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 Naprelan | VALROX | KENOSYN | Equiproxen | NAPRELAN | SYNFLEX | TIMPRON 500 EC | NYCOPREN | NAPROSYN 375 | RHEUFLEX 250 | EC-NAPROSYN | RIMOXYN | CONDROTEC | ARTHROSIN 250 EC | RS-3650 | ANAPROX DS | ALEVE | RS-3540 | RHEUFLEX 500 | ARTHROSIN 500 EC | VIMOVO | PROSAID | PRANOXEN CONTINUS | GRENOXAL | ARTHROSIN 500 | NAPROXEN SODIUM | TIMPRON | NAPROXEN | STIRLESCENT | ANAPROX | ARTHROSIN 250 | Anaprox | FEMINAX ULTRA | LARAFLEX | NAPRATEC OP | NAPROSYN EC | TIMPRON 250 EC | NAPROSYN
Max Phase 4 (Approved)
Trade Names ARTHROSIN 250 | Anaprox | FEMINAX ULTRA | LARAFLEX | NAPRATEC OP | NAPROSYN EC | TIMPRON 250 EC | VALROX | NAPROXEN | STIRLESCENT | NAPRELAN | Equiproxen | KENOSYN | NAPROSYN | RHEUFLEX 250 | SYNFLEX | ARTHROSIN 250 EC | CONDROTEC | ANAPROX DS | ARTHROSIN 500 EC | RHEUFLEX 500 | ARTHROSIN 500 | GRENOXAL | PRANOXEN CONTINUS | PROSAID | VIMOVO | EC-NAPROSYN | NAPROSYN 375 | NYCOPREN | TIMPRON 500 EC | ANAPROX | ALEVE | RIMOXYN | TIMPRON | 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
Migraine DisordersD008881EFO:0003821migraine disorder3ClinicalTrials
ClinicalTrials
MyalgiaD063806HP:0003326Myalgia4ATC
Peptic UlcerD010437HP:0004398Peptic ulcer3ClinicalTrials
ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000673prostate adenocarcinoma2ClinicalTrials
BursitisD002062EFO:1000941frozen shoulder4FDA
Arthritis, JuvenileD001171EFO:0002609chronic childhood arthritis3ClinicalTrials
Osteoarthritis, KneeD020370EFO:0004616osteoarthritis, knee2ClinicalTrials
ArthralgiaD018771HP:0002829arthralgia4ATC
DysmenorrheaD0044124ClinicalTrials
FDA
Arthritis, RheumatoidD001172EFO:0000685rheumatoid arthritis4ClinicalTrials
DailyMed
DailyMed
FDA
NeuralgiaD009437EFO:0005762neuropathic pain2ClinicalTrials
Alzheimer DiseaseD000544EFO:0000249Alzheimers disease3ClinicalTrials
ClinicalTrials
Colorectal Neoplasms, Hereditary NonpolyposisD003123Orphanet:144Lynch syndrome1ClinicalTrials
Distal MyopathiesD049310Orphanet:609Tibial muscular dystrophy1ClinicalTrials
GoutD006073EFO:0004274gout4ClinicalTrials
FDA
OsteoarthritisD010003EFO:0002506osteoarthritis4ClinicalTrials
DailyMed
DailyMed
FDA
TendinopathyD052256EFO:1001434Tendinopathy4FDA
Duodenal UlcerD004381EFO:0004607duodenal ulcer2ClinicalTrials
Osteoarthritis, HipD015207EFO:1000786osteoarthritis, hip3ClinicalTrials
Rheumatic DiseasesD012216EFO:0005755rheumatic disease4ATC
Spondylitis, AnkylosingD013167EFO:0003898ankylosing spondylitis4ClinicalTrials
DailyMed
DailyMed
FDA
VaginitisD014627EFO:0005757vaginal inflammation4ATC
Breast NeoplasmsD001943EFO:0000305breast carcinoma2ClinicalTrials
HeadacheD006261HP:0002315Headache3ClinicalTrials
Multiple SclerosisD009103EFO:0003885multiple sclerosis3ClinicalTrials
PainD010146EFO:0003843pain4ClinicalTrials
ClinicalTrials
FDA
Pleural EffusionD0109962ClinicalTrials
Stomach UlcerD0132764DailyMed
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
CHEMBL2949 Cyclooxygenase-1 Ovis aries 1.000
CHEMBL5141 Cytochrome P450 26A1 Homo sapiens 0.997
CHEMBL312 Arachidonate 5-lipoxygenase Rattus norvegicus 0.996
CHEMBL221 Cyclooxygenase-1 Homo sapiens 0.924
CHEMBL5645 Cysteinyl leukotriene receptor 1 Cavia porcellus 0.825
CHEMBL1946 Melatonin receptor 1B Homo sapiens 0.807
CHEMBL235 Peroxisome proliferator-activated receptor gamma Homo sapiens 0.701
CHEMBL215 Arachidonate 5-lipoxygenase Homo sapiens 0.686
CHEMBL1945 Melatonin receptor 1A Homo sapiens 0.507
CHEMBL239 Peroxisome proliferator-activated receptor alpha Homo sapiens 0.449
CHEMBL230 Cyclooxygenase-2 Homo sapiens 0.438



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL2949 Cyclooxygenase-1 Ovis aries 1.000
CHEMBL5141 Cytochrome P450 26A1 Homo sapiens 1.000
CHEMBL312 Arachidonate 5-lipoxygenase Rattus norvegicus 0.956
CHEMBL2977 Cyclooxygenase-2 Rattus norvegicus 0.894
CHEMBL235 Peroxisome proliferator-activated receptor gamma Homo sapiens 0.861
CHEMBL5645 Cysteinyl leukotriene receptor 1 Cavia porcellus 0.860
CHEMBL221 Cyclooxygenase-1 Homo sapiens 0.780
CHEMBL230 Cyclooxygenase-2 Homo sapiens 0.775
CHEMBL4681 Aldo-keto-reductase family 1 member C3 Homo sapiens 0.699
CHEMBL215 Arachidonate 5-lipoxygenase Homo sapiens 0.577
CHEMBL1946 Melatonin receptor 1B Homo sapiens 0.577
CHEMBL239 Peroxisome proliferator-activated receptor alpha Homo sapiens 0.471
CHEMBL3949 Endothelin receptor ET-B Sus scrofa 0.372
CHEMBL1878 Calcium sensing receptor Homo sapiens 0.266
CHEMBL1945 Melatonin receptor 1A Homo sapiens 0.234

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
230.3 230.0943 3.04 3 46.53 ACID


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
2 1 0 3 1 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
4.84 - 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 174908 38412
ChEBI 7476
ChemicalBook CB8274937
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