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Naproxen

CHEMBL154 Phase 4 Одобрено Small molecule
Half-Life
12-17 hours
Bioavailability
—
Protein Binding
—
Molecular Weight
230.3 g/mol
LogP
3.3
Phase
4

Naproxen relieves pain, fever, and inflammation as a nonsteroidal anti-inflammatory drug, inhibiting the cyclooxygenase enzymes that generate prostaglandins. Among NSAIDs it stands out for a comparatively long half-life of 12 to 17 hours, which allows less frequent dosing than shorter-acting agents in the class. It is used for arthritis, menstrual cramps, headaches, and muscle aches. A small molecule (C14H14O3), it blocks both COX-1 and COX-2 without selectivity, so alongside symptom relief it can affect the stomach and kidneys that rely on baseline prostaglandin activity. Its extended duration reflects slow clearance rather than any difference in the underlying enzyme block. Naproxen is an approved analgesic and anti-inflammatory sold both over the counter and by prescription.

This non-steroidal anti-inflammatory drug (NSAID) is widely used to relieve pain, reduce fever, and decrease inflammation from conditions such as arthritis, menstrual cramps, headaches, and muscle aches. It works by blocking enzymes that produce prostaglandins, the chemicals responsible for pain and inflammation.

Молекулярная масса

230,2590 g/mol

LogP

3,30

TPSA

46,50 Ų

Правило пяти Липинского

Соответствует

Терапевтические области

Endometriosis Cardiovascular Disease Hematology Pain Management Rheumatoid Arthritis Migraine Generalized Anxiety Disorder Multiple Sclerosis Non-Alcoholic Fatty Liver Disease Hypertension Breast Cancer Gout Chronic Pain Tuberculosis Prostate Cancer Colorectal Cancer

Классы препаратов

M — M - Musculo-Skeletal System

Механизм действия

Non-selective COX inhibitor.

Pharmacokinetics (PK)

Half-Life 12-17 hours

Pharmacodynamics (PD)

Механизм

Non-selective COX inhibitor.

2D Структура

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Cite this structure


                        

                            
                            
                        

                    

                


                
                

                    

                    

                        
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SMILES

                    
COc1ccc2cc([C@H](C)C(=O)O)ccc2c1

                

                

                
                

                    
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

                

                

                

                    
                    

                        
Molecular Formula

                        
C14H14O3

                    

                    
                    

                        
HBD / HBA

                        
1 / 3

                    

                    
                    

                        
Вращаемые Связи

                        
3

                    

                    
                    
                    

                        
Тяжёлые Атомы

                        
17

                    

                    
                

            


            
            

                
                

                    
                    

                        

                            PTGS2 (Cyclooxygenase-2)
                            Inhibitor
                        

                        
                        Primary Target
                        
                    

                    
                    

                        

                            PTGS1 (Cyclooxygenase-1)
                            Inhibitor
                        

                        
                    

                    
                    

                        

                            ABCB1 (P-glycoprotein)
                            Substrate
                        

                        
                    

                    
                

                
            


            
            

                
                

                    
                    
                        

                            

  
  Major


                            
                                Naproxen + Warfarin
                            
                        

                        
                        
Naproxen combined with warfarin increases the risk of GI and other hemorrhagic complications through additive effects on hemostasis and direct gastric mucosal damage.

                        
                    
                    
                    
                        

                            

  
  Moderate


                            
                                Naproxen + Spironolactone
                            
                        

                        
                        
NSAIDs reduce the natriuretic and diuretic efficacy of spironolactone, potentially leading to sodium retention and worsening edema or hypertension.

                        
                    
                    
                    
                        

                            

  
  Moderate


                            
                                Naproxen + Sertraline
                            
                        

                        
                        
Naproxen combined with sertraline increases the risk of upper GI bleeding through complementary impairment of platelet function and gastric mucosal defense.

                        
                    
                    
                    
                        

                            

  
  Major


                            
                                Naproxen + Apixaban
                            
                        

                        
                        
Naproxen with apixaban significantly increases GI bleeding risk through additive effects on hemostasis and direct gastric mucosal damage.

                        
                    
                    
                    
                        

                            

  
  Major


                            
                                Naproxen + Lithium Carbonate
                            
                        

                        
                        
Naproxen, like all NSAIDs, reduces renal prostaglandin synthesis, impairing lithium excretion and causing lithium toxicity.

                        
                    
                    
                    
                        

                            

  
  Major


                            
                                Naproxen + Methotrexate
                            
                        

                        
                        
NSAIDs reduce methotrexate renal elimination, raising its plasma levels and significantly increasing the risk of methotrexate toxicity (myelosuppression, mucositis, nephrotoxicity).

                        
                    
                    
                    
                        

                            

  
  Moderate


                            
                                Naproxen + Hydrochlorothiazide
                            
                        

                        
                        
Naproxen reduces the diuretic and antihypertensive efficacy of thiazide diuretics, blunting blood pressure control.

                        
                    
                    
                    
                        

                            

  
  Moderate


                            
                                Naproxen + Furosemide
                            
                        

                        
                        
Naproxen reduces the diuretic response to furosemide by inhibiting prostaglandin synthesis, potentially causing fluid retention and worsening edema or heart failure.

                        
                    
                    
                

                
            


            
            

                
                


    
    
        
    
    
    
No side effects recorded

    
    
Side effect data is not yet available for this drug.

    



                
            


            
            
            

                
Часто задаваемые вопросы

                

                    
                    

                        
                        

                            
This non-steroidal anti-inflammatory drug (NSAID) is widely used to relieve pain, reduce fever, and decrease inflammation from conditions such as arthritis, menstrual cramps, headaches, and muscle aches. It works by blocking enzymes that produce prostaglandins, the chemicals responsible for pain and inflammation.

                        

                    

                    

                    

                    
                    

                        
                        

                            
Non-selective COX inhibitor.

                        

                    

                    

                    
                    

                        
                        

                            
Key pharmacokinetic parameters for Naproxen: Half-life: 12-17 hours.

                        

                    

                    

                    

                        
                        

                            
Yes, Naproxen is an approved drug. It has reached clinical phase 4. It is classified as a Small molecule.

                        

                    

                

            

            

            
            

            
            
            

                
Related Drugs


                
                

                    
Same Drug Class

                    

                        
                        
                            Ibuprofen
                            Small molecule
                        
                        
                        
                            Celecoxib
                            Small molecule
                        
                        
                        
                            Allopurinol
                            Small molecule
                        
                        
                        
                            Colchicine
                            Small molecule
                        
                        
                    

                

                

                
                
                
            

            

            
            
{# References & Data Sources section for drug detail pages.
   Renders standard pharmacological database links plus the drug's data_sources field. #}


    
References & Data Sources

    
    
        
        
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                ChEMBL — European Bioinformatics Institute (EBI).
                CHEMBL154.
                Open-access bioactivity database.
            
        
    • 
        
        
        
  • 
            
            
                PubChem — National Center for Biotechnology Information (NCBI).
                CID 156391.
                Chemical information database.
            
        
    • 
        
        
        
        
    

    
Data aggregated from publicly available pharmacological databases. Last updated 2026-03-28.




        


        
        
    


    



    
Медицинский отказ от ответственности

    

        This content is for educational and informational purposes only. It is not a substitute for professional medical advice, diagnosis, or treatment. Always consult a qualified healthcare provider before making medication decisions.
    

    

        Data sources:
        ChEMBL,
        PubChem,
        DailyMed.