meclofenamic acid Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
anti-inflammatory, anthranilic acid derivatives 1650 644-62-2

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • meclofenamic acid
  • meclophenamic acid
  • meclofenamate sodium
  • meclofenamate
A non-steroidal anti-inflammatory agent with antipyretic and antigranulation activities. It also inhibits prostaglandin biosynthesis.
  • Molecular weight: 296.15
  • Formula: C14H11Cl2NO2
  • CLOGP: 6.26
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 2
  • TPSA: 49.33
  • ALOGS: -4.91
  • ROTB: 3

  • Status: OFP

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

Drug dosage:

None

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 19.30 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Hosey CM, Chan R, Benet LZ
BA (Bioavailability) 65.10 % Kim MT, Sedykh A, Chakravarti SK, Saiakhov RD, Zhu H

Approvals:

DateAgencyCompanyOrphan
June 25, 1980 FDA

FDA Adverse Event Reporting System (Female)

None

FDA Adverse Event Reporting System (Male)

None

Pharmacologic Action:

SourceCodeDescription
ATC M01AG04 MUSCULO-SKELETAL SYSTEM
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS
ANTIINFLAMMATORY AND ANTIRHEUMATIC PRODUCTS, NON-STEROIDS
Fenamates
ATC M02AA18 MUSCULO-SKELETAL SYSTEM
TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
TOPICAL PRODUCTS FOR JOINT AND MUSCULAR PAIN
Antiinflammatory preparations, non-steroids for topical use
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 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:35493 anti-pyretic
CHEBI has role CHEBI:35544 cyclooxygenase inhibitors
CHEBI has role CHEBI:35610 cytostatic
CHEBI has role CHEBI:35623 antiepileptic
CHEBI has role CHEBI:35842 antirheumatic agent
CHEBI has role CHEBI:64964 5-lipoxygenase inhibitor

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Pain indication 22253000
Rheumatoid arthritis indication 69896004 DOID:7148
Dysmenorrhea indication 266599000
Menorrhagia indication 386692008
Osteoarthritis indication 396275006
Ankylosing spondylitis off-label use 9631008 DOID:7147
Vascular headache off-label use 128187005
Alcoholism contraindication 7200002
Peptic ulcer contraindication 13200003 DOID:750
Myocardial infarction contraindication 22298006 DOID:5844
Hypertensive disorder contraindication 38341003 DOID:10763
Gastrointestinal ulcer contraindication 40845000
Chronic heart failure contraindication 48447003
Disorder of cardiovascular system contraindication 49601007 DOID:1287
Gastrointestinal hemorrhage contraindication 74474003
Kidney disease contraindication 90708001 DOID:557
Liver function tests abnormal contraindication 166603001
Coronary artery bypass graft contraindication 232717009
Disease of liver contraindication 235856003 DOID:409
Anemia contraindication 271737000 DOID:2355
Peripheral edema contraindication 271809000
Pregnancy, function contraindication 289908002
Cardiovascular event risk contraindication 395112001
Smokes tobacco daily contraindication 449868002

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 4.2 acidic

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 IC50 6.70 WOMBAT-PK CHEMBL
Prostaglandin G/H synthase 1 Enzyme INHIBITOR IC50 6.66 WOMBAT-PK CHEMBL
Arachidonate 5-lipoxygenase Enzyme INHIBITOR IC50 4.33 WOMBAT-PK CHEMBL
Fatty acid-binding protein, intestinal Cytosolic other Ki 5.05 CHEMBL
Aldo-keto reductase family 1 member C2 Enzyme IC50 5.06 CHEMBL
Aldo-keto reductase family 1 member C1 Enzyme IC50 5.50 CHEMBL
Androgen receptor Nuclear hormone receptor IC50 4.19 WOMBAT-PK
Transthyretin Secreted IC50 4.30 CHEMBL
Mitogen-activated protein kinase 1 Kinase IC50 5.50 DRUG MATRIX
Aldo-keto reductase family 1 member C3 Enzyme IC50 6.27 CHEMBL
Prostaglandin G/H synthase 2 Enzyme IC50 6.70 CHEMBL
Fatty acid-binding protein, liver Unclassified Ki 6.59 CHEMBL
Cyclooxygenase Enzyme IC50 7 CHEMBL
Arachidonate 5-lipoxygenase Enzyme IC50 4.62 CHEMBL
Prostaglandin G/H synthase 1 Enzyme IC50 7.30 CHEMBL

External reference:

IDSource
4019080 VUID
N0000147341 NUI
D00169 KEGG_DRUG
67254-91-5 SECONDARY_CAS_RN
4019079 VANDF
4019080 VANDF
4022843 VANDF
C1289957 UMLSCUI
CHEBI:76230 CHEBI
JMS PDB_CHEM_ID
CHEMBL509 ChEMBL_ID
CHEMBL876 ChEMBL_ID
CHEMBL1562610 ChEMBL_ID
D008469 MESH_DESCRIPTOR_UI
DB00939 DRUGBANK_ID
7219 IUPHAR_LIGAND_ID
2165 INN_ID
94NJ818U2W UNII
4037 PUBCHEM_CID
588003 RXNORM
1713 MMSL
5031 MMSL
d00283 MMSL
002387 NDDF
002388 NDDF
117178002 SNOMEDCT_US
58233009 SNOMEDCT_US
770315008 SNOMEDCT_US
96172003 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Meclofenamate Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0378-2150 CAPSULE 50 mg ORAL ANDA 27 sections
Meclofenamate Sodium HUMAN PRESCRIPTION DRUG LABEL 1 0378-3000 CAPSULE 100 mg ORAL ANDA 27 sections