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
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)
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11695255 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | ACULAR LS Approved UseACULAR LS ophthalmic solution is indicated for the reduction of ocular pain and burning/stinging following corneal refractive surgery. Launch Date2003 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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
Dose | Population | Adverse 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%) Sources: Constipation (29%) Vomiting (28%) Nasal passage irritation (24%) Headache (24%) Flatulence (23%) Anemia (19%) Tachycardia (14%) Pruritis (11%) Dizziness (6%) |
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) Sources: Thrombocytopenia (below serious, 3 patients) Hyponatraemia (below serious, 3 patients) Hypokalaemia (below serious, 2 patients) Leucopenia (below serious, 1 patient) |
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) Sources: 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) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
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: |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
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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 |
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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 |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18324898
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
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C1323
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NDF-RT |
N0000000160
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WHO-ATC |
S01FB51
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NDF-RT |
N0000175721
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WHO-ATC |
S01BC05
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WHO-ATC |
M01AB15
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WHO-VATC |
QM01AB15
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NDF-RT |
N0000175722
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WHO-VATC |
QS01BC05
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LIVERTOX |
NBK548459
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NDF-RT |
N0000175939
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74103-06-3
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C1219
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35827
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DB00465
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1529
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KETOROLAC
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CHEMBL469
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Ketorolac
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YZI5105V0L
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m6623
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PRIMARY | Merck Index |
ACTIVE MOIETY
METABOLITE INACTIVE (PARENT)
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)