nabumetone Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
1863 42924-53-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • nabumetone
  • nabucox
  • nabumeton
  • nabuton
A butanone non-steroidal anti-inflammatory drug and cyclooxygenase-2 (COX2) inhibitor that is used in the management of pain associated with OSTEOARTHRITIS and RHEUMATOID ARTHRITIS.
  • Molecular weight: 228.29
  • Formula: C15H16O2
  • CLOGP: 2.98
  • LIPINSKI: 0
  • HAC: 2
  • HDO: 0
  • TPSA: 26.30
  • ALOGS: -5.07
  • ROTB: 4

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
1 g O

ADMET properties:

PropertyValueReference
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI
S (Water solubility) 0.02 mg/mL Benet LZ, Broccatelli F, Oprea TI
EoM (Fraction excreted unchanged in urine) 0 % Benet LZ, Broccatelli F, Oprea TI
MRTD (Maximum Recommended Therapeutic Daily Dose) 125.15 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BA (Bioavailability) 35 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
Dec. 24, 1991 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 88.28 12.86 168 9252 243657 46432985
Retinopathy 33.28 12.86 14 9406 2442 46674200
Periarticular disorder 25.66 12.86 5 9415 49 46676593
Rubella 19.24 12.86 5 9415 191 46676451
Injury 17.92 12.86 32 9388 43995 46632647
Gastrooesophageal reflux disease 17.33 12.86 43 9377 74301 46602341
Off label use 15.10 12.86 34 9386 379807 46296835
Death 15.07 12.86 28 9392 335520 46341122
Depression 15.00 12.86 71 9349 170033 46506609
Emotional distress 14.71 12.86 24 9396 30683 46645959
Hypersensitivity myocarditis 14.55 12.86 3 9417 40 46676602
Cerebrovascular accident 14.40 12.86 49 9371 100990 46575652

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
Coronary artery disease 32.76 17.63 35 3591 49677 29899175
Pain 27.66 17.63 63 3563 172578 29776274
Psoriatic arthropathy 26.62 17.63 19 3607 15742 29933110
Intervertebral disc degeneration 23.91 17.63 12 3614 5239 29943613
Drug abuser 19.87 17.63 10 3616 4391 29944461
Splenic embolism 18.59 17.63 4 3622 113 29948739
Sideroblastic anaemia 18.08 17.63 4 3622 129 29948723

Pharmacologic Action:

SourceCodeDescription
ATC M01AX01 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Other antiinflammatory and antirheumatic agents, non-steroids
FDA CS M0001335 Anti-Inflammatory Agents, Non-Steroidal
FDA MoA N0000000160 Cyclooxygenase Inhibitors
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 D052246 Cyclooxygenase 2 Inhibitors
MeSH PA D016861 Cyclooxygenase Inhibitors
MeSH PA D004791 Enzyme Inhibitors
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drugs
CHEBI has role CHEBI:50266 prodrugs
CHEBI has role CHEBI:50629 cyclooxygenase-2 inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Rheumatoid arthritis indication 69896004 DOID:7148
Osteoarthritis indication 396275006
Ankylosing spondylitis off-label use 9631008 DOID:7147
Juvenile rheumatoid arthritis off-label use 410795001
Alcoholism contraindication 7200002
Peptic ulcer contraindication 13200003 DOID:750
Acute gastric ulcer with perforation contraindication 19850005
Myocardial infarction contraindication 22298006 DOID:5844
Hypertensive disorder contraindication 38341003 DOID:10763
Gastrointestinal ulcer contraindication 40845000
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Acute nephropathy contraindication 58574008
Blood coagulation disorder contraindication 64779008 DOID:1247
Gastrointestinal hemorrhage contraindication 74474003
Kidney disease contraindication 90708001 DOID:557
Coronary artery bypass graft contraindication 232717009
Disease of liver contraindication 235856003 DOID:409
Pregnancy, function contraindication 289908002
Cardiovascular event risk contraindication 395112001
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

None

Orange Book patent data (new drug applications)

None

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 CHEMBL CHEMBL
Sodium-dependent noradrenaline transporter Transporter Ki 5.73 DRUG MATRIX
Cytochrome P450 1A2 Enzyme IC50 5.30 DRUG MATRIX
Amine oxidase [flavin-containing] A Enzyme IC50 6.00 DRUG MATRIX
Prostaglandin G/H synthase 1 Enzyme IC50 3.34 WOMBAT-PK

External reference:

IDSource
4020284 VUID
N0000148161 NUI
D00425 KEGG_DRUG
4020284 VANDF
C1436146 UMLSCUI
CHEBI:76252 CHEBI
NBO PDB_CHEM_ID
CHEMBL1070 ChEMBL_ID
D000077430 MESH_DESCRIPTOR_UI
DB00461 DRUGBANK_ID
7245 IUPHAR_LIGAND_ID
4855 INN_ID
LW0TIW155Z UNII
4409 PUBCHEM_CID
31448 RXNORM
41877 MMSL
5142 MMSL
d00310 MMSL
003622 NDDF
108508000 SNOMEDCT_US
386859000 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 0115-1657 TABLET, FILM COATED 500 mg ORAL ANDA 28 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 0115-1658 TABLET, FILM COATED 750 mg ORAL ANDA 28 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 0185-0145 TABLET 500 mg ORAL ANDA 26 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 0185-0146 TABLET 750 mg ORAL ANDA 26 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 0440-5843 TABLET, FILM COATED 500 mg ORAL ANDA 26 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 0440-5844 TABLET, FILM COATED 750 mg ORAL ANDA 26 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 0591-3670 TABLET, FILM COATED 500 mg ORAL ANDA 26 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 0591-3671 TABLET, FILM COATED 750 mg ORAL ANDA 26 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 0615-7630 TABLET, FILM COATED 750 mg ORAL ANDA 25 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 0615-7645 TABLET, FILM COATED 500 mg ORAL ANDA 25 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 0615-7666 TABLET, FILM COATED 500 mg ORAL ANDA 28 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 0615-7667 TABLET, FILM COATED 750 mg ORAL ANDA 28 sections
Nabumetone 500 mg HUMAN PRESCRIPTION DRUG LABEL 1 0722-7076 TABLET, FILM COATED 500 mg ORAL ANDA 28 sections
Nabumetone 750 mg HUMAN PRESCRIPTION DRUG LABEL 1 0722-7077 TABLET, FILM COATED 750 mg ORAL ANDA 28 sections
Nabumetone 1000 mg HUMAN PRESCRIPTION DRUG LABEL 1 0722-7078 TABLET, FILM COATED 1000 mg ORAL ANDA 28 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 10544-003 TABLET, FILM COATED 500 mg ORAL ANDA 29 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 10544-120 TABLET, FILM COATED 500 mg ORAL ANDA 28 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 10544-271 TABLET, FILM COATED 750 mg ORAL ANDA 29 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 10544-273 TABLET 500 mg ORAL ANDA 25 sections
RELAFEN DS HUMAN PRESCRIPTION DRUG LABEL 1 15370-170 TABLET 1000 mg ORAL ANDA 30 sections
NULLBUMETONE HUMAN PRESCRIPTION DRUG LABEL 1 16590-160 TABLET 750 mg ORAL ANDA 25 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 21695-230 TABLET, FILM COATED 500 mg ORAL ANDA 29 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 21695-231 TABLET, FILM COATED 750 mg ORAL ANDA 29 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 33261-077 TABLET, FILM COATED 500 mg ORAL ANDA 28 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 33261-078 TABLET, FILM COATED 750 mg ORAL ANDA 29 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 33358-251 TABLET, FILM COATED 500 mg ORAL ANDA 29 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 33358-252 TABLET, FILM COATED 750 mg ORAL ANDA 29 sections
Nabumetone HUMAN PRESCRIPTION DRUG LABEL 1 35356-687 TABLET, FILM COATED 500 mg ORAL ANDA 28 sections
NULLBUMETONE HUMAN PRESCRIPTION DRUG LABEL 1 42549-523 TABLET, FILM COATED 500 mg ORAL ANDA 23 sections
NULLBUMETONE HUMAN PRESCRIPTION DRUG LABEL 1 42549-648 TABLET, FILM COATED 750 mg ORAL ANDA 29 sections