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Record Information
Version4.0
Creation Date2012-09-06 15:16:51 UTC
Update Date2017-10-23 19:06:29 UTC
HMDB IDHMDB0015275
Secondary Accession Numbers
  • HMDB15275
Metabolite Identification
Common NameDichlorphenamide
DescriptionDichlorphenamide is only found in individuals that have used or taken this drug. It is a carbonic anhydrase inhibitor that is used in the treatment of glaucoma. [PubChem]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.
Structure
Thumb
Synonyms
ValueSource
1,3-Disulfamoyl-4,5-dichlorobenzeneChEBI
1,3-Disulfamyl-4,5-dichlorobenzeneChEBI
3,4-dichloro-5-SulfamylbenzenesulfonamideChEBI
4,5-dichloro-1,3-BenzenedisulfonamideChEBI
4,5-dichloro-1,3-DisulfamoylbenzeneChEBI
4,5-dichloro-Benzene-1,3-disulfonic acid diamideChEBI
4,5-dichloro-m-BenzenedisulfonamideChEBI
4,5-DICHLOROBENZENE-1,3-disulfonamideChEBI
DichlofenamideChEBI
DichlorophenamideChEBI
DiclofenamidaChEBI
DiclofenamidumChEBI
1,3-Disulphamoyl-4,5-dichlorobenzeneGenerator
1,3-Disulphamyl-4,5-dichlorobenzeneGenerator
3,4-dichloro-5-SulphamylbenzenesulphonamideGenerator
4,5-dichloro-1,3-BenzenedisulphonamideGenerator
4,5-dichloro-1,3-DisulphamoylbenzeneGenerator
4,5-dichloro-Benzene-1,3-disulfonate diamideGenerator
4,5-dichloro-Benzene-1,3-disulphonate diamideGenerator
4,5-dichloro-Benzene-1,3-disulphonic acid diamideGenerator
4,5-dichloro-m-BenzenedisulphonamideGenerator
4,5-DICHLOROBENZENE-1,3-disulphonamideGenerator
4,5-Dicholorobenzene-1,3-disulfonamideHMDB
DichlorphenamidHMDB
DiclofenamideHMDB
DiclofenamidMeSH
DaranideMeSH
GlauconideMeSH
Llorens brand OF dichlorphenamideMeSH
Merck brand OF dichlorphenamideMeSH
Chemical FormulaC6H6Cl2N2O4S2
Average Molecular Weight305.159
Monoisotopic Molecular Weight303.914603484
IUPAC Name4,5-dichlorobenzene-1,3-disulfonamide
Traditional Namedichlorphenamide
CAS Registry Number120-97-8
SMILES
NS(=O)(=O)C1=CC(=C(Cl)C(Cl)=C1)S(N)(=O)=O
InChI Identifier
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)
InChI KeyGJQPMPFPNINLKP-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of chemical entities known as benzenesulfonamides. These are organic compounds containing a sulfonamide group that is S-linked to a benzene ring.
KingdomChemical entities
Super ClassOrganic compounds
ClassBenzenoids
Sub ClassBenzene and substituted derivatives
Direct ParentBenzenesulfonamides
Alternative Parents
Substituents
  • Benzenesulfonamide
  • Benzenesulfonyl group
  • 1,2-dichlorobenzene
  • Chlorobenzene
  • Halobenzene
  • Aryl chloride
  • Aryl halide
  • Organosulfonic acid amide
  • Aminosulfonyl compound
  • Sulfonyl
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Organohalogen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Organochloride
  • Organosulfur compound
  • Organic oxygen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Disposition

Biological Location:

  Subcellular:

  Biofluid and excreta:

Role

Industrial application:

  Pharmaceutical industry:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point228.7 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.4 g/LNot Available
LogP0.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP0.92ALOGPS
logP0.39ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)7.94ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area120.32 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity59.98 m³·mol⁻¹ChemAxon
Polarizability25.04 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash Key
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-00fr-1190000000-05ac58ca7b0d878559c9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0009000000-96143650a7f633efcdfbView in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0019000000-bbe52404fad8ebabeb95View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-056r-0290000000-935d4eff121cbb4795c4View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0009000000-a20a034f8bd3c1f4b339View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-0049000000-f461bd5e7ade13a53282View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9030000000-9d1ed58d3493bfa5183fView in MoNA
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
NameSMPDB/PathwhizKEGG
No entries found
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01144 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB01144 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01144
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2930
KEGG Compound IDC07459
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDichlorphenamide
METLIN IDNot Available
PubChem Compound3038
PDB IDI7A
ChEBI ID101085
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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:1364383 ]
  2. 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:10632100 ]

Enzymes

General function:
Involved in monooxygenase activity
Specific function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenytoin, tolbutamide and losartan.
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular weight:
55627.365
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular weight:
28870.0
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:14684332 ]
  2. Lindskog S: Structure and mechanism of carbonic anhydrase. Pharmacol Ther. 1997;74(1):1-20. [PubMed:9336012 ]
  3. 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:17228881 ]
  4. 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. [PubMed:19648295 ]
  5. 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. [PubMed:19019313 ]
General function:
Involved in carbonate dehydratase activity
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 into the anterior chamber of the eye.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular weight:
29245.895
References
  1. 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. [PubMed:18336310 ]
General function:
Involved in carbonate dehydratase activity
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 and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:
CA4
Uniprot ID:
P22748
Molecular weight:
35032.075
References
  1. 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. [PubMed:18336310 ]
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide.
Gene Name:
CA7
Uniprot ID:
P43166
Molecular weight:
23451.435
References
  1. 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. [PubMed:18336310 ]