Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H14O3 |
Molecular Weight | 254.2806 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(C(O)=O)C1=CC=CC(=C1)C(=O)C2=CC=CC=C2
InChI
InChIKey=DKYWVDODHFEZIM-UHFFFAOYSA-N
InChI=1S/C16H14O3/c1-11(16(18)19)13-8-5-9-14(10-13)15(17)12-6-3-2-4-7-12/h2-11H,1H3,(H,18,19)
Molecular Formula | C16H14O3 |
Molecular Weight | 254.2806 |
Charge | 0 |
Count |
|
Stereochemistry | RACEMIC |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Optical Activity | ( + / - ) |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/21052564https://www.drugs.com/international/dexketoprofen.htmlCurator's Comment: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT02159547 | https://www.ncbi.nlm.nih.gov/pubmed/28540716 | https://clinicaltrials.gov/ct2/show/NCT03122314 | https://www.ncbi.nlm.nih.gov/pubmed/28326850 | https://clinicaltrials.gov/ct2/show/NCT02092012
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21052564https://www.drugs.com/international/dexketoprofen.html
Curator's Comment: The description was created based on several sources, including
https://clinicaltrials.gov/ct2/show/NCT02159547 | https://www.ncbi.nlm.nih.gov/pubmed/28540716 | https://clinicaltrials.gov/ct2/show/NCT03122314 | https://www.ncbi.nlm.nih.gov/pubmed/28326850 | https://clinicaltrials.gov/ct2/show/NCT02092012
Dexketoprofen is a nonsteroidal anti-inflammatory drug (NSAID), manufactured by Menarini under the tradename Keral. Dexketoprofen is indicated for short-term treatment of mild to moderate pain, including dysmenorrhoea. Dexketoprofen works by blocking the action of a substance in the body called cyclo-oxygenase, which is involved in the production of chemicals in the body called prostaglandins. Prostaglandins are produced in response to injury or certain diseases and would otherwise go on to cause swelling, inflammation, and pain. By blocking cyclo-oxygenase, dexketoprofen prevents the production of prostaglandins and therefore reduces inflammation and pain. Along with peripheral analgesic action, it possesses central analgesic action. Dexketoprofen may cause dizziness, and patients should not, therefore, drive or operate heavy machinery or vehicles until they are familiar with how dexketoprofen affects them. Concomitant use of alcohol and other sedatives may potentiate this effect. In a small subset of individuals, the dizziness may be intolerable and require the transition to an alternative treatment.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/4076328
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/9176993
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/3526298ZA6800524
Curator's Comment: 1967
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10841807 |
1.9 nM [IC50] | ||
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10841807 |
27.0 nM [IC50] | ||
Target ID: CHEMBL2096909 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15974585 |
50.0 nM [IC50] | ||
Target ID: CHEMBL230 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14510637 |
0.52 µM [IC50] | ||
Target ID: CHEMBL221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14510637 |
0.019 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Keral Approved UseUnknown |
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Primary | Keral Approved UseUnknown |
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Primary | Keral Approved UseUnknown |
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Primary | KETOPROFEN Approved UseKetoprofen capsules USP are indicated for the management of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Ketoprofen capsules USP are indicated for the management of pain. Ketoprofen capsules USP are also indicated for treatment of primary dysmenorrhea. Launch Date1992 |
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Primary | KETOPROFEN Approved UseKetoprofen capsules USP are indicated for the management of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Ketoprofen capsules USP are indicated for the management of pain. Ketoprofen capsules USP are also indicated for treatment of primary dysmenorrhea. Launch Date1992 |
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Primary | KETOPROFEN Approved UseKetoprofen capsules USP are indicated for the management of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Ketoprofen capsules USP are indicated for the management of pain. Ketoprofen capsules USP are also indicated for treatment of primary dysmenorrhea. Launch Date1992 |
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Primary | KETOPROFEN Approved UseKetoprofen capsules USP are indicated for the management of the signs and symptoms of rheumatoid arthritis and osteoarthritis. Ketoprofen capsules USP are indicated for the management of pain. Ketoprofen capsules USP are also indicated for treatment of primary dysmenorrhea. Launch Date1992 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
10.1 μg/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7439263 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
KETOPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
21.91 μg × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7439263 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
KETOPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1.13 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/7439263 |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
KETOPROFEN plasma | Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED |
Doses
Dose | Population | Adverse events |
---|---|---|
12.5 mg single, oral Dose: 12.5 mg Route: oral Route: single Dose: 12.5 mg Sources: Page: p. 34 |
unhealthy, 36.8 years (range: 18 - 65 years) n = 90 Health Status: unhealthy Age Group: 36.8 years (range: 18 - 65 years) Sex: M+F Population Size: 90 Sources: Page: p. 34 |
Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (mild, 1 patient) Sources: Page: p. 34 |
2400 mg single, oral Overdose Dose: 2400 mg Route: oral Route: single Dose: 2400 mg Sources: |
unhealthy, 45 years Health Status: unhealthy Age Group: 45 years Sex: F Sources: |
Other AEs: Epigastric pain... Other AEs: Epigastric pain (mild, 1 patient) Sources: |
100 mg 1 times / day multiple, topical Dose: 100 mg, 1 times / day Route: topical Route: multiple Dose: 100 mg, 1 times / day Sources: |
unhealthy, adult n = 172 Health Status: unhealthy Condition: tendinitis Age Group: adult Population Size: 172 Sources: |
|
100 ug 3 times / day steady, oral (max) Dose: 100 ug, 3 times / day Route: oral Route: steady Dose: 100 ug, 3 times / day Sources: |
unhealthy n = 50 Health Status: unhealthy Condition: Lymphedema Population Size: 50 Sources: |
Other AEs: Cellulitis... Other AEs: Cellulitis (below serious, 3 patients) Sources: |
75 ug 3 times / day steady, oral Dose: 75 ug, 3 times / day Route: oral Route: steady Dose: 75 ug, 3 times / day Sources: |
unhealthy n = 19 Health Status: unhealthy Condition: Lymphedema Population Size: 19 Sources: |
Other AEs: Rash... |
75 ug 3 times / day steady, oral Dose: 75 ug, 3 times / day Route: oral Route: steady Dose: 75 ug, 3 times / day Sources: |
unhealthy n = 23 Health Status: unhealthy Condition: Lymphedema Population Size: 23 Sources: |
Other AEs: Cellulitis... Other AEs: Cellulitis (below serious, 1 patient) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Rash | mild, 1 patient Disc. AE |
12.5 mg single, oral Dose: 12.5 mg Route: oral Route: single Dose: 12.5 mg Sources: Page: p. 34 |
unhealthy, 36.8 years (range: 18 - 65 years) n = 90 Health Status: unhealthy Age Group: 36.8 years (range: 18 - 65 years) Sex: M+F Population Size: 90 Sources: Page: p. 34 |
Epigastric pain | mild, 1 patient | 2400 mg single, oral Overdose Dose: 2400 mg Route: oral Route: single Dose: 2400 mg Sources: |
unhealthy, 45 years Health Status: unhealthy Age Group: 45 years Sex: F Sources: |
Cellulitis | below serious, 3 patients | 100 ug 3 times / day steady, oral (max) Dose: 100 ug, 3 times / day Route: oral Route: steady Dose: 100 ug, 3 times / day Sources: |
unhealthy n = 50 Health Status: unhealthy Condition: Lymphedema Population Size: 50 Sources: |
Rash | below serious, 1 patient | 75 ug 3 times / day steady, oral Dose: 75 ug, 3 times / day Route: oral Route: steady Dose: 75 ug, 3 times / day Sources: |
unhealthy n = 19 Health Status: unhealthy Condition: Lymphedema Population Size: 19 Sources: |
Cellulitis | below serious, 1 patient | 75 ug 3 times / day steady, oral Dose: 75 ug, 3 times / day Route: oral Route: steady Dose: 75 ug, 3 times / day Sources: |
unhealthy n = 23 Health Status: unhealthy Condition: Lymphedema Population Size: 23 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as perpetrator
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
yes [IC50 1.3 uM] | ||||
yes [IC50 1.4 uM] | ||||
yes [IC50 11.9 uM] | ||||
yes [IC50 400 uM] | ||||
yes [IC50 5.98 uM] | ||||
yes [IC50 70.3 uM] |
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/19422321/ Page: 2.0 |
minor | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0 |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0 |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/15843492/ Page: 8.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Effects of nonsteroidal anti-inflammatory drugs on hemostasis in patients with aneurysmal subarachnoid hemorrhage. | 1999 Jul |
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Use of continuous fluid drainage for severe polyhydramnios due to twin to twin transfusion syndrome. | 2001 |
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Intravenous ketoprofen in thyroid and parathyroid surgery. | 2001 Apr |
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In vitro distribution of ketoprofen enantiomers in articular tissues of osteoarthritic patients. | 2001 Dec |
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UV-induces formation of hydrogen peroxide based on the photochemistry of ketoprofen. | 2001 Feb |
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Determination of diclofenac sodium, flufenamic acid, indomethacin and ketoprofen by LC-APCI-MS. | 2001 Feb |
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Effects of grinding with microcrystalline cellulose and cyclodextrins on the ketoprofen physicochemical properties. | 2001 Feb |
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Behavioural effects of laparotomy and analgesic effects of ketoprofen and carprofen in rats. | 2001 Feb 1 |
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A comparative experimental study of the effects of diclofenac and ketoprofen on the small-bowel mucosa of canines. | 2001 Jan |
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Evaluation and structure-activity relationship of synthesized cyclohexanol derivatives on percutaneous absorption of ketoprofen using artificial neural network. | 2001 Jan 16 |
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Novel enzymological profiles of human 11beta-hydroxysteroid dehydrogenase type 1. | 2001 Jan 30 |
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Comparison of tissue concentrations after intramuscular and topical administration of ketoprofen. | 2001 Jul |
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Age-related changes in skin permeability of hydrophilic and lipophilic compounds in rats. | 2001 Mar |
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Neuroprotective effects of non-steroidal anti-inflammatory drugs by direct scavenging of nitric oxide radicals. | 2001 Mar |
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[Allergies to ketoprofen gels]. | 2001 Mar 31 |
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Chiral resolution of flurbiprofen and ketoprofen enantiomers by HPLC on a glycopeptide-type column chiral stationary phase. | 2001 May |
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Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation. | 2001 May-Jun |
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Measurement of ketoprofen in horse urine using gas chromatography-mass spectrometry. | 2001 Oct |
|
Transdermal delivery of ketoprofen using microemulsions. | 2001 Oct 9 |
|
[ Ambulatory laparoscopic gynecological surgery in Africa: feasibility]. | 2001 Sep |
Patents
Sample Use Guides
Rheumatoid Arthritis and Osteoarthritis: 75 mg three times or 50 mg four times a day. The recommended maximum daily dose of ketoprofen capsules is 300 mg/day.
Pain and Dysmenorrhea: 25 to 50 mg every 6 to 8 hours as necessary.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18565185
Curator's Comment: In cultivation of freshly isolated epidermal cells, 5 mM Ketoprofen inhibited the culture-promoted expression of PCl-augmented expression of major histocompatibility complex class II and CD86 on Langerhans cells
5 mM Ketoprofen (mouse isolated epidermal cells)
Substance Class |
Chemical
Created
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Record UNII |
90Y4QC304K
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Record Status |
Validated (UNII)
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Classification Tree | Code System | Code | ||
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WHO-ATC |
M01AE03
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WHO-VATC |
QM01AE53
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WHO-VATC |
QM01AE03
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NDF-RT |
N0000175722
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LIVERTOX |
NBK548678
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NDF-RT |
N0000175721
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M02AA10
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NCI_THESAURUS |
C257
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NDF-RT |
N0000000160
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QM02AA10
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CFR |
21 CFR 522.1225
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WHO-ATC |
M01AE53
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6128
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3284
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KETOPROFEN
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172964-50-0
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SUB08374MIG
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m6622
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Ketoprofen
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1528
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758144
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C47578
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Related Record | Type | Details | ||
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TRANSPORTER -> INHIBITOR |
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TRANSPORTER -> INHIBITOR | |||
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ENANTIOMER -> RACEMATE | |||
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ENANTIOMER -> RACEMATE | |||
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SALT/SOLVATE -> PARENT | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
EP
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SALT/SOLVATE -> PARENT | |||
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BINDER->LIGAND |
BINDING
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (TITRATION)
USP
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TRANSPORTER -> INHIBITOR | |||
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TRANSPORTER -> INHIBITOR |
Related Record | Type | Details | ||
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT |
UNSPECIFIED
EP
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT | |||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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