CHEBI:76263 - proglumetacin

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ChEBI Name proglumetacin
ChEBI ID CHEBI:76263
Definition A carboxylic ester obtained by formal condensation of the carboxy group of indometacin with the hydroxy group of 3-[4-(2-hydroxyethyl)piperazin-1-yl]propyl N2-benzoyl-N,N-dipropyl-α-glutaminate. Used (as its dimaleate salt) to control pain and inflammation associated with musculoskeletal and joint disorders. Following oral administration, it is metabolised to indometacin and proglumide, a drug with antisecretory effects that helps prevent injury to the stomach lining.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C46H58ClN5O8
Net Charge 0
Average Mass 844.43400
Monoisotopic Mass 843.397
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)
InChIKey PTXGHCGBYMQQIG-UHFFFAOYSA-N
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
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
lipoxygenase inhibitor
A compound or agent that combines with lipoxygenase and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of the icosanoid products hydroxyicosatetraenoic acid and various leukotrienes.
EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor
A compound or agent that combines with cyclooxygenases (EC 1.14.99.1) and thereby prevents its substrate-enzyme combination with arachidonic acid and the formation of icosanoids, prostaglandins, and thromboxanes.
Application(s): non-steroidal anti-inflammatory drug
An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
antipyretic
A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
prodrug
A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
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ChEBI Ontology
Outgoing proglumetacin (CHEBI:76263) has functional parent indometacin (CHEBI:49662)
proglumetacin (CHEBI:76263) has functional parent proglumide (CHEBI:32058)
proglumetacin (CHEBI:76263) has role antipyretic (CHEBI:35493)
proglumetacin (CHEBI:76263) has role EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor (CHEBI:35544)
proglumetacin (CHEBI:76263) has role lipoxygenase inhibitor (CHEBI:35856)
proglumetacin (CHEBI:76263) has role non-narcotic analgesic (CHEBI:35481)
proglumetacin (CHEBI:76263) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
proglumetacin (CHEBI:76263) has role prodrug (CHEBI:50266)
proglumetacin (CHEBI:76263) is a N-acylindole (CHEBI:75884)
proglumetacin (CHEBI:76263) is a N-alkylpiperazine (CHEBI:46845)
proglumetacin (CHEBI:76263) is a aromatic ether (CHEBI:35618)
proglumetacin (CHEBI:76263) is a benzamides (CHEBI:22702)
proglumetacin (CHEBI:76263) is a carboxylic ester (CHEBI:33308)
proglumetacin (CHEBI:76263) is a monochlorobenzenes (CHEBI:83403)
Incoming proglumetacin dimaleate (CHEBI:32057) has part proglumetacin (CHEBI:76263)
IUPAC Name
3-[4-(2-{2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetoxy}ethyl)piperazin-1-yl]propyl N2-benzoyl-N,N-dipropyl-α-glutaminate
INNs Sources
proglumetacin KEGG DRUG
proglumetacina ChemIDplus
proglumétacine WHO MedNet
proglumetacinum ChemIDplus
Manual Xrefs Databases
2280 DrugCentral
D08427 KEGG DRUG
Proglumetacin Wikipedia
US6599529 Patent
View more database links
Registry Numbers Types Sources
57132-53-3 CAS Registry Number KEGG DRUG
57132-53-3 CAS Registry Number ChemIDplus
876871 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
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Last Modified
22 February 2017