increased (P<0.05). Compared to Indomethacin group and oxaliplatin group, the protein and mRNA expressions of EGFR, ICAM-1 and CD44v6 in combination therapy groups were significantly reduced (P<0.05), and the protein and mRNA expressions of E-cad expression were significantly increased (P<0.05). There was no significant difference between Indomethacin and oxaliplatin groups. Indomethacin and oxaliplatin have synergistic effect on expressions of lymph node metastasis related factors in lung cancer cell lines.

How to select patients and timing for rectal indomethacin to prevent post-ERCP pancreatitis: a systematic review and meta-analysis.[Pubmed:28298192]

BMC Gastroenterol. 2017 Mar 15;17(1):43.

BACKGROUND: Acute pancreatitis is a severe complication of endoscopic retrograde cholangiopancreatography (ERCP). Previous meta-analyses have shown that Indomethacin effectively prevents this complication; however, the data are limited. We performed a systematic review and meta-analysis to clarify the applications for rectal Indomethacin. METHODS: A systematic search was performed in June 2016. Human prospective, randomized, placebo-controlled trials that compared rectally administered Indomethacin with a placebo for the prevention of post-ERCP pancreatitis (PEP) were included. A meta-analysis was performed using a random-effects model to assess the outcomes (PEP) using Review Manager 5.0. RESULTS: Seven randomized controlled trials met the inclusion criteria (n = 3013). The overall incidence of PEP was significantly lower after prophylactic administration of rectal Indomethacin than after administration of the placebo (RR, 0.58, 95% CI, 0.40-0.83; P = 0.004). A subgroup analysis was performed for rectal Indomethacin administration compared to a placebo in high-risk patients (RR, 0.46; 95% CI, 0.32-0.65; P < 0.00001) and average-risk patients (RR, 0.75; 95% CI, 0.46-1.22; P = 0.25) and for administration before ERCP (RR, 0.56; 95% CI, 0.39-0.79; P = 0.001) and after the procedure (RR, 0.61; 95% CI, 0.26-1.44; P = 0.26). CONCLUSIONS: This meta-analysis indicated that prophylactic rectal Indomethacin is not suitable for all patients undergoing ERCP but it is safe and effective to prevent PEP in high-risk patients. In addition, rectal Indomethacin administration before ERCP is superior to its administration after ERCP for the prevention of PEP.

Indomethacin-containing interpolyelectrolyte complexes based on Eudragit((R)) E PO/S 100 copolymers as a novel drug delivery system.[Pubmed:28366803]

Int J Pharm. 2017 May 30;524(1-2):121-133.

Potential applications of a novel system composed of two oppositely-charged (meth)acrylate copolymers, Eudragit((R)) capital IE, Cyrilliccapital ER, Cyrilliccapital O, Cyrillic (EPO) and Eudragit((R)) S100 (S100), loaded with Indomethacin (IND) in oral drug delivery were evaluated. The particles based on drug-interpolyelectrolyte complexes (DIPEC), (EPO-IND)/S100, were prepared by mixing aqueous solutions of both copolymers at fixed pH. Particles of drug-polyelectrolyte complex (DPC), (EPO-IND) have a positive zeta potential, pointing to the surface location of free EPO chains and IND bound to EPO sequences. The formation and composition of both DPC and DIPEC were established by gravimetry, UV-spectrophotometry, capillary viscosity and elemental analysis. The structure and solid state properties of the formulated DIPEC were investigated using FTIR/NIR, Raman spectroscopy, XRPD and modulated DSC. DIPEC is a chemically homogenous material, characterized by a single Tg. DIPEC have an IR absorption band at 1560cm(-1), which can be assigned to the stretching vibration of the carboxylate groups (S100, IND) that form ionic bonds with the dimethylamino groups of EPO. XRPD, NIR and Raman-shifts confirm that during the preparation of this formulation, IND is converted into its amorphous form. The release of IND from DPC EPO/IND (3:1) and DIPEC EPO/L100/IND (4.5:1:1) is sustained and is completed within 7h under GIT mimicking conditions. However, S100 within DIPEC makes the release process slower making this system suitable for colon-specific delivery. Finally, DPC and DIPEC with Indomethacin were used to prepare tablets, which can be potentially used as oral dosage forms for their slower Indomethacin release in case of DIPEC which could be suitable for sustained delivery.

Dimethyl sulfoxide but not indomethacin is efficient for healing in hydrofluoric acid eye burns.[Pubmed:28341026]

Burns. 2017 Feb;43(1):232-244.

INTRODUCTION: In this study, we aimed to investigate the effect of Indomethacin and dimethyl sulfoxide (DMSO), well-known antioxidant and anti-inflammatory agents, to heal eye burns induced with hydrofluoric acid in rabbits. METHODS: After general anesthesia, the right eye of 72 male New Zealand rabbits were burned by instillation of 2% hydrofluoric acid for 60s. Following this, the eyes were irrigated with 500 cc normal saline. The rabbits were then divided into four groups of 18 rabbits each. Group D was instilled dimethyl sulfoxide 40%, Group I Indomethacin 0.1%, and Group DI dimethyl sulfoxide together with Indomethacin for 2, 7, and 14 treatment days, respectively. Group C received no instilled drug as control. Treatment efficacies were evaluated as clinical (corneal haziness, conjunctival status, conjunctivitis, corneal erosion area, and intraocular pressure) and histopathological (inflammatory cell infiltration, vascularization, stromal thickness, reepithelization, proliferating cell nuclear antigen [PCNA], apoptosis, and inducible nitric oxide synthases [iNOS]). RESULTS: In terms of corneal haziness and erosion area at days 7 and 14, group D showed the best result statistically as compared to the other groups. This group also showed the best result statistically for reepithelization rate, stromal thickness, and inflammatory cell end at day 14 as compared to the other groups. CONCLUSIONS: Dimethyl sulfoxide (40%) was efficient to induce reepithelization on mild hydrofluoric acid eye burns, whereas 0.1% Indomethacin both alone and along with DMSO poorly induced reepithelization and exacerbated inflammation. Thus, 40% DMSO could be used for the treatment of corneal disorders.

Identification of novel cyclooxygenase-2 selective inhibitors using pharmacophore models.[Pubmed:11906281]

J Med Chem. 2002 Mar 28;45(7):1402-11.

In the present study we have investigated whether pharmacophore models may account for the activity and selectivity of the known cyclooxygenase-2 (COX-2) selective inhibitors of the phenylsulfonyl tricyclic series, i.e., Celecoxib (1) and Rofecoxib (3), and whether transferring this structural information onto the frame of a nonsteroidal antiinflammatory drug (NSAID), known to tightly bind the enzyme active site, may be useful for designing novel COX-2 selective inhibitors. With this aim we have developed a pharmacophore based on the geometric disposition of chemical features in the most favorable conformation of the COX-2 selective inhibitors SC-558 (2; analogue of Celecoxib (1)) and Rofecoxib (3) and the more restrained compounds 4 (DFU) and 5. The pharmacophore model contains a sulfonyl S atom, an aromatic ring (ring plane A) with a fixed position of the normal to the plane, and an additional aromatic ring (ring plane B), both rings forming a dihedral angle of 290 degrees +/- 10 degrees. The final disposition of the pharmacophoric groups parallels the geometry of the ligand SC-558 (2) in the known crystal structure of the COX-2 complex. Moreover, the nonconserved residue 523 is known to be important for COX-2 selective inhibition; thus, the crystallographic information was used to position an excluded volume in the pharmacophore, accounting for the space limits imposed by this nonconserved residue. The geometry of the final five-feature pharmacophore was found to be consistent with the crystal structure of the nonselective NSAID Indomethacin (6) in the COX-2 complex. This result was used to design Indomethacin analogues 8 and 9 that exhibited consistent structure-activity relationships leading to the potent and selective COX-2 inhibitor 8a. Compound 8a (LM-1685) was selected as a promising candidate for further pharmacological evaluation.

Description

Indomethacin (Indometacin) is a potent and nonselective inhibitor of COX1 and COX2, with IC50s of 18 nM and 26 nM for human COX-1 and COX-2, respectively, in CHO cells.

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