Proglumetacin

Proglumetacin (usually as the maleate salt, trade names Afloxan, Protaxon and Proxil) is a nonsteroidal anti-inflammatory drug (NSAID). It is metabolized in the body to indometacin and proglumide,[1] a drug with antisecretory effects that helps prevent injury to the stomach lining.

Proglumetacin
Clinical data
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. Undergoes enterohepatic recirculation
Identifiers
IUPAC name
  • 3-{4-[2-({[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl}oxy)ethyl]piperazin-1-yl}propyl N2-benzoyl-N,N-dipropyl-α-glutaminate
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC46H58ClN5O8
Molar mass844.45 g·mol−1
3D model (JSmol)
SMILES
  • Clc1ccc(cc1)C(=O)n3c2ccc(OC)cc2c(c3C)CC(=O)OCCN4CCN(CC4)CCCOC(=O)CCC(C(=O)N(CCC)CCC)NC(=O)c5ccccc5
InChI
  • 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) Y
  • Key:PTXGHCGBYMQQIG-UHFFFAOYSA-N Y
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References
  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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