General
Preferred name
NAPROXEN
Synonyms
(S)-Naproxen ()
NAPROXEN SODIUM ()
PN400 COMPONENT NAPROXEN ()
Nycopren ()
Laraflex ()
Arthrosin 500 EC ()
NSC-757239 ()
Naprosyn ()
Naproxeno ()
Ec-Naprosyn ()
Rheuflex 500 ()
Napratec OP ()
Arthrosin 250 EC ()
Anaprox ()
Vimovo ()
Rimoxyn ()
Arthrosin 500 ()
Naprosyn EC ()
Timpron 500 EC ()
Condrotec ()
Naprosyn 375 ()
Naprelan ()
Stirlescent ()
Equiproxen ()
Timpron ()
Grenoxal ()
Feminax Ultra ()
Timpron 250 EC ()
Naproxene ()
Valrox ()
Pranoxen Continus ()
Kenosyn ()
Aleve ()
Arthrosin 250 ()
NSC-750183 ()
Rheuflex 250 ()
Prosaid ()
RS-3540 ()
P&D ID
PD001844
CAS
22204-53-1
131991-52-1
Tags
available
drug
Approved by
FDA
First approval
1976
Drug indication
Analgesic
Pain
Antipyretic
Anti-Inflammatory
Endometriosis
Osteoarthritis
Analgesic,Antipyretic
Drug Status
approved
vet_approved
Max Phase
4.0
Structure
Probe scores
P&D probe-likeness score
[[ v.score ]]%
Structure formats
[[ format ]]
[[ compound[format === 'MOL' ? 'molblock' : format.toLowerCase()] ]]
Description
(extracted from source data)
ABSORPTION Naproxen is available as a free acid and sodium salt.[A179098] At comparable doses, (naproxen 500 mg = naproxen sodium 550 mg) they differ slightly in their rates of absorption, but otherwise they are therapeutically and pharmacologically equivalent.[A179098] Naproxen sodium achieves a peak plasma concentration after 1 hour, while peak plasma concentration is observed after 2 hours with naproxen (free acid).[A179098] There are no differences between the 2 forms in the post-absorption phase pharmacokinetics.[A179098] The difference in initial absorption should be considered when treating acute pain, since naproxen sodium may offer a quicker onset of action.[A179098]; ; Overall, naproxen is rapidly and completely absorbed when administered orally and rectally.[A179110][A179098] Food may contribute to a delay in the absorption of orally administered naproxen, but will not affect the extent of absorption.[A179098]
TOXICITY Although the over-the-counter (OTC) availability of naproxen provides convenience to patients, it also increases the likelihood of overdose.[A178975] Thankfully, the extent of overdose is typically mild with adverse effects normally limited to drowsiness, lethargy, epigastric pain, nausea and vomiting.[A178975][L6582][L6583] Although there is no antidote for naproxen overdose, symptoms will typically subside with appropriate supportive care.[L6582][L6583][A178975]; ; Naproxen is classified as Category B during the first 2 trimesters of pregnancy, and as Category D during the third trimester.[L6595] Naproxen is contraindicated in the 3rd trimester since it increases the risk of premature closure of the fetal ductus arteriosus and should be avoided in pregnant women starting at 30 weeks gestation.[L6582][L6583]
PHARMACODYNAMICS Naproxen is an established non-selective NSAID and is useful as an analgesic, anti-inflammatory and antipyretic.[A179098] Similar to other NSAIDs, the pharmacological activity of naproxen can be attributed to the inhibition of cyclo-oxygenase, which in turn reduces prostaglandin synthesis in various tissues and fluids including the synovial fluid, gastric mucosa, and the blood.[A179098] ; ; Although naproxen is a an effective analgesic, it can have unintended deleterious effects in the patient. For instance, naproxen can adversely effect blood pressure control.[A179224] A study found that use of naproxen induced an increase in blood pressure, although the increase was not as significant as that found with ibuprofen use.[A179224]; ; Further, studies have found that the risk of upper gastrointestinal bleeding is on average four-fold higher for individuals taking NSAIDs.[A179227] Other factors that increase the risk of upper gastrointestinal bleeding include concurrent use of corticosteroids or anticoagulants, and history of gastrointestinal ulcers.[A179227]
DESCRIPTION Naproxen is one of the 2-arylpropionic acid ('profen') family of nonsteroidal anti-inflammatory drugs (NSAIDs), like . (GtoPdb)
METABOLISM Naproxen is heavily metabolized in the liver and undergoes both Phase I and Phase II metabolism.[L6582][L6583][A179197] The first step involves demethylation of naproxen via CYP 1A2, 2C8, and 2C9[A179191][A38985]. Both compounds proceed to Phase II metabolism; however, desmethylnaproxen can form both acyl and phenolic glucoronide products, while naproxen only produces the acyl glucuronide.[A179191][A179197] The acyl glucuronidation process involves UGT 1A1, 1A3, 1A6, 1A7, 1A9, 1A10 and 2B7, while phenolic glucuronidation is catalyzed by UGT 1A1, 1A7,1A9, and 1A10.[A179191] Desmethylnaproxen also undergoes sulphation which is mediated by SULT 1A1, 1B1 and 1E1.[A179197]
INDICATION Naproxen is indicated for the management of rheumatoid arthritis, osteoarthritis, ankylosing spondylitis, polyarticular juvenile idiopathic arthritis, tendinitis, bursitis, acute gout, primary dysmenorrhea, and for the relief of mild to moderate pain.[L6582][L6583][A178975] Further, it is first-line therapy for osteoarthritis, acute gouty arthritis, dysmenorrhea, and musculoskeletal inflammation and pain.[A178975]
MOA As with other non-selective NSAIDs, naproxen exerts it's clinical effects by blocking COX-1 and COX-2 enzymes leading to decreased prostaglandin synthesis.[A178975] Although both enzymes contribute to prostaglandin production, they have unique functional differences.[A178975] The COX-1 enzymes is constitutively active and can be found in normal tissues such as the stomach lining, while the COX-2 enzyme is inducible and produces prostaglandins that mediate pain, fever and inflammation.[A178990] The COX-2 enzyme mediates the desired antipyretic, analgesic and anti-inflammatory properties offered by Naproxen, while undesired adverse effects such as gastrointestinal upset and renal toxicities are linked to the COX-1 enzyme.[A178990]
ROE After oral administration, about 95% of naproxen and it's metabolites can be recovered in the urine with 66-92% recovered as conjugated metabolite and less than 1% recovered as naproxen or desmethylnaproxen.[A179197][L6582][L6583] Less than 5% of naproxen is excreted in the feces.[L6582][L6583]
HALF-LIFE The half-life of naproxen is reported to be 12-17 hours.[A178975]
Cell lines
1
Organisms
2
Compound Sets
22
Cayman Chemical Bioactives
70290
ChEMBL Approved Drugs
CHEMBL154
ChEMBL Drugs
CHEMBL154
Drug Repurposing Hub
DrugBank
DB00788
DrugBank Approved Drugs
DB00788
DrugCentral
1883
DrugCentral Approved Drugs
1883
DrugMAP
DMZ5RGV
DrugMAP Approved Drugs
DMZ5RGV
Enamine BioReference Compounds
Guide to Pharmacology
5230
LSP-MoA library (Laboratory of Systems Pharmacology)
CHEMBL154
MedChem Express Bioactive Compound Library
HY-15030
NCATS Inxight Approved Drugs
57Y76R9ATQ
Novartis Chemogenetic Library (NIBR MoA Box)
NPC Screening Collection
Prestwick Chemical Library
ReFrame library
Selleckchem Bioactive Compound Library
naproxen
TargetMol Bioactive Compound Library
T1582
The Spectrum Collection
External IDs
59
Properties
(calculated by RDKit )
Molecular Weight
230.09
Hydrogen Bond Acceptors
2
Hydrogen Bond Donors
1
Rotatable Bonds
3
Ring Count
2
Aromatic Ring Count
2
cLogP
3.04
TPSA
46.53
Fraction CSP3
0.21
Chiral centers
1.0
Largest ring
6.0
QED
0.88
Structural alerts
0
No structural alerts detected
Related compounds
Custom attributes
(extracted from source data)
Pathway
Immunology/Inflammation
Neuroscience
Autophagy
Target
COX
PTGS1, PTGS2
Member status
member
MOA
Non-Steroidal Antiinflammatory Drugs
cyclooxygenase inhibitor
Indication
pain relief, rheumatoid arthritis, headache, toothache, backache, muscle pain, common cold, fever
Disease Area
neurology/psychiatry, rheumatology, dental, otolaryngology, endocrinology
Source data