NAPROXEN

Search structure
Trade Names:
Synonyms:
Status: Approved (1976)
Entry Type: Small molecule
Molecule Category: Parent
ATC: G02CC02
UNII: 57Y76R9ATQ

Structure
InChI Key CMWTZPSULFXXJA-VIFPVBQESA-N
Smile COc1ccc2cc([C@H](C)C(=O)O)ccc2c1
InChI
InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10/h3-9H,1-2H3,(H,15,16)/t9-/m0/s1

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H14O3
Molecular Weight 230.26
AlogP 3.04
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 3.0
Polar Surface Area 46.53
Molecular species ACID
Aromatic Rings 2.0
Heavy Atoms 17.0

Experimental and Estimated Properties

Property Name Value Unit Method
log P (octanol-water) 3.18 - EXP
pKa Dissociation Constant 4.15 - EXP
Henry's Law Constant 3.39E-10 atm-m3/mole EST
Atmospheric OH Rate Constant 1.16E-10 cm3/molecule-sec EST
Melting Point 153 deg C EXP
Water Solubility 15.9 mg/L EXP
Vapor Pressure 1.89E-06 mm Hg EST

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Cyclooxygenase inhibitor PubMed PubMed PubMed PubMed
Primary Target
COX-1
COX-2
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Hydrolase
- 1200 - - 64
Enzyme Isomerase
- 13000 - - -
Enzyme Oxidoreductase
- 61-52200 - - 55-88
Enzyme Protease Aspartic protease Aspartic protease AD clan Aspartic protease A22A subfamily Aspartic protease A22A regulatory subfamily
- - - - 3
Enzyme
- 61-52200 - - 55-88
Ion channel Other ion channel Miscellaneous ion channel Presenilin ER Ca2+ leak channel family
- - - - 3
Membrane receptor Family A G protein-coupled receptor Peptide receptor (family A GPCR) Chemokine receptor CXC chemokine receptor
- - - - 35
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - 104

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Pain 4 D010146 ClinicalTrials
Stomach Ulcer 4 D013276 ClinicalTrials
Toothache 4 D014098 ClinicalTrials
Multiple Sclerosis 3 D009103 ClinicalTrials
Peptic Ulcer 3 D010437 ClinicalTrials
Migraine Disorders 3 D008881 ClinicalTrials
Severe Acute Respiratory Syndrome 3 D045169 ClinicalTrials
Osteoarthritis, Hip 3 D015207 ClinicalTrials
Osteoarthritis, Knee 3 D020370 ClinicalTrials
Low Back Pain 3 D017116 ClinicalTrials
Neuralgia 2 D009437 ClinicalTrials
Pleural Effusion 2 D010996 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Duodenal Ulcer 2 D004381 ClinicalTrials
Alzheimer Disease 2 D000544 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Colorectal Neoplasms, Hereditary Nonpolyposis 1 D003123 ClinicalTrials
Distal Myopathies 1 D049310 ClinicalTrials
Inflammation 0 D007249 ClinicalTrials

Related Entries

MCS

Scaffolds

Salt
Mixture
Mixture
Mixture

Side Effects from Label

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
General disorders and administration site conditions
12.1
Gastrointestinal disorders
11.78
Nervous system disorders
8.3
Vascular disorders
7.42
Musculoskeletal and connective tissue disorders
7.02
Respiratory, thoracic and mediastinal disorders
6.65
Skin and subcutaneous tissue disorders
6.61
Immune system disorders
5.7
Injury, poisoning and procedural complications
5.26
Cardiac disorders
5.02
Investigations
4.61
Psychiatric disorders
4.27
Infections and infestations
3.87
Metabolism and nutrition disorders
2.43
Renal and urinary disorders
2.18

Cross References

Resources Reference
CAS NUMBER 22204-53-1
ChEBI 7476
ChEMBL CHEMBL154
DrugBank DB00788
DrugCentral 1883
EPA CompTox DTXSID4040686
FDA SRS 57Y76R9ATQ
Human Metabolome Database HMDB0001923
Guide to Pharmacology 5230
PDB NPS
PubChem 156391
SureChEMBL SCHEMBL3046
ZINC ZINC000000105216
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