indomethacin Indications/Contra | FAERs-F | FAERs-M | Orange Bk | 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

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

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

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.00 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 15 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 7.99 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 99 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H
Vd (Volume of distribution) 0.10 L/kg Lombardo F, Berellini G, Obach RS
CL (Clearance) 1.30 mL/min/kg Lombardo F, Berellini G, Obach RS
fu (Fraction unbound in plasma) 0.01 % Lombardo F, Berellini G, Obach RS
t_half (Half-life) 1.40 hours Lombardo F, Berellini G, Obach RS

Approvals:

DateAgencyCompanyOrphan
June 10, 1965 FDA

FDA Adverse Event Reporting System (Female)

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 688.36 44.01 191 614 46452 2310828
Neck deformity 177.27 44.01 23 782 59 2357221
Drug ineffective 168.53 44.01 85 720 101539 2255741
Neck mass 150.12 44.01 24 781 342 2356938
Premature baby 145.64 44.01 33 772 3171 2354109
Anti-cyclic citrullinated peptide antibody positive 140.88 44.01 21 784 182 2357098
Exposure during pregnancy 128.42 44.01 47 758 25172 2332108
Bone density abnormal 125.28 44.01 21 784 406 2356874
Acute kidney injury 119.81 44.01 46 759 28076 2329204
Disability 117.63 44.01 22 783 810 2356470
Premature delivery 103.33 44.01 25 780 3175 2354105
Rheumatoid factor positive 101.31 44.01 18 787 494 2356786
Maternal exposure during pregnancy 99.44 44.01 34 771 14829 2342451
Mood swings 97.70 44.01 24 781 3245 2354035
Joint swelling 91.54 44.01 33 772 16786 2340494
Rheumatoid arthritis 87.38 44.01 33 772 19107 2338173
Vomiting 84.13 44.01 48 757 71554 2285726
Neonatal disorder 83.94 44.01 14 791 261 2357019
Arthralgia 79.12 44.01 42 763 54243 2303037
Asthenia 78.97 44.01 40 765 46886 2310394
Treatment failure 78.80 44.01 24 781 7215 2350065
Maternal drugs affecting foetus 75.95 44.01 17 788 1530 2355750
Joint stiffness 73.63 44.01 20 785 4003 2353277
Musculoskeletal stiffness 70.19 44.01 25 780 12222 2345058
Pain 68.59 44.01 40 765 61817 2295463
Nausea 66.66 44.01 49 756 112140 2245140
Headache 66.37 44.01 43 762 80136 2277144
Therapeutic product effect decreased 61.71 44.01 22 783 10767 2346513
Metabolic acidosis 61.48 44.01 19 786 5979 2351301
Neonatal respiratory distress syndrome 61.40 44.01 12 793 556 2356724
Product use issue 51.87 44.01 20 785 12149 2345131
Foetal exposure during pregnancy 51.12 44.01 16 789 5236 2352044
Oligohydramnios 49.56 44.01 11 794 949 2356331
Cerebral vasoconstriction 48.60 44.01 9 796 311 2356969
Low birth weight baby 45.56 44.01 10 795 819 2356461

FDA Adverse Event Reporting System (Male)

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 211.02 40.00 67 700 15068 1730946
Acute kidney injury 180.08 40.00 74 693 34870 1711144
Gastrointestinal haemorrhage 126.11 40.00 45 722 14222 1731792
Ductus arteriosus premature closure 120.50 40.00 16 751 27 1745987
Melaena 92.82 40.00 28 739 5182 1740832
Completed suicide 74.65 40.00 32 735 16280 1729734
Drug ineffective 71.59 40.00 49 718 63752 1682262
Gastric ulcer 68.04 40.00 19 748 2666 1743348
Gastric haemorrhage 66.09 40.00 19 748 2959 1743055
Gout 63.95 40.00 18 749 2598 1743416
Mast cell activation syndrome 63.09 40.00 8 759 7 1746007
Premature baby 61.86 40.00 18 749 2924 1743090
Hypoaldosteronism 54.13 40.00 8 759 38 1745976
Blood urea increased 53.51 40.00 18 749 4693 1741321
Dehydration 53.41 40.00 26 741 17632 1728382
Blood creatinine increased 46.59 40.00 22 745 13924 1732090
Hyperkalaemia 46.47 40.00 19 748 8528 1737486
Anaemia 46.05 40.00 28 739 29429 1716585
Hydrops foetalis 44.80 40.00 7 760 51 1745963
Neonatal disorder 43.74 40.00 9 758 340 1745674
Duodenal perforation 42.67 40.00 8 759 185 1745829
Duodenal ulcer 42.48 40.00 12 755 1748 1744266
Tricuspid valve incompetence 41.75 40.00 11 756 1235 1744779
Dyspnoea 40.07 40.00 32 735 52027 1693987

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