ChEMBL logo

ChEMBL

spacer
ChEMBL Statistics
  Loading Statistics...
spacer

Compound Report Card

Compound Name and Classification

Compound ID CHEMBL154
CHEMBL154
Compound Name NAPROXEN
ChEMBL Synonyms Anaprox DS | NAPROXEN SODIUM | Aleve | Ec-naprosyn | RS-3540 | RS-3650 | Equiproxen | NAPROSYN | Naprelan | NAPROXEN | ALEVE | Anaprox | NAPRELAN
Max Phase 4 (Approved)
Trade Names Anaprox | NAPRELAN | Equiproxen | NAPROSYN | Naproxen | Ec-naprosyn | ALEVE | Anaprox DS | NAPROXEN SODIUM
Molecular Formula C14H14O3

Additional synonyms for CHEMBL154 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES COc1ccc2cc(ccc2c1)[C@H](C)C(=O)O
Standard InChI InChI=1S/C14H14O3/c1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(1 ...
Download InChI
Standard InChI Key CMWTZPSULFXXJA-VIFPVBQESA-N

Sources

  • AstraZeneca Deposited Data
  • British National Formulary
  • DrugMatrix
  • Gene Expression Atlas Compounds
  • Open TG-GATEs
  • Orange Book
  • PubChem BioAssays
  • Scientific Literature
  • TP-search Transporter Database
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL154

Molecule Features

CHEMBL154 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Single Stereoisomer Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:Y Availability Type:Over-The-Counter

Mechanism of Action

Mechanism of Action ChEMBL Target References
Cyclooxygenase inhibitor Cyclooxygenase PubMed PubMed PubMed PubMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
DISTAL MYOPATHIESD049310Orphanet:609TIBIAL MUSCULAR DYSTROPHY1ClinicalTrials
OSTEOARTHRITIS, HIPD015207EFO:1000786OSTEOARTHRITIS, HIP3ClinicalTrials
PEPTIC ULCERD010437HP:0004398PEPTIC ULCER3ClinicalTrials
RHEUMATIC DISEASESD012216EFO:0005755RHEUMATIC DISEASE4ATC
GOUTD006073EFO:0004274GOUT4DailyMed
ALZHEIMER DISEASED000544EFO:0000249ALZHEIMERS DISEASE2ClinicalTrials
DUODENAL ULCERD004381EFO:0004607DUODENAL ULCER2ClinicalTrials
MYALGIAD063806HP:0003326MYALGIA4ATC
OSTEOARTHRITISD010003EFO:0002506OSTEOARTHRITIS4ClinicalTrials
DailyMed
DailyMed
DailyMed
OSTEOARTHRITIS, KNEED020370EFO:0004616OSTEOARTHRITIS, KNEE2ClinicalTrials
PLEURAL EFFUSIOND010996HP:0002202PLEURAL EFFUSION2ClinicalTrials
VAGINITISD014627EFO:0005757VAGINAL INFLAMMATION4ATC
TENDINOPATHYD052256EFO:1001434TENDINOPATHY4DailyMed
ARTHRITIS, JUVENILED001171EFO:0002609CHRONIC CHILDHOOD ARTHRITIS3ClinicalTrials
ARTHRITIS, RHEUMATOIDD001172EFO:0000685RHEUMATOID ARTHRITIS4DailyMed
DailyMed
ClinicalTrials
DailyMed
PAIND010146EFO:0003843PAIN4ClinicalTrials
ClinicalTrials
DailyMed
BURSITISD002062EFO:1000941FROZEN SHOULDER4DailyMed
ARTHRALGIAD018771HP:0002829ARTHRALGIA4ATC
COLORECTAL NEOPLASMS, HEREDITARY NONPOLYPOSISD003123Orphanet:144LYNCH SYNDROME1ClinicalTrials
SPONDYLITIS, ANKYLOSINGD013167EFO:0003898ANKYLOSING SPONDYLITIS4ClinicalTrials
DailyMed
DailyMed
DailyMed
STOMACH ULCERD013276HP:0002592GASTRIC ULCER4DailyMed
DailyMed
DYSMENORRHEAD004412HP:0100607DYSMENORRHEA4ClinicalTrials
DailyMed

Clinical Data

ClinicalTrials.gov NAPROXEN
The Cochrane Collaboration NAPROXEN

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL154. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL5141 Cytochrome P450 26A1 Homo sapiens 0.997
CHEMBL312 Arachidonate 5-lipoxygenase Rattus norvegicus 0.997
CHEMBL2949 Cyclooxygenase-1 Ovis aries 0.968
CHEMBL221 Cyclooxygenase-1 Homo sapiens 0.868
CHEMBL1946 Melatonin receptor 1B Homo sapiens 0.862
CHEMBL215 Arachidonate 5-lipoxygenase Homo sapiens 0.671
CHEMBL1945 Melatonin receptor 1A Homo sapiens 0.648
CHEMBL235 Peroxisome proliferator-activated receptor gamma Homo sapiens 0.546
CHEMBL5645 Cysteinyl leukotriene receptor 1 Cavia porcellus 0.503
CHEMBL239 Peroxisome proliferator-activated receptor alpha Homo sapiens 0.411



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5141 Cytochrome P450 26A1 Homo sapiens 1.000
CHEMBL2949 Cyclooxygenase-1 Ovis aries 0.998
CHEMBL312 Arachidonate 5-lipoxygenase Rattus norvegicus 0.967
CHEMBL4681 Aldo-keto-reductase family 1 member C3 Homo sapiens 0.944
CHEMBL235 Peroxisome proliferator-activated receptor gamma Homo sapiens 0.790
CHEMBL1946 Melatonin receptor 1B Homo sapiens 0.734
CHEMBL5645 Cysteinyl leukotriene receptor 1 Cavia porcellus 0.619
CHEMBL221 Cyclooxygenase-1 Homo sapiens 0.617
CHEMBL215 Arachidonate 5-lipoxygenase Homo sapiens 0.566
CHEMBL239 Peroxisome proliferator-activated receptor alpha Homo sapiens 0.430
CHEMBL2977 Cyclooxygenase-2 Rattus norvegicus 0.362
CHEMBL1945 Melatonin receptor 1A Homo sapiens 0.354
CHEMBL3949 Endothelin receptor ET-B Sus scrofa 0.300

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
230.3 230.0943 2.85 3 46.53 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 1 0 3 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.85 - 2.88 .35 2 17 0.88

Structural Alerts

There are no structural alerts for CHEMBL154

Compound Cross References

ATC G - GENITO URINARY SYSTEM AND SEX HORMONES
G02 - OTHER GYNECOLOGICALS
G02C - OTHER GYNECOLOGICALS
G02CC - Antiinflammatory products for vaginal administration
G02CC02 - naproxen

M - MUSCULO-SKELETAL SYSTEM
M01 - ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
M01A - ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
M01AE - Propionic acid derivatives
M01AE02 - naproxen

M - MUSCULO-SKELETAL SYSTEM
M02 - TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
M02A - TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
M02AA - Antiinflammatory preparations, non-steroids for topical use
M02AA12 - naproxen

ChemSpider ChemSpider:CMWTZPSULFXXJA-VIFPVBQESA-N
DailyMed naproxen naproxen sodium
PubChem SID: 11112669 SID: 144212270 SID: 26755231 SID: 90341518
Wikipedia Naproxen

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL154



ACToR 22204-53-1
Atlas naproxen
BindingDB 50339185
Brenda 7679 69452 38412 174908
ChEBI 7476
DrugBank DB00788
DrugCentral 1883
eMolecules 494695
EPA CompTox Dashboard DTXSID4040686
FDA SRS 57Y76R9ATQ
Guide to Pharmacology 5230
Human Metabolome Database HMDB0001923
IBM Patent System 90759B9A8F1684E106E5CEF70D722F77
LINCS LSM-5689
Mcule MCULE-8718466451 MCULE-2589082817
MolPort MolPort-000-145-960
NMRShiftDB 20209411
PDBe NPS
PubChem 156391
PubChem: Thomson Pharma 15172373 15172374
SureChEMBL SCHEMBL3046
ZINC ZINC000000105216

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/CMWTZPSULFXXJA-VIFPVBQESA-N spacer
spacer