Naproxen
Highest phase reached
Approved
Drug type
Small molecule
First approval year
1976
- First approval year
- 1976
- Listing at source
- Listed
- Highest phase reached
- Approved
- Drug type
- Small molecule
- Drug name
- Naproxen
- Molecular weight
- 230.26
- Structure (SMILES)
- COc1ccc2cc([C@H](C)C(=O)O)ccc2c1
- arthrosin 250
- Arthrosin 250
- arthrosin 250 ec
- Arthrosin 250 ec
- arthrosin 500
- Arthrosin 500
- arthrosin 500 ec
- Arthrosin 500 ec
- condrotec
- Condrotec
- ec naprosyn
- Ec-naprosyn
- feminax ultra
- Feminax ultra
- grenoxal
- Grenoxal
- kenosyn
- Kenosyn
- laraflex
- Laraflex
- napratec op
- Napratec op
- naprosyn
- Naprosyn
- naprosyn 375
And 29 more, listed on the interactive page.
- 2 naphthaleneacetic acid 6 methoxy alpha methyl s
- 2-NAPHTHALENEACETIC ACID, 6-METHOXY-.ALPHA.-METHYL-, (S)-
- naprosyn
- Naprosyn
- naprosyn 500 mg
- Naprosyn 500 mg
- Naprosyn®
- naproxen
- Naproxen
- NAPROXEN [EP MONOGRAPH]
- NAPROXEN [GREEN BOOK]
- NAPROXEN [HSDB]
- naproxen [INN]
- NAPROXEN [JAN]
- NAPROXEN [MART.]
- NAPROXEN [MI]
- NAPROXEN [ORANGE BOOK]
- NAPROXEN [USAN]
- NAPROXEN [USP MONOGRAPH]
- NAPROXEN [USP-RS]
- NAPROXEN [VANDF]
- Naproxen [WHO-DD]
- naproxen component of pn400
- NAPROXEN COMPONENT OF PN400
- naproxen ep monograph
And 26 more, listed on the interactive page.
- CAS registry numbers
- 22204-53-1
- ChEMBL ID
- CHEMBL154
- InChIKey
- CMWTZPSULFXXJA-VIFPVBQESA-N
- PubChem compound IDs
- 156391
- RxNorm IDs (RxCUI)
- 7258
- FDA ingredient codes (UNII)
- 57Y76R9ATQ
- G02CC02
- M01AE02
- M02AA12
Sources for recorded values
- Applicant
- ATNAHS PHARMA US
- Approval date
- 23 Mar 1987
- Application number
- NDA018965
- First in class
- No
- Orphan designation
- No
- Availability
- Over the counter
- Boxed warning
- Yes
- Pharmacology name
- naproxen
- Type
- Synthetic organic
- Approval recorded by Guide to Pharmacology
- Yes
Administration routes
- Oral
- Action
- Inhibition
- Action type
- Inhibitor
- Target
- COX-1
- Gene symbol
- PTGS1
- Protein identifier
- P23219
- Median affinity
- 5.49
- Affinity units
- pIC50
- Primary target
- Yes
- Action
- Inhibition
- Action type
- Inhibitor
- Target
- COX-2
- Gene symbol
- PTGS2
- Protein identifier
- P35354
- Median affinity
- 5.6
- Affinity units
- pIC50
- Primary target
- Yes
- Mechanism
- Cyclooxygenase inhibitor
- Action type
- Inhibitor
- Target
- Cyclooxygenase
- Protein identifier
- P23219
- Mechanism
- Cyclooxygenase inhibitor
- Action type
- Inhibitor
- Target
- Cyclooxygenase
- Protein identifier
- P35354
Open Targets mechanisms
- Mechanism
- Cyclooxygenase inhibitor
- Action type
- Inhibitor
- Target
- Cyclooxygenase
- Action type
- Inhibitor
- Gene symbol
- PTGS1
- Protein identifier
- P23219
- Organism
- Homo sapiens
- Target development level
- Clinical
- Action type
- Inhibitor
- Gene symbol
- PTGS2
- Protein identifier
- P35354
- Organism
- Homo sapiens
- Target development level
- Clinical
- Condition
- Wounds and Injuries
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000546
- Subject identifier
- D014947
- Condition
- Prostatic Neoplasms
- Highest recorded phase
- 2
- Condition identifier
- EFO:0000673
- Subject identifier
- D011471
- Condition
- Arthritis, Rheumatoid
- Highest recorded phase
- 4
- Condition identifier
- EFO:0000685
- Subject identifier
- D001172
- Condition
- Arthritis, Juvenile
- Highest recorded phase
- 4
- Condition identifier
- EFO:0002609
- Subject identifier
- D001171
- Condition
- Pain
- Highest recorded phase
- 4
- Condition identifier
- EFO:0003843
- Subject identifier
- D010146
- Condition
- Acute Pain
- Highest recorded phase
- 4
- Condition identifier
- EFO:0003843
- Subject identifier
- D059787
- Condition
- Spondylitis, Ankylosing
- Highest recorded phase
- 4
- Condition identifier
- EFO:0003898
- Subject identifier
- D013167
- Condition
- Gout
- Highest recorded phase
- 4
- Condition identifier
- EFO:0004274
- Subject identifier
- D006073
- Condition
- Arthritis, Gouty
- Highest recorded phase
- 4
- Condition identifier
- EFO:0004274
- Subject identifier
- D015210
- Condition
- Duodenal Ulcer
- Highest recorded phase
- 2
- Condition identifier
- EFO:0004607
- Subject identifier
- D004381
- Condition
- Osteoarthritis, Knee
- Highest recorded phase
- 3
- Condition identifier
- EFO:0004616
- Subject identifier
- D020370
- Condition
- Rheumatic Diseases
- Highest recorded phase
- 4
- Condition identifier
- EFO:0005755
- Subject identifier
- D012216
- Condition
- Vaginitis
- Highest recorded phase
- 4
- Condition identifier
- EFO:0005757
- Subject identifier
- D014627
- Condition
- Neuralgia
- Highest recorded phase
- 2
- Condition identifier
- EFO:0005762
- Subject identifier
- D009437
- Condition
- Arthritis
- Highest recorded phase
- 4
- Condition identifier
- EFO:0005856
- Subject identifier
- D001168
- Condition
- Common Cold
- Highest recorded phase
- 4
- Condition identifier
- EFO:0007214
- Subject identifier
- D003139
- Condition
- Stomach Ulcer
- Highest recorded phase
- 4
- Condition identifier
- EFO:0009454
- Subject identifier
- D013276
- Condition
- Pleural Effusion
- Highest recorded phase
- 2
- Condition identifier
- EFO:0009637
- Subject identifier
- D010996
- Condition
- Muscle Cramp
- Highest recorded phase
- 4
- Condition identifier
- EFO:0009846
- Subject identifier
- D009120
- Condition
- Toothache
- Highest recorded phase
- 4
- Condition identifier
- EFO:0010072
- Subject identifier
- D014098
- Condition
- Osteoarthritis, Hip
- Highest recorded phase
- 3
- Condition identifier
- EFO:1000786
- Subject identifier
- D015207
- Condition
- Fever
- Highest recorded phase
- 4
- Condition identifier
- HP:0001945
- Subject identifier
- D005334
- Condition
- Headache
- Highest recorded phase
- 4
- Condition identifier
- HP:0002315
- Subject identifier
- D006261
- Condition
- Arthralgia
- Highest recorded phase
- 4
- Condition identifier
- HP:0002829
- Subject identifier
- D018771
- Condition
- Myalgia
- Highest recorded phase
- 4
- Condition identifier
- HP:0003326
- Subject identifier
- D063806
And 16 more, listed on the interactive page.
- Condition identifier
- EFO_0000546
- Highest recorded phase
- 2
- Condition identifier
- EFO_0000685
- Condition identifier
- EFO_0001065
- Condition identifier
- EFO_0002609
- Condition identifier
- EFO_0003898
- Condition identifier
- EFO_0004274
- Condition identifier
- EFO_0004607
- Highest recorded phase
- 2
- Condition identifier
- EFO_0004616
- Highest recorded phase
- 3
- Condition identifier
- EFO_0005279
- Highest recorded phase
- 1
- Condition identifier
- EFO_0005755
- Condition identifier
- EFO_0005757
- Condition identifier
- EFO_0005757
- Highest recorded phase
- 4
- Condition identifier
- EFO_0005762
- Highest recorded phase
- 2
- Condition identifier
- EFO_0005856
- Condition identifier
- EFO_0007214
- Condition identifier
- EFO_0009454
- Condition identifier
- EFO_0009760
- Condition identifier
- EFO_0009846
- Condition identifier
- EFO_0009846
- Highest recorded phase
- 4
- Condition identifier
- EFO_0010072
- Condition identifier
- EFO_0010072
- Highest recorded phase
- 4
- Condition identifier
- EFO_0022861
- Highest recorded phase
- 2
- Condition identifier
- EFO_1001412
- Highest recorded phase
- 1
- Condition identifier
- EFO_1001801
- Condition identifier
- EFO_1001896
And 78 more, listed on the interactive page.
- Warning
- Black Box Warning
- Effect
- cardiotoxicity
- Warning
- Black Box Warning
- Effect
- gastrointestinal toxicity
- Warning
- Black Box Warning
- Effect
- neurotoxicity
- Warning
- Black Box Warning
- Effect
- cardiotoxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- gastrointestinal toxicity
- Country
- United States
- Warning
- Black Box Warning
- Effect
- neurotoxicity
- Country
- United States
- Event
- abdominal discomfort
- Reports
- 440
- Reporting signal score
- 431.818
- Event
- abdominal pain
- Reports
- 437
- Reporting signal score
- 165.523
- Event
- abdominal pain upper
- Reports
- 414
- Reporting signal score
- 286.673
- Event
- acne cystic
- Reports
- 44
- Reporting signal score
- 141.273
- Event
- acute kidney injury
- Reports
- 502
- Reporting signal score
- 362.433
- Event
- adrenal insufficiency
- Reports
- 130
- Reporting signal score
- 223.182
- Event
- angioedema
- Reports
- 219
- Reporting signal score
- 159.11
- Event
- arthralgia
- Reports
- 646
- Reporting signal score
- 279.219
- Event
- arthropathy
- Reports
- 414
- Reporting signal score
- 648.131
- Event
- body height below normal
- Reports
- 83
- Reporting signal score
- 317.383
- Event
- bone density decreased
- Reports
- 81
- Reporting signal score
- 148.835
- Event
- c-reactive protein abnormal
- Reports
- 211
- Reporting signal score
- 622.23
- Event
- c-reactive protein increased
- Reports
- 204
- Reporting signal score
- 215.696
- Event
- condition aggravated
- Reports
- 592
- Reporting signal score
- 308.437
- Event
- deafness transitory
- Reports
- 100
- Reporting signal score
- 402.581
- Event
- disability
- Reports
- 87
- Reporting signal score
- 170.874
- Event
- dizziness
- Reports
- 690
- Reporting signal score
- 210.906
- Event
- drug hypersensitivity
- Reports
- 977
- Reporting signal score
- 863.487
- Event
- drug intolerance
- Reports
- 538
- Reporting signal score
- 597.014
- Event
- duodenal ulcer
- Reports
- 165
- Reporting signal score
- 349.214
- Event
- duodenal ulcer haemorrhage
- Reports
- 94
- Reporting signal score
- 239.107
- Event
- duodenal ulcer perforation
- Reports
- 86
- Reporting signal score
- 213.678
- Event
- ear infection
- Reports
- 166
- Reporting signal score
- 257.062
- Event
- faeces discoloured
- Reports
- 133
- Reporting signal score
- 189.271
- Event
- femur fracture
- Reports
- 170
- Reporting signal score
- 211.69
And 44 more, listed on the interactive page.
- NCT00004845
- NCT00034853
- NCT00279747
- NCT00652925
- NCT00807846
- NCT01358383
- NCT01544114
- NCT00157872
- NCT00346216
- NCT00626275
- NCT00650455
- NCT00959439
- NCT02451748
- NCT00175032
- NCT00367211
- NCT00392080
- NCT00418782
- NCT00435292
- NCT00504127
- NCT00542555
- NCT00648258
- NCT00652808
- NCT00664560
- NCT00665431
- NCT00665743
And 71 more, listed on the interactive page.
- Dose
- 1 capsule
- How often
- Every 8 to 12 hours
- Do not exceed 2 capsules in any 8 to 12-hour period
- Do not exceed 3 capsules in 24 hours
- Drink a full glass of water with each dose
- For the first dose, you may take 2 capsules within the first hour
- If taken with food, it may take longer to work
- Hydrogen bond acceptors
- 2
- Hydrogen bond donors
- 1
- Polar surface area
- 46.53
- Calculated partition coefficient (ALogP)
- 3.04
- Calculated partition coefficient (XLogP)
- 3.3
- Prodrug
- No
- Chirality
- Single enantiomer
- Inorganic
- No
- Rule-of-five violations
- 0
- Rotatable bonds
- 3
- Heavy atoms
- 17
- Molecular formula
- C14H14O3
- Monoisotopic mass
- 230.094294304
- Natural product
- Yes
- 0054-3630
- 0615-8094
- 11534-211
- 11534-212
- 25000-138
- 25000-139
- 25000-140
- 27241-202
- 27241-203
- 31722-682
- 42192-619
- 42494-453
- 42494-454
- 42708-043
- 42708-140
- 43063-600
- 43063-650
- 43063-920
- 43353-211
- 43353-216
- 43353-218
- 45865-238
- 49483-617
- 49483-618
- 49483-619
And 169 more, listed on the interactive page.
- Recorded assays
- 5,015
- Active assays
- 57
- Confirmatory
- Other
- Summary
- Anti-Inflammatory Agents, Non-Steroidal
- Gout Suppressants
- Cyclooxygenase Inhibitors
Distribution coefficient (LogD)
- Median
- 1.09
- Mean
- 1.42
- Minimum
- 0.2
- Maximum
- 3.3
- Unit
- unitless
- Assays
- 4
- Standard deviation
- 1.32232
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- LogD
Solubility
- Median
- 20,860
- Mean
- 21,156
- Minimum
- 3,580
- Maximum
- 40,930
- Unit
- ug/mL
- Assays
- 20
- Standard deviation
- 12,066
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- Solubility
Oral bioavailability
- Median
- 100
- Mean
- 100
- Minimum
- 100
- Maximum
- 100
- Unit
- %
- Assays
- 1
- Standard deviation
- 0
- Summary method
- median
- Censored results excluded
- 0
- Other units excluded
- 0
- Unknown units excluded
- 0
Measurement types
- F
Related records
Trials (197)
- A Clinical Study to Investigate the Effect on Pain Relief of a Single Dose of JNJ-39439335 in Patients With Chronic Osteoarthritis Pain of the Knee
- A Clinical Trial to Compare Safety and Effectiveness for Relieving Tenderness of 10% Naproxen Gel vs. a 2.32% Diclofenac Diethylamine Gel in the Treatment of Strains and Bruises of the Legs.
- A Comparison of Safety and Treatment in Subjects With Osteoarthritis Taking Low Dose Aspirin
- A Double-Blind, Double Dummy, Randomized Comparison Study Of The Efficacy And Safety Of Valdecoxib 10mg Once Daily And Naproxen 500mg Twice Daily In Treating The Signs And Symptoms Of Osteoarthritis Of The Knee Or Hip In Taiwan
- A Multicenter Trial of Rofecoxib and Naproxen in Alzheimer's Disease (NSAID Study)
- A Multiple Dose Study to Evaluate the Safety, Tolerability, Pharmacokinetics, and Pharmacodynamics of JNJ-39439335 in Patients With Osteoarthritis
- A One Year Double-blind Trial to Investigate the Efficacy and Safety of Meloxicam Oral Suspension in Juvenile Rheumatoid Arthritis (JRA/JIA)
- A Pharmacokinetic (PK) Study Evaluating Naproxen and Esomeprazole Plasma Levels
- A Phase IIa Randomized, Double-Blinded Clinical Trial of Naproxen or Aspirin for Cancer Immune Interception in Lynch Syndrome
- A Proof-of-Concept Study Assessing NEO6860 in Osteoarthritis Pain
- A Randomized Controlled Trial of Oral Naproxen and Transdermal Estradiol for Bleeding in LNG-IUC
- A Randomized Study of Three Medication Regimens for Acute Low Back Pain
- A Safety and Effectiveness Study of Acetaminophen (4000 mg/Day) and Naproxen (750 mg/Day) in the Treatment of Osteoarthritis of the Hip or Knee
- A Safety Trial to Compare Different Analgesics in Combination With Low Dose Aspirin to Study Their Bleeding Properties and Their Effects on the Stomach
- A Study of ABT-652 in Adults With Osteoarthritis Pain of the Knee
- A Study of Tanezumab in Adults With Chronic Low Back Pain
- A Study Of The Effect Of CE-224535 On Knee OA (Osteoarthritis) Pain
- A Study Of The Effect Of CJ-023,423 On The Incidence Of Stomach Ulcers
- A Study Of The Safety And Efficacy Of PF-04191834 In Patients With Osteoarthritis Of The Knee
- A Study To Assess The Ability Of Tramadol, Naproxen And Oxycodone To Affect The Pain Thresholds Of Patients With Osteoarthritis Of The Thumb
Approved for (14)
- Ankylosing spondylitis
- Arthritic joint disease
- Bursitis
- Common cold
- Dysmenorrhea
- Gastric ulcer
- Gout
- Juvenile idiopathic arthritis
- Osteoarthritis
- Rheumatic disorder
- Rheumatoid arthritis
- Spondylitis
- Tendinitis
- Vaginitis
In development for (17)
- Alzheimer disease Phase 2
- Breast cancer Phase 2
- COVID-19 Phase 3
- Duodenal ulcer Phase 2
- Injury Phase 2
- Lynch syndrome Phase 1
- Migraine disorder Phase 3
- Multiple sclerosis Phase 3
- Neuralgia Phase 2
- Osteoarthritis, hip Phase 3
- Osteoarthritis, knee Phase 3
- Peptic ulcer disease Phase 3
- Prostate adenocarcinoma Phase 2
- Prostate cancer Phase 2
- Temporomandibular joint disorder Phase 1
- Tibial muscular dystrophy Phase 1
- Transient myeloproliferative syndrome Phase 1