Indomethacin heptyl ester
Basic information
- CAS
282728-47-6- Standard SMILES
CCCCCCCOC(=O)Cc1c(C)n(C(=O)c2ccc(Cl)cc2)c2ccc(OC)cc12- InChIKey
PYBCHCVNKGZCOH-UHFFFAOYSA-N- Molecular formula
- C26H30ClNO4
- Average molar mass
- 456 g/mol
Overview
Indomethacin heptyl ester is a N-acylindole.
Names & identifiers
- Preferred name
- Indomethacin heptyl ester
- IUPAC
- heptyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetate
- English name
- Indomethacin ester, n-heptyl-
- Molecular formula
- C26H30ClNO4
- Molecular weight
- 455.97
Names & synonyms
Indomethacin heptyl ester282728-47-6INDOMETHACIN ESTER, N-HEPTYL-heptyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetateCHEMBL330194C26H30ClNO4orb1306099CHEBI:184056Indomethacin heptyl ester, >98%HMS3649K19BDBM50090775Heptyl 2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-indol-3-yl]acetate
Show more names
PYBCHCVNKGZCOH-UHFFFAOYSA-NIndomethacin heptyl ester, 10 mM in DMSOHeptyl [1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acet ate1H-Indole-3-acetic acid, 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-, heptyl ester1-(P-CHLOROBENZOYL)-5-METHOXY-2-METHYL-1H-INDOLE-3-ACETIC ACID, N-HEPTYL ESTER1-(P-CHLOROBENZOYL)-5-METHOXY-3-METHYL-1H-INDOLE-3-ACETIC ACID, N-HEPTYL ESTER
MFCD03412025AKOS0407449801-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetic acid, 1-heptyl esterTS-08230DS-016148HY-114795CS-0064341T22092
Database identifiers
- CAS
282728-47-6- ChEMBL
CHEMBL330194- ChEBI
CHEBI:184056- Nikkaji
- J1.403.214B
Properties
Computed structural properties
- XLogP
- 7.5
- Topological polar surface area
- 57.5 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 4
- Rotatable bonds
- 11
- Heavy atoms
- 32
- Formal charge
- 0
- Complexity
- 607
Physicochemical properties
- Flash point
- -16 °C · -16 °C
- storage temp.
- 20 °C · −20°C
- solubility
- 17 mg/ml · ≤17mg/ml in ethanol;17mg/ml in DMSO;17mg/ml in dimethyl formamide
- form
- methyl acetate solution
- Symbol(GHS)
- 2 · GHS02,GHS07
- Signal word
- Danger
- Hazard statements
- 225 · H225-H319-H336
- Precautionary statements
- 210 · P210-P240-P241-P242-P243-P261-P264-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501
- Hazard Codes
- F,Xi
- Risk Statements
- 11 · 11-36-66-67
- Safety Statements
- 16 · 16-26-29-33-36
- RIDADR
- 1231 · UN 1231 3/PG 2
- WGK Germany
- 1 · 1
- RTECS
- 9100000 · AI9100000
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
Safety data
- wgk
- 1
- rtecs
- AI9100000
- ridadr
- UN 1231 3/PG 2
- risk_code
- 11-36-66-67
- Signal word
- Danger
- Symbol(GHS)
- GHS02,GHS07
- hazard_code
- F,Xi
- safety_code
- 16-26-29-33-36
- Hazard statements
- H225-H319-H336
- Precautionary statements
- P210-P240-P241-P242-P243-P261-P264-P271-P280-P303+P361+P353-P304+P340-P305+P351+P338-P312-P337+P313-P370+P378-P403+P233-P403+P235-P405-P501
Chemistry & industry
Applications
DescriptionIndomethacin is a potent but non-selective inhibitor of both COX-1 and COX-2 in sheep and humans. Structurally, indomethacin is a substituted indole acetic acid, wherein the carboxylate can be derivatized as an ester or amide. These derivatives show enhanced selectivity for the COX-2 isoform. For example, the IC50 for indomethacin heptyl ester for the inhibition of human recombinant COX-2 is 0.04 μM, making it more than 1,700 times more potent as an inhibitor of COX-2 than COX-1. While indomethacin itself has an IC50 of 0.05 μM for the inhibition of COX-2, it also inhibits COX-1 with a corresponding IC50 of 0.67 μM.
UsesIndomethacin heptyl ester is a selective COX-2 inhibitor with IC50 of 0.04 μM, exhibits anti-inflammatory activity[1].
Additional notes
DefinitionChEBI: Indomethacin heptyl ester is a N-acylindole.
Related reactions
0 records
No reaction records under the current filter.
Compound notes
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