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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:49 UTC
Update Date2018-05-20 20:51:25 UTC
HMDB IDHMDB0014608
Secondary Accession Numbers
  • HMDB14608
Metabolite Identification
Common NameKetorolac
DescriptionKetorolac is only found in individuals that have used or taken this drug. It is a pyrrolizine carboxylic acid derivative structurally related to indomethacin. It is an NSAID and is used principally for its analgesic activity (from Martindale The Extra Pharmacopoeia, 31st ed). Ketorolac is a nonsteroidal anti-inflammatory drug (NSAID) chemically related to indomethacin and tolmetin. Ketorolac tromethamine is a racemic mixture of [-]S- and [+]R-enantiomeric forms, with the S-form having analgesic activity. Its antiinflammatory effects are believed to be due to inhibition of both cylooxygenase-1 (COX-1) and cylooxygenase-2 (COX-2) which leads to the inhibition of prostaglandin synthesis leading to decreased formation of precursors of prostaglandins and thromboxanes from arachidonic acid. The resultant reduction in prostaglandin synthesis and activity may be at least partially responsible for many of the adverse, as well as the therapeutic, effects of these medications. Analgesia is probably produced via a peripheral action in which blockade of pain impulse generation results from decreased prostaglandin activity. However, inhibition of the synthesis or actions of other substances that sensitize pain receptors to mechanical or chemical stimulation may also contribute to the analgesic effect. In terms of the ophthalmic applications of ketorolac - ocular administration of ketorolac reduces prostaglandin E2 levels in aqueous humor, secondary to inhibition of prostaglandin biosynthesis.
Structure
Thumb
Synonyms
ValueSource
ToradolKegg
KetoralacHMDB
Ketorolac tromethamineHMDB
Chemical FormulaC15H13NO3
Average Molecular Weight255.2686
Monoisotopic Molecular Weight255.089543287
IUPAC Name5-benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid
Traditional Nameketorolac
CAS Registry Number66635-83-4
SMILES
OC(=O)C1CCN2C1=CC=C2C(=O)C1=CC=CC=C1
InChI Identifier
InChI=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
DescriptionThis compound 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
Ontology
Disposition

Biological location:

Process

Naturally occurring process:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point165 - 167 °C (tromethamine salt)Not Available
Boiling PointNot AvailableNot Available
Water Solubility0.51 g/LNot Available
LogP2.1Not 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 RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0a4i-1920000000-a5c8bba9af16159033c0View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (1 TMS) - 70eV, Positivesplash10-0a4i-7961000000-17a94cd0a49d06b5b243View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0190000000-cc495a56f46ce2f38f4cView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-0900000000-49260d5fd66684718972View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-0a4i-3900000000-cf3a2eedecd98f879db6View in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-056r-9500000000-a993ea029f81823db36eView in MoNA
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QTOF , positivesplash10-004i-9200000000-238f6cde2fac6b0ba421View in MoNA
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0a4i-1590000000-070501bbf446e4fc9feaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0190000000-9fdb0e54aaff0cd5b8e1View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0a4i-0940000000-413e5ee90a211ec8dd55View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0pb9-1900000000-6434b0035bdf19334abaView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0ik9-0090000000-1d743b79312994c4708aView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-0390000000-fa8da911a286c2522b7dView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-090r-4920000000-dad9f60ce69ed5b49dbbView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00465 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00465 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00465
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID3694
KEGG Compound IDC07062
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkKetorolac
METLIN IDNot Available
PubChem Compound3826
PDB IDNot Available
ChEBI ID76223
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in peroxidase activity
Specific function:
Mediates the formation of prostaglandins from arachidonate. May have a role as a major mediator of inflammation and/or a role for prostanoid signaling in activity-dependent plasticity.
Gene Name:
PTGS2
Uniprot ID:
P35354
Molecular weight:
68995.625
References
  1. Hocherl K, Kammerl MC, Schumacher K, Endemann D, Grobecker HF, Kurtz A: Role of prostanoids in regulation of the renin-angiotensin-aldosterone system by salt intake. Am J Physiol Renal Physiol. 2002 Aug;283(2):F294-301. [PubMed:12110513 ]
  2. Blais V, Zhang J, Rivest S: In altering the release of glucocorticoids, ketorolac exacerbates the effects of systemic immune stimuli on expression of proinflammatory genes in the brain. Endocrinology. 2002 Dec;143(12):4820-7. [PubMed:12446609 ]
  3. Ma W, Eisenach JC: Intraplantar injection of a cyclooxygenase inhibitor ketorolac reduces immunoreactivities of substance P, calcitonin gene-related peptide, and dynorphin in the dorsal horn of rats with nerve injury or inflammation. Neuroscience. 2003;121(3):681-90. [PubMed:14568028 ]
  4. Ma W, Eisenach JC: Cyclooxygenase 2 in infiltrating inflammatory cells in injured nerve is universally up-regulated following various types of peripheral nerve injury. Neuroscience. 2003;121(3):691-704. [PubMed:14568029 ]
  5. Padi SS, Jain NK, Singh S, Kulkarni SK: Pharmacological profile of parecoxib: a novel, potent injectable selective cyclooxygenase-2 inhibitor. Eur J Pharmacol. 2004 Apr 26;491(1):69-76. [PubMed:15102535 ]
General function:
Involved in peroxidase activity
Specific function:
May play an important role in regulating or promoting cell proliferation in some normal and neoplastically transformed cells.
Gene Name:
PTGS1
Uniprot ID:
P23219
Molecular weight:
68685.82
References
  1. Bosch-Marce M, Claria J, Titos E, Masferrer JL, Altuna R, Poo JL, Jimenez W, Arroyo V, Rivera F, Rodes J: Selective inhibition of cyclooxygenase 2 spares renal function and prostaglandin synthesis in cirrhotic rats with ascites. Gastroenterology. 1999 May;116(5):1167-75. [PubMed:10220509 ]
  2. Lashbrook JM, Ossipov MH, Hunter JC, Raffa RB, Tallarida RJ, Porreca F: Synergistic antiallodynic effects of spinal morphine with ketorolac and selective COX1- and COX2-inhibitors in nerve-injured rats. Pain. 1999 Jul;82(1):65-72. [PubMed:10422661 ]
  3. Dionne RA, Khan AA, Gordon SM: Analgesia and COX-2 inhibition. Clin Exp Rheumatol. 2001 Nov-Dec;19(6 Suppl 25):S63-70. [PubMed:11695255 ]
  4. Uzan A: The unexpected side effects of new nonsteroidal anti-inflammatory drugs. Expert Opin Emerg Drugs. 2005 Nov;10(4):687-8. [PubMed:16262557 ]
  5. Blais V, Turrin NP, Rivest S: Cyclooxygenase 2 (COX-2) inhibition increases the inflammatory response in the brain during systemic immune stimuli. J Neurochem. 2005 Dec;95(6):1563-74. Epub 2005 Nov 8. [PubMed:16277613 ]