Proglumetacin

Proglumetacin (usually supplied as the maleate salt) is a nonsteroidal anti-inflammatory drug (NSAID). It is a codrug (that is, a mutual prodrug) of indometacin and proglumide^[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.

Proglumetacin

Structure of proglumetacin
Structures of the two metabolites
Clinical data
Trade names	Afloxan, Protaxon, Proxil
Other names	3-[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.com	International Drug Names
ATC code	M01AB14 (WHO)
Pharmacokinetic data
Metabolism	Hepatic. 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	57132-53-3 59209-40-4
PubChem CID	4921
ChemSpider	4752 Y
UNII	FV919079LU
ChEBI	CHEBI:76263
CompTox Dashboard (EPA)	DTXSID0048842
Chemical and physical data
Formula	C46H58ClN5O8
Molar mass	844.45 g·mol−1
3D model (JSmol)	Interactive image
SMILES 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 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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Indometacin contributes to the anti-inflammatory effect, while proglumide has antisecretory effects that helps prevent injury to the stomach lining.