Ketorolac (CHEM022112)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-25 18:20:36 UTC
Update Date2016-11-09 01:17:25 UTC
Accession NumberCHEM022112
Identification
Common NameKetorolac
ClassSmall Molecule
DescriptionA racemate comprising equimolar amounts of (R)-(+)- and (S)-(-)-5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid. While only the (S)-(-) enantiomer is a COX1 and COX2 inhibitor, the (R)-(+) enantiomer exhibits potent analgesic activity. A non-steroidal anti-inflammatory drug, ketorolac is mainly used (generally as the tromethamine salt) for its potent analgesic properties in the short-term management of post-operative pain, and in eye drops to relieve the ocular itching associated with seasonal allergic conjunctivitis. It was withdrawn from the market in many countries in 1993 following association with haemorrhage and renal failure.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
(+-)-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acidChEBI
(+-)-KetorolacChEBI
KetorolacoChEBI
KetorolacumChEBI
rac-KetorolacChEBI
ToradolKegg
(+-)-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylateGenerator
KetoralacHMDB
Ketorolac tromethamineHMDB
Chemical FormulaC15H13NO3
Average Molecular Mass255.269 g/mol
Monoisotopic Mass255.090 g/mol
CAS Registry Number66635-83-4
IUPAC Name5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
Traditional Nameketorolac
SMILESOC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1
InChI IdentifierInChI=1S/C15H13NO3/c17-14(10-4-2-1-3-5-10)13-7-6-12-11(15(18)19)8-9-16(12)13/h1-7,11H,8-9H2,(H,18,19)
InChI KeyOZWKMVRBQXNZKK-UHFFFAOYSA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as aryl-phenylketones. These are aromatic compounds containing a ketone substituted by one aryl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAryl-phenylketones
Alternative Parents
Substituents
  • Aryl-phenylketone
  • Benzoyl
  • Pyrrolizine
  • Monocyclic benzene moiety
  • Substituted pyrrole
  • Benzenoid
  • Pyrrole
  • Heteroaromatic compound
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Organoheterocyclic compound
  • Azacycle
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Organonitrogen compound
  • Organopnictogen 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 Solubility0.51 g/LALOGPS
logP2.66ALOGPS
logP2.28ChemAxon
logS-2.7ALOGPS
pKa (Strongest Acidic)3.84ChemAxon
pKa (Strongest Basic)-7.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.3 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity70.19 m³·mol⁻¹ChemAxon
Polarizability26.67 ųChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1920000000-a5c8bba9af16159033c0Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-7961000000-17a94cd0a49d06b5b243Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (TBDMS_1_1) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0190000000-cc495a56f46ce2f38f4cSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-49260d5fd66684718972Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-3900000000-cf3a2eedecd98f879db6Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-056r-9500000000-a993ea029f81823db36eSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-9200000000-238f6cde2fac6b0ba421Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-1590000000-070501bbf446e4fc9feaSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-3900000000-cf3a2eedecd98f879db6Spectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-fbb6114acc4083df7784Spectrum
LC-MS/MSLC-MS/MS Spectrum - 40V, Positivesplash10-056r-9500000000-a993ea029f81823db36eSpectrum
LC-MS/MSLC-MS/MS Spectrum - 30V, Positivesplash10-0a4i-3900000000-ee0dc6dc8e4e5458f031Spectrum
LC-MS/MSLC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-cc495a56f46ce2f38f4cSpectrum
LC-MS/MSLC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0900000000-49260d5fd66684718972Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Positivesplash10-0a4i-1900000000-4b05ed1bfbbaf89c98d5Spectrum
LC-MS/MSLC-MS/MS Spectrum - 50V, Positivesplash10-004i-9200000000-238f6cde2fac6b0ba421Spectrum
LC-MS/MSLC-MS/MS Spectrum - 35V, Negativesplash10-03di-0090000000-cf2413a3f637dd2e4920Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-9fdb0e54aaff0cd5b8e1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0940000000-413e5ee90a211ec8dd55Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-1900000000-6434b0035bdf19334abaSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-0090000000-1d743b79312994c4708aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0390000000-fa8da911a286c2522b7dSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-090r-4920000000-dad9f60ce69ed5b49dbbSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0w29-0090000000-4148685fc3bd851d8294Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0290000000-9e7b9f6d61338222e28bSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kh9-2930000000-5b75c695a6356577b1b1Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0090000000-37bb3aa601b3716743cfSpectrum
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 IDDB00465
HMDB IDHMDB0014608
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkKetorolac
Chemspider ID3694
ChEBI ID6129
PubChem Compound ID3826
Kegg Compound IDC07062
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10027870
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=10223774
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=10593468
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=17456651
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=19281996
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=22191998
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=23088994
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=23126437
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=23179562
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=23298250
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=23447046
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=23473380
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=23562034
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=23653032
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=23702435
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=24022643
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=24112670
18. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217
19. https://www.ncbi.nlm.nih.gov/pubmed/?term=9549656