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Indoprofen

From Wikipedia, the free encyclopedia
Withdrawn NSAID drug
Pharmaceutical compound
Indoprofen
Clinical data
Routes of
administration
Oral
ATC code
Legal status
Legal status
  • Withdrawn
Pharmacokinetic data
BioavailabilityHigh (rapid and complete absorption)
MetabolismGlucuronidation
Eliminationhalf-life2.3 hours
ExcretionRenal
Identifiers
  • 2-[4-(1-oxo-1,3-dihydro-2H-isoindol-2-yl)
    phenyl]propanoic acid
CAS Number
PubChemCID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard(EPA)
ECHA InfoCard100.046.197Edit this at Wikidata
Chemical and physical data
FormulaC17H15NO3
Molar mass281.311 g·mol−1
3D model (JSmol)
  • O=C(O)C(c1ccc(cc1)N3C(=O)c2ccccc2C3)C
  • InChI=1S/C17H15NO3/c1-11(17(20)21)12-6-8-14(9-7-12)18-10-13-4-2-3-5-15(13)16(18)19/h2-9,11H,10H2,1H3,(H,20,21) checkY
  • Key:RJMIEHBSYVWVIN-UHFFFAOYSA-N checkY

Indoprofen is anonsteroidal anti-inflammatory drug (NSAID). It was withdrawn worldwide in the 1980s after postmarketing reports of severegastrointestinal bleeding.[1]

A 2004 study usinghigh-throughput screening found indoprofen to increase production of thesurvival of motor neuron protein, suggesting it may provide insight into treatments forspinal muscular atrophies.[1][2]

Synthesis

[edit]

Theisoindolone ring system forms the nucleus for thisprofen NSAID.

The nitro group in 2-(4-nitrophenyl)propionic acid (1) is reduced using iron and hydrochloric acid to give 2-(4-aminophenyl)propionic acid (2). Reaction withphthalic anhydride then gives thephthalimide (4). Treatment with zinc in acetic acid yields indoprofen afterreduction of one of theamide groups.[3][4][5]

See also

[edit]

References

[edit]
  1. ^abFrazin N (March 9, 2005)."Pain Reliever May Provide Clues for Treating Spinal Muscular Atrophy". United StatesNational Institute of Neurological Disorders and Stroke. Archived fromthe original on 2008-07-04. Retrieved2007-10-06.
  2. ^Lunn MR, Root DE, Martino AM, Flaherty SP, Kelley BP, Coovert DD, et al. (November 2004)."Indoprofen upregulates the survival motor neuron protein through a cyclooxygenase-independent mechanism".Chemistry & Biology.11 (11):1489–93.doi:10.1016/j.chembiol.2004.08.024.PMC 3160629.PMID 15555999.
  3. ^US patent 4316850, Richard W. J. Carney and George de Stevens, "Tertiary aminoacids", issued 1982-02-23, assigned to Ciba Geigy Corp 
  4. ^Nannini G, Giraldi PN, Molgora G, Biasoli G, Spinelli F, Logemann W, et al. (August 1973). "New analgesic-anti-inflammatory drugs. 1-Oxo-2-substituted isoindoline derivatives".Arzneimittel-Forschung.23 (8):1090–100.doi:10.1002/chin.197344288.PMID 4801034.
  5. ^"Indoprofen".Pharmaceutical Substances. Thieme. Retrieved2024-07-11.
pyrazolones /
pyrazolidines
salicylates
acetic acid derivatives
and related substances
oxicams
propionic acid
derivatives (profens)
n-arylanthranilic
acids (fenamates)
COX-2 inhibitors
(coxibs)
other
NSAID
combinations
Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;withdrawn drugs;veterinary use.
Receptor
(ligands)
DP (D2)Tooltip Prostaglandin D2 receptor
DP1Tooltip Prostaglandin D2 receptor 1
DP2Tooltip Prostaglandin D2 receptor 2
EP (E2)Tooltip Prostaglandin E2 receptor
EP1Tooltip Prostaglandin EP1 receptor
EP2Tooltip Prostaglandin EP2 receptor
EP3Tooltip Prostaglandin EP3 receptor
EP4Tooltip Prostaglandin EP4 receptor
Unsorted
FP (F)Tooltip Prostaglandin F receptor
IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
Unsorted
Enzyme
(inhibitors)
COX
(
PTGS)
PGD2STooltip Prostaglandin D synthase
PGESTooltip Prostaglandin E synthase
PGFSTooltip Prostaglandin F synthase
PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
Others
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