ChemFOnt: Showing chemical card for Etodolac (CFc000009218)

Record Information

Version

1.0

Creation Date

2022-08-28 10:25:12 UTC

Update Date

2022-09-13 18:56:17 UTC

Chemfont ID

CFc000009218

Molecule Identification

Common Name

Etodolac

Definition

Etodolac is only found in individuals that have used or taken this drug. It is a non-steroidal anti-inflammatory drug (NSAID) with anti-inflammatory, analgesic and antipyretic properties. Its therapeutic effects are due to its ability to inhibit prostaglandin synthesis. It is indicated for relief of signs and symptoms of rheumatoid arthritis and osteoarthritis. Similar to other NSAIDs, the anti-inflammatory effects of etodolac result from inhibition of the enzyme cycooxygenase (COX). This decreases the synthesis of peripheral prostaglandins involved in mediating inflammation. Etodolac binds to the upper portion of the COX enzyme active site and prevents its substrate, arachidonic acid, from entering the active site. Etodolac was previously thought to be a non-selective COX inhibitor, but it is now known to be 5 â€“ 50 times more selective for COX-2 than COX-1. Antipyresis may occur by central action on the hypothalamus, resulting in peripheral dilation, increased cutaneous blood flow, and subsequent heat loss.

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid	ChEBI
(1,8-Diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid	ChEBI
1,3,4,9-Tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetic acid	ChEBI
1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetic acid	ChEBI
1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-ylacetic acid	ChEBI
Etodolaco	ChEBI
Etodolacum	ChEBI
ETODOLIC ACID	ChEBI
Lodine	Kegg
(+-)-1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetate	Generator
(1,8-Diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetate	Generator
1,3,4,9-Tetrahydro-1,8-diethylpyrano(3,4-b)indole-1-acetate	Generator
1,8-Diethyl-1,3,4,9-tetrahydropyrano(3,4-b)indole-1-acetate	Generator
1,8-Diethyl-1,3,4,9-tetrahydropyrano[3,4-b]indol-1-ylacetate	Generator
ETODOLate	Generator
Etodolac, (-)-isomer	MeSH, HMDB
Etodolac, monosodium salt	MeSH, HMDB
Etodolac, (+-)-isomer	MeSH, HMDB
Etodolac, monosodium salt, (S)-isomer	MeSH, HMDB
Etodolac, monosodium salt, (+-) isomer	MeSH, HMDB
Ultradol	MeSH, HMDB
Acid, etodolic	MeSH, HMDB
Etodolac, (S)-isomer	MeSH, HMDB
Ramodar	MeSH, HMDB

Chemical Formula

C₁₇H₂₁NO₃

Average Molecular Weight

287.3535

Monoisotopic Molecular Weight

287.152143543

IUPAC Name

2-{1,8-diethyl-1H,3H,4H,9H-pyrano[3,4-b]indol-1-yl}acetic acid

Traditional Name

etodolac

CAS Registry Number

41340-25-4

SMILES

CCC1=C2NC3=C(CCOC3(CC)CC(O)=O)C2=CC=C1

InChI Identifier

InChI=1S/C17H21NO3/c1-3-11-6-5-7-12-13-8-9-21-17(4-2,10-14(19)20)16(13)18-15(11)12/h5-7,18H,3-4,8-10H2,1-2H3,(H,19,20)

InChI Key

NNYBQONXHNTVIJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as indolyl carboxylic acids and derivatives. Indolyl carboxylic acids and derivatives are compounds containing a carboxylic acid chain (of at least 2 carbon atoms) linked to an indole ring.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Indoles and derivatives

Sub Class

Indolyl carboxylic acids and derivatives

Direct Parent

Indolyl carboxylic acids and derivatives

Alternative Parents

Substituents

Indolyl carboxylic acid derivative
3-alkylindole
Indole
Benzenoid
Pyrrole
Heteroaromatic compound
Oxacycle
Azacycle
Monocarboxylic acid or derivatives
Ether
Dialkyl ether
Carboxylic acid
Carboxylic acid derivative
Organic oxide
Organopnictogen compound
Organooxygen compound
Organonitrogen compound
Organic oxygen compound
Organic nitrogen compound
Carbonyl group
Hydrocarbon derivative
Aromatic heteropolycyclic compound

Molecular Framework

Aromatic heteropolycyclic compounds

External Descriptors

monocarboxylic acid (CHEBI:4909 )
organic heterotricyclic compound (CHEBI:4909 )

Functional Ontology

Physiological effect

Not Available

Disposition

Biological location

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 21059682)

Excreta

Biofluid or Excreta

Urine (PMID: 21059682)

Cellular substructure

Source

Exogenous

Exogenous (HMDB: HMDB0014887)

Process

Naturally occurring process

Biological process

Biochemical pathway

Drug action pathway

Etodolac Action Pathway (PathBank: SMP0000084)

Role

Not Available

Physical Properties

Predicted Properties

Property	Value	Source
Water Solubility	0.039 g/L	ALOGPS
logP	3.39	ALOGPS
logP	3.44	ChemAxon
logS	-3.9	ALOGPS
pKa (Strongest Acidic)	4.73	ChemAxon
pKa (Strongest Basic)	-4.2	ChemAxon
Physiological Charge	-1	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	2	ChemAxon
Polar Surface Area	62.32 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	81.16 m³·mol⁻¹	ChemAxon
Polarizability	31.94 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

3192

KEGG Compound ID

C06991

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Etodolac

METLIN ID

Not Available

PubChem Compound

Not Available

PDB ID

Not Available

ChEBI ID

4909

Food Biomarker Ontology

Not Available

References

Synthesis Reference

Not Available

Showing chemical card for Etodolac (CFc000009218)

MOL for CFc000009218 (Etodolac)

3D MOL for CFc000009218 (Etodolac)

3D SDF for CFc000009218 (Etodolac)

3D-SDF for CFc000009218 (Etodolac)

PDB for CFc000009218 (Etodolac)

3D PDB for CFc000009218 (Etodolac)

SMILES for CFc000009218 (Etodolac)

INCHI for CFc000009218 (Etodolac)

Structure for CFc000009218 (Etodolac)

3D Structure for CFc000009218 (Etodolac)