Proglumetacin (CHEM020062)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 06:44:50 UTC
Update Date2016-11-09 01:16:07 UTC
Accession NumberCHEM020062
Identification
Common NameProglumetacin
ClassSmall Molecule
DescriptionA 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.
Contaminant Sources
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
ProglumetacinaChEBI
ProglumetacineChEBI
ProglumetacinumChEBI
BruxelKegg
3-[4-[2-[2-[1-(4-Chlorobenzoyl)-5-methoxy-2-methylindol-3-yl]acetyl]oxyethyl]piperazin-1-yl]propyl 4-benzamido-5-(dipropylamino)-5-oxopentanoic acidGenerator
Proglumetacin maleateMeSH
ProtaxilMeSH
ProglumetacinMeSH
3'-(4-(2-(1-P-Chlorobenzoyl-5-methoxy-2-methylindol-3-ylacetoxy)ethyl)piperazin-1-yl)propyl-4-benzamido-N,N-dipropylglutaramate (+-) dimaleateMeSH
ProtaxonMeSH
ProdamoxMeSH
Proglumetacin dimaleateMeSH
ProtacineMeSH
Chemical FormulaC46H58ClN5O8
Average Molecular Mass844.450 g/mol
Monoisotopic Mass843.397 g/mol
CAS Registry Number57132-53-3
IUPAC NameN-[4-(3-{4-[2-({2-[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl}oxy)ethyl]piperazin-1-yl}propoxy)-1-(dipropylcarbamoyl)-4-oxobutyl]benzenecarboximidic acid
Traditional Nameproglumetacin
SMILESCCCN(CCC)C(=O)C(CCC(=O)OCCCN1CCN(CCOC(=O)CC2=C(C)N(C(=O)C3=CC=C(Cl)C=C3)C3=C2C=C(OC)C=C3)CC1)N=C(O)C1=CC=CC=C1
InChI IdentifierInChI=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)
InChI KeyPTXGHCGBYMQQIG-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as benzoylindoles. These are organic compounds containing an indole attached to a benzoyl moiety through the acyl group.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassIndoles and derivatives
Sub ClassBenzoylindoles
Direct ParentBenzoylindoles
Alternative Parents
Substituents
  • Benzoylindole
  • Glutamic acid or derivatives
  • N-acyl-alpha amino acid or derivatives
  • Indole-3-acetic acid derivative
  • Alpha-amino acid amide
  • Indolecarboxylic acid derivative
  • Alpha-amino acid or derivatives
  • 4-halobenzoic acid or derivatives
  • Halobenzoic acid or derivatives
  • 3-alkylindole
  • Indole
  • Benzoic acid or derivatives
  • Benzoyl
  • Anisole
  • Chlorobenzene
  • N-alkylpiperazine
  • Alkyl aryl ether
  • Fatty acid ester
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Fatty acyl
  • 1,4-diazinane
  • Dicarboxylic acid or derivatives
  • Benzenoid
  • N-acyl-amine
  • Piperazine
  • Substituted pyrrole
  • Pyrrole
  • Tertiary carboxylic acid amide
  • Heteroaromatic compound
  • Tertiary aliphatic amine
  • Tertiary amine
  • Amino acid or derivatives
  • Carboxylic acid ester
  • Carboxamide group
  • Propargyl-type 1,3-dipolar organic compound
  • Organic 1,3-dipolar compound
  • Ether
  • Carboxylic acid derivative
  • Carboximidic acid derivative
  • Carboximidic acid
  • Azacycle
  • Organopnictogen compound
  • Carbonyl group
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Organic oxide
  • Organohalogen compound
  • Organochloride
  • Organonitrogen compound
  • Organooxygen compound
  • Organic oxygen compound
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.0011 g/LALOGPS
logP5.82ALOGPS
logP6.01ChemAxon
logS-5.9ALOGPS
pKa (Strongest Acidic)8.69ChemAxon
pKa (Strongest Basic)8.03ChemAxon
Physiological Charge2ChemAxon
Hydrogen Acceptor Count9ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area143.21 ŲChemAxon
Rotatable Bond Count23ChemAxon
Refractivity233.4 m³·mol⁻¹ChemAxon
Polarizability94.39 ųChemAxon
Number of Rings5ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0006-2409330370-19666391c0e8952af68fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-06r6-3809130100-4fbcd1a37e958a4f9558Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9302010100-efc6163b9b6be0eeb3b5Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-00ku-0009110030-b53a613b0e8b503682fbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0fs9-0439110210-faf3ec9036dd23476d8dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-05bv-9747200510-9f4318692332d37050a8Spectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
DrugBank IDDB13527
HMDB IDHMDB0256795
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkProglumetacin
Chemspider ID4752
ChEBI ID76263
PubChem Compound IDNot Available
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=1626095
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=1778279
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=2491526
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=2653004
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=2974384
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=3663267
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=3860726
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=3887221
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=3905222
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=4074450
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=6222270
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=6222271
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=6343924
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=6381269
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=6602308
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=6602309
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=6602310
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=6728264
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=6728268
20. https://www.ncbi.nlm.nih.gov/pubmed/?term=6856162
21. https://www.ncbi.nlm.nih.gov/pubmed/?term=6856163
22. https://www.ncbi.nlm.nih.gov/pubmed/?term=6856164
23. https://www.ncbi.nlm.nih.gov/pubmed/?term=6856165
24. https://www.ncbi.nlm.nih.gov/pubmed/?term=6856166
25. https://www.ncbi.nlm.nih.gov/pubmed/?term=6856167