dichlorphenamide 🐶 Veterinary Use | 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 µM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
S (Water solubility) 0.10 mg/mL Bocci G, Oprea TI, Benet LZ
BDDCS (Biopharmaceutical Drug Disposition Classification System) 4 Bocci G, Oprea TI, Benet LZ

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 188.31 41.42 85 1395 156881 63330661
Wrong technique in product usage process 169.63 41.42 61 1419 62279 63425263
Disease recurrence 138.30 41.42 43 1437 27987 63459555
Feeling abnormal 85.06 41.42 49 1431 148343 63339199
Blood potassium decreased 73.92 41.42 30 1450 41996 63445546
Muscular weakness 71.63 41.42 41 1439 122312 63365230
Dysgeusia 67.54 41.42 29 1451 46681 63440861
Confusional state 45.21 41.42 40 1440 236340 63251202

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 176.99 55.49 49 775 21441 34934666
Paraesthesia 145.93 55.49 55 769 64117 34891990
Muscular weakness 72.89 55.49 35 789 72862 34883245
Wrong technique in product usage process 71.21 55.49 28 796 35958 34920149
Blood potassium decreased 57.81 55.49 20 804 17895 34938212

FDA Adverse Event Reporting System (Geriatric)

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 261.70 48.37 75 1502 44034 79698777
Paraesthesia 225.16 48.37 95 1482 176228 79566583
Muscular weakness 94.46 48.37 51 1526 160678 79582133
Blood potassium decreased 93.65 48.37 35 1542 46477 79696334
Feeling abnormal 75.73 48.37 44 1533 159155 79583656
Wrong technique in product usage process 74.81 48.37 34 1543 73841 79668970
Dysgeusia 73.06 48.37 31 1546 57146 79685665

FDA Adverse Event Reporting System (Pediatric)

None

Pharmacologic Action:

SourceCodeDescription
ATC S01EC02 SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIGLAUCOMA PREPARATIONS AND MIOTICS
Carbonic anhydrase inhibitors
FDA CS M0020790 Sulfonamides
FDA MoA N0000000235 Carbonic Anhydrase Inhibitors
FDA EPC N0000175517 Carbonic Anhydrase Inhibitor
MeSH PA D002257 Carbonic Anhydrase Inhibitors
MeSH PA D004791 Enzyme Inhibitors
CHEBI has role CHEBI:23018 EC 4.2.1.1 inhibitor
CHEBI has role CHEBI:39456 antiglaucoma agent
CHEBI has role CHEBI:66981 ophthalmology drugs

Drug Use | Suggest Off label Use Form| |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




🐶 Veterinary Drug Use

None

🐶 Veterinary products

None

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)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])		Mechanism
action		Bioact sourceMoA source
Carbonic anhydrase 12 Enzyme INHIBITOR Ki 7.30 WOMBAT-PK CHEMBL
Carbonic anhydrase 1 Enzyme INHIBITOR IC50 8.30 WOMBAT-PK CHEMBL
Carbonic anhydrase 4 Enzyme INHIBITOR Ki 7.02 CHEMBL CHEMBL
Carbonic anhydrase 2 Enzyme INHIBITOR Ki 7.42 WOMBAT-PK CHEMBL
Carbonic anhydrase 5B, mitochondrial Enzyme INHIBITOR Ki 7.68 WOMBAT-PK
Carbonic anhydrase 7 Enzyme INHIBITOR Ki 7.58 WOMBAT-PK
Carbonic anhydrase 6 Enzyme Ki 7.10 CHEMBL
Carbonic anhydrase 14 Enzyme Ki 6.46 CHEMBL
Carbonic anhydrase 13 Enzyme Ki 7.64 CHEMBL
Cytochrome P450 2C9 Enzyme EC50 5.60 WOMBAT-PK
Carbonic anhydrase 9 Enzyme INHIBITOR Ki 7.30 WOMBAT-PK
Carbonic anhydrase 5A, mitochondrial Enzyme Ki 6.20 WOMBAT-PK
Carbonic anhydrase Enzyme Ki 6.42 WOMBAT-PK
Carbonic anhydrase 13 Enzyme Ki 7.64 CHEMBL
Carbonic anhydrase 4 Enzyme Ki 6.42 CHEMBL
Carbonic anhydrase Enzyme Ki 6.82 CHEMBL
Carbonic anhydrase 15 Enzyme Ki 7.02 CHEMBL
Carbonic anhydrase Enzyme Ki 6.99 CHEMBL
Carbonic anhydrase Enzyme Ki 7.42 CHEMBL
Carbonic anhydrase Enzyme Ki 6.95 CHEMBL
Alpha carbonic anhydrase Enzyme Ki 6.37 CHEMBL
Carbonic anhydrase Enzyme Ki 7.10 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 5.92 CHEMBL
Astrosclerin-3 Enzyme Ki 7.21 CHEMBL
Beta-carbonic anhydrase 1 Enzyme Ki 6.06 CHEMBL
Delta carbonic anhydrase Unclassified Ki 6.34 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 5.70 CHEMBL
Carbonic anhydrase Enzyme Ki 6.20 CHEMBL
Carbonic anhydrase, alpha family Unclassified Ki 7.61 CHEMBL
Carbonate dehydratase Enzyme Ki 8.07 CHEMBL

External reference:

IDSource
4017928 VUID
N0000146279 NUI
D00518 KEGG_DRUG
3353 RXNORM
4017928 VANDF
C0012086 UMLSCUI
CHEBI:101085 CHEBI
I7A PDB_CHEM_ID
CHEMBL17 ChEMBL_ID
DB01144 DRUGBANK_ID
6807 IUPHAR_LIGAND_ID
639 INN_ID
VVJ6673MHY UNII
3038 PUBCHEM_CID
364734 MMSL
4581 MMSL
d00639 MMSL
002288 NDDF
19583005 SNOMEDCT_US
387111009 SNOMEDCT_US
D004005 MESH_DESCRIPTOR_UI

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Dichlorphenamide HUMAN PRESCRIPTION DRUG LABEL 1 13668-676 TABLET 50 mg ORAL ANDA 26 sections
Keveyis HUMAN PRESCRIPTION DRUG LABEL 1 51672-4177 TABLET 50 mg ORAL NDA 27 sections
Keveyis HUMAN PRESCRIPTION DRUG LABEL 1 71090-001 TABLET 50 mg ORAL NDA 26 sections
Keveyis HUMAN PRESCRIPTION DRUG LABEL 1 72065-001 TABLET 50 mg ORAL NDA 26 sections
Keveyis HUMAN PRESCRIPTION DRUG LABEL 1 72065-001 TABLET 50 mg ORAL NDA 26 sections
Dichlorphenamide HUMAN PRESCRIPTION DRUG LABEL 1 72065-002 TABLET 50 mg ORAL NDA authorized generic 25 sections