Etodolac: The chemistry, pharmacology, metabolic disposition, and clinical profile of a novel anti‐inflammatory pyranocarboxylic acid

Humber, Leslie G.

doi:10.1002/med.2610070102

Cited by 55 publications

(28 citation statements)

References 51 publications

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“…The title compound is a derivative of the non-steroidal antiinflammatory drugs (NSAIDs) etodolac [3]. Etodolac is an indoleacetic acid derivative with analgesic and limited antiinflammatory properties.…”

Section: Discussionmentioning

confidence: 99%

Crystal structure of (1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol- 1-yl)acetic acid (2-hydroxy-benzylidene)hydrazide, C24H27N3O3

Q.-B.

Zhang

2006

Zeitschrift Für Kristallographie - New Crystal Structures

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Source of materialThe compound, (1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)acetic acid (2-hydroxy-benzylidene)hydrazide, is obtained from the condensation reaction of (1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid hydrazide with salicylaldehyde [1,2]. A mixture of 1 g (3.3 mmol) of (1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol-1-yl)-acetic acid hydrazide, 0.41 g (3.32 mmol) of salicylaldehyde, 50 mL of anhydrous ethanol was vigorously stirred at reflux for 1.5 hours. Then the reaction mixture was filtrated and washed with 30 ml ethanol to give 1.21 g of the title compound (yield 89.9 %). The crystals were obtained from a solution of the compound in anhydrous ethanol after two days at room temperature (m.p. 462-463 K). Experimental detailsThe positions of H1 (at N1), H2 (at N3) and H3 (at O3) were found from Fourier difference maps and refined freely. The other H atoms were placed in calculated positions and allowed to ride on their parent atoms at distances of 0.93 Å 0.97 Å for CH. Isotropic displacement parameters were set at 1.2 to 1.5 times U eq of the parent atom. One ethyl group was found to be disordered over two positions caused by rotation around the C3C16 single bond with approximately equal occupancies. The C17 atom was split into two positions and refined anisotropically. The corresponding H atoms at C16 and C17 were added geometrically in accord with the C16C17A and C16C17B bonds. DiscussionThe title compound is a derivative of the non-steroidal antiinflammatory drugs (NSAIDs) etodolac [3]. Etodolac is an indoleacetic acid derivative with analgesic and limited antiinflammatory properties. Etodolac is rapidly absorbed from the gastrointestinal tract, with a bioavailability of approximately 80 %. Like other NSAIDs, etodolac is highly (more than 99 %) bound to plasma proteins and extensively metabolized in the liver, with a half-life of approximately six to seven hours [4]. Also, gastrointestinal effect is the most common adverse reactions associated with etodolac [5]. In the title crystal structure, the molecules are interlinked by intermolecular hydrogen bonds N3HA···O1 and O1HA···N3 bonds into centrosymmetric dimers. There are two intramolecular hydrogen bonds O3HA···N2, O2HA···N1 forming two closed sixmembered loops in each molecule. The phenyl ring and the pyrrole ring are nearly coplanar. In phenyl ring part, the maximum CC bond length is 1.406(3) Å, the minimum is 1.363(3) Å, and the average CC bond length for the phenyl ring is 1.389(3) Å. In the pyrrole ring part, the longer CC bond is 1.406(3) Å and the other is 1.356(3) Å. The pyran ring has a chair form configuration. Other bond lengths and angles are in normal range.

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Section: Discussionmentioning

confidence: 99%

Crystal structure of (1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol- 1-yl)acetic acid (2-hydroxy-benzylidene)hydrazide, C24H27N3O3

Q.-B.

Zhang

2006

Zeitschrift Für Kristallographie - New Crystal Structures

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“…fig.1), is a chiral nonsteroidal anti-inflammatory drug. It is used as analgesic and anti-inflammatory in the treatment of rheumatoid arthritis and osteoarthritis (10). It prohibits the synthesis of inflammatory peripheral prostaglandins by inhibition of the cycloxygenase-2 enzyme.…”

Section: Introductionmentioning

confidence: 99%

Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release

Gadade¹,

Pekamwar²,

Lahoti³

et al. 2016

Marmara Pharmaceutical Journal

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“…7-ethyl tryptophol mainly used for the synthesis of Etodolac 5 . Etodolac is a nonsteroidal anti-inflammatory drug (NSAID) 6 . The U.S. Food and Drug Administration approved etodolac in January 1991.…”

Section: Introductionmentioning

confidence: 99%

A optimized process for the synthesis of a key starting material for etodolac, a non steroidal anti- inflammatory drug.

2013

IOSR-JAC

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Etodolac: The chemistry, pharmacology, metabolic disposition, and clinical profile of a novel anti‐inflammatory pyranocarboxylic acid

Cited by 55 publications

References 51 publications

Crystal structure of (1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol- 1-yl)acetic acid (2-hydroxy-benzylidene)hydrazide, C24H27N3O3

Crystal structure of (1,8-diethyl-1,3,4,9-tetrahydro-pyrano[3,4-b]indol- 1-yl)acetic acid (2-hydroxy-benzylidene)hydrazide, C24H27N3O3

Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release

A optimized process for the synthesis of a key starting material for etodolac, a non steroidal anti- inflammatory drug.

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