U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C15H13NO3
Molecular Weight 255.2686
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of KETOROLAC

SMILES

OC(=O)C1CCN2C1=CC=C2C(=O)C3=CC=CC=C3

InChI

InChIKey=OZWKMVRBQXNZKK-UHFFFAOYSA-N
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)

HIDE SMILES / InChI
Ketorolac is a pyrrolizine carboxylic acid derivative structurally related to indomethacin. It is an NSAID and is used principally for its analgesic activity and has been shown to decrease opioid requirements in post-operative patients. It does not affect consciousness or respiration but does have effects on gastric mucosa, renal perfusion, and platelet function. Ketorolac tromethamine ophthalmic solution is sold under brand name acular LS and is indicated for the reduction of ocular pain and burning/stinging following corneal refractive surgery. 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 medication. Analgesia is probably produced via a peripheral action in which blockade of pain impulse generation results from decreased prostaglandin activity.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ACULAR LS

Approved Use

ACULAR LS ophthalmic solution is indicated for the reduction of ocular pain and burning/stinging following corneal refractive surgery.

Launch Date

2003
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2382.2 ng/mL
30 mg single, intramuscular
dose: 30 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
KETOROLAC plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
1805.8 ng/mL
31.5 mg single, nasal
dose: 31.5 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
KETOROLAC plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
11152.8 ng × h/mL
30 mg single, intramuscular
dose: 30 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
KETOROLAC plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
7477.3 ng × h/mL
31.5 mg single, nasal
dose: 31.5 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
KETOROLAC plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.8 h
30 mg single, intramuscular
dose: 30 mg
route of administration: Intramuscular
experiment type: SINGLE
co-administered:
KETOROLAC plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
5.24 h
31.5 mg single, nasal
dose: 31.5 mg
route of administration: Nasal
experiment type: SINGLE
co-administered:
KETOROLAC plasma
Homo sapiens
population: HEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
2 mg single, intrathecal
Highest studied dose
Dose: 2 mg
Route: intrathecal
Route: single
Dose: 2 mg
Sources:
healthy, 18-50
n = 5
Health Status: healthy
Age Group: 18-50
Sex: M+F
Population Size: 5
Sources:
30 mg single, intramuscular
Highest studied dose
Dose: 30 mg
Route: intramuscular
Route: single
Dose: 30 mg
Sources:
healthy, 19-45
n = 15
Health Status: healthy
Age Group: 19-45
Sex: M+F
Population Size: 15
Sources:
30 mg single, intranasal
Highest studied dose
Dose: 30 mg
Route: intranasal
Route: single
Dose: 30 mg
Sources:
healthy, 19-45
n = 15
Health Status: healthy
Age Group: 19-45
Sex: M+F
Population Size: 15
Sources:
31.5 mg 3 times / day multiple, intranasal
Recommended
Dose: 31.5 mg, 3 times / day
Route: intranasal
Route: multiple
Dose: 31.5 mg, 3 times / day
Sources:
unhealthy, 51.7
n = 199
Health Status: unhealthy
Condition: pain
Age Group: 51.7
Sex: M+F
Population Size: 199
Sources:
Other AEs: Nausea, Constipation...
Other AEs:
Nausea (58%)
Constipation (29%)
Vomiting (28%)
Nasal passage irritation (24%)
Headache (24%)
Flatulence (23%)
Anemia (19%)
Tachycardia (14%)
Pruritis (11%)
Dizziness (6%)
Sources:
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
unhealthy
n = 8
Health Status: unhealthy
Condition: Percutaneous Nephrolithotomy operation
Population Size: 8
Sources:
Other AEs: Anaemia, Thrombocytopenia...
Other AEs:
Anaemia (below serious, 7 patients)
Thrombocytopenia (below serious, 3 patients)
Hyponatraemia (below serious, 3 patients)
Hypokalaemia (below serious, 2 patients)
Leucopenia (below serious, 1 patient)
Sources:
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
unhealthy
n = 57
Health Status: unhealthy
Condition: Laparoscopic Donor Nephrectomy
Population Size: 57
Sources:
Other AEs: Hypercapnia, Thrombocytopenia...
Other AEs:
Hypercapnia (below serious, 12 patients)
Thrombocytopenia (below serious, 12 patients)
Leukocytosis (below serious, 38 patients)
Hypokalaemia (below serious, 20 patients)
Hyperkalaemia (below serious, 3 patients)
Hyponatraemia (below serious, 10 patients)
Sources:
AEs

AEs

AESignificanceDosePopulation
Pruritis 11%
31.5 mg 3 times / day multiple, intranasal
Recommended
Dose: 31.5 mg, 3 times / day
Route: intranasal
Route: multiple
Dose: 31.5 mg, 3 times / day
Sources:
unhealthy, 51.7
n = 199
Health Status: unhealthy
Condition: pain
Age Group: 51.7
Sex: M+F
Population Size: 199
Sources:
Tachycardia 14%
31.5 mg 3 times / day multiple, intranasal
Recommended
Dose: 31.5 mg, 3 times / day
Route: intranasal
Route: multiple
Dose: 31.5 mg, 3 times / day
Sources:
unhealthy, 51.7
n = 199
Health Status: unhealthy
Condition: pain
Age Group: 51.7
Sex: M+F
Population Size: 199
Sources:
Anemia 19%
31.5 mg 3 times / day multiple, intranasal
Recommended
Dose: 31.5 mg, 3 times / day
Route: intranasal
Route: multiple
Dose: 31.5 mg, 3 times / day
Sources:
unhealthy, 51.7
n = 199
Health Status: unhealthy
Condition: pain
Age Group: 51.7
Sex: M+F
Population Size: 199
Sources:
Flatulence 23%
31.5 mg 3 times / day multiple, intranasal
Recommended
Dose: 31.5 mg, 3 times / day
Route: intranasal
Route: multiple
Dose: 31.5 mg, 3 times / day
Sources:
unhealthy, 51.7
n = 199
Health Status: unhealthy
Condition: pain
Age Group: 51.7
Sex: M+F
Population Size: 199
Sources:
Headache 24%
31.5 mg 3 times / day multiple, intranasal
Recommended
Dose: 31.5 mg, 3 times / day
Route: intranasal
Route: multiple
Dose: 31.5 mg, 3 times / day
Sources:
unhealthy, 51.7
n = 199
Health Status: unhealthy
Condition: pain
Age Group: 51.7
Sex: M+F
Population Size: 199
Sources:
Nasal passage irritation 24%
31.5 mg 3 times / day multiple, intranasal
Recommended
Dose: 31.5 mg, 3 times / day
Route: intranasal
Route: multiple
Dose: 31.5 mg, 3 times / day
Sources:
unhealthy, 51.7
n = 199
Health Status: unhealthy
Condition: pain
Age Group: 51.7
Sex: M+F
Population Size: 199
Sources:
Vomiting 28%
31.5 mg 3 times / day multiple, intranasal
Recommended
Dose: 31.5 mg, 3 times / day
Route: intranasal
Route: multiple
Dose: 31.5 mg, 3 times / day
Sources:
unhealthy, 51.7
n = 199
Health Status: unhealthy
Condition: pain
Age Group: 51.7
Sex: M+F
Population Size: 199
Sources:
Constipation 29%
31.5 mg 3 times / day multiple, intranasal
Recommended
Dose: 31.5 mg, 3 times / day
Route: intranasal
Route: multiple
Dose: 31.5 mg, 3 times / day
Sources:
unhealthy, 51.7
n = 199
Health Status: unhealthy
Condition: pain
Age Group: 51.7
Sex: M+F
Population Size: 199
Sources:
Nausea 58%
31.5 mg 3 times / day multiple, intranasal
Recommended
Dose: 31.5 mg, 3 times / day
Route: intranasal
Route: multiple
Dose: 31.5 mg, 3 times / day
Sources:
unhealthy, 51.7
n = 199
Health Status: unhealthy
Condition: pain
Age Group: 51.7
Sex: M+F
Population Size: 199
Sources:
Dizziness 6%
31.5 mg 3 times / day multiple, intranasal
Recommended
Dose: 31.5 mg, 3 times / day
Route: intranasal
Route: multiple
Dose: 31.5 mg, 3 times / day
Sources:
unhealthy, 51.7
n = 199
Health Status: unhealthy
Condition: pain
Age Group: 51.7
Sex: M+F
Population Size: 199
Sources:
Leucopenia below serious, 1 patient
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
unhealthy
n = 8
Health Status: unhealthy
Condition: Percutaneous Nephrolithotomy operation
Population Size: 8
Sources:
Hypokalaemia below serious, 2 patients
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
unhealthy
n = 8
Health Status: unhealthy
Condition: Percutaneous Nephrolithotomy operation
Population Size: 8
Sources:
Hyponatraemia below serious, 3 patients
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
unhealthy
n = 8
Health Status: unhealthy
Condition: Percutaneous Nephrolithotomy operation
Population Size: 8
Sources:
Thrombocytopenia below serious, 3 patients
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
unhealthy
n = 8
Health Status: unhealthy
Condition: Percutaneous Nephrolithotomy operation
Population Size: 8
Sources:
Anaemia below serious, 7 patients
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
unhealthy
n = 8
Health Status: unhealthy
Condition: Percutaneous Nephrolithotomy operation
Population Size: 8
Sources:
Hyponatraemia below serious, 10 patients
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
unhealthy
n = 57
Health Status: unhealthy
Condition: Laparoscopic Donor Nephrectomy
Population Size: 57
Sources:
Hypercapnia below serious, 12 patients
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
unhealthy
n = 57
Health Status: unhealthy
Condition: Laparoscopic Donor Nephrectomy
Population Size: 57
Sources:
Thrombocytopenia below serious, 12 patients
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
unhealthy
n = 57
Health Status: unhealthy
Condition: Laparoscopic Donor Nephrectomy
Population Size: 57
Sources:
Hypokalaemia below serious, 20 patients
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
unhealthy
n = 57
Health Status: unhealthy
Condition: Laparoscopic Donor Nephrectomy
Population Size: 57
Sources:
Hyperkalaemia below serious, 3 patients
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
unhealthy
n = 57
Health Status: unhealthy
Condition: Laparoscopic Donor Nephrectomy
Population Size: 57
Sources:
Leukocytosis below serious, 38 patients
90 mg single, intravenous
Dose: 90 mg
Route: intravenous
Route: single
Dose: 90 mg
Sources:
unhealthy
n = 57
Health Status: unhealthy
Condition: Laparoscopic Donor Nephrectomy
Population Size: 57
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer




Drug as perpetrator​
PubMed

PubMed

TitleDatePubMed
Effects of nonsteroidal anti-inflammatory drugs on post-operative renal function in normal adults.
2001
The risk of upper gastrointestinal complications associated with nonsteroidal anti-inflammatory drugs, glucocorticoids, acetaminophen, and combinations of these agents.
2001
New advances in the treatment of sickle cell disease: focus on perioperative significance.
2001 Aug
Topical ketorolac tromethamine 0.5% ophthalmic solution in ocular inflammation after cataract surgery.
2001 Feb
Double-blind parallel comparison of multiple doses of ketorolac, ketoprofen and placebo administered orally to patients with postoperative dental pain.
2001 Feb 1
Effects of diclofenac or ketorolac on the inhibitory activity of cidofovir in the Ad5/NZW rabbit model.
2001 Jan
In vitro effects of NSAIDS and paracetamol on oxidative stress-related parameters of human erythrocytes.
2001 Jun
Headache in the emergency department.
2001 Jun
Children's use of PCA following spinal fusion.
2001 Mar-Apr
Effect of preemptive multimodal analgesia for arthroscopic knee ligament repair.
2001 Mar-Apr
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients.
2001 Nov
Analgesia and COX-2 inhibition.
2001 Nov-Dec
Effect of 10 pharmacologic probes on mRNA levels of inducible nitric oxide synthetase and selected inflammatory cytokines in a rat model of acute otitis media.
2002 Apr
Preemptive analgesic effect or short delay for inflammation?
2002 Feb
A systematic review of adjuncts for intravenous regional anesthesia for surgical procedures.
2002 Jan
Epidural hematoma after outpatient epidural anesthesia.
2002 Jan
Effect of ketorolac on renal function after donor nephrectomy.
2002 Jun
Intra-muscular ketorolac administered as a supplemental analgesic for removal of impacted third molar teeth: a prospective study.
2002 Mar
Morphological and pharmacological evidence for the role of peripheral prostaglandins in the pathogenesis of neuropathic pain.
2002 Mar
Effect of topical diclofenac and ketorolac on patient discomfort and corneal sensitivity.
2002 Mar-Apr
Pain reduction after laser in situ keratomileusis with ketorolac tromethamine ophthalmic solution 0.5%: a randomized, double-masked, placebo-controlled trial.
2002 Mar-Apr
Comparison of the morphine-sparing effects of diclofenac sodium and ketorolac tromethamine after major orthopedic surgery.
2002 May
Role for both spinal cord COX-1 and COX-2 in maintenance of mechanical hypersensitivity following peripheral nerve injury.
2002 May 24
Patents

Sample Use Guides

The recommended dose of ACULAR LS (ketorolac tromethamine ophthalmic solution) is one drop four times a day in the operated eye as needed for pain and burning/stinging for up to 4 days following corneal refractive surgery. Ketorolac tromethamine ophthalmic solution has been safely administered in conjunction with other ophthalmic medications such as antibiotics, beta blockers, carbonic anhydrase inhibitors, cycloplegics, and mydriatics.
Route of Administration: Other
It was discovered, that ketorolac inhibition of stretch-induced ureteral contractility was concentration-dependent between 1 nM and 1 microM. Local administration of ketorolac at these doses may be useful during the management of stones while at the same time limiting the risk for adverse effects. Porcine ureter strips attached to force displacement transducers were suspended in organ tissue baths that contained aerated Krebs buffer. Tissues equilibrated for 1 hour, and a spontaneous contractility rate was established. Tissues were incubated with a concentration-response curve of ketorolac (0.1 nM-10 microM) for 90 minutes and compared with indomethacin (1 muM) and dimethyl sulfoxide (DMSO) 0.1%. Contractility rates were recorded on a polygraph and analyzed for changes over exposure time
Name Type Language
KETOROLAC
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
KETOROLAC [VANDF]
Common Name English
(±)-5-BENZOYL-2,3-DIHYDRO-1H-PYRROLIZINE-1-CARBOXYLIC ACID
Systematic Name English
1H-PYRROLIZINE-1-CARBOXYLIC ACID, 5-BENZOYL-2,3-DIHYDRO, (±)-
Common Name English
ketorolac [INN]
Common Name English
Ketorolac [WHO-DD]
Common Name English
KETOROLAC [MI]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1323
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
NDF-RT N0000000160
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
WHO-ATC S01FB51
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
NDF-RT N0000175721
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
WHO-ATC S01BC05
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
WHO-ATC M01AB15
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
WHO-VATC QM01AB15
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
NDF-RT N0000175722
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
WHO-VATC QS01BC05
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
LIVERTOX NBK548459
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
NDF-RT N0000175939
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
Code System Code Type Description
CAS
74103-06-3
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
NCI_THESAURUS
C1219
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
RXCUI
35827
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY RxNorm
DRUG BANK
DB00465
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
IUPHAR
6661
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
EPA CompTox
DTXSID8023189
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
MESH
D020910
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
FDA UNII
YZI5105V0L
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
EVMPD
SUB08376MIG
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
PUBCHEM
3826
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
SMS_ID
100000083097
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
DRUG CENTRAL
1529
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
WIKIPEDIA
KETOROLAC
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
INN
5558
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
CHEBI
6129
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
ChEMBL
CHEMBL469
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
LACTMED
Ketorolac
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
DAILYMED
YZI5105V0L
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY
MERCK INDEX
m6623
Created by admin on Fri Dec 15 15:22:24 GMT 2023 , Edited by admin on Fri Dec 15 15:22:24 GMT 2023
PRIMARY Merck Index