CHEBI:7476 - naproxen

Main ChEBI Ontology Automatic Xrefs Reactions Pathways
ChEBI Name naproxen
ChEBI ID CHEBI:7476
Definition A 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.
Stars This entity has been manually annotated by the ChEBI Team.
Secondary ChEBI IDs CHEBI:603695
Supplier Information
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Formula C14H14O3
Net Charge 0
Average Mass 230.25920
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
InChIKey CMWTZPSULFXXJA-VIFPVBQESA-N
SMILES COc1ccc2cc(ccc2c1)[C@H](C)C(O)=O
Roles Classification
Chemical Role(s): 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 (Bronsted base).
(via oxoacid )
Biological Role(s): 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.
cyclooxygenase 1 inhibitor
A cyclooxygenase inhibitor that interferes with the action of cyclooxygenase 1.
non-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
Application(s): 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.
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.
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-narcotic analgesic
A drug that has principally analgesic, antipyretic and anti-inflammatory actions. Non-narcotic analgesics do not bind to opioid receptors.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing 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 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 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 Sources
naproxen DrugBank
naproxene ChemIDplus
naproxeno ChemIDplus
naproxenum ChemIDplus
Synonyms Sources
(+)-(S)-6-Methoxy-α-methyl-2-naphthaleneacetic acid ChemIDplus
(+)-(S)-Naproxen ChemIDplus
(+)-2-(6-Methoxy-2-naphthyl)propionic acid ChemIDplus
(+)-2-(Methoxy-2-naphthyl)-propionic acid ChemIDplus
(+)-2-(Methoxy-2-naphthyl)-propionsäure ChemIDplus
(+)-Naproxen ChemIDplus
(S)-(+)-2-(6-Methoxy-2-naphthyl)propionic acid ChemIDplus
(S)-(+)-Naproxen ChemIDplus
(S)-2-(6-Methoxy-2-naphthyl)propanoic acid ChemIDplus
(S)-2-(6-Methoxy-2-naphthyl)propionic acid ChemIDplus
(S)-6-Methoxy-alpha-methyl-2-naphthaleneacetic acid ChemIDplus
(S)-Naproxen ChemIDplus
naproxen ChEMBL
Naproxen KEGG COMPOUND
Database Links Databases
D00118 KEGG DRUG
DB00788 DrugBank
HMDB01923 HMDB
LSM-5689 LINCS
Naproxen Wikipedia
US3904682 Patent
US4009197 Patent
View more database links
Registry Numbers Types Sources
22204-53-1 CAS Registry Number ChemIDplus
3591067 Beilstein Registry Number Beilstein
Citations Waiting for Citations Types Sources
18044350 PubMed citation CiteXplore
24478225 PubMed citation CiteXplore
9784154 PubMed citation ChEMBL
Last Modified
25 February 2016