Identification
- Summary
Diclofenamide is a carbonic anhydrase inhibitor used for the management of open-angle and secondary glaucoma, as well as acute angle-closure glaucoma in delayed pre-operative setting requiring a reduction in intraocular pressure.
- Brand Names
- Keveyis
- Generic Name
- Diclofenamide
- DrugBank Accession Number
- DB01144
- Background
A carbonic anhydrase inhibitor that is used in the treatment of glaucoma.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Diclofenamide (DB01144)
- Weight
- Average: 305.159
Monoisotopic: 303.914603484 - Chemical Formula
- C6H6Cl2N2O4S2
- 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
Pharmacology
- Indication
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
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Hyperkalemic periodic paralysis •••••••••••• •••••• Treatment of Hypokalemic periodic paralysis •••••••••••• •••••• - Contraindications & Blackbox Warnings
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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).
- 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.
Target Actions Organism ACarbonic anhydrase 2 inhibitorHumans ACarbonic anhydrase 1 inhibitorHumans ACarbonic anhydrase 4 inhibitorHumans ACarbonic anhydrase 7 inhibitorHumans UCarbonic anhydrase 3 inhibitorHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
55%
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Diclofenamide may increase the excretion rate of Abacavir which could result in a lower serum level and potentially a reduction in efficacy. Abaloparatide The risk or severity of adverse effects can be increased when Diclofenamide is combined with Abaloparatide. Acarbose The therapeutic efficacy of Acarbose can be increased when used in combination with Diclofenamide. Acebutolol The risk or severity of adverse effects can be increased when Diclofenamide is combined with Acebutolol. Aceclofenac Diclofenamide may increase the excretion rate of Aceclofenac which could result in a lower serum level and potentially a reduction in efficacy. - Food Interactions
- Increase consumption of potassium-rich foods. Diclofenamide may cause hypokalemia, therefore consuming more potassium-rich foods may help prevent hypokalemia.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Oratrol (Alcon)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Daranide Tablet 50 mg/1 Oral Taro Pharmaceuticals U.S.A., Inc. 2012-03-16 2020-01-17 US 
Keveyis Tablet 50 mg/1 Oral Taro Pharmaceuticals U.S.A., Inc. 2015-08-07 Not applicable US Keveyis Tablet 50 mg/1 Oral Xeris Pharmaceuticals, Inc. 2021-12-13 Not applicable US Keveyis Tablet 50 mg/1 Oral Strongbridge Us Inc. 2015-08-07 2025-10-23 US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Dichlorphenamide Tablet 50 mg/1 Oral Xeris Pharmaceuticals, Inc. 2023-03-10 Not applicable US Dichlorphenamide Tablet 50 mg/1 Oral Torrent Pharmaceuticals Limited 2022-12-29 Not applicable US
Categories
- ATC Codes
- G01AE10 — Combinations of sulfonamides
- G01AE — Sulfonamides
- G01A — ANTIINFECTIVES AND ANTISEPTICS, EXCL. COMBINATIONS WITH CORTICOSTEROIDS
- G01 — GYNECOLOGICAL ANTIINFECTIVES AND ANTISEPTICS
- G — GENITO URINARY SYSTEM AND SEX HORMONES
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- 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.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Benzenesulfonamides
- Direct Parent
- Benzenesulfonamides
- Alternative Parents
- Benzenesulfonyl compounds / Dichlorobenzenes / Organosulfonamides / Aryl chlorides / Aminosulfonyl compounds / Organochlorides / Organic oxides / Organic nitrogen compounds / Hydrocarbon derivatives
- Substituents
- 1,2-dichlorobenzene / Aminosulfonyl compound / Aromatic homomonocyclic compound / Aryl chloride / Aryl halide / Benzenesulfonamide / Benzenesulfonyl group / Chlorobenzene / Halobenzene / Hydrocarbon derivative
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- sulfonamide, dichlorobenzene (CHEBI:101085)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- VVJ6673MHY
- CAS number
- 120-97-8
- InChI Key
- GJQPMPFPNINLKP-UHFFFAOYSA-N
- 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)
- IUPAC Name
- 4,5-dichlorobenzene-1,3-disulfonamide
- SMILES
- NS(=O)(=O)C1=CC(=C(Cl)C(Cl)=C1)S(N)(=O)=O
References
- Synthesis Reference
Schultz,E.M.; U.S.Patent 2,835,702; May 20, 1958; assigned to Merck & Co.,Inc.
- General References
- Tawil R, McDermott MP, Brown R Jr, Shapiro BC, Ptacek LJ, McManis PG, Dalakas MC, Spector SA, Mendell JR, Hahn AF, Griggs RC: Randomized trials of dichlorphenamide in the periodic paralyses. Working Group on Periodic Paralysis. Ann Neurol. 2000 Jan;47(1):46-53. [Article]
- Okada S, Izumi W, Murai M, Komatsu H, Ishimitsu S: [Diclofenamide Reference Standard (Control 891) of National Institute of Hygienic Sciences]. Eisei Shikenjo Hokoku. 1991;(109):148-50. [Article]
- External Links
- Human Metabolome Database
- HMDB0015275
- KEGG Drug
- D00518
- KEGG Compound
- C07459
- PubChem Compound
- 3038
- PubChem Substance
- 46505039
- ChemSpider
- 2930
- BindingDB
- 10883
- 3353
- ChEBI
- 101085
- ChEMBL
- CHEMBL17
- ZINC
- ZINC000000896918
- Therapeutic Targets Database
- DAP000601
- PharmGKB
- PA164745512
- PDBe Ligand
- I7A
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Diclofenamide
- PDB Entries
- 2pou
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 3 Completed Treatment Hyperkalemic Periodic Paralysis / Hypokalemic Periodic Paralysis 1 3 Completed Treatment Hyperkalemic Periodic Paralysis / Hypokalemic Periodic Paralysis / Paramyotonia Congenita 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Injection, powder, for solution Intravenous Tablet Oral Tablet Oral 50 mg/1 - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 228.5 Schultz,E.M.; U.S.Patent 2,835,702; May 20, 1958; assigned to Merck & Co.,Inc. logP 0.2 Not Available - Predicted Properties
Property Value Source Water Solubility 0.398 mg/mL ALOGPS logP 0.92 ALOGPS logP 0.39 Chemaxon logS -2.9 ALOGPS pKa (Strongest Acidic) 7.94 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 120.32 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 59.98 m3·mol-1 Chemaxon Polarizability 25.04 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9913 Blood Brain Barrier + 0.8167 Caco-2 permeable - 0.54 P-glycoprotein substrate Non-substrate 0.8835 P-glycoprotein inhibitor I Non-inhibitor 0.9593 P-glycoprotein inhibitor II Non-inhibitor 0.9922 Renal organic cation transporter Non-inhibitor 0.9254 CYP450 2C9 substrate Non-substrate 0.8101 CYP450 2D6 substrate Non-substrate 0.9085 CYP450 3A4 substrate Non-substrate 0.7198 CYP450 1A2 substrate Non-inhibitor 0.9044 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.957 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9691 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8017 Ames test Non AMES toxic 0.7954 Carcinogenicity Non-carcinogens 0.7986 Biodegradation Not ready biodegradable 0.9872 Rat acute toxicity 2.1828 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9697 hERG inhibition (predictor II) Non-inhibitor 0.9558
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-00fr-1190000000-05ac58ca7b0d878559c9 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0udr-0069000000-3159637d522a97ffeeca Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-0009000000-08dacb1f7b52adff8a10 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0udr-0069000000-849b3b392f27f602edb2 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0udi-2009000000-6177fa0b693e36068b74 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0ug0-2972000000-d87ec97eee6bc079cff5 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-004i-9000000000-d29977fbf9d5722cf329 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 155.1558893 predictedDarkChem Lite v0.1.0 [M-H]- 154.36731 predictedDeepCCS 1.0 (2019) [M+H]+ 156.75955 predictedDeepCCS 1.0 (2019) [M+Na]+ 162.81845 predictedDeepCCS 1.0 (2019)
Targets
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Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion in...
- Gene Name
- CA2
- Uniprot ID
- P00918
- Uniprot Name
- Carbonic anhydrase 2
- Molecular Weight
- 29245.895 Da
References
- Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
- Gene Name
- CA1
- Uniprot ID
- P00915
- Uniprot Name
- Carbonic anhydrase 1
- Molecular Weight
- 28870.0 Da
References
- Winum JY, Casini A, Mincione F, Starnotti M, Montero JL, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: N-(p-sulfamoylphenyl)-alpha-D-glycopyranosylamines as topically acting antiglaucoma agents in hypertensive rabbits. Bioorg Med Chem Lett. 2004 Jan 5;14(1):225-9. [Article]
- Lindskog S: Structure and mechanism of carbonic anhydrase. Pharmacol Ther. 1997;74(1):1-20. [Article]
- Nishimori I, Minakuchi T, Onishi S, Vullo D, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. DNA cloning, characterization, and inhibition studies of the human secretory isoform VI, a new target for sulfonamide and sulfamate inhibitors. J Med Chem. 2007 Jan 25;50(2):381-8. [Article]
- Giacomotto J, Pertl C, Borrel C, Walter MC, Bulst S, Johnsen B, Baillie DL, Lochmuller H, Thirion C, Segalat L: Evaluation of the therapeutic potential of carbonic anhydrase inhibitors in two animal models of dystrophin deficient muscular dystrophy. Hum Mol Genet. 2009 Nov 1;18(21):4089-101. doi: 10.1093/hmg/ddp358. Epub 2009 Jul 31. [Article]
- Cleland JC, Griggs RC: Treatment of neuromuscular channelopathies: current concepts and future prospects. Neurotherapeutics. 2008 Oct;5(4):607-12. doi: 10.1016/j.nurt.2008.09.001. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina an...
- Gene Name
- CA4
- Uniprot ID
- P22748
- Uniprot Name
- Carbonic anhydrase 4
- Molecular Weight
- 35032.075 Da
References
- Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Reversible hydration of carbon dioxide.
- Gene Name
- CA7
- Uniprot ID
- P43166
- Uniprot Name
- Carbonic anhydrase 7
- Molecular Weight
- 29658.235 Da
References
- Mincione F, Scozzafava A, Supuran CT: The development of topically acting carbonic anhydrase inhibitors as antiglaucoma agents. Curr Pharm Des. 2008;14(7):649-54. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Zinc ion binding
- Specific Function
- Reversible hydration of carbon dioxide.
- Gene Name
- CA3
- Uniprot ID
- P07451
- Uniprot Name
- Carbonic anhydrase 3
- Molecular Weight
- 29557.215 Da
References
- Nishimori I, Minakuchi T, Onishi S, Vullo D, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. Bioorg Med Chem. 2007 Dec 1;15(23):7229-36. Epub 2007 Aug 25. [Article]
Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:24