| 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 |
|
| Name |
Dichlorphenamide |
| Drug Type |
|
| Description |
A carbonic anhydrase inhibitor that is used in the treatment of glaucoma. [PubChem] |
| Synonyms |
- Dichlofenamide
- Dichlorophenamide
- Dichlorphenamid
- Diclofenamida [INN-Spanish]
- Diclofenamide
- Diclofenamidum [INN-Latin]
|
| Brand Names |
- Antidrasi
- Daranide
- Dasanide
- Glaucol
- Oratrol
|
| Brand Mixtures |
Not Available |
| Chemical IUPAC Name |
4,5-dichlorobenzene-1,3-disulfonamide |
| Chemical Formula |
C6H6Cl2N2O4S2 |
| Chemical 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  |
| KEGG Compound |
C07459  |
| PubChem Compound |
3038  |
| PubChem Substance |
9662  |
| ChEBI ID |
Not Available |
| PharmGKB ID |
PA449292  |
| HET ID |
Not Available |
| GenBank ID |
Not Available |
| Drug ID Number [DIN] |
Not Available |
| RxList Link |
http://www.rxlist.com/cgi/generic/dichlorphen.htm  |
| PDRhealth Link |
Not Available |
| Wikipedia Link |
http://en.wikipedia.org/wiki/Dichlorphenamide  |
| 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 | Download  |
| SDF File |
Show | Download  |
| PDB File |
Show | Download  |
| 2D Structure |
|
| 3D Structure |
|
| Experimental PDB ID |
1CZM  |
| 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 |
|
| Patient Information |
Not Available |
| Contraindications |
Show  |
| Interactions |
Show  |
| Drug Interactions |
Not Available
|
| Food Interactions |
Not Available
|
| Pathways |
Not Available
|
| 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. [PubMed
]
- 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
]
- Drugs.com

- Wikipedia

- RxList

|
| Organisms Affected |
|
| Targets |
- Carbonic anhydrase 1
|
|
Drug Target 1
[top]
|
| Target 1 ID |
295 |
| Target 1 Name |
Carbonic anhydrase 1 |
| Target 1 Synonyms |
- CA-I
- Carbonate dehydratase I
- Carbonic anhydrase I
- 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  |
|
| Target 1 Reactions |
|
| Target 1 Pfam Domain Function |
|
| Target 1 Signals |
|
| Target 1 Transmembrane Regions |
|
| Target 1 Essentiality |
Non-Essential |
| Target 1 GenBank ID Protein |
29600  |
| Target 1 UniProtKB/Swiss-Prot ID |
P00915  |
| Target 1 UniProtKB/Swiss-Prot Entry Name |
CAH1_HUMAN  |
| Target 1 PDB ID |
1CZM  |
| Target 1 PDB File |
Show |
| Target 1 3D Structure |
|
| Target 1 Cellular Location |
|
| 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  |
| Target 1 GenAtlas ID |
CA1  |
| Target 1 HGNC ID |
HGNC:1368  |
| Target 1 Chromosome Location |
8 |
| Target 1 Locus |
8q13-q22.1 |
| Target 1 SNPs |
SNPJam Report  |
| Target 1 General References |
- 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
]
- Barlow JH, Lowe N, Edwards YH, Butterworth PH: Human carbonic anhydrase I cDNA. Nucleic Acids Res. 1987 Mar 11;15(5):2386. [PubMed
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
- 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
]
|
| Target 1 Drug 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. [PubMed
]
- 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
]
- Lindskog S: Structure and mechanism of carbonic anhydrase. Pharmacol Ther. 1997;74(1):1-20. [PubMed
]
|