dichlorphenamide 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DDR1,DYRK1B,EGFR,EIF2AK3,ERBB2,FLT3,GRK2,GSK3B,IKBKB,ITK,JAK2,MAP2K6,MAP3K21,MAP3K7,MAPK1,MAPK10,MAPK7,MAPK8,MAPK9,MAPKAPK2,MAPKAPK3,MTOR,NTRK2,PDK1,PDK2,PDK4,PDPK1,PIK3CA,PIK3CB,PIK3CD,PIK3CG,PIM2,PRKCD,PRKDC,SIK2,SIK3,STK33,SYK,TEK,TTK,ULK1,ZAP70 52
kinase-selectivity-class AXL,GRK2,MAP2K6,MAPK7,MAPKAPK3,PDK1,PDK2,PDK4,PIK3CB,PIK3CD,TEK,UHMK1,ZAP70 13
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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
Wrong technique in product usage process 185.08 39.00 62 1456 71509 90555420
Paraesthesia 180.25 39.00 86 1432 250240 90376689
Disease recurrence 139.78 39.00 43 1475 37610 90589319
Feeling abnormal 94.74 39.00 49 1469 167186 90459743
Blood potassium decreased 79.83 39.00 30 1488 47697 90579232
Dysgeusia 73.49 39.00 29 1489 52531 90574398
Muscular weakness 64.28 39.00 41 1477 206625 90420304
Confusional state 39.72 39.00 40 1478 386165 90240764

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 169.22 53.95 49 804 29629 42590853
Paraesthesia 154.81 53.95 57 796 73402 42547080
Muscular weakness 73.80 53.95 35 818 83463 42537019
Wrong technique in product usage process 71.04 53.95 28 825 42607 42577875
Blood potassium decreased 58.48 53.95 20 833 20364 42600118

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 259.99 43.19 75 1548 60709 110526967
Paraesthesia 214.43 43.19 96 1527 276425 110311251
Blood potassium decreased 98.66 43.19 35 1588 54079 110533597
Muscular weakness 87.89 43.19 51 1572 248417 110339259
Feeling abnormal 82.77 43.19 44 1579 180667 110407009
Wrong technique in product usage process 82.38 43.19 35 1588 87313 110500363
Dysgeusia 75.93 43.19 31 1592 69954 110517722
Fatigue 48.64 43.19 73 1550 1215885 109371791

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 (carbonic anhydrase) inhibitor
CHEBI has role CHEBI:39456 antiglaucoma drug
CHEBI has role CHEBI:66981 ophthalmology drug

Related Drugs by ATC class:

S01EC Carbonic anhydrase inhibitors 4 drugs
acetazolamidebrinzolamidedorzolamidemethazolamide

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 Enzyme Ki 6.34 CHEMBL
Carbonic anhydrase 2 Enzyme Ki 5.70 CHEMBL
Carbonic anhydrase Enzyme Ki 6.20 CHEMBL
Carbonic anhydrase, alpha family Enzyme 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
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
6807 IUPHAR_LIGAND_ID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Dichlorphenamide HUMAN PRESCRIPTION DRUG LABEL 1 13668-676 TABLET 50 mg ORAL ANDA 26 sections
Dichlorphenamide HUMAN PRESCRIPTION DRUG LABEL 1 16571-242 TABLET 50 mg ORAL ANDA 26 sections
ORMALVI HUMAN PRESCRIPTION DRUG LABEL 1 70709-085 TABLET 50 mg ORAL ANDA 26 sections
ORMALVI HUMAN PRESCRIPTION DRUG LABEL 1 70709-085 TABLET 50 mg ORAL ANDA 26 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 25 sections