Target Information

Target General Infomation
Target ID
T43920
Former ID
TTDS00304
Target Name
Carbonic anhydrase
Target Type
Successful
Disease Breast cancer [ICD9: 174, 175; ICD10: C50]
Cancer [ICD9: 140-229; ICD10: C00-C96]
Hypertension; Congestive heart failure [ICD9:401, 428; ICD10: I10-I16, I50]
Obesity [ICD9: 278; ICD10: E66]
BioChemical Class
Carbon-oxygen lyases
Target Validation
T43920
EC Number
EC 4.2.1.1
Drugs and Mode of Action
Drug(s) MAFENIDE Drug Info Approved Bacterial infection [1]
Quinethazone Drug Info Approved Hypertension; Congestive heart failure [2], [3], [4]
SALICYLATE Drug Info Phase 4 Discovery agent [5]
Curcumin Drug Info Phase 3 Cancer [6], [7]
PARABEN Drug Info Phase 3 Discovery agent [8]
Phentermine+topiramate Drug Info Phase 3 Obesity [9]
PHENOL Drug Info Phase 2/3 Discovery agent [10]
COUMATE Drug Info Phase 2 Breast cancer [11]
SULFAMIDE Drug Info Phase 1 Discovery agent [12]
CLIOQUINOL Drug Info Withdrawn from market Discovery agent [13]
SPERMINE Drug Info Terminated Discovery agent [14], [15]
Inhibitor (2-bromophenyl)difluoromethanesulfonamide Drug Info [16]
(4-bromophenyl)difluoromethanesulfonamide Drug Info [16]
1-(3,4-dichlorophenyl)-3-hydroxyurea Drug Info [17]
2,3-dihydro-1H-indene-5-sulfonamide Drug Info [18]
2,4-Disulfamyltrifluoromethylaniline Drug Info [19]
2,5-difluorophenol Drug Info [20]
2-acetamido-2,3-dihydro-1H-indene-5-sulfonic acid Drug Info [18]
2-amino-2,3-dihydro-1H-indene-5-sulfonamide Drug Info [18]
2-Amino-benzenesulfonamide Drug Info [19]
2-Amino-indan-5-sulfonic acid Drug Info [18]
2-hydrazinylbenzenesulfonamide Drug Info [19]
2-oxo-2H-chromene-3-carboxylic acid Drug Info [21]
2-oxo-2H-thiochromene-3-carboxylic acid Drug Info [21]
3,5-difluorophenol Drug Info [22]
3-(4-sulfamoylphenyl)propanoic acid Drug Info [23]
3-Amino-benzenesulfonamide Drug Info [24]
3-bromophenyl-difluoromethanesulfonamide Drug Info [16]
3-Nitro-benzenesulfonamide Drug Info [25]
4-(2-Amino-ethyl)-benzenesulfonamide Drug Info [26]
4-(2-aminopyrimidin-4-ylamino)benzenesulfonamide Drug Info [19]
4-(2-Hydroxy-ethyl)-benzenesulfonamide Drug Info [19]
4-(2-Phenylacetamido)-3-bromobenzenesulfonamide Drug Info [27]
4-(2-Phenylacetamido)-3-chlorobenzenesulfonamide Drug Info [27]
4-(2-Phenylacetamido)-3-fluorobenzenesulfonamide Drug Info [27]
4-(2-Phenylacetamido)benzenesulfonamide Drug Info [27]
4-(2-Phenylacetamidoethyl)benzenesulfonamide Drug Info [27]
4-(2-Phenylacetamidomethyl)benzenesulfonamide Drug Info [27]
4-(2-Pyridin-2-ylacetamido)benzenesulfonamide Drug Info [27]
4-(2-Pyridin-4-ylacetamido)benzenesulfonamide Drug Info [27]
4-(hydroxymethyl)benzenesulfonamide Drug Info [19]
4-amino-3,5-dibromobenzenesulfonamide Drug Info [28]
4-Amino-3-bromo-benzenesulfonamide Drug Info [19]
4-Amino-3-chloro-benzenesulfonamide Drug Info [19]
4-amino-3-fluoro-5-iodobenzenesulfonamide Drug Info [28]
4-Amino-3-fluoro-benzenesulfonamide Drug Info [19]
4-Amino-3-iodo-benzenesulfonamide Drug Info [19]
4-amino-6-chlorobenzene-1,3-disulfonamide Drug Info [19]
4-amino-N-(4-sulfamoylbenzyl)benzenesulfonamide Drug Info [19]
4-AMINOPHENOL Drug Info [20]
4-azidobenzenesulfonamide Drug Info [29]
4-bromophenylboronic acid Drug Info [30]
4-butylphenylboronic acid Drug Info [30]
4-CYANOPHENOL Drug Info [20]
4-Hydrazino-benzenesulfonamide Drug Info [19]
4-methoxyphenylboronic acid Drug Info [30]
4-methylphenyl-difluoromethanesulfonamide Drug Info [16]
4-Nitro-benzenesulfonamide Drug Info [25]
4-nitrophenyl phosphate Drug Info [31]
4-nitrophenyl-difluoromethanesulfonamide Drug Info [16]
4-phenoxyphenylboronic acid Drug Info [30]
4-Thiocyanato-benzenesulfonamide Drug Info [25]
4-[2-(2-Thienyl)acetamidoethyl]benzenesulfonamide Drug Info [27]
4-[2-(2-Thienyl)acetamido]benzenesulfonamide Drug Info [27]
5-amino-1,3,4-thiadiazole-2-sulfonamide Drug Info [32]
6-(aminomethyl)-2H-chromen-2-one Drug Info [21]
6-(hydroxymethyl)-2H-chromen-2-one Drug Info [21]
6-Hydroxy-benzothiazole-2-sulfonic acid amide Drug Info [19]
6-methoxy-2-oxo-2H-chromene-3-carboxylic acid Drug Info [21]
6-methyl-2-oxo-2H-chromene-3-carboxylic acid Drug Info [21]
7-(benzyloxy)-2H-chromen-2-one Drug Info [21]
7-butoxy-2H-chromen-2-one Drug Info [21]
7-methoxy-2-oxo-2H-chromene-4-carboxylic acid Drug Info [21]
7-phenethoxy-2H-chromen-2-one Drug Info [21]
7-propoxy-2H-chromen-2-one Drug Info [21]
8-methoxy-2-oxo-2H-chromene-3-carboxylic acid Drug Info [21]
BENZOLAMIDE Drug Info [19]
Benzothiazole-2-sulfonic acid amide Drug Info [26]
Beta-Mercaptoethanol Drug Info [33]
Beta-naphthylboronic acid Drug Info [30]
Biphenyl-4-ylboronic acid Drug Info [30]
Carzenide Drug Info [19]
CATECHIN Drug Info [34]
CATECHOL Drug Info [35]
CLIOQUINOL Drug Info [22]
COUMARIN Drug Info [21]
COUMATE Drug Info [36]
Curcumin Drug Info [34]
Decane-1,10-diyl disulfamate Drug Info [37]
Decyl sulfamate Drug Info [37]
ELLAGIC ACID Drug Info [35]
ETHOXYCOUMARIN Drug Info [21]
Ethyl 7-methoxy-2-oxo-2H-chromene-3-carboxylate Drug Info [21]
FERULIC ACID Drug Info [35]
GALLICACID Drug Info [35]
HERNIARIN Drug Info [21]
Hexane-1,6-diamine Drug Info [38]
MAFENIDE Drug Info [19]
N-(5-ethyl-1,3,4-thiadiazol-2-yl)sulfamide Drug Info [39]
N-(5-phenyl-1,3,4-thiadiazol-2-yl)sulfamide Drug Info [39]
N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)sulfamide Drug Info [39]
N-[5-(ethylthio)-1,3,4-thiadiazol-2-yl]sulfamide Drug Info [39]
N-[5-(methylthio)-1,3,4-thiadiazol-2-yl]sulfamide Drug Info [39]
N1-(2-aminoethyl)ethane-1,2-diamine Drug Info [38]
N1-(naphthalen-1-yl)ethane-1,2-diamine Drug Info [38]
Octane-1,8-diyl disulfamate Drug Info [37]
Octyl sulfamate Drug Info [37]
P-Coumaric Acid Drug Info [35]
P-TOLUENESULFONAMIDE Drug Info [19]
P-tolylboronic acid Drug Info [30]
PARABEN Drug Info [35]
PARAOXON Drug Info [31]
Pentane-1,5-diamine Drug Info [38]
PHENOL Drug Info [34]
Phentermine+topiramate Drug Info [40]
Phenyl Boronic acid Drug Info [41]
Phenylarsonic acid Drug Info [41]
PHENYLDIFLUOROMETHANESULFONAMIDE Drug Info [16]
PHENYLMETHANESULFONAMIDE Drug Info [16]
PRONTOCIL Drug Info [28]
Quinethazone Drug Info [42]
RESORCINOL Drug Info [20]
SACCHARIN Drug Info [43]
SALICYLATE Drug Info [22]
Sodium maleate Drug Info [44]
SPERMINE Drug Info [38]
SULFAMATE Drug Info [41]
SULFAMIDE Drug Info [45]
Syringic Acid Drug Info [35]
References
REF 1J Med Chem. 2010 Apr 8;53(7):2913-26.Sulfonamide linked neoglycoconjugates--a new class of inhibitors for cancer-associated carbonic anhydrases.
REF 2FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 013264.
REF 3(http://www.guidetopharmacology.org/) Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7289).
REF 4Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
REF 5ClinicalTrials.gov (NCT01712295) 17% Salicylate Versus 17% Salicylate-Ethyl Pyruvate for Plantar Foot Warts. U.S. National Institutes of Health.
REF 6Nanocurcumin: a promising therapeutic advancement over native curcumin. Crit Rev Ther Drug Carrier Syst. 2013;30(4):331-68.
REF 7(http://www.guidetopharmacology.org/) Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7000).
REF 8ClinicalTrials.gov (NCT01688479) Trial Comparing Calendula Officinalis With Aqueous Cream "Essex" to Treat Skin Reactions From Radiotherapy of Breast Cancer. U.S. National Institutes of Health.
REF 9Adjunctive topiramate enhances the risk of hypothermia associated with valproic acid therapy. J Clin Pharm Ther. 2008 Oct;33(5):513-9.
REF 10ClinicalTrials.gov (NCT02527187) Determination of the Sensitivity and Specificity of Prick Test Betula Verrucosa.
REF 11Irosustat: a first-generation steroid sulfatase inhibitor in breast cancer. Expert Rev Anticancer Ther. 2011 Feb;11(2):179-83.
REF 12ClinicalTrials.gov (NCT02216669) Trial to Determine Optimal Phase II Dose of the Oral Dual CAIX Inhibitor/ Radiosensitizer. U.S. National Institutes of Health.
REF 13ClinicalTrials.gov (NCT00963495) Study Evaluating the Tolerance and Biological Activity of Oral Clioquinol in Patients With Relapsed or Refractory Hematological Malignancy. U.S. National Institutes of Health.
REF 14(http://www.guidetopharmacology.org/) Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 710).
REF 15Trusted, scientifically sound profiles of drug programs, clinical trials, safety reports, and company deals, written by scientists. Springer. 2015. Adis Insight (drug id 800008464)
REF 16Bioorg 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.
REF 17Bioorg 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.
REF 18Eur 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.
REF 19J 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.
REF 20Bioorg 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.
REF 21J Med Chem. 2010 Jan 14;53(1):335-44.Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins.
REF 22Bioorg 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.
REF 23Bioorg 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.
REF 24Bioorg 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.
REF 25Bioorg 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.
REF 26Bioorg 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.
REF 27Bioorg 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.
REF 28Bioorg 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.
REF 29Bioorg 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.
REF 30Bioorg 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.
REF 31Bioorg Med Chem Lett. 2010 Nov 1;20(21):6208-12. Epub 2010 Aug 26.Paraoxon, 4-nitrophenyl phosphate and acetate are substrates of |A- but not of |A-, |?- and |?-carbonic anhydrases.
REF 32Bioorg 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 acetazolamideresides in a less utilized binding pocket than most hydrophobic inhibitors.
REF 33How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
REF 34Bioorg 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.
REF 35Bioorg 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.
REF 36Bioorg 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.
REF 37J 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.
REF 38J Med Chem. 2010 Aug 12;53(15):5511-22.Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule.
REF 39Bioorg 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.
REF 40Anti-obesity drugs. Expert Opin Pharmacother. 2008 Jun;9(8):1339-50.
REF 41Bioorg 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.
REF 42Carbonic 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.
REF 43Bioorg 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.
REF 44Bioorg 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.
REF 45Bioorg 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.

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