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Proglumetacin

Proglumetacin structure

CAS No:
57132-53-3
Formula:
C46H58ClN5O8
Chemical Name:
Proglumetacin
Synonyms:
1H-Indole-3-acetic acid,1-(4-chlorobenzoyl)-5-methoxy-2-methyl-,2-[4-[3-[[4-(benzoylamino)-5-(dipropylamino)-1,5-dioxopentyl]oxy]propyl]-1-piperazinyl]ethyl ester;1H-Indole-3-acetic acid,1-(4-chlorobenzoyl)-5-methoxy-2-methyl-,2-[4-[3-[[4-(benzoylamino)-5-(dipropylamino)-1,5-dioxopentyl]oxy]propyl]-1-piperazinyl]ethyl ester,(±)-;Proglumetacin
Categories:
Pharmaceutical Intermediates > Anti-inflammatory Agents

Description

Proglumetacin is 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 N(2)-benzoyl-N,N-dipropyl-alpha-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. It has a role as a non-steroidal anti-inflammatory drug, a non-narcotic analgesic, a lipoxygenase inhibitor, an EC 1.14.99.1 (prostaglandin-endoperoxide synthase) inhibitor, an antipyretic and a prodrug. It is a N-acylindole, an aromatic ether, a carboxylic ester, a N-alkylpiperazine, a member of benzamides and a member of monochlorobenzenes. It derives from an indometacin and a proglumide.

Proglumetacin Basic Attributes

Molecular Weight：

844.43400

Exact Mass：

844.43

DSSTox ID：

DTXSID0048842

ATC Code：

M - Musculo-skeletal system

Characteristics

PSA：

139.72000

XLogP3：

6.43090

Density：

1.22g/cm3

Boiling Point：

904ºC

Flash Point：

498.3ºC

Refractive Index：

1.592

Drug Information

MeSH：

Anti-inflammatory agents that are non-steroidal in nature. In addition to anti-inflammatory actions, they 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. Inhibition of prostaglandin synthesis accounts for their analgesic, antipyretic, and platelet-inhibitory actions; other mechanisms may contribute to their anti-inflammatory effects. (See all compounds classified as Anti-Inflammatory Agents, Non-Steroidal.)

MeSH Entry Terms：

3'-(4-(2-(1-p-chlorobenzoyl-5-methoxy-2-methylindol-3-ylacetoxy)ethyl)piperazin-1-yl)propyl-4-benzamido-N,N-dipropylglutaramate (+-) dimaleate

Computed Properties

Molecular Weight:844.4
XLogP3:7.3
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:10
Rotatable Bond Count:23
Exact Mass:843.3973915
Monoisotopic Mass:843.3973915
Topological Polar Surface Area:140
Heavy Atom Count:60
Complexity:1360
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes