16401-99-3

Basic information

• Product Name: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-Methoxy-2-Methyl-, ethyl ester
• Synonyms: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-Methoxy-2-Methyl-, ethyl ester;Indometacin EP Impurity I
• CAS NO: 16401-99-3
• Molecular Formula: C₂₁H₂₀ClNO₄
• Molecular Weight: 385.8408
• Mol File: 16401-99-3.mol
• Article Data: 17

Chemical Properties

• Melting Point: 95-96 °C
• Boiling Point: 475.3°Cat760mmHg
• Flash Point: 241.3°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 3.35E-09mmHg at 25°C
• Refractive Index: 1.586
• CAS DataBase Reference: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-Methoxy-2-Methyl-, ethyl ester(CAS DataBase Reference)
• NIST Chemistry Reference: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-Methoxy-2-Methyl-, ethyl ester(16401-99-3)
• EPA Substance Registry System: 1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-Methoxy-2-Methyl-, ethyl ester(16401-99-3)

Safety Data

• Hazardous Substances Data: 16401-99-3(Hazardous Substances Data)

Usage

Uses

Indomethacin Ethyl Ester (Indomethacin EP Impurity I) is the ethyl ester of the nonsteroidal anti-inflammatory drug Indomethacin (I641000). Indomethacin Ethyl Ester is a selective COX-2 inhibitor and is used (along with Indomethacin) as loaded nanocapsules as anticancer treatment showing a decrease in glioma cell proliferation.

InChI:InChI=1/C21H20ClNO4/c1-4-27-20(24)12-17-13(2)23(19-10-9-16(26-3)11-18(17)19)21(25)14-5-7-15(22)8-6-14/h5-11H,4,12H2,1-3H3

Upstream product

• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 97716-74-0 3-ethyl-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide 
• 106698-10-6 1-(5-methoxy-2-methyl-1H-indol-1-yl)ethanone 
• 51-66-1 4-methoxyacetanilide 
• 1076-74-0 5-methoxy-2-methyl-1H-indole 
• 64-17-5 ethanol 
• 541-41-3 chloroformic acid ethyl ester 
• 122-01-0 4-chloro-benzoyl chloride 
• 17536-38-8 ethyl 2-(5-methoxy-2-methyl-1H-indol-3-yl)acetate 

Downstream Products

• 53-86-1 [1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetic acid 
• 867154-24-3 N₁-[2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-acetyl]-N₄-cyclohexyl thiosemicarbazide 
• 867154-23-2 N₁-[2-(1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl)-acetyl]-N₄-n-butyl thiosemicarbazide 
• 867154-15-2 [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]-acetic acid hydrazide 

Relevant articles and documents

Lipid-core nanocapsules restrained the indomethacin ethyl ester hydrolysis in the gastrointestinal lumen and wall acting as mucoadhesive reservoirs

The aim of this work was to investigate if the indomethacin ethyl ester (IndOEt) released from lipid-core nanocapsules (NC) is converted into indomethacin (IndOH) in the intestine lumen, intestine wall or after the particles reach the blood stream. NC-IndOEt had monomodal size distribution (242 nm; PDI 0.2) and zeta potential of -11 mV. The everted rat gut sac model showed IndOEt passage of 0.16 μmol m-2 through the serosal fluid (30 min). From 15 to 120 min, the IndOEt concentrations in the tissue increased from 6.13 to 27.47 μmol m-2. No IndOH was formed ex vivo. A fluorescent-NC formulation was used to determine the copolymer bioadhesion (0.012 μmol m-2). After NC-IndOEt oral administration to rats, IndOEt and IndOH were detected in the gastrointestinal tract (contents and tissues). In the tissues, the IndOEt concentrations decreased from 459 to 5 μg g-1 after scrapping, demonstrating the NC mucoadhesion. In plasma (peripheric and portal vein), in spleen and liver, exclusively IndOH was detected. In conclusion, after oral dosing of NC-IndOEt, IndOEt is converted into IndOH in the intestinal lumen and wall before reaching the blood stream. The complexity of a living system was not predicted by the ex vivo gut sac model.

Effects of steric hindrance and electron density of ester prodrugs on controlling the metabolic activation by human carboxylesterase

Carboxylesterase (CES) plays an important role in the hydrolysis metabolism of ester–type drugs and prodrugs. In this study, we investigated the change in the hydrolysis rate of hCE1 by focusing on the steric hindrance of the ester structure and the elect

Cross-Coupling of Chloro(hetero)arenes with Thiolates Employing a Ni(0)-Precatalyst

A general and efficient Ni-catalyzed coupling of challenging aryl chlorides and in situ generated aliphatic and aromatic thiolates is described. The employed on-cycle, air-stable defined Ni precatalysts allow for transformation of a broad scope of substrates. A variety of functional groups and heterocyclic motifs as well as structurally varied thiols are tolerated at unprecedented moderate catalyst loadings and reaction temperatures. Depending on reaction conditions, aryl thiols can selectively undergo C-S or C-C couplings.