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CHEBI:76263 - proglumetacin

Default Structure
ChEBI IDCHEBI:76263
ChEBI Nameproglumetacin
Stars
DefinitionA 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.
Last Modified22 February 2017
SubmitterSteve
DownloadsMolfile
FormulaC46H58ClN5O8
Net Charge0
Average Mass844.450
Monoisotopic Mass843.39739
SMILESCCCN(CCC)C(=O)C(CCC(=O)OCCCN1CCN(CCOC(=O)Cc2c(C)n(C(=O)c3ccc(Cl)cc3)c3ccc(OC)cc23)CC1)NC(=O)c1ccccc1
InChIInChI=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)
InChIKeyPTXGHCGBYMQQIG-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Biological Roles:
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.
Applications:
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.
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.
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.
ChEBI Ontology
Outgoing Relation(s)
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 Relation(s)
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  Source
proglumetacinKEGG DRUG
proglumetacinaChemIDplus
proglumétacineWHO MedNet
proglumetacinumChemIDplus
Manual XrefsDatabases
2280DrugCentral
D08427KEGG DRUG
ProglumetacinWikipedia
US6599529Patent
Registry NumbersSources
Reaxys:876871Reaxys
CAS:57132-53-3KEGG DRUG
CAS:57132-53-3ChemIDplus
Citations