indomethacin Indications/Contra | FAERs | Orange Book | BioActivity |

Stem definitionDrug idCAS RN
anti-inflammatory, indometacin derivatives 1440 53-86-1

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • indomethacin hydrochloride
  • indomethacin HCl
  • indocin
  • indomethacin
  • indometacine
  • indomethacine
  • indometacin
  • indomethacin sodium
A non-steroidal anti-inflammatory agent (NSAID) that inhibits CYCLOOXYGENASE, which is necessary for the formation of PROSTAGLANDINS and other AUTACOIDS. It also inhibits the motility of POLYMORPHONUCLEAR LEUKOCYTES.
  • Molecular weight: 357.79
  • Formula: C19H16ClNO4
  • CLOGP: 4.18
  • LIPINSKI: 0
  • HAC: 5
  • HDO: 1
  • TPSA: 68.53
  • ALOGS: -5.17
  • ROTB: 4

Drug dosage:

DoseUnitRoute
0.10 g O
0.10 g P
0.10 g R
0.10 g O
0.10 g R

Approvals:

DateAgencyCompanyOrphan
June 10, 1965 FDA

FDA Adverse Event Reporting System

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 888.93 39.01 281 1785 68119 4568807
Retinopathy of prematurity 446.40 39.01 63 2003 220 4636706
Premature baby 325.40 39.01 85 1981 9966 4626960
Foetal exposure during pregnancy 316.68 39.01 100 1966 23069 4613857
Acute kidney injury 308.18 39.01 131 1935 70300 4566626
Necrotising colitis 254.42 39.01 43 2023 576 4636350
Drug ineffective 247.67 39.01 155 1911 185906 4451020
Ductus arteriosus premature closure 238.25 39.01 34 2032 130 4636796
Gastrointestinal haemorrhage 163.85 39.01 66 2000 30469 4606457
Neck deformity 156.42 39.01 23 2043 113 4636813
Exposure during pregnancy 155.57 39.01 65 2001 32906 4604020
Vomiting 131.70 39.01 89 1977 119610 4517316
Intraventricular haemorrhage neonatal 130.09 39.01 20 2046 139 4636787
Neck mass 128.03 39.01 24 2042 592 4636334
Ductus arteriosus stenosis foetal 127.95 39.01 20 2046 157 4636769
Anti-cyclic citrullinated peptide antibody positive 126.82 39.01 21 2045 245 4636681
Neonatal disorder 116.18 39.01 23 2043 761 4636165
Bronchopulmonary dysplasia 113.87 39.01 20 2046 338 4636588
Bone density abnormal 113.13 39.01 21 2045 490 4636436
Periventricular leukomalacia 113.01 39.01 17 2049 100 4636826
Melaena 111.16 39.01 37 2029 9921 4627005
Maternal exposure during pregnancy 109.26 39.01 42 2024 17051 4619875
Tricuspid valve incompetence 103.65 39.01 27 2039 3087 4633839
Neonatal respiratory distress syndrome 103.17 39.01 24 2042 1717 4635209
Metabolic acidosis 99.34 39.01 36 2030 12404 4624522
Disability 96.23 39.01 22 2044 1457 4635469
Rheumatoid factor positive 91.63 39.01 18 2048 571 4636355
Premature delivery 91.23 39.01 26 2040 4158 4632768
Hyperkalaemia 90.88 39.01 36 2030 15801 4621125
Nausea 90.66 39.01 84 1982 177249 4459677
Hydrops foetalis 86.64 39.01 15 2051 232 4636694
Rheumatoid arthritis 84.34 39.01 39 2027 24960 4611966
Maternal drugs affecting foetus 83.57 39.01 24 2042 3941 4632985
Arthralgia 80.50 39.01 57 2009 81937 4554989
Gastric haemorrhage 77.31 39.01 23 2043 4271 4632655
Treatment failure 77.12 39.01 31 2035 14116 4622810
Asthenia 75.69 39.01 56 2010 86107 4550819
Mood swings 75.50 39.01 24 2042 5553 4631373
Intraventricular haemorrhage 74.19 39.01 17 2049 1136 4635790
Low birth weight baby 73.55 39.01 20 2046 2690 4634236
Gastric ulcer 73.29 39.01 24 2042 6099 4630827
Gout 72.58 39.01 22 2044 4351 4632575
Joint swelling 70.26 39.01 34 2032 24044 4612882
Completed suicide 70.13 39.01 41 2025 42404 4594522
Product use issue 68.99 39.01 34 2032 25002 4611924
Blood urea increased 68.61 39.01 25 2041 8725 4628201
Ankylosing spondylitis 68.53 39.01 17 2049 1595 4635331
Dizziness 68.36 39.01 56 2010 99815 4537111
Dehydration 67.63 39.01 40 2026 42250 4594676
Drug interaction 65.92 39.01 46 2020 64462 4572464
Pain 65.49 39.01 53 2013 92817 4544109
Blood creatinine increased 63.78 39.01 33 2033 26867 4610059
Musculoskeletal stiffness 62.19 39.01 29 2037 18873 4618053
Urticaria 62.14 39.01 37 2029 39536 4597390
Mast cell activation syndrome 59.52 39.01 9 2057 55 4636871
Headache 58.51 39.01 56 2010 122317 4514609
Joint stiffness 57.84 39.01 20 2046 5991 4630935
Off label use 57.83 39.01 57 2009 129056 4507870
Sepsis neonatal 57.66 39.01 11 2055 298 4636628
Intestinal perforation 57.62 39.01 18 2048 3930 4632996
Oligohydramnios 57.46 39.01 14 2052 1218 4635708
Caesarean section 57.06 39.01 19 2047 5079 4631847
Condition aggravated 55.97 39.01 40 2026 58131 4578795
Corneal perforation 55.22 39.01 10 2056 202 4636724
Anaphylactic reaction 54.36 39.01 26 2040 17884 4619042
Renal impairment 54.13 39.01 29 2037 25309 4611617
Therapeutic product effect decreased 53.23 39.01 26 2040 18727 4618199
Patent ductus arteriosus 53.20 39.01 14 2052 1660 4635266
Faeces discoloured 52.96 39.01 18 2048 5119 4631807
Angioedema 51.93 39.01 26 2040 19739 4617187
Placental transfusion syndrome 51.48 39.01 8 2058 60 4636866
Haemoglobin decreased 50.89 39.01 32 2034 37625 4599301
Abdominal pain 50.34 39.01 38 2028 59986 4576940
Thrombocytopenia 48.65 39.01 34 2032 47639 4589287
Hypoaldosteronism 48.00 39.01 8 2058 97 4636829
Shock 46.70 39.01 19 2047 8897 4628029
Anaemia 46.51 39.01 39 2027 71521 4565405
Necrotising enterocolitis neonatal 46.00 39.01 8 2058 127 4636799
Dyspnoea 45.55 39.01 52 2014 138933 4497993
Ileal perforation 45.22 39.01 9 2057 305 4636621
Coronary artery insufficiency 44.30 39.01 8 2058 159 4636767
Toxicity to various agents 44.23 39.01 38 2028 72002 4564924
Therapeutic product effect incomplete 43.33 39.01 22 2044 17186 4619740
Procedural vomiting 42.94 39.01 8 2058 190 4636736
Gastrointestinal ulcer 42.48 39.01 10 2056 751 4636175
Cerebral vasoconstriction 42.26 39.01 9 2057 428 4636498
Gastrointestinal perforation 42.21 39.01 12 2054 1896 4635030
Oliguria 41.98 39.01 13 2053 2754 4634172
Rash 41.44 39.01 44 2022 108344 4528582
Duodenal ulcer 40.41 39.01 13 2053 3117 4633809
Intestinal diaphragm disease 40.08 39.01 7 2059 114 4636812
Right ventricular hypertrophy 39.08 39.01 8 2058 313 4636613
Diarrhoea 39.07 39.01 50 2016 150135 4486791

Pharmacologic Action:

SourceCodeDescription
ATC C01EB03 CARDIOVASCULAR SYSTEM
CARDIAC THERAPY
OTHER CARDIAC PREPARATIONS
Other cardiac preparations
ATC M01AB01 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Acetic acid derivatives and related substances
ATC M02AA23 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 S01BC01 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFLAMMATORY AGENTS
Antiinflammatory agents, non-steroids
ATC M01AB51 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Acetic acid derivatives and related substances
ATC S01CC02 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIINFLAMMATORY AGENTS AND ANTIINFECTIVES IN COMBINATION
Antiinflammatory agents, non-steroids and antiinfectives in combination
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 D002317 Cardiovascular 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 D012102 Reproductive Control Agents
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:35480 analgesic
CHEBI has role CHEBI:35845 gout suppressant
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
FDA Chemical/Ingredient N0000175721 Nonsteroidal Anti-inflammatory Compounds
MeSH PA D015149 Tocolytic Agents

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Ankylosing spondylitis indication 9631008 DOID:7147
Tendinitis indication 34840004 DOID:971
Tenosynovitis indication 67801009 DOID:970
Rheumatoid arthritis indication 69896004 DOID:7148
Patent ductus arteriosus indication 83330001 DOID:13832
Bursitis indication 84017003 DOID:2965
Gout indication 90560007 DOID:13189
Bursitis of shoulder indication 239961006
Osteoarthritis indication 396275006
Synovitis indication 416209007 DOID:2703
Shoulder Tendonitis indication
Pericarditis off-label use 3238004 DOID:1787
Premature labor off-label use 6383007
Renal colic off-label use 7093002
Pseudoprimary hyperaldosteronism off-label use 71275003
Nephrogenic diabetes insipidus off-label use 111395007 DOID:12387
Dysmenorrhea off-label use 266599000
Fever off-label use 386661006
Twin reversal arterial perfusion syndrome off-label use 417006004
Necrotizing enterocolitis in fetus OR newborn contraindication 2707005
Proctitis contraindication 3951002 DOID:3127
Acute hemorrhage contraindication 8573003
Rectal hemorrhage contraindication 12063002
Hyperkalemia contraindication 14140009
Myocardial infarction contraindication 22298006 DOID:5844
Parkinsonism contraindication 32798002
Dehydration contraindication 34095006
Depressive disorder contraindication 35489007
Hypertensive disorder contraindication 38341003 DOID:10763
Gastrointestinal ulcer contraindication 40845000
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Duodenal ulcer disease contraindication 51868009 DOID:1724
Gastrointestinal perforation contraindication 51875005
Stomatitis contraindication 61170000 DOID:9637
Ulcerative colitis contraindication 64766004 DOID:8577
Blood coagulation disorder contraindication 64779008 DOID:1247
Hemorrhoids contraindication 70153002 DOID:9746
Corneal deposit contraindication 74460005 DOID:11547
Gastrointestinal hemorrhage contraindication 74474003
Heart failure contraindication 84114007 DOID:6000
Epilepsy contraindication 84757009 DOID:1826
Bacterial infectious disease contraindication 87628006
Hyponatremia contraindication 89627008
Kidney disease contraindication 90708001 DOID:557
Blurring of visual image contraindication 111516008
Seizure disorder contraindication 128613002
Liver function tests abnormal contraindication 166603001
Asthma contraindication 195967001 DOID:2841
Sepsis of the newborn contraindication 206376005
Coronary artery bypass graft contraindication 232717009
Disease of liver contraindication 235856003 DOID:409
Esophageal dysmotility contraindication 266434009 DOID:9192
Cerebral hemorrhage contraindication 274100004
Pregnancy, function contraindication 289908002
Thrombocytopenic disorder contraindication 302215000 DOID:1588
Malignant tumor of colon contraindication 363406005 DOID:219
Cardiovascular event risk contraindication 395112001
Gastric ulcer contraindication 397825006 DOID:10808
Diverticular disease contraindication 397881000
Smokes tobacco daily contraindication 449868002
Psychiatric Disturbance contraindication
Intraventricular Hemorrhage In Newborn contraindication
Congenital Heart Defect Requiring Open Patent Ductus Arteriosus contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.45 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
20MG TIVORBEX GENUS N204768 Feb. 24, 2014 RX CAPSULE ORAL 9089471 April 23, 2030 TREATMENT OF PAIN
40MG TIVORBEX GENUS N204768 Feb. 24, 2014 RX CAPSULE ORAL 9089471 April 23, 2030 TREATMENT OF PAIN

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Prostaglandin G/H synthase 2 Enzyme INHIBITOR IC50 6.33 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 1 Enzyme INHIBITOR IC50 7.21 WOMBAT-PK CHEMBL
Prostaglandin D2 receptor 2 GPCR Ki 6.53 WOMBAT-PK
Aldo-keto reductase family 1 member C3 Enzyme IC50 7 CHEMBL
Interleukin-8 Cytokine IC50 7.30 CHEMBL
Prostaglandin E synthase Enzyme IC50 4.39 CHEMBL
Aldo-keto reductase family 1 member C4 Enzyme IC50 4.27 CHEMBL
Androgen receptor Nuclear hormone receptor EC50 9.85 CHEMBL
Multidrug resistance-associated protein 1 Transporter IC50 4.92 CHEMBL
Aldo-keto reductase family 1 member C2 Enzyme IC50 4.44 CHEMBL
Dehydrogenase/reductase SDR family member 9 Enzyme IC50 4.85 CHEMBL
Lactoylglutathione lyase Enzyme Ki 4.74 CHEMBL
Aldose reductase Enzyme IC50 5.22 CHEMBL
Potassium voltage-gated channel subfamily A member 7 Ion channel Ki 7.50 WOMBAT-PK
Multidrug resistance protein 1 Transporter IC50 4.49 CHEMBL
Prostaglandin E2 receptor EP2 subtype GPCR Ki 7.69 PDSP
Peroxisome proliferator-activated receptor gamma Nuclear hormone receptor AGONIST Kd 7.38 IUPHAR
Aldose reductase Enzyme IC50 5.44 DRUG MATRIX
Aldose reductase Enzyme IC50 5.30 CHEMBL
Prostaglandin G/H synthase (cyclooxygenase) Enzyme IC50 6.82 CHEMBL
Prostaglandin G/H synthase 1 Enzyme Ki 5.10 CHEMBL
Prostaglandin-H2 D-isomerase Enzyme IC50 6.30 CHEMBL
Prostaglandin G/H synthase 2 Enzyme IC50 6.47 CHEMBL
Prostaglandin G/H synthase 2 Enzyme IC50 8.19 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 8.70 CHEMBL
Cyclooxygenase Enzyme IC50 7 CHEMBL
Prostaglandin G/H synthase 2 Enzyme IC50 8 CHEMBL
Cyclooxygenase Enzyme IC50 6.37 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 8.22 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 8.39 CHEMBL
Nitric oxide synthase, inducible Enzyme IC50 4.70 CHEMBL
Prostaglandin D2 receptor 2 Unclassified AGONIST Ki 6 IUPHAR

External reference:

IDSource
D007213 MESH_DESCRIPTOR_UI
C0700798 UMLSCUI
D00141 KEGG_DRUG
0IMX38M2GG UNII
74252-25-8 SECONDARY_CAS_RN
373513008 SNOMEDCT_US
60149003 SNOMEDCT_US
2393 MMSL
5781 RXNORM
4877 MMSL
d00039 MMSL
4017890 VANDF
002373 NDDF
CHEMBL6 ChEMBL_ID
DB00328 DRUGBANK_ID
IMN PDB_CHEM_ID
CHEBI:49662 CHEBI
1524 INN_ID
CHEMBL3989410 ChEMBL_ID
3715 PUBCHEM_CID
1909 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 0409-1113 INJECTION, POWDER, LYOPHILIZED, FOR SOLUTION 1 mg INTRAVENOUS ANDA 10 sections
INDOMETHACIN HUMAN PRESCRIPTION DRUG LABEL 1 0713-0176 SUPPOSITORY 50 mg RECTAL ANDA 14 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 10544-083 CAPSULE 50 mg ORAL ANDA 15 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 10544-919 CAPSULE, EXTENDED RELEASE 75 mg ORAL ANDA 13 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 10544-935 CAPSULE, EXTENDED RELEASE 75 mg ORAL ANDA 13 sections
INDOMETHACIN HUMAN PRESCRIPTION DRUG LABEL 1 10702-016 CAPSULE, EXTENDED RELEASE 75 mg ORAL ANDA 13 sections
INDOMETHACIN ER HUMAN PRESCRIPTION DRUG LABEL 1 12634-160 CAPSULE 75 mg ORAL ANDA 14 sections
INDOMETHACIN ER HUMAN PRESCRIPTION DRUG LABEL 1 12634-838 CAPSULE 75 mg ORAL ANDA 14 sections
INDOMETHACIN HUMAN PRESCRIPTION DRUG LABEL 1 16590-130 CAPSULE 50 mg ORAL ANDA 13 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 21695-522 CAPSULE 25 mg ORAL ANDA 15 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 21695-523 CAPSULE 50 mg ORAL ANDA 13 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 23155-010 CAPSULE 25 mg ORAL NDA 18 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 23155-011 CAPSULE 50 mg ORAL NDA 18 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 31722-542 CAPSULE 25 mg ORAL ANDA 19 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 31722-543 CAPSULE 50 mg ORAL ANDA 19 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 31722-565 CAPSULE, EXTENDED RELEASE 75 mg ORAL ANDA 13 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 35356-697 CAPSULE 50 mg ORAL ANDA 14 sections
INDOCIN HUMAN PRESCRIPTION DRUG LABEL 1 42211-101 SUSPENSION 25 mg ORAL NDA 19 sections
INDOCIN HUMAN PRESCRIPTION DRUG LABEL 1 42211-102 SUPPOSITORY 50 mg RECTAL ANDA 19 sections
Tivorbex HUMAN PRESCRIPTION DRUG LABEL 1 42211-201 CAPSULE 20 mg ORAL NDA 19 sections
Tivorbex HUMAN PRESCRIPTION DRUG LABEL 1 42211-202 CAPSULE 40 mg ORAL NDA 19 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 42254-081 CAPSULE 50 mg ORAL ANDA 15 sections
INDOMETHACIN HUMAN PRESCRIPTION DRUG LABEL 1 42254-237 CAPSULE 25 mg ORAL ANDA 12 sections
indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 42708-030 CAPSULE 50 mg ORAL ANDA 20 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 43063-368 CAPSULE 25 mg ORAL ANDA 19 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 43063-594 CAPSULE 25 mg ORAL NDA 18 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 43063-773 CAPSULE 25 mg ORAL ANDA 19 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 43063-777 CAPSULE 50 mg ORAL ANDA 19 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 43063-929 CAPSULE 50 mg ORAL ANDA 19 sections
Indomethacin HUMAN PRESCRIPTION DRUG LABEL 1 43063-930 CAPSULE 50 mg ORAL ANDA 19 sections