Indometacin
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| Category | Enzyme inhibitors |
| Catalog number | BBF-04026 |
| CAS | 53-86-1 |
| Molecular Weight | 357.79 |
| Molecular Formula | C19H16ClNO4 |
| Purity | 98% |
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Description
A nonselective COX1 and COX2 inhibitor with IC50 of 0.1 μg/mL and 5 μg/mL, respectively.
Specification
| Synonyms | 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid |
| Storage | Store at -20°C |
| IUPAC Name | 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid |
| Canonical SMILES | CC1=C(C2=C(N1C(=O)C3=CC=C(C=C3)Cl)C=CC(=C2)OC)CC(=O)O |
| 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) |
| InChI Key | CGIGDMFJXJATDK-UHFFFAOYSA-N |
Properties
| Appearance | Off-white Solid |
| Application | API |
| Boiling Point | 499.4°C at 760 mmHg |
| Melting Point | 159-161°C |
| Density | 1.32 g/cm3 |
| LogP | 4.27 |
Toxicity
| Carcinogenicity | No indication of carcinogenicity to humans (not listed by IARC). |
| Mechanism Of Toxicity | Antiinflammatory effects of Indomethacin are believed to be due to inhibition of cylooxygenase in platelets which leads to the blockage of prostaglandin synthesis. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Indomethacin is a prostaglandin G/H synthase (also known as cyclooxygenase or COX) inhibitor that acts on both prostaglandin G/H synthase 1 and 2 (COX-1 and -2). Prostaglandin G/H synthase catalyzes the conversion of arachidonic acid to a number of prostaglandins involved in fever, pain, swelling, inflammation, and platelet aggregation. Indomethacin antagonizes COX by binding to the upper portion of the active site, preventing its substrate, arachidonic acid, from entering the active site. Indomethacin, unlike other NSAIDs, also inhibits phospholipase A2, the enzyme responsible for releasing arachidonic acid from phospholipids. Indomethacin is more selective for COX-1 than COX-2, which accounts for its increased adverse gastric effects relative to other NSAIDs. COX-1 is required for maintaining the protective gastric mucosal layer. The analgesic, antipyretic and anti-inflammatory effects of indomethacin occur as a result of decreased prostaglandin synthesis. Its antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. |
| Toxicity | LD50: 50 mg/kg (oral, mice) (based on 14 day mortality response); LD50: 12 mg/kg (oral, rat) (based on 14 day mortality response). |
Reference Reading
1.Psychological stress exacerbates NSAID-induced small bowel injury by inducing changes in intestinal microbiota and permeability via glucocorticoid receptor signaling.
Yoshikawa K1,2, Kurihara C3, Furuhashi H3, Takajo T3, Maruta K3, Yasutake Y3, Sato H3, Narimatsu K3, Okada Y3, Higashiyama M3, Watanabe C3, Komoto S4, Tomita K3, Nagao S4, Miura S5, Tajiri H6, Hokari R3. J Gastroenterol. 2016 Apr 13. [Epub ahead of print]
BACKGROUND: Nonsteroidal anti-inflammatory drugs (NSAIDs) are popular painkillers, but they have serious side effects, not only in the upper gastrointestinal tract but also in the small intestine. It is well known that psychological stress may exacerbate various gastrointestinal diseases. The aim of this study was to determine whether psychological stress exacerbates NSAID enteropathy and to determine the possible underlying mechanisms for this.
2.Simultaneous determination of cucurbitacin IIa and cucurbitacin IIb of Hemsleya amabilis by HPLC-MS/MS and their pharmacokinetic study in normal and indomethacin-induced rats.
Wang S1, Guan X1, Zhong X2, Yang Z1, Huang W1, Jia B1, Cui T1. Biomed Chromatogr. 2016 Apr 8. doi: 10.1002/bmc.3733. [Epub ahead of print]
A selective and sensitive HPLC-MS/MS method was developed for the simultaneous determination of cucurbitacin IIa (cuIIa) and cucurbitacin IIb (cuIIb), the major bioactive cucurbitacins of Hemsleya amabilis, in rat plasma using euphadienol as internal standard (IS). After liquid-liquid extraction with dichloromethane, separation was achieved on a Syncronis HPLC C18 column (150 mm × 4.6 mm, 5 µm) using an isocratic mobile phase system consisting of acetonitrile-water (85:15, v/v) at a flow rate of 0.6 mL/min with a split ratio of 1:2. Detection was performed on a TSQ QUANTUM ULTRA mass spectrometer equipped with an positive-ion electrospray ionization source. The lower limits of quantification (LLOQs) were 0.25 and 0.15 ng/mL for cuIIa and cuIIb, respectively. The intra- and inter-day precision was less than 11.5% for the LLOQs and each QC level of the analytes, and accuracy was between -9.1% and 7.6%. The extraction recoveries of the analytes and IS from rat plasma were all more than 87.
3.[Effect of radiotherapy and indomethacin together in the prevention of recurrence of ectopic ossification around the elbow after resection].
Liu XH1, Jiang XY1, Gong MQ1, Zha YJ1. Beijing Da Xue Xue Bao. 2016 Apr 18;48(2):230-3.
OBJECTIVE: To discuss the effect of single low dose local radiotherapy and indomethacin together in the prevention of recurrence of ectopic ossification around the elbow after resection.
4.Deficiency of sex hormones does not affect 17-ß-estradiol-induced coronary vasodilation in the isolated rat heart.
Santos RL1, Lima JT1, Rouver WN1, Moysés MR1. Braz J Med Biol Res. 2016;49(5):e5058. doi: 10.1590/1414-431X20165058. Epub 2016 Apr 12.
The relaxation of coronary arteries by estrogens in the coronary vascular beds of naive and hypertensive rats has been well described. However, little is known about this action in gonadectomized rats. We investigated the effect of 17-ß-estradiol (E2) in coronary arteries from gonadectomized rats, as well as the contributions of endothelium-derived factors and potassium channels. Eight-week-old female and male Wistar rats weighing 220-300 g were divided into sham-operated and gonadectomized groups (n=9-12 animals per group). The baseline coronary perfusion pressure (CPP) was determined, and the vasoactive effects of 10 μM E2 were assessed by bolus administration before and after endothelium denudation or by perfusion with NG-nitro-L-arginine methyl ester (L-NAME), indomethacin, clotrimazole, L-NAME plus indomethacin, L-NAME plus clotrimazole or tetraethylammonium (TEA). The CPP differed significantly between the female and sham-operated male animals.
Spectrum
GC-MS Spectrum - EI-B (Non-derivatized)
Experimental Conditions
Instrument Type: EI-B
Ionization Mode: positive
Chromatography Type: GC
Ionization Mode: positive
Chromatography Type: GC
Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive
Experimental Conditions
Ionization Mode: Positive
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C19H16ClNO4
Molecular Weight (Monoisotopic Mass): 357.0768 Da
Molecular Weight (Avergae Mass): 357.788 Da
Ionization Energy: 70 eV
Chromatography Type: Gas Chromatography Column (GC)
Instrument Type: Single quadrupole, spectrum predicted by CFM-ID(EI)
Mass Resolution: 0.0001 Da
Molecular Formula: C19H16ClNO4
Molecular Weight (Monoisotopic Mass): 357.0768 Da
Molecular Weight (Avergae Mass): 357.788 Da
LC-MS/MS Spectrum - LC-ESI-qTof , Positive
Experimental Conditions
Instrument Type: LC-ESI-qTof
Ionization Mode: Positive
Ionization Mode: Positive
Predicted LC-MS/MS Spectrum - 10V, Positive
Experimental Conditions
Ionization Mode: Positive
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C19H16ClNO4
Molecular Weight (Monoisotopic Mass): 357.0768 Da
Molecular Weight (Avergae Mass): 357.788 Da
Collision Energy: 10 eV
Instrument Type: QTOF (generic), spectrum predicted by CFM-ID
Mass Resolution: 0.0001 Da
Molecular Formula: C19H16ClNO4
Molecular Weight (Monoisotopic Mass): 357.0768 Da
Molecular Weight (Avergae Mass): 357.788 Da
Mass Spectrum (Electron Ionization)
1H NMR Spectrum
Experimental Conditions
Solvent: CDCl3
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS
Instrument Type: JEOL
Nucleus: 1H
Frequency: 400 MHz
Chemical Shift Reference: TMS
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Bio Calculators
* Our calculator is based on the following equation:
Concentration (start) x Volume (start) = Concentration (final) x Volume (final)
It is commonly abbreviated as: C1V1 = C2V2
* Total Molecular Weight:
g/mol
Tip: Chemical formula is case sensitive. C22H30N4O √ c22h30n40 ╳
