Therapeutic Targets Database
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TTD Target ID: TTDS00304

Target Information
NameCarbonic anhydrase    
Type of targetSuccessful target    
DiseaseGlaucoma
[ICD9: 365   ICD10: H40-H42]
[1]
Ocular hypertension
[ICD9: 365.04   ICD10: H40.0]
[1]
Drug(s)AcetazolamideApprovedGlaucoma[2][3][4][5]
BrinzolamideApprovedOpen-angle glaucoma and ocular hypertension[2][6]
DiazoxideApprovedHypertension[7]
DichlorphenamideApprovedChronic glaucoma[2][8][6]
EthoxzolamideApprovedGlaucoma, duodenal ulcers[2][9]
MethazolamideApprovedChronic and acute open-angle glaucoma[10][11][12][5]
QuinethazoneApprovedHypertension[7]
Phentermine+topiramatePhase IIIObesity[13]
BioChemical ClassCarbon-oxygen lyases    
EC NumberEC 4.2.1.1
PathwayNitrogen metabolism
Related US Patent6,316,443
Target ValidationClick to Find Target Validation Information.    
QSAR ModelClick to Find Target QSAR Model.    
Inhibitor (2-bromophenyl)difluoromethanesulfonamide[14]
(4-bromophenyl)difluoromethanesulfonamide[14]
1- (3,4-dichlorophenyl)-3-hydroxyurea[15]
2,3-dihydro-1H-indene-5-sulfonamide[16]
2,4-Disulfamyltrifluoromethylaniline[17]
2,5-difluorophenol[18]
2-acetamido-2,3-dihydro-1H-indene-5-sulfonic acid[16]
2-amino-2,3-dihydro-1H-indene-5-sulfonamide[16]
2-amino-2,3-dihydro-1H-indene-5-sulfonic acid[16]
2-aminobenzenesulfonamide[17]
2-hydrazinylbenzenesulfonamide[17]
2-oxo-2H-chromene-3-carboxylic acid[19]
2-oxo-2H-thiochromene-3-carboxylic acid[19]
3,5-difluorophenol[20]
3- (4-sulfamoylphenyl)propanoic acid[21]
3-Amino-benzenesulfonamide[22]
3-Nitro-benzenesulfonamide[23]
3-bromophenyl-difluoromethanesulfonamide[14]
4- (2-Amino-ethyl)-benzenesulfonamide[24]
4- (2-Phenylacetamido)-3-bromobenzenesulfonamide[25]
4- (2-Phenylacetamido)-3-chlorobenzenesulfonamide[25]
4- (2-Phenylacetamido)-3-fluorobenzenesulfonamide[25]
4- (2-Phenylacetamido)benzenesulfonamide[25]
4- (2-Phenylacetamidoethyl)benzenesulfonamide[25]
4- (2-Phenylacetamidomethyl)benzenesulfonamide[25]
4- (2-Pyridin-2-ylacetamido)benzenesulfonamide[25]
4- (2-Pyridin-4-ylacetamido)benzenesulfonamide[25]
4- (2-aminopyrimidin-4-ylamino)benzenesulfonamide[17]
4- (2-hydroxyethyl)benzenesulfonamide[17]
4- (hydroxymethyl)benzenesulfonamide[17]
4-AMINOPHENOL[18]
4-CYANOPHENOL[18]
4-Nitro-benzenesulfonamide[23]
4-Thiocyanato-benzenesulfonamide[23]
4-[2- (2-Thienyl)acetamido]benzenesulfonamide[25]
4-[2- (2-Thienyl)acetamidoethyl]benzenesulfonamide[25]
4-amino-3,5-dibromobenzenesulfonamide[26]
4-amino-3-bromobenzenesulfonamide[17]
4-amino-3-chlorobenzenesulfonamide[17]
4-amino-3-fluoro-5-iodobenzenesulfonamide[26]
4-amino-3-fluorobenzenesulfonamide[17]
4-amino-3-iodobenzenesulfonamide[17]
4-amino-6-chlorobenzene-1,3-disulfonamide[17]
4-amino-N- (4-sulfamoylbenzyl)benzenesulfonamide[17]
4-azidobenzenesulfonamide[27]
4-bromophenylboronic acid[28]
4-butylphenylboronic acid[28]
4-hydrazinylbenzenesulfonamide[17]
4-methoxyphenylboronic acid[28]
4-methylphenyl-difluoromethanesulfonamide[14]
4-nitrophenyl phosphate[29]
4-nitrophenyl-difluoromethanesulfonamide[14]
4-phenoxyphenylboronic acid[28]
5-amino-1,3,4-thiadiazole-2-sulfonamide[30]
6- (aminomethyl)-2H-chromen-2-one[19]
6- (hydroxymethyl)-2H-chromen-2-one[19]
6-hydroxybenzo[d]thiazole-2-sulfonamide[17]
6-methoxy-2-oxo-2H-chromene-3-carboxylic acid[19]
6-methyl-2-oxo-2H-chromene-3-carboxylic acid[19]
7- (benzyloxy)-2H-chromen-2-one[19]
7-butoxy-2H-chromen-2-one[19]
7-methoxy-2-oxo-2H-chromene-4-carboxylic acid[19]
7-phenethoxy-2H-chromen-2-one[19]
7-propoxy-2H-chromen-2-one[19]
8-methoxy-2-oxo-2H-chromene-3-carboxylic acid[19]
Acetazolamide[2][3][4][5]
BENZOLAMIDE[17]
Benzothiazole-2-sulfonic acid amide[24]
Beta-Mercaptoethanol[31]
Brinzolamide[2][6]
CATECHIN[32]
CATECHOL[33]
CLIOQUINOL[20]
COUMARIN[19]
COUMATE[34]
CURCUMIN[32]
Carzenide,   Para-Carboxybenzenesulfonamide (Weak Carbonic Anhydrase Inhibitor)[17]
Diazoxide[7]
Dichlorphenamide[2][8][6]
ELLAGIC ACID[33]
ETHOXYCOUMARIN[19]
Ethoxzolamide[2][9]
FERULIC ACID[33]
GALLICACID[33]
HERNIARIN[19]
INDISULAM[17]
MAFENIDE[17]
Methazolamide[10][11][12][5]
N- (5-ethyl-1,3,4-thiadiazol-2-yl)sulfamide[35]
N- (5-phenyl-1,3,4-thiadiazol-2-yl)sulfamide[35]
N- (5-tert-butyl-1,3,4-thiadiazol-2-yl)sulfamide[35]
N-[5- (ethylthio)-1,3,4-thiadiazol-2-yl]sulfamide[35]
N-[5- (methylthio)-1,3,4-thiadiazol-2-yl]sulfamide[35]
N1- (2-aminoethyl)ethane-1,2-diamine[36]
N1- (naphthalen-1-yl)ethane-1,2-diamine[36]
P-TOLUENESULFONAMIDE[17]
PARABEN[33]
PARAOXON[29]
PHENOL[32]
PHENYLDIFLUOROMETHANESULFONAMIDE[14]
PHENYLMETHANESULFONAMIDE[14]
PRONTOCIL[26]
Phentermine+topiramate[13]
Quinethazone[7]
RESORCINOL[18]
SACCHARIN[37]
SALICYLATE[20]
SPERMINE[36]
SULFAMATE[38]
SULFAMIDE[39]
Syringic Acid[33]
beta-naphthylboronic acid[28]
biphenylboronic acid[28]
decane-1,10-diyl disulfamate[40]
decyl sulfamate[40]
ethyl 7-methoxy-2-oxo-2H-chromene-3-carboxylate[19]
hexane-1,6-diamine[36]
octane-1,8-diyl disulfamate[40]
octyl sulfamate[40]
p-Coumaric Acid[33]
p-tolylboronic acid[28]
pentane-1,5-diamine[36]
phenylarsonic acid[38]
phenylboronic acid[38]
sodium maleate[41]
MultitargetPhentermine+topiramate[13]
Cross References 3D Structure
Related Literature
On-Line Medical Dictionary
Ref 1Brinzolamide/timolol: in open-angle glaucoma and ocular hypertension. Drugs Aging. 2009;26(5):437-46. doi: 10.2165/00002512-200926050-00007. To Reference
Ref 2Bioorg Med Chem. 2009 Jul 15;17(14):5054-8. Epub 2009 May 30.Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. To Reference
Ref 3Vasodilatory effect of diuretics is dependent on inhibition of vascular smooth muscle carbonic anhydrase by a direct mechanism of action. Drugs Exp Clin Res. 1999;25(6):271-9. To Reference
Ref 4Nonsteroidal anti-inflammatory drugs activate carbonic anhydrase by a direct mechanism of action. J Pharmacol Exp Ther. 1996 Jun;277(3):1464-6. To Reference
Ref 5Interactions of human organic anion transporters with diuretics. J Pharmacol Exp Ther. 2004 Mar;308(3):1021-9. Epub 2003 Nov 10. To Reference
Ref 6Molecular cloning, characterization, and inhibition studies of the Rv1284 beta-carbonic anhydrase from Mycobacterium tuberculosis with sulfonamides and a sulfamate. J Med Chem. 2009 Apr 23;52(8):2226-32. To Reference
Ref 7Carbonic anhydrase inhibitors. Interaction of indapamide and related diuretics with 12 mammalian isozymes and X-ray crystallographic studies for the indapamide-isozyme II adduct. Bioorg Med Chem Lett. 2008 Apr 15;18(8):2567-73. Epub 2008 Mar 20. To Reference
Ref 8Carbonic anhydrase inhibitors. Cloning, characterization, and inhibition studies of a new beta-carbonic anhydrase from Mycobacterium tuberculosis. J Med Chem. 2009 May 14;52(9):3116-20. To Reference
Ref 9Retrospective cohort study of 163 pediatric glaucoma patients. Can J Ophthalmol. 2009 Jun;44(3):323-7. To Reference
Ref 10Carbonic anhydrase inhibitors: aromatic and heterocyclic sulfonamides incorporating adamantyl moieties with strong anticonvulsant activity. Bioorg Med Chem. 2004 May 15;12(10):2717-26. To Reference
Ref 11Carbonic anhydrase inhibitors: synthesis of membrane-impermeant low molecular weight sulfonamides possessing in vivo selectivity for the membrane-bound versus cytosolic isozymes. J Med Chem. 2000 Jan 27;43(2):292-300. To Reference
Ref 12Carbonic 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. To Reference
Ref 13Anti-obesity drugs. Expert Opin Pharmacother. 2008 Jun;9(8):1339-50. To Reference
Ref 14Bioorg Med Chem Lett. 2005 Dec 1;15(23):5192-6. Epub 2005 Oct 3.Carbonic anhydrase inhibitors: inhibition of the human isozymes I, II, VA, and IX with a library of substituted difluoromethanesulfonamides. To Reference
Ref 15Bioorg Med Chem Lett. 2006 Aug 15;16(16):4316-20. Epub 2006 Jun 12.N-hydroxyurea--a versatile zinc binding function in the design of metalloenzyme inhibitors. To Reference
Ref 16Eur J Med Chem. 2008 Dec;43(12):2853-60. Epub 2008 Feb 29.Indanesulfonamides as carbonic anhydrase inhibitors and anticonvulsant agents: structure-activity relationship and pharmacological evaluation. To Reference
Ref 17J Med Chem. 2009 Feb 12;52(3):646-54.Cloning, expression, post-translational modifications and inhibition studies on the latest mammalian carbonic anhydrase isoform, CA XV. To Reference
Ref 18Bioorg Med Chem. 2008 Aug 1;16(15):7424-8. Epub 2008 Jun 13.Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. To Reference
Ref 19J Med Chem. 2010 Jan 14;53(1):335-44.Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. To Reference
Ref 20Bioorg Med Chem Lett. 2008 Jun 15;18(12):3593-6. Epub 2008 May 4.Carbonic anhydrase inhibitors: Inhibition of the new membrane-associated isoform XV with phenols. To Reference
Ref 21Bioorg Med Chem. 2009 Jul 1;17(13):4503-9. Epub 2009 May 8.Carbonic anhydrase inhibitors. Inhibition and homology modeling studies of the fungal beta-carbonic anhydrase from Candida albicans with sulfonamides. To Reference
Ref 22Bioorg Med Chem Lett. 2004 Dec 20;14(24):6001-6.Carbonic anhydrase inhibitors. Inhibition of the prokariotic beta and gamma-class enzymes from Archaea with sulfonamides. To Reference
Ref 23Bioorg Med Chem Lett. 2004 Nov 15;14(22):5703-7.Carbonic anhydrase inhibitors: inhibition of human cytosolic isozyme II and mitochondrial isozyme V with a series of benzene sulfonamide derivatives. To Reference
Ref 24Bioorg Med Chem Lett. 2005 Feb 15;15(4):971-6.Carbonic anhydrase inhibitors. Inhibition of the human cytosolic isozyme VII with aromatic and heterocyclic sulfonamides. To Reference
Ref 25Bioorg Med Chem. 2009 Jul 15;17(14):4894-9. Epub 2009 Jun 9.Carbonic anhydrase inhibitors. Aromatic/heterocyclic sulfonamides incorporating phenacetyl, pyridylacetyl and thienylacetyl tails act as potent inhibitors of human mitochondrial isoforms VA and VB. To Reference
Ref 26Bioorg Med Chem. 2007 Dec 1;15(23):7229-36. Epub 2007 Aug 25.Carbonic anhydrase inhibitors: cloning, characterization, and inhibition studies of the cytosolic isozyme III with sulfonamides. To Reference
Ref 27Bioorg Med Chem Lett. 2008 Aug 15;18(16):4624-7. Epub 2008 Jul 10.Inhibition of human mitochondrial carbonic anhydrases VA and VB with para-(4-phenyltriazole-1-yl)-benzenesulfonamide derivatives. To Reference
Ref 28Bioorg Med Chem Lett. 2009 May 15;19(10):2642-5. Epub 2009 Apr 5.Carbonic anhydrase inhibitors. Inhibition of the fungal beta-carbonic anhydrases from Candida albicans and Cryptococcus neoformans with boronic acids. To Reference
Ref 29Bioorg Med Chem Lett. 2010 Nov 1;20(21):6208-12. Epub 2010 Aug 26.Paraoxon, 4-nitrophenyl phosphate and acetate are substrates of - but not of -, - and -carbonic anhydrases. To Reference
Ref 30Bioorg Med Chem Lett. 2010 Aug 1;20(15):4376-81. Epub 2010 Jun 17.Carbonic anhydrase inhibitors. The X-ray crystal structure of human isoform II in adduct with an adamantyl analogue of acetazolamide resides in a less utilized binding pocket than most hydrophobic inhibitors. To Reference
Ref 31Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. To Reference
Ref 32Bioorg Med Chem Lett. 2010 Sep 1;20(17):5050-3. Epub 2010 Jul 13.Carbonic anhydrase inhibitors. Antioxidant polyphenols effectively inhibit mammalian isoforms I-XV. To Reference
Ref 33Bioorg Med Chem. 2010 Mar 15;18(6):2159-64. Epub 2010 Feb 6.Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. To Reference
Ref 34Bioorg Med Chem Lett. 2008 Aug 1;18(15):4282-6. Epub 2008 Jul 5.Carbonic anhydrase inhibitors. Interaction of the antitumor sulfamate EMD 486019 with twelve mammalian carbonic anhydrase isoforms: Kinetic and X-ray crystallographic studies. To Reference
Ref 35Bioorg Med Chem Lett. 2008 Dec 15;18(24):6332-5. Epub 2008 Nov 1.Carbonic anhydrase inhibitors: 2-substituted-1,3,4-thiadiazole-5-sulfamides act as powerful and selective inhibitors of the mitochondrial isozymes VA and VB over the cytosolic and membrane-associated carbonic anhydrases I, II and IV. To Reference
Ref 36J Med Chem. 2010 Aug 12;53(15):5511-22.Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule. To Reference
Ref 37Bioorg Med Chem Lett. 2009 Dec 1;19(23):6649-54. Epub 2009 Oct 7.Carbonic anhydrase inhibitors. Characterization and inhibition studies of the most active beta-carbonic anhydrase from Mycobacterium tuberculosis, Rv3588c. To Reference
Ref 38Bioorg Med Chem Lett. 2006 Jun 15;16(12):3139-43. Epub 2006 Apr 18.Carbonic anhydrase inhibitors: inhibition of the cytosolic human isozyme VII with anions. To Reference
Ref 39Bioorg Med Chem Lett. 2010 Jun 15;20(12):3601-5. Epub 2010 Apr 28.Carbonic anhydrase inhibitors: crystallographic and solution binding studies for the interaction of a boron-containing aromatic sulfamide with mammalian isoforms I-XV. To Reference
Ref 40J Med Chem. 2009 Oct 8;52(19):5990-8.Carbonic anhydrase inhibitors. Comparison of aliphatic sulfamate/bis-sulfamate adducts with isozymes II and IX as a platform for designing tight-binding, more isoform-selective inhibitors. To Reference
Ref 41Bioorg Med Chem. 2009 Apr 1;17(7):2654-7. Epub 2009 Mar 5.Carbonic anhydrase inhibitors. Inhibition of the beta-class enzymes from the fungal pathogens Candida albicans and Cryptococcus neoformans with aliphatic and aromatic carboxylates. To Reference



 

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Professor in Department of Pharmacy
National University of Singapore, Singapore


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