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Proglumetacin

From Wikipedia, the free encyclopedia
Non-steroidal anti-inflammatory drug
Pharmaceutical compound
Proglumetacin
Structure of proglumetacin
Structures of the two metabolites
Clinical data
Trade namesAfloxan, Protaxon, Proxil
Other names3-[4-[2-[2-[1-(4-chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxyethyl]piperazin-1-yl]propyl 4-(benzoylamino)-5-(dipropylamino)-5-oxopentanoate
AHFS/Drugs.comInternational Drug Names
ATC code
Pharmacokinetic data
MetabolismHepatic. Undergoesenterohepatic recirculation
Identifiers
  • 3-{4-[2-({[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl}oxy)ethyl]piperazin-1-yl}propylN2-benzoyl-N,N-dipropyl-α-glutaminate
CAS Number
PubChemCID
ChemSpider
UNII
ChEBI
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC46H58ClN5O8
Molar mass844.45 g·mol−1
3D model (JSmol)
  • CCCN(CCC)C(=O)C(CCC(=O)OCCCN1CCN(CCOC(=O)Cc2c(C)n(C(=O)c3ccc(Cl)cc3)c3ccc(OC)cc23)CC1)NC(=O)c1ccccc1
  • InChI=1S/C46H58ClN5O8/c1-5-21-51(22-6-2)46(57)40(48-44(55)34-11-8-7-9-12-34)18-20-42(53)59-29-10-23-49-24-26-50(27-25-49)28-30-60-43(54)32-38-33(3)52(41-19-17-37(58-4)31-39(38)41)45(56)35-13-15-36(47)16-14-35/h7-9,11-17,19,31,40H,5-6,10,18,20-30,32H2,1-4H3,(H,48,55) checkY
  • Key:PTXGHCGBYMQQIG-UHFFFAOYSA-N checkY
  (verify)

Proglumetacin (usually supplied as themaleate salt) is anonsteroidal anti-inflammatory drug (NSAID). It is acodrug (that is, a mutualprodrug) ofindometacin andproglumide.[1] After oral intake, it is absorbed and metabolized to indometacin and proglumide. These two substances are then released into the system in a 1:1 molar ratio.

Indometacin contributes to the anti-inflammatory effect, while proglumide hasantisecretory effects that helps prevent injury to the stomach lining.

References

[edit]
  1. ^Setnikar I, Arigoni R, Chisté R, Makovec F, Revel L (1987). "Plasma levels of proglumetacin and its metabolites after intravenous or oral administration in the dog".Arzneimittel-Forschung.37 (6):698–702.PMID 3663267.
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Key:underline indicates initially developed first-in-class compound of specific group;#WHO-Essential Medicines;withdrawn drugs;veterinary use.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
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IP (I2)Tooltip Prostacyclin receptor
TP (TXA2)Tooltip Thromboxane receptor
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PGI2STooltip Prostacyclin synthase
TXASTooltip Thromboxane A synthase
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