Diclofenamide

Synonyms :
1,3-disulfamoyl-4,5-dichlorobenzene, 1,3-Disulfamyl-4,5-dichlorobenzene, 3,4-Dichloro-5-sulfamylbenzenesulfonamide, 4,5-Dichloro-1,3-benzenedisulfonamide, 4,5-dichloro-1,3-disulfamoylbenzene, 4,5-Dichloro-benzene-1,3-disulfonic acid diamide, 4,5-dichloro-m-benzenedisulfonamide, 4,5-DICHLOROBENZENE-1,3-disulfonamide, Dichlofenamide, Dichlorophenamide, Dichlorphenamide, Diclofenamida, Diclofenamide, Diclofenamidum

Status : approved

Category

Carbonic Anhydrase Inhibitors

Therapeutic Classification

ANTIGLAUCOMA PREPARATIONS AND MIOTICS

SENSORY ORGANS
OPHTHALMOLOGICALS
ANTIGLAUCOMA PREPARATIONS AND MIOTICS
Anti-glaucoma Agents

Description

A carbonic anhydrase inhibitor that is used in the treatment of glaucoma. [PubChem]

Used

For adjunctive treatment of: chronic simple (open-angle) glaucoma, secondary glaucoma, and preoperatively in acute angle-closure glaucoma where delay of surgery is desired in order to lower intraocular pressure

Mechanism Of Action

Carbonic anhydrase inhibitors reduce intraocular pressure by partially suppressing the secretion of aqueous humor (inflow), although the mechanism by which they do this is not fully understood. Evidence suggests that HCO3- ions are produced in the ciliary body by hydration of carbon dioxide under the influence of carbonic anhydrase and diffuse into the posterior chamber which contains more Na+ and HCO3- ions than does plasma and consequently is hypertonic. Water is then attracted to the posterior chamber by osmosis, resulting in a drop in pressure.

Dosage

Form Route Strength
Tablet oral 50 mg

Pharmacodynamics

Dichlorphenamide is an oral carbonic anhydrase inhibitor indicated for adjunctive treatment of: chronic simple (open-angle) glaucoma, secondary glaucoma, and preoperatively in acute angle-closure glaucoma where delay of surgery is desired in order to lower intraocular pressure. Carbonic anhydrase inhibitors reduce intraocular pressure by partially suppressing the secretion of aqueous humor (inflow).

Protein Binding

55%

Chemical Classification

This compound belongs to the class of organic compounds known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.

Benzenesulfonamides

Organic compounds

Benzenoids

Benzene and substituted derivatives

Benzenesulfonamides

Chemical Name

1,3-disulfamoyl-4,5-dichlorobenzene

Brands

name Dosage form Country
Daranide tablet US
Keveyis tablet US

Drug Drug Interactions

  •  Acetazolamide  : May enhance the adverse/toxic effect of other Carbonic Anhydrase Inhibitors. The development of acid-base disorders with concurrent use of ophthalmic and oral carbonic anhydrase inhibitors has been reported.
  •  Acetylsalicylic acid  : Salicylates may enhance the adverse/toxic effect of Carbonic Anhydrase Inhibitors. Salicylate toxicity might be enhanced by this same combination.
  •  Aminosalicylic Acid  : Salicylates may enhance the adverse/toxic effect of Carbonic Anhydrase Inhibitors. Salicylate toxicity might be enhanced by this same combination.
  •  Amphetamine  : May decrease the excretion of Amphetamines.
  •  Benzphetamine  : May decrease the excretion of Amphetamines.
  •  Bismuth Subsalicylate  : Salicylates may enhance the adverse/toxic effect of Carbonic Anhydrase Inhibitors. Salicylate toxicity might be enhanced by this same combination.
  •  Brinzolamide  : May enhance the adverse/toxic effect of other Carbonic Anhydrase Inhibitors. The development of acid-base disorders with concurrent use of ophthalmic and oral carbonic anhydrase inhibitors has been reported.
  •  Butabarbital  : May enhance the hypotensive effect of Hypotensive Agents.
  •  Butethal  : May enhance the hypotensive effect of Hypotensive Agents.
  •  Canagliflozin  : May enhance the adverse/toxic effect of MetFORMIN. Specifically, the risk of developing lactic acidosis may be increased.
  •  Carbamazepine  : Carbonic Anhydrase Inhibitors may increase the serum concentration of Carbamazepine.
  •  Cathinone  : Carbonic Anhydrase Inhibitors may decrease the excretion of Amphetamines.
  •  Dextroamphetamine  : May decrease the excretion of Amphetamines.
  •  Dihydrocodeine  : Salicylates may enhance the adverse/toxic effect of Carbonic Anhydrase Inhibitors. Salicylate toxicity might be enhanced by this same combination.
  •  Dorzolamide  : May enhance the adverse/toxic effect of other Carbonic Anhydrase Inhibitors. The development of acid-base disorders with concurrent use of ophthalmic and oral carbonic anhydrase inhibitors has been reported.
  •  Duloxetine  : Hypotensive Agents may enhance the orthostatic hypotensive effect of Duloxetine.
  •  Ephedrine  : May increase the serum concentration of Alpha-/Beta-Agonists (Indirect-Acting).
  •  Ethoxzolamide  : May enhance the adverse/toxic effect of other Carbonic Anhydrase Inhibitors. The development of acid-base disorders with concurrent use of ophthalmic and oral carbonic anhydrase inhibitors has been reported.
  •  Flecainide  : Carbonic Anhydrase Inhibitors may increase the serum concentration of Flecainide.
  •  Fosphenytoin  : May enhance the adverse/toxic effect of Fosphenytoin-Phenytoin. Specifically, the risk for osteomalacia or rickets may be increased.
  •  Heptabarbital  : May enhance the hypotensive effect of Hypotensive Agents.
  •  Hexamethylenetetramine  : May diminish the therapeutic effect of Methenamine.
  •  Hexobarbital  : May enhance the hypotensive effect of Hypotensive Agents.
  •  Levodopa  : Hypotensive Agents may enhance the orthostatic hypotensive effect of Levodopa.
  •  Lisdexamfetamine  : May decrease the excretion of Amphetamines.
  •  Lithium  : Carbonic Anhydrase Inhibitors may decrease the serum concentration of Lithium.
  •  Magnesium salicylate  : Salicylates may enhance the adverse/toxic effect of Carbonic Anhydrase Inhibitors. Salicylate toxicity might be enhanced by this same combination.
  •  Memantine  : Carbonic Anhydrase Inhibitors may decrease the excretion of Memantine.
  •  Metformin  : Carbonic Anhydrase Inhibitors may enhance the adverse/toxic effect of Metformin. Specifically, the risk of developing lactic acidosis may be increased.
  •  Methamphetamine  : May decrease the excretion of Amphetamines.
  •  Methazolamide  : May enhance the adverse/toxic effect of other Carbonic Anhydrase Inhibitors. The development of acid-base disorders with concurrent use of ophthalmic and oral carbonic anhydrase inhibitors has been reported.
  •  Methohexital  : May enhance the hypotensive effect of Hypotensive Agents.
  •  Pentobarbital  : May enhance the hypotensive effect of Hypotensive Agents.
  •  Phendimetrazine  : May decrease the excretion of Amphetamines.
  •  Phentermine  : May decrease the excretion of Amphetamines.
  •  Phenytoin  : May enhance the adverse/toxic effect of Fosphenytoin-Phenytoin. Specifically, the risk for osteomalacia or rickets may be increased.
  •  Primidone  : Carbonic Anhydrase Inhibitors may enhance the adverse/toxic effect of Primidone. Specifically, osteomalacia and rickets. Carbonic Anhydrase Inhibitors may decrease the serum concentration of Primidone.
  •  Pseudoephedrine  : May increase the serum concentration of Alpha-/Beta-Agonists (Indirect-Acting).
  •  Quinidine  : Carbonic Anhydrase Inhibitors may decrease the excretion of Quinidine.
  •  Risperidone  : Hypotensive Agents may enhance the hypotensive effect of Risperidone.
  •  Salicylate-sodium  : May enhance the adverse/toxic effect of Carbonic Anhydrase Inhibitors. Salicylate toxicity might be enhanced by this same combination.
  •  Salsalate  : Salicylates may enhance the adverse/toxic effect of Carbonic Anhydrase Inhibitors. Salicylate toxicity might be enhanced by this same combination.
  •  Secobarbital  : May enhance the hypotensive effect of Hypotensive Agents.
  •  Topiramate  : May enhance the adverse/toxic effect of other Carbonic Anhydrase Inhibitors. The development of acid-base disorders with concurrent use of ophthalmic and oral carbonic anhydrase inhibitors has been reported.
  •  Triprolidine  : May increase the serum concentration of Alpha-/Beta-Agonists (Indirect-Acting).
  •  Zonisamide  : May enhance the adverse/toxic effect of other Carbonic Anhydrase Inhibitors. The development of acid-base disorders with concurrent use of ophthalmic and oral carbonic anhydrase inhibitors has been reported.

Calculated Property

kind Value Source
logP 0.92 ALOGPS
logS -2.9 ALOGPS
Water Solubility 3.98e-01 g/l ALOGPS
logP 0.39 ChemAxon
IUPAC Name 4,5-dichlorobenzene-1,3-disulfonamide ChemAxon
Traditional IUPAC Name dichlorphenamide ChemAxon
Molecular Weight 305.159 ChemAxon
Monoisotopic Weight 303.914603484 ChemAxon
SMILES NS(=O)(=O)C1=CC(=C(Cl)C(Cl)=C1)S(N)(=O)=O ChemAxon
Molecular Formula C6H6Cl2N2O4S2 ChemAxon
InChI InChI=1S/C6H6Cl2N2O4S2/c7-4-1-3(15(9,11)12)2-5(6(4)8)16(10,13)14/h1-2H,(H2,9,11,12)(H2,10,13,14) ChemAxon
InChIKey InChIKey=GJQPMPFPNINLKP-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 120.32 ChemAxon
Refractivity 59.98 ChemAxon
Polarizability 25.04 ChemAxon
Rotatable Bond Count 2 ChemAxon
H Bond Acceptor Count 4 ChemAxon
H Bond Donor Count 2 ChemAxon
pKa (strongest acidic) 7.94 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 1 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • Carbonic anhydrase 1 : in Human
  • Carbonic anhydrase 2 : in Human
  • Carbonic anhydrase 4 : in Human
  • Carbonic anhydrase 7 : in Human