Details
Stereochemistry | RACEMIC |
Molecular Formula | C15H13NO3.C4H11NO3 |
Molecular Weight | 376.4037 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
NC(CO)(CO)CO.OC(=O)C1CCN2C1=CC=C2C(=O)C3=CC=CC=C3
InChI
InChIKey=BWHLPLXXIDYSNW-UHFFFAOYSA-N
InChI=1S/C15H13NO3.C4H11NO3/c17-14(10-4-2-1-3-5-10)13-7-6-12-11(15(18)19)8-9-16(12)13;5-4(1-6,2-7)3-8/h1-7,11H,8-9H2,(H,18,19);6-8H,1-3,5H2
Molecular Formula | C15H13NO3 |
Molecular Weight | 255.2686 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
Molecular Formula | C4H11NO3 |
Molecular Weight | 121.135 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
---|---|---|---|---|
Primary | ACULAR LS Approved UseACULAR LS ophthalmic solution is indicated for the reduction of ocular pain and burning/stinging following corneal refractive surgery. Launch Date1.05425279E12 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
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 |
---|---|---|
Risks and benefits of nonsteroidal anti-inflammatory drugs in children: a comparison with paracetamol. | 2001 |
|
Single-dose dipyrone for acute postoperative pain. | 2001 |
|
Analgesic efficacy of ketorolac and morphine in neonatal rats. | 2001 Apr |
|
Preemptive analgesic effects of ketorolac in ankle fracture surgery. | 2001 Apr |
|
[Control of postoperative pain in heart surgery. Comparison of analgesics]. | 2001 Apr |
|
[Factors affecting postoperative pain]. | 2001 Apr |
|
Bilateral symmetric inflammatory reaction to hylan G-F 20 injection. | 2001 Apr |
|
Corneal complications associated with topical ophthalmic use of nonsteroidal antiinflammatory drugs. | 2001 Apr |
|
Intravenous ketorolac in the emergency department management of sickle cell pain and predictors of its effectiveness. | 2001 Apr |
|
Randomised controlled trial of ketorolac in the management of corneal abrasions. | 2001 Apr |
|
Ketorolac is not nephrotoxic in connection with sevoflurane anesthesia in patients undergoing breast surgery. | 2001 Apr |
|
The effect of intravenous ketorolac on opioid requirement and pain after cesarean delivery. | 2001 Apr |
|
New advances in the treatment of sickle cell disease: focus on perioperative significance. | 2001 Aug |
|
Treatment of vinorelbine-associated tumor pain. | 2001 Aug |
|
Participation of the nitric oxide-cyclic GMP-ATP-sensitive K(+) channel pathway in the antinociceptive action of ketorolac. | 2001 Aug 24 |
|
Chiral pharmacokinetics of ketorolac in sheep after intravenous and intramuscular administration of the racemate. | 2001 Dec |
|
Topical ketorolac after cataract surgery. | 2001 Dec |
|
[Bupivacaine in continuous epidural infusion using a portable mechanical devise for postoperative analgesia after surgery for hernia of the lumbar disk]. | 2001 Feb |
|
[Infiltration of the surgical wound with local anesthetic for postoperative analgesia in patients operated on for lumbar disc herniation. Comparative study of ropivacaine and bupivacaine]. | 2001 Jan |
|
Effects of a non-steroidal (ketorolac tromethamine) and a steroidal (dexamethasone) anti-inflammatory drug on refractive state and ocular growth. | 2001 Jun |
|
Propacetamol versus ketorolac for treatment of acute postoperative pain after total hip or knee replacement. | 2001 Jun |
|
Prospective double-blind study of effect of ketorolac administration after laparoscopic urologic surgery. | 2001 Mar |
|
Methadone in treatment of tenesmus not responding to morphine escalation. | 2001 Mar |
|
Plasma levels of interleukin-6 and interleukin-10 are affected by ketorolac as an adjunct to patient-controlled morphine after abdominal hysterectomy. | 2001 Mar |
|
Postoperative narcotic requirement after microscopic lumbar discectomy is not affected by intraoperative ketorolac or bupivacaine. | 2001 Mar 15 |
|
Effect of preemptive multimodal analgesia for arthroscopic knee ligament repair. | 2001 Mar-Apr |
|
Precipitation in Manchester: ketorolac/cyclizine. | 2001 May |
|
Retrospective analysis of drug-induced urticaria and angioedema: a survey of 2287 patients. | 2001 Nov |
|
Opioid analgesics versus ketorolac in spine and joint procedures: impact on healthcare resources. | 2001 Nov |
|
Pain control after knee arthroplasty: intraarticular versus epidural anesthesia. | 2001 Nov |
|
The effect of ketorolac and sevoflurane anesthesia on renal glomerular and tubular function. | 2001 Nov |
|
Safety of ketorolac in the pediatric population after ureteroneocystostomy. | 2001 Nov |
|
Analgesia and COX-2 inhibition. | 2001 Nov-Dec |
|
Nonsteroidal anti-inflammatory drugs for perioperative pain control. | 2001 Oct |
|
Ketorolac vs tramadol in the treatment of postoperative pain during maxillofacial surgery. | 2001 Sep |
|
Upper gastrointestinal safety evaluation of parecoxib sodium, a new parenteral cyclooxygenase-2-specific inhibitor, compared with ketorolac, naproxen, and placebo. | 2001 Sep |
|
Preemptive analgesic effect or short delay for inflammation? | 2002 Feb |
|
Age-stratified pharmacokinetics of ketorolac tromethamine in pediatric surgical patients. | 2002 Feb |
|
Upper GI mucosal effects of parecoxib sodium in healthy elderly subjects. | 2002 Jan |
|
A systematic review of adjuncts for intravenous regional anesthesia for surgical procedures. | 2002 Jan |
|
Epidural hematoma after outpatient epidural anesthesia. | 2002 Jan |
|
The influence of timing and route of administration of intravenous ketorolac on analgesia after hand surgery. | 2002 Jun |
|
Early hospital discharge for intravesical ureteroneocystostomy. | 2002 Jun |
|
Effects of intravenous ketorolac and fentanyl combined with midazolam on analgesia and side effects during extracorporeal shock wave lithotripsy. | 2002 Mar |
|
Topical ketorolac tromethamine 0.5% versus diclofenac sodium 0.1% to inhibit miosis during cataract surgery. | 2002 Mar |
|
Morphological and pharmacological evidence for the role of peripheral prostaglandins in the pathogenesis of neuropathic pain. | 2002 Mar |
|
Ketorolac for pain management after abdominal surgical procedures in infants. | 2002 Mar |
|
Comparison of the morphine-sparing effects of diclofenac sodium and ketorolac tromethamine after major orthopedic surgery. | 2002 May |
|
Protective role of cyclooxygenase (COX) inhibitors in burn-induced intestinal and liver damage. | 2002 May |
|
Low-dose ketorolac improves analgesia and reduces morphine requirements following posterior spinal fusion in adolescents. | 2002 May |
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Wed Jul 05 23:06:07 UTC 2023
by
admin
on
Wed Jul 05 23:06:07 UTC 2023
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Record UNII |
4EVE5946BQ
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C1323
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CHEMBL469
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Related Record | Type | Details | ||
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PARENT -> SALT/SOLVATE | |||
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ENANTIOMER -> RACEMATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
---|---|---|---|---|
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT | |||
|
IMPURITY -> PARENT |
unspecified
UNKNOWN
EP
|
||
|
IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
unspecified
UNKNOWN
EP
|
||
|
IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 0.67
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 0.52
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
|
||
|
IMPURITY -> PARENT |
For the calculation of contents, multiply the peak areas by 2.2
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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||
|
IMPURITY -> PARENT |
unspecified
UNKNOWN
EP
|
||
|
IMPURITY -> PARENT |
unspecified
UNKNOWN
EP
|
||
|
IMPURITY -> PARENT |
unspecified
UNKNOWN
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |