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

Stem definitionDrug idCAS RN
864 120-97-8

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • diclofenamide
  • dichlofenamide
  • dichlorophenamide
  • dichlorphenamide
  • diclofenamid
A carbonic anhydrase inhibitor that is used in the treatment of glaucoma.
  • Molecular weight: 305.14
  • Formula: C6H6Cl2N2O4S2
  • CLOGP: 0.24
  • LIPINSKI: 0
  • HAC: 6
  • HDO: 2
  • TPSA: 120.32
  • ALOGS: -2.88
  • ROTB: 2

  • Status: OFP

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

Drug dosage:

DoseUnitRoute
0.10 g O

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 9.36 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD

Approvals:

DateAgencyCompanyOrphan
July 22, 1958 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
Paraesthesia 204.06 40.15 47 152 22041 2335845
Disease recurrence 105.29 40.15 20 179 3431 2354455
Fatigue 86.52 40.15 33 166 84840 2273046
Feeling abnormal 85.06 40.15 24 175 23557 2334329
Confusional state 79.76 40.15 23 176 24321 2333565
Muscular weakness 76.16 40.15 20 179 14877 2343009
Dysgeusia 61.07 40.15 15 184 8444 2349442
Blood potassium decreased 51.67 40.15 12 187 5293 2352593
Intentional product use issue 50.62 40.15 11 188 3591 2354295
Asthenia 46.26 40.15 18 181 46908 2310978

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
Disease recurrence 159.29 45.82 28 126 2554 1744073
Paraesthesia 120.24 45.82 28 126 10423 1736204
Muscular weakness 69.10 45.82 18 136 10231 1736396
Confusional state 47.90 45.82 16 138 21262 1725365
Fatigue 47.53 45.82 20 134 50761 1695866

Pharmacologic Action:

SourceCodeDescription
ATC S01EC02 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIGLAUCOMA PREPARATIONS AND MIOTICS
Carbonic anhydrase inhibitors
FDA EPC N0000175517 Carbonic Anhydrase Inhibitor
FDA CS M0020790 Sulfonamides
CHEBI has role CHEBI:39456 antiglaucoma drug
CHEBI has role CHEBI:66981 ophthalmology drug
MeSH PA D002257 Carbonic Anhydrase Inhibitors
MeSH PA D004791 Enzyme Inhibitors

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Open-angle glaucoma indication 84494001 DOID:1067
Secondary glaucoma indication 95717004
Angle-closure glaucoma indication 392291006 DOID:13550
Malignant glaucoma off-label use 10100008
Renal tubular acidosis contraindication 1776003 DOID:14219
Respiratory acidosis contraindication 12326000
Hyperkalemia contraindication 14140009
Metabolic acidosis, normal anion gap, acidifying salts contraindication 18104000
Diabetes mellitus type 2 contraindication 44054006 DOID:9352
Diabetes mellitus type 1 contraindication 46635009 DOID:9744
Acute nephropathy contraindication 58574008
Hepatic failure contraindication 59927004
Decreased respiratory function contraindication 80954004
Hyponatremia contraindication 89627008
Gout contraindication 90560007 DOID:13189
Kidney disease contraindication 90708001 DOID:557
Disease of blood AND/OR blood-forming organ contraindication 191124002 DOID:74
Disease of liver contraindication 235856003 DOID:409
Disorder of electrolytes contraindication 237840007
Primary adrenocortical insufficiency contraindication 373662000
Recurrent Calcium Renal Calculi contraindication

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 7.51 acidic
pKa2 9.19 acidic

Orange Book patent data (new drug applications)

None

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
50MG KEVEYIS STRONGBRIDGE US N011366 Aug. 7, 2015 RX TABLET ORAL Aug. 7, 2022 TREATMENT OF PRIMARY HYPERKALEMIC PERIODIC PARALYSIS, PRIMARY HYPOKALEMIC PERIOD PARALYSIS, AND RELATED VARIANTS

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Carbonic anhydrase 1 Enzyme INHIBITOR IC50 8.30 WOMBAT-PK CHEMBL
Carbonic anhydrase 2 Enzyme INHIBITOR Ki 7.42 WOMBAT-PK CHEMBL
Carbonic anhydrase 12 Enzyme INHIBITOR Ki 7.30 WOMBAT-PK CHEMBL
Carbonic anhydrase 4 Enzyme INHIBITOR Ki 7.02 CHEMBL CHEMBL
Carbonic anhydrase 13 Enzyme Ki 7.64 CHEMBL
Carbonic anhydrase 14 Enzyme Ki 6.46 CHEMBL
Carbonic anhydrase 6 Enzyme Ki 7.10 CHEMBL
Carbonic anhydrase 5A, mitochondrial Enzyme Ki 6.20 WOMBAT-PK
Cytochrome P450 2C9 Enzyme EC50 5.60 WOMBAT-PK
Carbonic anhydrase 7 Enzyme INHIBITOR Ki 7.58 WOMBAT-PK
Carbonic anhydrase 5B, mitochondrial Enzyme INHIBITOR Ki 7.68 WOMBAT-PK
Carbonic anhydrase 9 Enzyme INHIBITOR Ki 7.30 WOMBAT-PK
Alpha carbonic anhydrase Unclassified Ki 6.37 CHEMBL
Astrosclerin-3 Unclassified Ki 7.21 CHEMBL
Beta-carbonic anhydrase 1 Enzyme Ki 6.06 CHEMBL
Carbonic anhydrase Unclassified Ki 7.10 CHEMBL
Delta carbonic anhydrase Unclassified Ki 6.34 CHEMBL
Carbonic anhydrase Enzyme Ki 6.99 CHEMBL
Carbonic anhydrase 15 Enzyme Ki 7.02 CHEMBL
Carbonic anhydrase Enzyme Ki 7.42 CHEMBL
Carbonic anhydrase Enzyme Ki 6.82 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 5.70 CHEMBL
Carbonic anhydrase 4 Enzyme Ki 6.42 CHEMBL
Carbonic anhydrase Enzyme Ki 6.42 WOMBAT-PK
Carbonic anhydrase 2 Unclassified Ki 5.92 CHEMBL
Carbonic anhydrase Unclassified Ki 6.20 CHEMBL
Carbonic anhydrase Enzyme Ki 6.95 CHEMBL
Carbonic anhydrase 13 Enzyme Ki 7.64 CHEMBL

External reference:

IDSource
D004005 MESH_DESCRIPTOR_UI
4017928 VUID
N0000146279 NUI
C0012086 UMLSCUI
D00518 KEGG_DRUG
3353 RXNORM
387111009 SNOMEDCT_US
4581 MMSL
d00639 MMSL
19583005 SNOMEDCT_US
4017928 VANDF
002288 NDDF
CHEBI:101085 CHEBI
CHEMBL17 ChEMBL_ID
VVJ6673MHY UNII
639 INN_ID
DB01144 DRUGBANK_ID
6807 IUPHAR_LIGAND_ID
3038 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Keveyis HUMAN PRESCRIPTION DRUG LABEL 1 51672-4177 TABLET 50 mg ORAL NDA 18 sections
Keveyis HUMAN PRESCRIPTION DRUG LABEL 1 71090-001 TABLET 50 mg ORAL NDA 18 sections