Details
Stereochemistry | RACEMIC |
Molecular Formula | C13H17O2.K |
Molecular Weight | 244.3712 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[K+].CC(C)CC1=CC=C(C=C1)C(C)C([O-])=O
InChI
InChIKey=XJELUCTZEAQYGF-UHFFFAOYSA-M
InChI=1S/C13H18O2.K/c1-9(2)8-11-4-6-12(7-5-11)10(3)13(14)15;/h4-7,9-10H,8H2,1-3H3,(H,14,15);/q;+1/p-1
DescriptionSources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2f516c51-a1b5-4585-8de3-6271ad161608Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20718179
Sources: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=2f516c51-a1b5-4585-8de3-6271ad161608
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/20718179
Ibuprofen is a nonsteroidal anti-inflammatory agent (NSAIA) or nonsteroidal anti-inflammatory drug (NSAID), with analgesic and antipyretic properties. Ibuprofen has pharmacologic actions similar to those of other prototypical NSAIAs, which are thought to act through inhibition of prostaglandin synthesis. It’s used temporarily relieves minor aches and pains due to: headache; the common cold; muscular aches; backache; toothache; minor pain of arthritis; menstrual cramps and temporarily reduces fever. The exact mechanism of action of ibuprofen is unknown. Ibuprofen is a non-selective inhibitor of cyclooxygenase, an enzyme invovled in prostaglandin synthesis via the arachidonic acid pathway. Its pharmacological effects are believed to be due to inhibition cylooxygenase-2 (COX-2) which decreases the synthesis of prostaglandins involved in mediating inflammation, pain, fever and swelling. Antipyretic effects may be due to action on the hypothalamus, resulting in an increased peripheral blood flow, vasodilation, and subsequent heat dissipation. Inhibition of COX-1 is thought to cause some of the side effects of ibuprofen including GI ulceration. Ibuprofen is administered as a racemic mixture. The R-enantiomer undergoes extensive interconversion to the S-enantiomer in vivo. The S-enantiomer is believed to be the more pharmacologically active enantiomer.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094253 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15481334 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Palliative | IBU-TAB Approved Usetemporarily relieves minor aches and pains due to: headache; the common cold; muscular aches; backache; toothache; minor pain of arthritis; menstrual cramps; temporarily reduces fever Launch Date1988 |
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Palliative | IBU-TAB Approved Usetemporarily relieves minor aches and pains due to: headache; the common cold; muscular aches; backache; toothache; minor pain of arthritis; menstrual cramps; temporarily reduces fever Launch Date1988 |
|||
Palliative | IBU-TAB Approved Usetemporarily relieves minor aches and pains due to: headache; the common cold; muscular aches; backache; toothache; minor pain of arthritis; menstrual cramps; temporarily reduces fever Launch Date1988 |
|||
Palliative | IBU-TAB Approved Usetemporarily relieves minor aches and pains due to: headache; the common cold; muscular aches; backache; toothache; minor pain of arthritis; menstrual cramps; temporarily reduces fever Launch Date1988 |
|||
Palliative | IBU-TAB Approved Usetemporarily relieves minor aches and pains due to: headache; the common cold; muscular aches; backache; toothache; minor pain of arthritis; menstrual cramps; temporarily reduces fever Launch Date1988 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
27.9 μg/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
IBUPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
103 μg × h/mL |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
IBUPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
2.2 h |
400 mg single, oral dose: 400 mg route of administration: Oral experiment type: SINGLE co-administered: |
IBUPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1% |
IBUPROFEN plasma | Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
199800 mg single, oral Overdose Dose: 199800 mg Route: oral Route: single Dose: 199800 mg Sources: |
unknown, 17 years |
Other AEs: Cardiovascular collapse, Acidosis... Other AEs: Cardiovascular collapse (grade 5, 1 patient) Sources: Acidosis (grade 5, 1 patient) Hypothermia (grade 5, 1 patient) |
90 g single, oral Overdose |
unknown, 19 years |
Other AEs: Polyuria, Acidosis... |
800 mg 4 times / day multiple, intravenous Recommended Dose: 800 mg, 4 times / day Route: intravenous Route: multiple Dose: 800 mg, 4 times / day Sources: |
unhealthy, 33 years n = 40 Health Status: unhealthy Age Group: 33 years Sex: M+F Population Size: 40 Sources: |
Other AEs: Acute respiratory distress syndrome, Tachypnea... Other AEs: Acute respiratory distress syndrome (serious, 1 patient) Sources: Tachypnea (serious, 1 patient) Septic shock (serious, 1 patient) Breathlessness (serious, 1 patient) Septicemia (serious, 1 patient) |
400 mg 4 times / day multiple, intravenous Recommended Dose: 400 mg, 4 times / day Route: intravenous Route: multiple Dose: 400 mg, 4 times / day Sources: Page: p.87 |
unhealthy, 42 years (range: 17-73 years) n = 195 Health Status: unhealthy Age Group: 42 years (range: 17-73 years) Sex: M+F Population Size: 195 Sources: Page: p.87 |
Disc. AE: Dizziness, Headache... AEs leading to discontinuation/dose reduction: Dizziness (2%) Sources: Page: p.87Headache (1 patient) |
800 mg 4 times / day multiple, intravenous Recommended Dose: 800 mg, 4 times / day Route: intravenous Route: multiple Dose: 800 mg, 4 times / day Sources: Page: p.87 |
unhealthy, 44 years (range: 20-69 years) n = 304 Health Status: unhealthy Age Group: 44 years (range: 20-69 years) Sex: M+F Population Size: 304 Sources: Page: p.87 |
Disc. AE: Headache... AEs leading to discontinuation/dose reduction: Headache (2 patients) Sources: Page: p.87 |
240000 mg single, oral Overdose Dose: 240000 mg Route: oral Route: single Dose: 240000 mg Co-administed with:: divalproex sodium Sources: |
unknown, 49 years |
Other AEs: Cardiovascular collapse... Other AEs: Cardiovascular collapse (grade 5, 1 patient) Sources: |
240000 mg single, oral Overdose Dose: 240000 mg Route: oral Route: single Dose: 240000 mg Sources: |
unknown, 49 years |
Other AEs: Acidosis, Hypothermia... Other AEs: Acidosis (grade 5, 1 patient) Sources: Hypothermia (grade 5, 1 patient) |
400 mg 4 times / day multiple, intravenous Recommended Dose: 400 mg, 4 times / day Route: intravenous Route: multiple Dose: 400 mg, 4 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: Pain Age Group: adult Sources: |
Other AEs: Myocardial infarction, Stroke... Other AEs: Myocardial infarction (serious|grade 5) Sources: Stroke (serious|grade 5) |
400 mg 6 times / day multiple, oral Recommended Dose: 400 mg, 6 times / day Route: oral Route: multiple Dose: 400 mg, 6 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: pain Age Group: adult Sources: |
Other AEs: Myocardial infarction, Stroke... Other AEs: Myocardial infarction (serious|grade 5) Sources: Stroke (serious|grade 5) |
200 mg single, oral Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: |
unhealthy n = 62 Health Status: unhealthy Condition: Episodic Tension Type Headache Population Size: 62 Sources: |
Other AEs: Depression, Insomnia... Other AEs: Depression (below serious, 1 patient) Sources: Insomnia (below serious, 1 patient) Oropharyngeal pain (below serious, 1 patient) Sinus congestion (below serious, 1 patient) |
97.5 mg 4 times / day multiple, oral Dose: 97.5 mg, 4 times / day Route: oral Route: multiple Dose: 97.5 mg, 4 times / day Sources: |
unhealthy n = 112 Health Status: unhealthy Condition: Dental Pain Population Size: 112 Sources: |
Other AEs: Facial swelling... Other AEs: Facial swelling (below serious, 8 patients) Sources: |
10 mg/kg single, oral Dose: 10 mg/kg Route: oral Route: single Dose: 10 mg/kg Sources: |
unhealthy n = 29 Health Status: unhealthy Condition: Post-ERCP Pancreatitis Population Size: 29 Sources: |
Other AEs: Bleeding, Perforation... Other AEs: Bleeding (below serious, 2 patients) Sources: Perforation (below serious, 1 patient) |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Acidosis | grade 5, 1 patient | 199800 mg single, oral Overdose Dose: 199800 mg Route: oral Route: single Dose: 199800 mg Sources: |
unknown, 17 years |
Cardiovascular collapse | grade 5, 1 patient | 199800 mg single, oral Overdose Dose: 199800 mg Route: oral Route: single Dose: 199800 mg Sources: |
unknown, 17 years |
Hypothermia | grade 5, 1 patient | 199800 mg single, oral Overdose Dose: 199800 mg Route: oral Route: single Dose: 199800 mg Sources: |
unknown, 17 years |
Acidosis | 1 patient | 90 g single, oral Overdose |
unknown, 19 years |
Polyuria | 1 patient | 90 g single, oral Overdose |
unknown, 19 years |
Acute respiratory distress syndrome | serious, 1 patient | 800 mg 4 times / day multiple, intravenous Recommended Dose: 800 mg, 4 times / day Route: intravenous Route: multiple Dose: 800 mg, 4 times / day Sources: |
unhealthy, 33 years n = 40 Health Status: unhealthy Age Group: 33 years Sex: M+F Population Size: 40 Sources: |
Breathlessness | serious, 1 patient | 800 mg 4 times / day multiple, intravenous Recommended Dose: 800 mg, 4 times / day Route: intravenous Route: multiple Dose: 800 mg, 4 times / day Sources: |
unhealthy, 33 years n = 40 Health Status: unhealthy Age Group: 33 years Sex: M+F Population Size: 40 Sources: |
Septic shock | serious, 1 patient | 800 mg 4 times / day multiple, intravenous Recommended Dose: 800 mg, 4 times / day Route: intravenous Route: multiple Dose: 800 mg, 4 times / day Sources: |
unhealthy, 33 years n = 40 Health Status: unhealthy Age Group: 33 years Sex: M+F Population Size: 40 Sources: |
Septicemia | serious, 1 patient | 800 mg 4 times / day multiple, intravenous Recommended Dose: 800 mg, 4 times / day Route: intravenous Route: multiple Dose: 800 mg, 4 times / day Sources: |
unhealthy, 33 years n = 40 Health Status: unhealthy Age Group: 33 years Sex: M+F Population Size: 40 Sources: |
Tachypnea | serious, 1 patient | 800 mg 4 times / day multiple, intravenous Recommended Dose: 800 mg, 4 times / day Route: intravenous Route: multiple Dose: 800 mg, 4 times / day Sources: |
unhealthy, 33 years n = 40 Health Status: unhealthy Age Group: 33 years Sex: M+F Population Size: 40 Sources: |
Headache | 1 patient Disc. AE |
400 mg 4 times / day multiple, intravenous Recommended Dose: 400 mg, 4 times / day Route: intravenous Route: multiple Dose: 400 mg, 4 times / day Sources: Page: p.87 |
unhealthy, 42 years (range: 17-73 years) n = 195 Health Status: unhealthy Age Group: 42 years (range: 17-73 years) Sex: M+F Population Size: 195 Sources: Page: p.87 |
Dizziness | 2% Disc. AE |
400 mg 4 times / day multiple, intravenous Recommended Dose: 400 mg, 4 times / day Route: intravenous Route: multiple Dose: 400 mg, 4 times / day Sources: Page: p.87 |
unhealthy, 42 years (range: 17-73 years) n = 195 Health Status: unhealthy Age Group: 42 years (range: 17-73 years) Sex: M+F Population Size: 195 Sources: Page: p.87 |
Headache | 2 patients Disc. AE |
800 mg 4 times / day multiple, intravenous Recommended Dose: 800 mg, 4 times / day Route: intravenous Route: multiple Dose: 800 mg, 4 times / day Sources: Page: p.87 |
unhealthy, 44 years (range: 20-69 years) n = 304 Health Status: unhealthy Age Group: 44 years (range: 20-69 years) Sex: M+F Population Size: 304 Sources: Page: p.87 |
Cardiovascular collapse | grade 5, 1 patient | 240000 mg single, oral Overdose Dose: 240000 mg Route: oral Route: single Dose: 240000 mg Co-administed with:: divalproex sodium Sources: |
unknown, 49 years |
Acidosis | grade 5, 1 patient | 240000 mg single, oral Overdose Dose: 240000 mg Route: oral Route: single Dose: 240000 mg Sources: |
unknown, 49 years |
Hypothermia | grade 5, 1 patient | 240000 mg single, oral Overdose Dose: 240000 mg Route: oral Route: single Dose: 240000 mg Sources: |
unknown, 49 years |
Myocardial infarction | serious|grade 5 | 400 mg 4 times / day multiple, intravenous Recommended Dose: 400 mg, 4 times / day Route: intravenous Route: multiple Dose: 400 mg, 4 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: Pain Age Group: adult Sources: |
Stroke | serious|grade 5 | 400 mg 4 times / day multiple, intravenous Recommended Dose: 400 mg, 4 times / day Route: intravenous Route: multiple Dose: 400 mg, 4 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: Pain Age Group: adult Sources: |
Myocardial infarction | serious|grade 5 | 400 mg 6 times / day multiple, oral Recommended Dose: 400 mg, 6 times / day Route: oral Route: multiple Dose: 400 mg, 6 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: pain Age Group: adult Sources: |
Stroke | serious|grade 5 | 400 mg 6 times / day multiple, oral Recommended Dose: 400 mg, 6 times / day Route: oral Route: multiple Dose: 400 mg, 6 times / day Sources: |
unhealthy, adult Health Status: unhealthy Condition: pain Age Group: adult Sources: |
Depression | below serious, 1 patient | 200 mg single, oral Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: |
unhealthy n = 62 Health Status: unhealthy Condition: Episodic Tension Type Headache Population Size: 62 Sources: |
Insomnia | below serious, 1 patient | 200 mg single, oral Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: |
unhealthy n = 62 Health Status: unhealthy Condition: Episodic Tension Type Headache Population Size: 62 Sources: |
Oropharyngeal pain | below serious, 1 patient | 200 mg single, oral Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: |
unhealthy n = 62 Health Status: unhealthy Condition: Episodic Tension Type Headache Population Size: 62 Sources: |
Sinus congestion | below serious, 1 patient | 200 mg single, oral Dose: 200 mg Route: oral Route: single Dose: 200 mg Sources: |
unhealthy n = 62 Health Status: unhealthy Condition: Episodic Tension Type Headache Population Size: 62 Sources: |
Facial swelling | below serious, 8 patients | 97.5 mg 4 times / day multiple, oral Dose: 97.5 mg, 4 times / day Route: oral Route: multiple Dose: 97.5 mg, 4 times / day Sources: |
unhealthy n = 112 Health Status: unhealthy Condition: Dental Pain Population Size: 112 Sources: |
Perforation | below serious, 1 patient | 10 mg/kg single, oral Dose: 10 mg/kg Route: oral Route: single Dose: 10 mg/kg Sources: |
unhealthy n = 29 Health Status: unhealthy Condition: Post-ERCP Pancreatitis Population Size: 29 Sources: |
Bleeding | below serious, 2 patients | 10 mg/kg single, oral Dose: 10 mg/kg Route: oral Route: single Dose: 10 mg/kg Sources: |
unhealthy n = 29 Health Status: unhealthy Condition: Post-ERCP Pancreatitis Population Size: 29 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
OverviewOther
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 26.0 |
no | |||
Page: abstract |
yes [IC50 4.4 uM] | |||
Page: 8.0 |
yes | |||
Page: abstract |
yes | |||
Page: 2.0 |
yes | |||
Page: 2.0 |
yes | |||
Page: 2.0 |
yes | |||
Page: 2.0 |
yes | |||
Page: 867.0 |
yes |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 37.0 |
minor | |||
Page: 2.0 |
minor | |||
Page: 2.0 |
minor | |||
Page: 37.0 |
no | |||
Page: 37.0 |
no | |||
Page: 37.0 |
no | |||
Page: 37.0 |
no | |||
Page: 2.0 |
no | |||
Page: 2.0 |
no | |||
Page: 701.0 |
yes | |||
Page: 2.0 |
yes | |||
Page: 2.0 |
yes | |||
Page: 2.0 |
yes | |||
Page: 2.0 |
yes | |||
Page: 2.0 |
yes | |||
Page: 2.0 |
yes | |||
Page: 2.0 |
yes | |||
Page: 2.0 |
yes |
Tox targets
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Page: 5.0 |
PubMed
Title | Date | PubMed |
---|---|---|
[Renal tubular acidosis with severe hypokalemic tetraparesis after ibuprofen intake]. | 1999 Apr 23 |
|
Constitutive activation of IkappaB kinase alpha and NF-kappaB in prostate cancer cells is inhibited by ibuprofen. | 1999 Dec 2 |
|
Topical non-steroidal drugs are systemically absorbed and may cause renal disease. | 1999 Jan |
|
Plasma levels after peroral and topical ibuprofen and effects upon low pH-induced cutaneous and muscle pain. | 2000 |
|
Interstitial nephritis in children with Crohn's disease. | 2000 Apr |
|
Ibuprofen protects dopaminergic neurons against glutamate toxicity in vitro. | 2000 Aug 11 |
|
Randomized double-blind controlled trial comparing the effects of ibuprofen with indomethacin on cerebral hemodynamics in preterm infants with patent ductus arteriosus. | 2000 Jan |
|
A comparison of ibuprofen and indomethacin for closure of patent ductus arteriosus. | 2000 Sep 7 |
|
Directed control of electroosmotic flow in nonaqueous electrolytes using poly(ethylene glycol) coated capillaries. | 2001 |
|
Non-steroidal anti-inflammatory drugs protect against chondrocyte apoptotic death. | 2001 |
|
Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations. | 2001 |
|
[Misuse of drugs in recreational sports]. | 2001 Apr |
|
Nitric oxide-releasing nonsteroidal anti-inflammatory drugs (NSAIDs) alter the kinetics of human colon cancer cell lines more effectively than traditional NSAIDs: implications for colon cancer chemoprevention. | 2001 Apr 15 |
|
IL-10 mediation of activation-induced TH1 cell apoptosis and lymphoid dysfunction in polymicrobial sepsis. | 2001 Apr 7 |
|
Ibuprofen affects pro- and anti-inflammatory cytokine production by mononuclear cells of preterm newborns. | 2001 Feb |
|
[Topical administration is better than oral administration]. | 2001 Feb 1 |
|
Functional evidence for an inward rectifier potassium current in rat renal afferent arterioles. | 2001 Feb 2 |
|
Determination of drug residues in water by the combination of liquid chromatography or capillary electrophoresis with electrospray mass spectrometry. | 2001 Feb 23 |
|
Ibuprofen versus indomethacin for closure of patent ductus arteriosus. | 2001 Feb 8 |
|
Effect of a single dose of ibuprofen lysinate before embryo transfer on pregnancy rates in cows. | 2001 Jan |
|
NSAID-induced nephrotoxicity from the fetus to the child. | 2001 Jan |
|
Using evidence from different sources: an example using paracetamol 1000 mg plus codeine 60 mg. | 2001 Jan 10 |
|
Investigation of foreign substances in food. | 2001 Jan-Feb |
|
Synthesis of N-pyridinyl(methyl)-1,2-dihydro-4-hydroxy-2-oxoquinoline-3-carboxamides and analogues and their anti-inflammatory activity in mice and rats. | 2001 Mar |
|
Synthesis and hydrolytic behaviour of glycerol-1,2-diibuprofenate-3-nitrate, a putative pro-drug of ibuprofen and glycerol-1-nitrate. | 2001 Mar |
|
Continuous low-level topical heat in the treatment of dysmenorrhea. | 2001 Mar |
|
NSAIDs bound to methacrylic carriers: microstructural characterization and in vitro release analysis. | 2001 Mar 12 |
|
Simultaneous quantification of neutral and acidic pharmaceuticals and pesticides at the low-ng/l level in surface and waste water. | 2001 Mar 16 |
|
Linear drug eruption. | 2001 Mar-Apr |
|
Identification and characterization of human organic anion transporter 3 expressing predominantly in the kidney. | 2001 May |
|
Indomethacin and telomerase activity in tumor growth retardation. | 2001 May |
|
Microencapsulation of ibuprofen and Eudragit RS 100 by the emulsion solvent diffusion technique. | 2001 May 7 |
Patents
Sample Use Guides
adults: take 1 tablet every 4 to 6 hours while symptoms persist. If pain or fever does not respond to 1 tablet, 2 tablets may be used; do not exceed 6 tablets in 24 hours. Children under 12 years: ask a doctor.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24481441
Ibuprofen, in a 400-μM concentration, decreased the expression of Hsp70 by 23% in comparison with untreated cells, whereas other NSAID had no effect. Ibuprofen also decreased the expression of Hsp70 in H358, a human lung adenocarcinoma cell line, in a dose-dependent manner (from 0-400 uM).
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DTXSID201000360
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279-122-3
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DBSALT002284
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48304089JJ
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79261-49-7
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Ibuprofen potassium
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23662458
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ACTIVE MOIETY
SUBSTANCE RECORD