CHEBI:7476 - naproxen

ChEBI IDCHEBI:7476
ChEBI Namenaproxen
Stars
DefinitionA methoxynaphthalene that is 2-methoxynaphthalene substituted by a carboxy ethyl group at position 6. Naproxen is a non-steroidal anti-inflammatory drug commonly used for the reduction of pain, fever, inflammation and stiffness caused by conditions such as osteoarthritis, kidney stones, rheumatoid arthritis, psoriatic arthritis, gout, ankylosing spondylitis, menstrual cramps, tendinitis, bursitis, and for the treatment of primary dysmenorrhea. It works by inhibiting both the COX-1 and COX-2 enzymes.
Secondary ChEBI IDCHEBI:603695
Last Modified12 March 2019
DownloadsMolfile
FormulaC14H14O3
Net Charge0
Average Mass230.263
Monoisotopic Mass230.09429
SMILESCOc1ccc2cc([C@H](C)C(=O)O)ccc2c1
InChIInChI=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
InChIKeyCMWTZPSULFXXJA-VIFPVBQESA-N
Wikipedia
Roles Classification
Chemical Roles:
environmental contaminant  Any minor or unwanted substance introduced into the environment that can have undesired effects.
Bronsted acid  A molecular entity capable of donating a hydron to an acceptor (Brønsted base).
Biological Roles:
drug allergen  Any drug which causes the onset of an allergic reaction.
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
cyclooxygenase 1 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
xenobiotic  A xenobiotic (Greek, xenos "foreign"; bios "life") is a compound that is foreign to a living organism. Principal xenobiotics include: drugs, carcinogens and various compounds that have been introduced into the environment by artificial means.
cyclooxygenase 2 inhibitor  A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 2.
Applications:
gout suppressant  A drug that increases uric acid excretion by the kidney (uricosuric drug), decreases uric acid production (antihyperuricemic), or alleviates the pain and inflammation of acute attacks of gout.
drug allergen  Any drug which causes the onset of an allergic reaction.
non-narcotic analgesic  A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
antipyretic  A drug that prevents or reduces fever by lowering the body temperature from a raised state. An antipyretic will not affect the normal body temperature if one does not have fever. Antipyretics cause the hypothalamus to override an interleukin-induced increase in temperature. The body will then work to lower the temperature and the result is a reduction in fever.
non-steroidal anti-inflammatory drug  An anti-inflammatory drug that is not a steroid. In addition to anti-inflammatory actions, non-steroidal anti-inflammatory drugs have analgesic, antipyretic, and platelet-inhibitory actions. They act by blocking the synthesis of prostaglandins by inhibiting cyclooxygenase, which converts arachidonic acid to cyclic endoperoxides, precursors of prostaglandins.
ChEBI Ontology
Outgoing Relation(s)
naproxen (CHEBI:7476) has role antipyretic (CHEBI:35493)
naproxen (CHEBI:7476) has role cyclooxygenase 1 inhibitor (CHEBI:50630)
naproxen (CHEBI:7476) has role cyclooxygenase 2 inhibitor (CHEBI:50629)
naproxen (CHEBI:7476) has role drug allergen (CHEBI:88188)
naproxen (CHEBI:7476) has role environmental contaminant (CHEBI:78298)
naproxen (CHEBI:7476) has role gout suppressant (CHEBI:35845)
naproxen (CHEBI:7476) has role non-narcotic analgesic (CHEBI:35481)
naproxen (CHEBI:7476) has role non-steroidal anti-inflammatory drug (CHEBI:35475)
naproxen (CHEBI:7476) has role xenobiotic (CHEBI:35703)
naproxen (CHEBI:7476) is a methoxynaphthalene (CHEBI:48851)
naproxen (CHEBI:7476) is a monocarboxylic acid (CHEBI:25384)
naproxen (CHEBI:7476) is conjugate acid of naproxen(1−) (CHEBI:59527)
Incoming Relation(s)
desmethylnaproxen sulfate (CHEBI:133458) has functional parent naproxen (CHEBI:7476)
naproxcinod (CHEBI:76254) has functional parent naproxen (CHEBI:7476)
naproxen(1−) (CHEBI:59527) is conjugate base of naproxen (CHEBI:7476)
IUPAC Name 
(2S)-2-(6-methoxynaphthalen-2-yl)propanoic acid
INNs  Source
naproxenoChemIDplus
naproxeneChemIDplus
naproxenumChemIDplus
naproxenDrugBank
Synonyms  Source
NaproxenKEGG COMPOUND
naproxenChEMBL
(+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acidChemIDplus
(+)-2-(6-Methoxy-2-naphthyl)propionic acidChemIDplus
(+)-NaproxenChemIDplus
(+)-2-(Methoxy-2-naphthyl)-propionsäureChemIDplus
Manual XrefsDatabases
D00118KEGG DRUG
DB00788DrugBank
US3904682Patent
US4009197Patent
NaproxenWikipedia
HMDB0001923HMDB
LSM-5689LINCS
1883DrugCentral
Registry NumbersSources
Beilstein:3591067Beilstein
CAS:22204-53-1KEGG COMPOUND
CAS:22204-53-1ChemIDplus
Citations