KETOPROFEN

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Trade Names:
Synonyms:
Status: Approved (1986)
Entry Type: Small molecule
Molecule Category: Parent
ATC: M01AE03
UNII: 90Y4QC304K

Structure
InChI Key DKYWVDODHFEZIM-UHFFFAOYSA-N
Smile CC(C(=O)O)c1cccc(C(=O)c2ccccc2)c1
InChI
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C16H14O3
Molecular Weight 254.29
AlogP 3.11
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 54.37
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 19.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 3.12 - EXP
pKa Dissociation Constant 4.45 - EXP
Henry's Law Constant 2.12E-11 atm-m3/mole EST
Atmospheric OH Rate Constant 6.06E-12 cm3/molecule-sec EST
Melting Point 94 deg C EXP
Water Solubility 51 mg/L EXP
Vapor Pressure 3.72E-07 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Cyclooxygenase inhibitor PubMed Wikipedia Wikipedia
Primary Target
COX-1
COX-2
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Oxidoreductase
- 26-3800 - - 0-40
Enzyme
- 26-3800 - - 0-40
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CXC chemokine receptor
- - - - 64
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 112
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -

Metabolites

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Indications

Mesh Heading Maximum Phase Mesh ID Reference
Arthralgia 4 D018771 ClinicalTrials
Pain 4 D010146 ClinicalTrials
Postoperative Nausea and Vomiting 3 D020250 ClinicalTrials
Tendinopathy 3 D052256 ClinicalTrials
Migraine Disorders 3 D008881 ClinicalTrials
Osteoarthritis, Knee 3 D020370 ClinicalTrials
Bursitis 3 D002062 ClinicalTrials
Inflammation 3 D007249 ClinicalTrials
Wounds and Injuries 3 D014947 ClinicalTrials
Sprains and Strains 3 D013180 ClinicalTrials
Low Back Pain 3 D017116 ClinicalTrials
Periodontitis 2 D010518 ClinicalTrials
Paget Disease, Extramammary 2 D010145 ClinicalTrials
Renal Colic 1 D056844 ClinicalTrials
Kidney Calculi 1 D007669 ClinicalTrials

Related Entries

MCS

Scaffolds

Side Effects from Label

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Skin and subcutaneous tissue disorders
11.62
Nervous system disorders
10.85
Vascular disorders
9.07
Gastrointestinal disorders
8.92
Immune system disorders
8.87
General disorders and administration site conditions
7.43
Injury, poisoning and procedural complications
6.76
Respiratory, thoracic and mediastinal disorders
6.32
Cardiac disorders
5.32
Psychiatric disorders
3.81
Renal and urinary disorders
3.35
Infections and infestations
2.46
Investigations
2.28
Metabolism and nutrition disorders
2.28
Blood and lymphatic system disorders
2.21
Musculoskeletal and connective tissue disorders
2.01

Cross References

Resources Reference
CAS NUMBER 22071-15-4
ChEBI 6128
ChEMBL CHEMBL571
DrugBank DB01009
DrugCentral 1528
EPA CompTox DTXSID6020771
FDA SRS 90Y4QC304K
Human Metabolome Database HMDB0015144
Guide to Pharmacology 4795
KEGG C01716
PharmGKB PA450149
PubChem 3825
SureChEMBL SCHEMBL2896
ZINC ZINC00005560
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