Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | 2C14H14O3.C4H10N2 |
| Molecular Weight | 546.6539 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C1CNCCN1.COC2=CC3=CC=C(C=C3C=C2)[C@H](C)C(O)=O.COC4=CC5=CC=C(C=C5C=C4)[C@H](C)C(O)=O
InChI
InChIKey=KRDCGZGYWRCHNN-NAWJVIAPSA-N
InChI=1S/2C14H14O3.C4H10N2/c2*1-9(14(15)16)10-3-4-12-8-13(17-2)6-5-11(12)7-10;1-2-6-4-3-5-1/h2*3-9H,1-2H3,(H,15,16);5-6H,1-4H2/t2*9-;/m00./s1
| Molecular Formula | C14H14O3 |
| Molecular Weight | 230.2592 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | C4H10N2 |
| Molecular Weight | 86.1356 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionSources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017581s112,018164s062,020067s019lbl.pdfCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68009288
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017581s112,018164s062,020067s019lbl.pdf
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/mesh/68009288
Naproxen (naproxen sodium, NAPROSYN®) is a propionic acid derivative related to the arylacetic acid group of nonsteroidal anti-inflammatory drugs (NSAIDs). It is an anti-inflammatory agent with analgesic and antipyretic properties. Both the acid and its sodium salt are used in the treatment of rheumatoid arthritis and other rheumatic or musculoskeletal disorders, dysmenorrhea, and acute gout. The mechanism of action of the naproxen (naproxen sodium, NAPROSYN®), like that of other NSAIDs, is not completely understood but involves inhibition of cyclooxygenase (COX-1 and COX-2).
CNS Activity
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2016/017581s112,018164s062,020067s019lbl.pdf
Curator's Comment: Naproxen is a potent inhibitor of prostaglandin synthesis in vitro. Naproxen concentrations reached during therapy have produced in vivo effects. Prostaglandins sensitize afferent nerves and potentiate the action of bradykinin in inducing pain in animal models.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL221 |
0.11 µM [IC50] | ||
Target ID: CHEMBL230 |
0.19 µM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | NAPROSYN Approved UseNAPROSYN is indicated:
For the relief of the signs and symptoms of rheumatoid arthritis.
For the relief of the signs and symptoms of osteoarthritis.
For the relief of the signs and symptoms of ankylosing spondylitis.
For the relief of the signs and symptoms of juvenile arthritis.
NAPROSYN is also indicated:
For relief of the signs and symptoms of tendonitis.
For relief of the signs and symptoms of bursitis.
For relief of the signs and symptoms of acute gout.
For the management of pain.
For the management of primary dysmenorrhea. Launch Date1.95350397E11 |
|||
| Primary | NAPROSYN Approved UseNAPROSYN is indicated:
For the relief of the signs and symptoms of rheumatoid arthritis.
For the relief of the signs and symptoms of osteoarthritis.
For the relief of the signs and symptoms of ankylosing spondylitis.
For the relief of the signs and symptoms of juvenile arthritis.
NAPROSYN is also indicated:
For relief of the signs and symptoms of tendonitis.
For relief of the signs and symptoms of bursitis.
For relief of the signs and symptoms of acute gout.
For the management of pain.
For the management of primary dysmenorrhea. Launch Date1.95350397E11 |
|||
| Primary | NAPROSYN Approved UseNAPROSYN is indicated:
For the relief of the signs and symptoms of rheumatoid arthritis.
For the relief of the signs and symptoms of osteoarthritis.
For the relief of the signs and symptoms of ankylosing spondylitis.
For the relief of the signs and symptoms of juvenile arthritis.
NAPROSYN is also indicated:
For relief of the signs and symptoms of tendonitis.
For relief of the signs and symptoms of bursitis.
For relief of the signs and symptoms of acute gout.
For the management of pain.
For the management of primary dysmenorrhea. Launch Date1.95350397E11 |
|||
| Primary | NAPROSYN Approved UseNAPROSYN is indicated:
For the relief of the signs and symptoms of rheumatoid arthritis.
For the relief of the signs and symptoms of osteoarthritis.
For the relief of the signs and symptoms of ankylosing spondylitis.
For the relief of the signs and symptoms of juvenile arthritis.
NAPROSYN is also indicated:
For relief of the signs and symptoms of tendonitis.
For relief of the signs and symptoms of bursitis.
For relief of the signs and symptoms of acute gout.
For the management of pain.
For the management of primary dysmenorrhea. Launch Date1.95350397E11 |
|||
| Primary | NAPROSYN Approved UseNAPROSYN is indicated:
For the relief of the signs and symptoms of rheumatoid arthritis.
For the relief of the signs and symptoms of osteoarthritis.
For the relief of the signs and symptoms of ankylosing spondylitis.
For the relief of the signs and symptoms of juvenile arthritis.
NAPROSYN is also indicated:
For relief of the signs and symptoms of tendonitis.
For relief of the signs and symptoms of bursitis.
For relief of the signs and symptoms of acute gout.
For the management of pain.
For the management of primary dysmenorrhea. Launch Date1.95350397E11 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
95 μg/L |
500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NAPROXEN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
94 μg/mL |
1000 mg 1 times / day steady-state, oral dose: 1000 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NAPROXEN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1446 μg × h/mL |
500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NAPROXEN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
|
1448 μg × h/mL |
1000 mg 1 times / day steady-state, oral dose: 1000 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NAPROXEN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
15 h |
500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NAPROXEN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Funbound
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1% |
500 mg 2 times / day steady-state, oral dose: 500 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
NAPROXEN plasma | Homo sapiens population: UNKNOWN age: ADULT sex: UNKNOWN food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
12.5 g single, oral Overdose Dose: 12.5 g Route: oral Route: single Dose: 12.5 g Sources: Page: 1102/129 |
healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: Page: 1102/129 |
Disc. AE: Abdominal pain, Nausea... AEs leading to discontinuation/dose reduction: Abdominal pain Sources: Page: 1102/129Nausea Dizziness Seizures Metabolic acidosis (severe) |
4 g single, oral Highest studied dose Dose: 4 g Route: oral Route: single Dose: 4 g Sources: Page: p.272 |
healthy, 20 n = 4 Health Status: healthy Age Group: 20 Sex: M Population Size: 4 Sources: Page: p.272 |
|
70.4 g single, oral Overdose Dose: 70.4 g Route: oral Route: single Dose: 70.4 g Co-administed with:: alcohol, p.o Sources: Page: p.103 |
healthy, 28 n = 1 Health Status: healthy Age Group: 28 Sex: M Population Size: 1 Sources: Page: p.103 |
Disc. AE: Sinus tachycardia, Drowsiness... AEs leading to discontinuation/dose reduction: Sinus tachycardia Sources: Page: p.103Drowsiness Metabolic acidosis Seizures |
26 g single, oral Overdose Dose: 26 g Route: oral Route: single Dose: 26 g Sources: Page: p.458 |
unhealthy, 58 n = 1 Health Status: unhealthy Condition: Depressive syndrome|Anxiety Age Group: 58 Sex: F Population Size: 1 Sources: Page: p.458 |
Disc. AE: Thrombopenia... AEs leading to discontinuation/dose reduction: Thrombopenia Sources: Page: p.458 |
550 mg 2 times / day multiple, oral Recommended Dose: 550 mg, 2 times / day Route: oral Route: multiple Dose: 550 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis Sources: Page: p.1 |
Disc. AE: Cardiac thrombosis, Myocardial infarction... AEs leading to discontinuation/dose reduction: Cardiac thrombosis (grade 3-5) Sources: Page: p.1Myocardial infarction (grade 3-5) Stroke (grade 3-5) Gastrointestinal disorder NOS (grade 3-5) Gastrointestinal bleeding (grade 3-5) Gastrointestinal ulcer (grade 3-5) Perforation stomach (grade 3-5) |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Abdominal pain | Disc. AE | 12.5 g single, oral Overdose Dose: 12.5 g Route: oral Route: single Dose: 12.5 g Sources: Page: 1102/129 |
healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: Page: 1102/129 |
| Dizziness | Disc. AE | 12.5 g single, oral Overdose Dose: 12.5 g Route: oral Route: single Dose: 12.5 g Sources: Page: 1102/129 |
healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: Page: 1102/129 |
| Nausea | Disc. AE | 12.5 g single, oral Overdose Dose: 12.5 g Route: oral Route: single Dose: 12.5 g Sources: Page: 1102/129 |
healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: Page: 1102/129 |
| Seizures | Disc. AE | 12.5 g single, oral Overdose Dose: 12.5 g Route: oral Route: single Dose: 12.5 g Sources: Page: 1102/129 |
healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: Page: 1102/129 |
| Metabolic acidosis | severe Disc. AE |
12.5 g single, oral Overdose Dose: 12.5 g Route: oral Route: single Dose: 12.5 g Sources: Page: 1102/129 |
healthy, 15 n = 1 Health Status: healthy Age Group: 15 Sex: F Population Size: 1 Sources: Page: 1102/129 |
| Drowsiness | Disc. AE | 70.4 g single, oral Overdose Dose: 70.4 g Route: oral Route: single Dose: 70.4 g Co-administed with:: alcohol, p.o Sources: Page: p.103 |
healthy, 28 n = 1 Health Status: healthy Age Group: 28 Sex: M Population Size: 1 Sources: Page: p.103 |
| Metabolic acidosis | Disc. AE | 70.4 g single, oral Overdose Dose: 70.4 g Route: oral Route: single Dose: 70.4 g Co-administed with:: alcohol, p.o Sources: Page: p.103 |
healthy, 28 n = 1 Health Status: healthy Age Group: 28 Sex: M Population Size: 1 Sources: Page: p.103 |
| Seizures | Disc. AE | 70.4 g single, oral Overdose Dose: 70.4 g Route: oral Route: single Dose: 70.4 g Co-administed with:: alcohol, p.o Sources: Page: p.103 |
healthy, 28 n = 1 Health Status: healthy Age Group: 28 Sex: M Population Size: 1 Sources: Page: p.103 |
| Sinus tachycardia | Disc. AE | 70.4 g single, oral Overdose Dose: 70.4 g Route: oral Route: single Dose: 70.4 g Co-administed with:: alcohol, p.o Sources: Page: p.103 |
healthy, 28 n = 1 Health Status: healthy Age Group: 28 Sex: M Population Size: 1 Sources: Page: p.103 |
| Thrombopenia | Disc. AE | 26 g single, oral Overdose Dose: 26 g Route: oral Route: single Dose: 26 g Sources: Page: p.458 |
unhealthy, 58 n = 1 Health Status: unhealthy Condition: Depressive syndrome|Anxiety Age Group: 58 Sex: F Population Size: 1 Sources: Page: p.458 |
| Cardiac thrombosis | grade 3-5 Disc. AE |
550 mg 2 times / day multiple, oral Recommended Dose: 550 mg, 2 times / day Route: oral Route: multiple Dose: 550 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis Sources: Page: p.1 |
| Gastrointestinal bleeding | grade 3-5 Disc. AE |
550 mg 2 times / day multiple, oral Recommended Dose: 550 mg, 2 times / day Route: oral Route: multiple Dose: 550 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis Sources: Page: p.1 |
| Gastrointestinal disorder NOS | grade 3-5 Disc. AE |
550 mg 2 times / day multiple, oral Recommended Dose: 550 mg, 2 times / day Route: oral Route: multiple Dose: 550 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis Sources: Page: p.1 |
| Gastrointestinal ulcer | grade 3-5 Disc. AE |
550 mg 2 times / day multiple, oral Recommended Dose: 550 mg, 2 times / day Route: oral Route: multiple Dose: 550 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis Sources: Page: p.1 |
| Myocardial infarction | grade 3-5 Disc. AE |
550 mg 2 times / day multiple, oral Recommended Dose: 550 mg, 2 times / day Route: oral Route: multiple Dose: 550 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis Sources: Page: p.1 |
| Perforation stomach | grade 3-5 Disc. AE |
550 mg 2 times / day multiple, oral Recommended Dose: 550 mg, 2 times / day Route: oral Route: multiple Dose: 550 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis Sources: Page: p.1 |
| Stroke | grade 3-5 Disc. AE |
550 mg 2 times / day multiple, oral Recommended Dose: 550 mg, 2 times / day Route: oral Route: multiple Dose: 550 mg, 2 times / day Sources: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Pain|Primary Dysmenorrhea| Acute Tendonitis| Acute Bursitis Sources: Page: p.1 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
Drug as perpetrator
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| yes [IC50 4.67 uM] | ||||
| yes [IC50 486 uM] | ||||
| yes [IC50 5.67 uM] | ||||
| yes [IC50 85.4 uM] |
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
| major | ||||
| minor | ||||
| minor | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes | ||||
| yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Persistent pulmonary hypertension after maternal naproxen ingestion in a term newborn: a case report. | 2000 |
|
| Simultaneous analysis of naproxen, nabumetone and its major metabolite 6-methoxy-2-naphthylacetic acid in pharmaceuticals and human urine by high-performance liquid chromatography. | 2000 Oct |
|
| Absence of pharmacokinetic interaction between orally co-administered naproxen sodium and diphenhydramine hydrochloride. | 2000 Sep |
|
| [Two complex suicidal poisonings with drugs and their medicolegal aspects]. | 2001 |
|
| Risk of upper gastrointestinal bleeding and perforation associated with low-dose aspirin as plain and enteric-coated formulations. | 2001 |
|
| Risk of ulcer soars with combination of arthritis drugs. | 2001 Apr |
|
| I'm taking over-the-counter ibuprofen every day for neck pain. Recently, my doctor gave me a prescription for naproxen for my arthritis. Should I be concerned about taking these two together? | 2001 Aug |
|
| Time and dose dependent augmentation of inhibitory effects of abciximab by aspirin. | 2001 Feb |
|
| Etoricoxib (MK-0663): preclinical profile and comparison with other agents that selectively inhibit cyclooxygenase-2. | 2001 Feb |
|
| [Drug-induced aphthae]. | 2001 Jan |
|
| Slow-release tramadol for treatment of chronic malignant pain--an open multicenter trial. | 2001 Jan |
|
| Review article: the gastrointestinal safety profile of rofecoxib, a highly selective inhibitor of cyclooxygenase-2, in humans. | 2001 Jan |
|
| A possible mechanism of naproxen-induced lipid peroxidation in rat liver microsomes. | 2001 Jul |
|
| New issues about nitric oxide and its effects on the gastrointestinal tract. | 2001 Jul |
|
| In vitro evaluation and intra-articular administration of biodegradable microspheres containing naproxen sodium. | 2001 Jul-Aug |
|
| Fixed drug eruption due to naproxen; lack of cross-reactivity with other propionic acid derivatives. | 2001 Jun |
|
| Inhibition of tendon cell proliferation and matrix glycosaminoglycan synthesis by non-steroidal anti-inflammatory drugs in vitro. | 2001 Jun |
|
| High-performance liquid chromatographic method development and validation for the simultaneous quantitation of naproxen sodium and pseudoephedrine hydrochloride impurities. | 2001 Mar |
|
| Effect of lipophilicity on in vivo iontophoretic delivery. I. NSAIDs. | 2001 Mar |
|
| Functional status and health-related quality of life of elderly osteoarthritic patients treated with celecoxib. | 2001 Mar |
|
| Synthesis, in vitro skin permeation studies, and PLS-analysis of new naproxen derivatives. | 2001 May |
|
| Stereoselective synthesis of (S)-(+)-Naproxen catalyzed by carboxyl esterase in a multicompartment electrolyzer. | 2001 May 28 |
|
| Isotachophoretic determination of naproxen in the presence of its metabolite in human serum. | 2001 May 4 |
|
| Screening procedure for detection of non-steroidal anti-inflammatory drugs and their metabolites in urine as part of a systematic toxicological analysis procedure for acidic drugs and poisons by gas chromatography-mass spectrometry after extractive methylation. | 2001 May-Jun |
Patents
Sample Use Guides
Rheumatoid Arthritis, Osteoarthritis and Ankylosing Spondylitis:
1 tablet of NAPROSYN® (250 mg or 375 mg or 500 mg) twice daily.
Acute Gout:
The recommended starting dose is 750 mg of NAPROSYN® followed by 250 mg every 8
hours until the attack has subsided.
Route of Administration:
Oral
There are data on the N-(3-methylpyridin-2-yl)amide derivatives of flurbiprofen and naproxen (Flu-AM1 and Nap-AM1, respectively) with respect to their properties towards fatty acid amide hydrolase (FAAH). Flu-AM1 and Nap-AM1 inhibited FAAH-catalysed hydrolysis of [(3)H]anandamide by rat brain homogenates with IC50 values of 0.44 and 0.74 uM. The corresponding values for flurbiprofen and naproxen were 29 and >100 uM, respectively.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 21:22:33 UTC 2022
by
admin
on
Fri Dec 16 21:22:33 UTC 2022
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| Record UNII |
R2A8B8HIPI
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| Record Status |
Validated (UNII)
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| Record Version |
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76968825
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M7769
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275-083-1
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R2A8B8HIPI
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SUB14897MIG
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C504545
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