Details of the Drug Metabolized by Drug-Metabolizing Enzyme (DME)

General Information of Drug (ID: DR0908)
Drug Name
Ketorolac
Synonyms
Ketoralac; Ketorolac [INN:BAN]; Ketorolaco; Ketorolaco [Spanish]; Ketorolacum; Ketorolacum [Latin]; Macril; OZWKMVRBQXNZKK-UHFFFAOYSA-N; RS 37619; RS-37619; Toradol (TN); ketorolac; (+-)-5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid; (+-)-Ketorolac; 1H-Pyrrolizine-1-carboxylic acid, 5-benzoyl-2,3-dihydro-; 5-(phenylcarbonyl)-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid; 5-Benzoyl-2,3-dihydro-1H-pyrrolizine-1-carboxylic acid; 66635-83-4; 74103-06-3; CHEBI:76223
Indication Rheumatoid arthritis [ICD11: FA20] Approved [1]
Structure
3D MOL 2D MOL
Pharmaceutical Properties Molecular Weight 255.27 Topological Polar Surface Area 59.3
Heavy Atom Count 19 Rotatable Bond Count 3
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Cross-matching ID
PubChem CID
3826
PubChem SID
9274 ; 5316934 ; 7979681 ; 8152424 ; 12013083 ; 14774471 ; 29222945 ; 46507019 ; 48416148 ; 49698948 ; 50040043 ; 50559242 ; 53787558 ; 56313647 ; 57322012 ; 85787389 ; 87245106 ; 90341692 ; 92719330 ; 96024794 ; 99281833 ; 103168363 ; 103922837 ; 104304637 ; 118314823 ; 124749910 ; 124896716 ; 125357028 ; 126449597 ; 126449602 ; 126621065 ; 126628266 ; 126648434 ; 126657726 ; 126670368 ; 126670856 ; 128885449 ; 131939830 ; 134337908 ; 135011243 ; 135039632 ; 136351611 ; 137035346 ; 142342166 ; 160654547 ; 160963811 ; 162178870 ; 162631206 ; 163414850 ; 164827307
ChEBI ID
CHEBI:76223
CAS Number
66635-83-4
TTD Drug ID
D0D9JW
Formula
C15H13NO3
Canonical SMILES
C1CN2C(=CC=C2C(=O)C3=CC=CC=C3)C1C(=O)O
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)
InChIKey
OZWKMVRBQXNZKK-UHFFFAOYSA-N
The Metabolic Roadmap of This Drug
The Full List of Drug Metabolites (DM) of This Drug
DM Name DM ID PubChem ID Reaction DM Level REF
4-hydroxy ketorolac DM002820
3082630
Oxidation - Hydroxylation 1 [4]
K1 DM002822
57357558
Unclear 1 [4]
K2 DM002827
71209516
Unclear 1 [4]
K6 DM002826
9921553
Conjugation - Methylation 1 [4]
K7 DM002825 N. A. Conjugation - Acetylation 1 [4]
K8 DM002824 N. A. Conjugation - Sulfation 1 [4]
Rac Ketorolac glucuronide DM002821
163285456
Conjugation - Glucuronidation 1 [4]
K10 DM002823 N. A. Conjugation - Glucuronidation 2 [4]
The Full List of Metabolic Reaction (MR) of This Drug
MR ID Reactant Product MR Type DME REF
MR001368 Ketorolac 4-hydroxy ketorolac Oxidation - Hydroxylation CYP2C8 ... [4]
MR001369 Ketorolac Rac Ketorolac glucuronide Conjugation - Glucuronidation UGT2B7 [4]
MR001370 Ketorolac K1 Unclear Unclear [4]
MR001371 Ketorolac K8 Conjugation - Sulfation Unclear [4]
MR001372 Ketorolac K7 Conjugation - Acetylation Unclear [4]
MR001373 Ketorolac K6 Conjugation - Methylation Unclear [4]
MR001374 Ketorolac K2 Unclear Unclear [4]
MR001367 K1 K10 Conjugation - Glucuronidation Unclear [4]
⏷ Show the Full List of 8 MR(s)
Drug-Metabolizing Enzyme(s) (DME) Metabolizing This Drug
DME Name DME Info Species Uniprot ID EC Number REF
Cytochrome P450 2C8 (CYP2C8) DME0018 Homo sapiens
CP2C8_HUMAN
1.14.14.1
[2]
Cytochrome P450 2C9 (CYP2C9) DME0019 Homo sapiens
CP2C9_HUMAN
1.14.14.1
[2]
UDP-glucuronosyltransferase 2B7 (UGT2B7) DME0040 Homo sapiens
UD2B7_HUMAN
2.4.1.17
[2]
Unclear metabolic mechanism (DME-unclear) DME1251 Bacteroides fragilis Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1256 Bacteroides sartorii Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1365 Bacteroides dorei Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1384 Bacteroides vulgatus Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1385 Bacteroides xylanisolvens Not Available Not Available [3]
Unclear metabolic mechanism (DME-unclear) DME1402 Clostridium botulinum Not Available Not Available [3]
⏷ Show the Full List of 9  DME(s)
References
1 Ketorolac was approved by FDA. The 2020 official website of the U.S. Food and Drug Administration.
2 Body weight, gender and pregnancy affect enantiomer-specific ketorolac pharmacokinetics. Br J Clin Pharmacol. 2017 Sep;83(9):1966-1975.
3 Mapping human microbiome drug metabolism by gut bacteria and their genes. Nature. 2019 Jun;570(7762):462-467.
4 Identification and structural characterization of in vivo metabolites of ketorolac using liquid chromatography electrospray ionization tandem mass spectrometry (LC/ESI-MS/MS) J Mass Spectrom. 2012 Jul;47(7):919-31. doi: 10.1002/jms.3043.

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