naproxen indications/contra

Stem definitionDrug idCAS RN
1883 22204-53-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • methoxypropiocin
  • naproxen
  • naprosyn
  • aproxen
  • naproxen sodium
  • aleve
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.
  • Molecular weight: 230.26
  • Formula: C14H14O3
  • CLOGP: 2.82
  • LIPINSKI: 0
  • HAC: 3
  • HDO: 1
  • TPSA: 46.53
  • ALOGS: -3.65
  • ROTB: 3

Drug dosage:

DoseUnitRoute
0.50 g O
0.50 g R
0.50 g O

Approvals:

DateAgencyCompanyOrphan
March 11, 1976 FDA ROCHE PALO

FDA Adverse Event Reporting System

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MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Drug hypersensitivity 2229.49 26.20 716 7218 34964 3342961
Completed suicide 1562.62 26.20 531 7403 30583 3347342
Gastrointestinal haemorrhage 1217.26 26.20 415 7519 23959 3353966
Acute kidney injury 1114.62 26.20 471 7463 49212 3328713
Toxicity to various agents 880.25 26.20 393 7541 46661 3331264
Gastric ulcer 790.16 26.20 206 7728 4579 3373346
Nausea 665.37 26.20 461 7473 129184 3248741
Haematemesis 653.74 26.20 192 7742 6693 3371232
Gastric haemorrhage 648.29 26.20 164 7770 3212 3374713
Upper gastrointestinal haemorrhage 628.51 26.20 166 7768 3877 3374048
Dizziness 610.20 26.20 360 7574 76152 3301773
Melaena 607.75 26.20 184 7750 7128 3370797
Duodenal ulcer 594.68 26.20 144 7790 2334 3375591
Vomiting 555.50 26.20 359 7575 89172 3288753
Haemoglobin decreased 551.75 26.20 249 7685 30045 3347880
Drug ineffective 525.29 26.20 383 7551 115707 3262218
Abdominal discomfort 453.95 26.20 189 7745 18695 3359230
Abdominal pain 438.15 26.20 244 7690 45981 3331944
Pain 416.03 26.20 276 7658 71281 3306644
Anaemia 393.74 26.20 241 7693 54092 3323833
Faeces discoloured 386.43 26.20 113 7821 3859 3374066
Gastritis 377.88 26.20 125 7809 6452 3371473
Overdose 373.42 26.20 198 7736 33780 3344145
Abdominal pain upper 372.88 26.20 179 7755 24737 3353188
Dyspnoea 368.41 26.20 296 7638 102638 3275287
Intentional overdose 367.75 26.20 153 7781 15072 3362853
Respiratory arrest 349.72 26.20 136 7798 11232 3366693
Rheumatoid arthritis 343.81 26.20 147 7787 15491 3362434
Cardiac arrest 327.97 26.20 169 7765 27150 3350775
Urticaria 325.66 26.20 171 7763 28556 3349369

Pharmacologic Action:

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SourceCodeDescription
ATC G02CC02 GENITO URINARY SYSTEM AND SEX HORMONES
OTHER GYNECOLOGICALS
OTHER GYNECOLOGICALS
Antiinflammatory products for vaginal administration
ATC M01AE02 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Propionic acid derivatives
ATC M02AA12 MUSCULO-SKELETAL SYSTEM
TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
Antiinflammatory preparations, non-steroids for topical use
ATC M01AE52 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Propionic acid derivatives
ATC M01AE56 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Propionic acid derivatives
FDA Chemical/Ingredient N0000175721 Nonsteroidal Anti-inflammatory Compounds
FDA EPC N0000175722 Nonsteroidal Anti-inflammatory Drug
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D018501 Antirheumatic Agents
MeSH PA D016861 Cyclooxygenase Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D006074 Gout Suppressants
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents

Drug Use (View source of the data)

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DiseaseRelationSNOMED_IDDOID
Sinus headache indication 4969004
Ankylosing spondylitis indication 9631008 DOID:7147
Pain indication 22253000
Toothache indication 27355003
Tendinitis indication 34840004 DOID:971
Migraine indication 37796009 DOID:6364
Joint pain indication 57676002
Nasal discharge indication 64531003
Muscle pain indication 68962001
Rheumatoid arthritis indication 69896004 DOID:7148
Bursitis indication 84017003 DOID:2965
Gout indication 90560007 DOID:13189
Headache disorder indication 230461009
Dysmenorrhea indication 266599000
Fever indication 386661006
Osteoarthritis indication 396275006 DOID:381
Juvenile rheumatoid arthritis indication 410795001
Tachyarrhythmia contraindication 6285003
Alcoholism contraindication 7200002
Hypercholesterolemia contraindication 13644009
Myocardial infarction contraindication 22298006 DOID:5844
Hypovolemia contraindication 28560003
Hyperthyroidism contraindication 34486009 DOID:7998
Hypertensive disorder contraindication 38341003 DOID:10763
Gastrointestinal ulcer contraindication 40845000
Body fluid retention contraindication 43498006
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Gastrointestinal perforation contraindication 51875005
Coronary arteriosclerosis contraindication 53741008 DOID:3393
Hemiplegic migraine contraindication 59292006
Hepatic failure contraindication 59927004
Blood coagulation disorder contraindication 64779008 DOID:1247
Osteoporosis contraindication 64859006 DOID:11476
Diabetes mellitus contraindication 73211009 DOID:9351
Gastrointestinal hemorrhage contraindication 74474003
Vascular insufficiency of intestine contraindication 82196007
Atrophic gastritis contraindication 84568007 DOID:8929
Epilepsy contraindication 84757009 DOID:1826
Prinzmetal angina contraindication 87343002
Kidney disease contraindication 90708001 DOID:2527
Fracture of bone contraindication 125605004
Liver function tests abnormal contraindication 166603001
Hypomagnesemia contraindication 190855004
Angina pectoris contraindication 194828000
Cerebrovascular accident contraindication 230690007 DOID:6713
Coronary artery bypass graft contraindication 232717009
Disease of liver contraindication 235856003 DOID:409
Transient ischemic attack contraindication 266257000 DOID:224
Esophageal dysmotility contraindication 266434009 DOID:9192
Benign prostatic hyperplasia contraindication 266569009 DOID:2883
Edema contraindication 267038008
Retention of urine contraindication 267064002
Anemia contraindication 271737000 DOID:2355
Cerebral ischemia contraindication 287731003
Pregnancy, function contraindication 289908002
Thromboembolic disorder contraindication 371039008
Serotonin syndrome contraindication 371089000
Angle-closure glaucoma contraindication 392291006 DOID:13550
Cardiovascular event risk contraindication 395112001
Peripheral vascular disease contraindication 400047006
Disorder of coronary artery contraindication 414024009
Myocardial ischemia contraindication 414795007 DOID:3393
Obesity contraindication 414916001 DOID:9970
Hypertensive urgency contraindication 443482000
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

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Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.36 acidic

Orange Book patent data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
375MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 6369085 May 25, 2018 RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER
375MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 7411070 May 25, 2018 RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER
500MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 6369085 May 25, 2018 RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER
500MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 7411070 May 25, 2018 RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER
375MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 7745466 Oct. 13, 2018 RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER
500MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 7745466 Oct. 13, 2018 RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER
375MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 8852636 May 31, 2022 RELIEF OF SIGNS AND SYMPTOMS OF ARTHRITIS AND RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER
375MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 8858996 May 31, 2022 RELIEF OF SIGNS AND SYMPTOMS OF ARTHRITIS AND RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER
375MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 9161920 May 31, 2022 RISK-REDUCTION OF NSAID GASTRIC ULCER IN PATIENTS REQUIRING CHRONIC NSAID TREATMENT
375MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 9198888 May 31, 2022 RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER IN PATIENTS REQUIRING NSAID TREATMENT
500MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 8852636 May 31, 2022 RELIEF OF SIGNS AND SYMPTOMS OF ARTHRITIS AND RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER
500MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 8858996 May 31, 2022 RELIEF OF SIGNS AND SYMPTOMS OF ARTHRITIS AND RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER
500MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 9161920 May 31, 2022 RISK-REDUCTION OF NSAID GASTRIC ULCER IN PATIENTS REQUIRING CHRONIC NSAID TREATMENT
500MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 9198888 May 31, 2022 RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER IN PATIENTS REQUIRING NSAID TREATMENT
375MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 6926907 Feb. 28, 2023 RELIEF OF SIGNS AND SYMPTOMS OF ARTHRITIS AND RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER
500MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 6926907 Feb. 28, 2023 RELIEF OF SIGNS AND SYMPTOMS OF ARTHRITIS AND RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER
500MG TREXIMET PERNIX IRELAND LTD N021926 April 15, 2008 RX TABLET ORAL 7332183 Oct. 2, 2025 TREATMENT OF MIGRAINE
60MG TREXIMET PERNIX IRELAND LTD N021926 May 14, 2015 RX TABLET ORAL 7332183 Oct. 2, 2025 ACUTE TREATMENT OF MIGRAINE
375MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 9393208 Sept. 3, 2029 RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER IN PATIENTS REQUIRING NSAID TREATMENT
500MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 9393208 Sept. 3, 2029 RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER IN PATIENTS REQUIRING NSAID TREATMENT
500MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 9220698 March 10, 2031 RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCER IN PATIENTS REQUIRING NSAID TREATMENT
375MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 8945621 Oct. 17, 2031 RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCERS IN PATIENTS ALSO TAKING LOW DOSE ASPIRIN
500MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL 8945621 Oct. 17, 2031 RISK-REDUCTION OF NSAID-ASSOCIATED GASTRIC ULCERS IN PATIENTS ALSO TAKING LOW DOSE ASPIRIN

Orange Book exclusivity data (new drug applications)

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Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
60MG TREXIMET PERNIX IRELAND LTD N021926 May 14, 2015 RX TABLET ORAL May 14, 2018 NEW PRODUCT
60MG TREXIMET PERNIX IRELAND LTD N021926 May 14, 2015 RX TABLET ORAL Nov. 14, 2018 PEDIATRIC EXCLUSIVITY
375MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL July 6, 2020 NEW PATIENT POPULATION
500MG VIMOVO HORIZON PHARMA USA N022511 April 30, 2010 RX TABLET, DELAYED RELEASE ORAL July 6, 2020 NEW PATIENT POPULATION

Bioactivity Summary:

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TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Prostaglandin G/H synthase 2 Enzyme INHIBITOR IC50 5.60 CHEMBL CHEMBL
Prostaglandin G/H synthase 1 Enzyme INHIBITOR IC50 5.16 WOMBAT-PK CHEMBL
Aldo-keto reductase family 1 member C2 Enzyme IC50 4.50 CHEMBL
Aldo-keto reductase family 1 member C3 Enzyme IC50 6.32 CHEMBL
Hormone-sensitive lipase Enzyme IC50 5.92 CHEMBL
Prostaglandin-H2 D-isomerase Enzyme IC50 4.89 CHEMBL
Cyclooxygenase Enzyme IC50 7.22 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 6.74 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 4.96 CHEMBL

External reference:

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IDSource
5230 IUPHAR_LIGAND_ID
4018847 VUID
N0000147149 NUI
C0027396 UMLSCUI
D00118 KEGG_DRUG
57Y76R9ATQ UNII
2979 INN_ID
DB00788 DRUGBANK_ID
CHEMBL154 ChEMBL_ID
156391 PUBCHEM_CID
4018847 VANDF
2111 MMSL
7258 RXNORM
11847009 SNOMEDCT_US
372588000 SNOMEDCT_US
5155 MMSL
d00019 MMSL
N0000007352 NDFRT
N0000147149 NDFRT
002380 NDDF
26159-34-2 SECONDARY_CAS_RN
CHEBI:59527 CHEBI
CHEMBL1200806 ChEMBL_ID
D009288 MESH_DESCRIPTOR_UI
NPS PDB_CHEM_ID

Pharmaceutical products:

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ProductCategoryIngredientsNDCFormQuantityRoute MarketingLabel
Anaprox DS HUMAN PRESCRIPTION DRUG LABEL 1 0004-6203 TABLET 550 mg ORAL NDA 15 sections
Naprosyn HUMAN PRESCRIPTION DRUG LABEL 1 0004-6316 TABLET 500 mg ORAL NDA 15 sections
EC-Naprosyn HUMAN PRESCRIPTION DRUG LABEL 1 0004-6415 TABLET, DELAYED RELEASE 375 mg ORAL NDA 15 sections
EC-Naprosyn HUMAN PRESCRIPTION DRUG LABEL 1 0004-6416 TABLET, DELAYED RELEASE 500 mg ORAL NDA 15 sections
Naproxen HUMAN PRESCRIPTION DRUG LABEL 1 0093-1005 TABLET, DELAYED RELEASE 375 mg ORAL ANDA 19 sections
Naproxen HUMAN PRESCRIPTION DRUG LABEL 1 0093-1006 TABLET, DELAYED RELEASE 500 mg ORAL ANDA 19 sections
Good Sense Naproxen Sodium HUMAN OTC DRUG LABEL 1 0113-0901 TABLET 220 mg ORAL ANDA 9 sections
sinus and cold d HUMAN OTC DRUG LABEL 2 0113-2417 TABLET, FILM COATED 220 mg ORAL ANDA 8 sections
Good Sense Naproxen Sodium HUMAN OTC DRUG LABEL 1 0113-4368 TABLET, FILM COATED 220 mg ORAL ANDA 9 sections
Basic Care Naproxen Sodium HUMAN OTC DRUG LABEL 1 0113-7368 TABLET, FILM COATED 220 mg ORAL ANDA 9 sections
Naproxen HUMAN PRESCRIPTION DRUG LABEL 1 0143-1346 TABLET 250 mg ORAL ANDA 15 sections
Naproxen HUMAN PRESCRIPTION DRUG LABEL 1 0143-1347 TABLET 375 mg ORAL ANDA 15 sections
Naproxen HUMAN PRESCRIPTION DRUG LABEL 1 0143-1348 TABLET 500 mg ORAL ANDA 15 sections
NAPROXEN HUMAN PRESCRIPTION DRUG LABEL 1 0143-9908 TABLET, FILM COATED 550 mg ORAL ANDA 14 sections
NAPROXEN HUMAN PRESCRIPTION DRUG LABEL 1 0143-9916 TABLET, FILM COATED 275 mg ORAL ANDA 14 sections
TREXIMET HUMAN PRESCRIPTION DRUG LABEL 2 0173-0750 TABLET, FILM COATED 500 mg ORAL NDA 16 sections
Naproxen HUMAN PRESCRIPTION DRUG LABEL 1 0179-1978 TABLET 500 mg ORAL ANDA 15 sections
Menstridol HUMAN OTC DRUG LABEL 1 0280-0270 TABLET 220 mg ORAL NDA 10 sections
Aleve PM HUMAN OTC DRUG LABEL 2 0280-1200 TABLET, FILM COATED 220 mg ORAL NDA 9 sections
Aleve HUMAN OTC DRUG LABEL 1 0280-6000 TABLET 220 mg ORAL NDA 10 sections
Aleve HUMAN OTC DRUG LABEL 1 0280-6010 TABLET 220 mg ORAL NDA 10 sections
Aleve HUMAN OTC DRUG LABEL 1 0280-6020 TABLET, COATED 220 mg ORAL NDA 10 sections
Aleve-D Sinus and Headache HUMAN OTC DRUG LABEL 2 0280-6045 TABLET 220 mg ORAL ANDA 16 sections
Aleve HUMAN OTC DRUG LABEL 1 0280-6050 TABLET 220 mg ORAL NDA 10 sections
Aleve HUMAN OTC DRUG LABEL 1 0280-6060 TABLET 220 mg ORAL NDA 10 sections
Aleve HUMAN OTC DRUG LABEL 1 0280-6070 TABLET, COATED 220 mg ORAL NDA 10 sections
Aleve HUMAN OTC DRUG LABEL 1 0280-6080 CAPSULE, LIQUID FILLED 220 mg ORAL NDA 10 sections
Aleve-D Sinus and Cold HUMAN OTC DRUG LABEL 2 0280-6090 TABLET 220 mg ORAL ANDA 17 sections
Aleve HUMAN OTC DRUG LABEL 1 0280-6091 CAPSULE, LIQUID FILLED 220 mg ORAL NDA 10 sections
Aleve Back and Muscle Pain HUMAN OTC DRUG LABEL 1 0280-6092 TABLET 220 mg ORAL NDA 17 sections