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)
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 | ( + / - ) |
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 Date2003 |
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 |
|
30 mg single, intramuscular Highest studied dose Dose: 30 mg Route: intramuscular Route: single Dose: 30 mg Sources: |
healthy, 19-45 |
|
30 mg single, intranasal Highest studied dose Dose: 30 mg Route: intranasal Route: single Dose: 30 mg Sources: |
healthy, 19-45 |
|
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
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 |
Leucopenia | below serious, 1 patient | 90 mg single, intravenous Dose: 90 mg Route: intravenous Route: single Dose: 90 mg Sources: |
unhealthy |
Hypokalaemia | below serious, 2 patients | 90 mg single, intravenous Dose: 90 mg Route: intravenous Route: single Dose: 90 mg Sources: |
unhealthy |
Hyponatraemia | below serious, 3 patients | 90 mg single, intravenous Dose: 90 mg Route: intravenous Route: single Dose: 90 mg Sources: |
unhealthy |
Thrombocytopenia | below serious, 3 patients | 90 mg single, intravenous Dose: 90 mg Route: intravenous Route: single Dose: 90 mg Sources: |
unhealthy |
Anaemia | below serious, 7 patients | 90 mg single, intravenous Dose: 90 mg Route: intravenous Route: single Dose: 90 mg Sources: |
unhealthy |
Hyponatraemia | below serious, 10 patients | 90 mg single, intravenous Dose: 90 mg Route: intravenous Route: single Dose: 90 mg Sources: |
unhealthy |
Hypercapnia | below serious, 12 patients | 90 mg single, intravenous Dose: 90 mg Route: intravenous Route: single Dose: 90 mg Sources: |
unhealthy |
Thrombocytopenia | below serious, 12 patients | 90 mg single, intravenous Dose: 90 mg Route: intravenous Route: single Dose: 90 mg Sources: |
unhealthy |
Hypokalaemia | below serious, 20 patients | 90 mg single, intravenous Dose: 90 mg Route: intravenous Route: single Dose: 90 mg Sources: |
unhealthy |
Hyperkalaemia | below serious, 3 patients | 90 mg single, intravenous Dose: 90 mg Route: intravenous Route: single Dose: 90 mg Sources: |
unhealthy |
Leukocytosis | below serious, 38 patients | 90 mg single, intravenous Dose: 90 mg Route: intravenous Route: single Dose: 90 mg Sources: |
unhealthy |
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 |
|
Therapeutic uses of non-steroidal anti-inflammatory drugs in dentistry. | 2001 |
|
New advances in the treatment of sickle cell disease: focus on perioperative significance. | 2001 Aug |
|
Chiral pharmacokinetics of ketorolac in sheep after intravenous and intramuscular administration of the racemate. | 2001 Dec |
|
[Aortic stent: the anesthesiologist's point of view]. | 2001 Dec |
|
Delayed diffuse lamellar keratitis after laser in situ keratomileusis. | 2001 Dec |
|
Topical ketorolac after cataract surgery. | 2001 Dec |
|
Children's use of PCA following spinal fusion. | 2001 Mar-Apr |
|
Efficacy of a single-dose ondansetron for preventing post-operative nausea and vomiting after laparoscopic cholecystectomy with sevoflurane and remifentanil infusion anaesthesia. | 2001 Mar-Apr |
|
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 |
|
Analgesia and COX-2 inhibition. | 2001 Nov-Dec |
|
Nonsteroidal anti-inflammatory drugs for perioperative pain control. | 2001 Oct |
|
Goal oriented general anesthesia for Cesarean section in a parturient with a large intracranial epidermoid cyst. | 2001 Oct |
|
Ketorolac vs tramadol in the treatment of postoperative pain during maxillofacial surgery. | 2001 Sep |
|
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 |
|
Ketorolac, diclofenac, and ketoprofen are equally safe for pain relief after major surgery. | 2002 Feb |
|
Drug-induced extrapyramidal reactions. | 2002 Feb |
|
Postoperative pain management: morphine versus ketorolac. | 2002 Feb |
|
Is the administration of ketorolac associated with preemptive analgesia? | 2002 Feb |
|
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 |
|
Opioid-free analgesia following total knee arthroplasty--a multimodal approach using continuous lumbar plexus (psoas compartment) block, acetaminophen, and ketorolac. | 2002 Jan-Feb |
|
Multimodal analgesia and intravenous nutrition preserves total body protein following major upper gastrointestinal surgery. | 2002 Jan-Feb |
|
Effect of ketorolac on renal function after donor nephrectomy. | 2002 Jun |
|
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 |
|
Subjective and objective comparison of critical care pathways for open donor nephrectomy. | 2002 Jun |
|
Novel 4,5-diaryl-3-hydroxy-2(5H)-furanones as anti-oxidants and anti-inflammatory agents. | 2002 Jun |
|
Intra-muscular ketorolac administered as a supplemental analgesic for removal of impacted third molar teeth: a prospective study. | 2002 Mar |
|
Parenteral ketorolac and risk of myocardial infarction. | 2002 Mar |
|
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 |
|
Treatment patterns of isolated benign headache in US emergency departments. | 2002 Mar |
|
Ketorolac-based analgesia improves outcomes for living kidney donors. | 2002 Mar 15 |
|
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 |
|
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 |
|
The role of spinal neuropeptides and prostaglandins in opioid physical dependence. | 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
Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 17:55:30 GMT 2025
by
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Record UNII |
YZI5105V0L
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Record Status |
Validated (UNII)
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Record Version |
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Preferred Name | English | ||
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Common Name | English | ||
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Common Name | English |
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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6661
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DTXSID8023189
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D020910
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YZI5105V0L
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SUB08376MIG
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3826
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100000083097
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1529
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KETOROLAC
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5558
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6129
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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 |
Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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ENANTIOMER -> RACEMATE |
Related Record | Type | Details | ||
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METABOLITE INACTIVE -> PARENT |
Related Record | Type | Details | ||
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ACTIVE MOIETY |