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Showing drug card for Dichlorphenamide (DB01144)

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Version 2.5
Creation Date 2005-06-13 13:24:05
Update Date 2009-06-23 18:06:23
Primary Accession Number DB01144
Secondary Accession Number
  • APRD00131
Name Dichlorphenamide
Drug Type
  • Approved
  • Small Molecule
Description A carbonic anhydrase inhibitor that is used in the treatment of glaucoma. [PubChem]
Synonyms
  1. Dichlofenamide
  2. Dichlorophenamide
  3. Dichlorphenamid
  4. Diclofenamida [INN-Spanish]
  5. Diclofenamide
  6. Diclofenamidum [INN-Latin]
Brand Names
  1. Antidrasi
  2. Daranide
  3. Dasanide
  4. Glaucol
  5. Oratrol
Brand Mixtures Not Available
Chemical IUPAC Name 4,5-dichlorobenzene-1,3-disulfonamide
Chemical Formula C6H6Cl2N2O4S2
Chemical Structure Structure
CAS Registry Number 120-97-8
InChI Identifier InChI=1/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)/f/h9-10H2
InChI Key GJQPMPFPNINLKP-IUIWLCSJCC
KEGG Drug D00518 Link Image
KEGG Compound C07459 Link Image
PubChem Compound 3038 Link Image
PubChem Substance 9662 Link Image
ChEBI ID Not Available
PharmGKB ID PA449292 Link Image
HET ID Not Available
GenBank ID Not Available
Drug ID Number [DIN] Not Available
RxList Link http://www.rxlist.com/cgi/generic/dichlorphen.htm Link Image
PDRhealth Link Not Available
Wikipedia Link http://en.wikipedia.org/wiki/Dichlorphenamide Link Image
FDA Label Not Available
Material Safety Data Sheet (MSDS) Not Available
Synthesis Reference Not Available
Average Molecular Weight 305.1590
Monoisotopic Molecular Weight 303.9146
State Solid
Melting Point 228.7 oC
Experimental Water Solubility Not Available Source: PhysProp
Predicted Water Solubility 3.98e-01 mg/mL Calculated using ALOGPS
Experimental LogP/Hydrophobicity 0.2 Source: PhysProp
Predicted LogP 0.92 Calculated using ALOGPS
Experimental LogS Not Available
Predicted LogS -2.88 Calculated using ALOGPS
Experimental Caco2 Permeability Not Available
pKa/Isoelectric Point Not Available
Mass Spectrum Not Available
MOL File Show Link Image | Download Link Image
SDF File Show Link Image | Download Link Image
PDB File Show Link Image | Download Link Image
2D Structure
3D Structure
Experimental PDB ID 1CZM Link Image
Experimental PDB File Show
Experimental PDB Structure
Isomeric SMILES NS(=O)(=O)C1=CC(=C(Cl)C(Cl)=C1)S(N)(=O)=O
Canonical SMILES NS(=O)(=O)C1=CC(=C(Cl)C(Cl)=C1)S(N)(=O)=O
Drug Category
  • Antiglaucomic Agents
  • Carbonic Anhydrase Inhibitors
  • Ophthalmics
ATC Codes
AHFS Codes Not Available
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
Pharmacology 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.
Absorption Not Available
Toxicity Not Available
Protein Binding 55%
Biotransformation Not Available
Half Life Not Available
Dosage Forms
Form Route
Tablet Oral
Patient Information Not Available
Contraindications Show Link Image
Interactions Show Link Image
Drug Interactions Not Available
Food Interactions Not Available
Pathways Not Available
General References
  1. 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. [PubMed Link Image]
  2. 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. [PubMed Link Image]
  3. Drugs.com Link Image
  4. Wikipedia Link Image
  5. RxList Link Image
Organisms Affected
  • Humans and other mammals
Targets
  1. Carbonic anhydrase 1
Drug Target 1 [top]
Target 1 ID 295
Target 1 Name Carbonic anhydrase 1
Target 1 Synonyms
  1. CA-I
  2. Carbonate dehydratase I
  3. Carbonic anhydrase I
  4. EC 4.2.1.1
Target 1 Gene Name CA1
Target 1 Protein Sequence >Carbonic anhydrase 1 
ASPDWGYDDKNGPEQWSKLYPIANGNNQSPVDIKTSETKHDTSLKPISVSYNPATAKEII
NVGHSFHVNFEDNDNRSVLKGGPFSDSYRLFQFHFHWGSTNEHGSEHTVDGVKYSAELHV
AHWNSAKYSSLAEAASKADGLAVIGVLMKVGEANPKLQKVLDALQAIKTKGKRAPFTNFD
PSTLLPSSLDFWTYPGSLTHPPLYESVTWIICKESISVSSEQLAQFRSLLSNVEGDNAVP
MQHNNRPTQPLKGRTVRASF
Target 1 Number of Residues 264
Target 1 Molecular Weight 28739
Target 1 Theoretical pI 7.14
Target 1 GO Classification
Function
binding
ion binding
cation binding
transition metal ion binding
zinc ion binding
catalytic activity
lyase activity
carbon-oxygen lyase activity
hydro-lyase activity
carbonate dehydratase activity
Process
physiological process
metabolism
cellular metabolism
one-carbon compound metabolism
Component
Not Available
Target 1 General Function Inorganic ion transport and metabolism
Target 1 Specific Function Reversible hydration of carbon dioxide
Target 1 Pathways
Name SMPDB Link KEGG Link
Nitrogen metabolism map00910 Link Image
Target 1 Reactions
  • H2CO3 = CO2 + H2O
Target 1 Pfam Domain Function
Target 1 Signals
  • None
Target 1 Transmembrane Regions
  • None
Target 1 Essentiality Non-Essential
Target 1 GenBank ID Protein 29600 Link Image
Target 1 UniProtKB/Swiss-Prot ID P00915 Link Image
Target 1 UniProtKB/Swiss-Prot Entry Name CAH1_HUMAN Link Image
Target 1 PDB ID 1CZM Link Image
Target 1 PDB File Show
Target 1 3D Structure
Target 1 Cellular Location
  • Cytoplasm
Target 1 Gene Sequence >786 bp 
ATGGCAAGTCCAGACTGGGGATATGATGACAAAAATGGTCCTGAACAATGGAGCAAGCTG
TATCCCATTGCCAATGGAAATAACCAATCCCCTGTTGATATTAAAACCAGTGAAACCAAA
CATGACACCTCTCTGAAACCTATTAGTGTCTCCTACAACCCAGCCACAGCCAAAGAAATT
ATCAATGTGGGGCATTCTTTCCATGTAAATTTTGAGGACAACGATAACCGATCAGTGCTG
AAAGGTGGTCCTTTCTCTGACAGCTACAGGCTCTTTCAGTTTCATTTTCACTGGGGCAGT
ACAAATGAGCATGGTTCAGAACATACAGTGGATGGAGTCAAATATTCTGCCGAGCTTCAC
GTAGCTCACTGGAATTCTGCAAAGTACTCCAGCCTTGCTGAAGCTGCCTCAAAGGCTGAT
GGTTTGGCAGTTATTGGTGTTTTGATGAAGGTTGGTGAGGCCAACCCAAAGCTGCAGAAA
GTACTTGATGCCCTCCAAGCAATTAAAACCAAGGGCAAACGAGCCCCATTCACAAATTTT
GACCCCTCTACTCTCCTTCCTTCATCCCTGGATTTCTGGACCTACCCTGGCTCTCTGACT
CATCCTCCTCTTTATGAGAGTGTAACTTGGATCATCTGTAAGGAGAGCATCAGTGTCAGC
TCAGAGCAGCTGGCACAATTCCGCAGCCTTCTATCAAATGTTGAAGGTGATAACGCTGTC
CCCATGCAGCACAACAACCGCCCAACCCAACCTCTGAAGGGCAGAACAGTGAGAGCTTCA
TTTTGA
Target 1 GenBank Gene ID
Target 1 GeneCard ID CA1 Link Image
Target 1 GenAtlas ID CA1 Link Image
Target 1 HGNC ID HGNC:1368 Link Image
Target 1 Chromosome Location 8
Target 1 Locus 8q13-q22.1
Target 1 SNPs SNPJam Report Link Image
Target 1 General References
  1. Lowe N, Brady HJ, Barlow JH, Sowden JC, Edwards M, Butterworth PH: Structure and methylation patterns of the gene encoding human carbonic anhydrase I. Gene. 1990 Sep 14;93(2):277-83. [PubMed Link Image]
  2. Barlow JH, Lowe N, Edwards YH, Butterworth PH: Human carbonic anhydrase I cDNA. Nucleic Acids Res. 1987 Mar 11;15(5):2386. [PubMed Link Image]
  3. Lin KT, Deutsch HF: Human carbonic anhydrases. XII. The complete primary structure of the C isozyme. J Biol Chem. 1974 Apr 25;249(8):2329-37. [PubMed Link Image]
  4. Giraud N, Marriq C, Laurent-Tabusse G: [Primary structure of human B erythrocyte carbonic anhydrase. 3. Sequence of CNBr fragment I and III (residues 149-260)] Biochimie. 1974;56(8):1031-43. [PubMed Link Image]
  5. Andersson B, Nyman PO, Strid L: Amino acid sequence of human erythrocyte carbonic anhydrase B. Biochem Biophys Res Commun. 1972 Aug 7;48(3):670-7. [PubMed Link Image]
  6. Lin KT, Deutsch HF: Human carbonic anhydrases. XI. The complete primary structure of carbonic anhydrase B. J Biol Chem. 1973 Mar 25;248(6):1885-93. [PubMed Link Image]
  7. Omoto K, Ueda S, Goriki K, Takahashi N, Misawa S, Pagaran IG: Population genetic studies of the Philippine Negritos. III. Identification of the carbonic anhydrase-1 variant with CA1 Guam. Am J Hum Genet. 1981 Jan;33(1):105-11. [PubMed Link Image]
  8. Chegwidden WR, Wagner LE, Venta PJ, Bergenhem NC, Yu YS, Tashian RE: Marked zinc activation of ester hydrolysis by a mutation, 67-His (CAT) to Arg (CGT), in the active site of human carbonic anhydrase I. Hum Mutat. 1994;4(4):294-6. [PubMed Link Image]
  9. Kannan KK, Notstrand B, Fridborg K, Lovgren S, Ohlsson A, Petef M: Crystal structure of human erythrocyte carbonic anhydrase B. Three-dimensional structure at a nominal 2.2-A resolution. Proc Natl Acad Sci U S A. 1975 Jan;72(1):51-5. [PubMed Link Image]
Target 1 Drug References
  1. 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. [PubMed Link Image]
  2. 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. [PubMed Link Image]
  3. Lindskog S: Structure and mechanism of carbonic anhydrase. Pharmacol Ther. 1997;74(1):1-20. [PubMed Link Image]

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.