Target Information

Target General Infomation
Target ID
T13201
Former ID
TTDR01224
Target Name
Carbonic anhydrase I
Gene Name
CA1
Synonyms
CA-I; Carbonate dehydratase I; Carbonic anhydrase B; CA1
Target Type
Successful
Disease Arthritis [ICD9: 710-719; ICD10: M00-M25]
Breast cancer [ICD9: 174, 175; ICD10: C50]
Cancer [ICD9: 140-229; ICD10: C00-C96]
Chronic glaucoma [ICD9: 365; ICD10: H40-H42]
Glaucoma; Duodenal ulcers [ICD9: 365, 531-534; ICD10: H40-H42, K25-K27]
Glaucoma [ICD9: 365; ICD10: H40-H42]
Function
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
BioChemical Class
Carbon-oxygen lyases
Target Validation
T13201
UniProt ID
P00915
EC Number
EC 4.2.1.1
Sequence
MASPDWGYDDKNGPEQWSKLYPIANGNNQSPVDIKTSETKHDTSLKPISVSYNPATAKEI
INVGHSFHVNFEDNDNRSVLKGGPFSDSYRLFQFHFHWGSTNEHGSEHTVDGVKYSAELH
VAHWNSAKYSSLAEAASKADGLAVIGVLMKVGEANPKLQKVLDALQAIKTKGKRAPFTNF
DPSTLLPSSLDFWTYPGSLTHPPLYESVTWIICKESISVSSEQLAQFRSLLSNVEGDNAV
PMQHNNRPTQPLKGRTVRASF
Drugs and Mode of Action
Drug(s) Acetazolamide Drug Info Approved Glaucoma [1], [2]
Dichlorphenamide Drug Info Approved Chronic glaucoma [3], [4]
Ethoxzolamide Drug Info Approved Glaucoma; Duodenal ulcers [5], [6]
Methazolamide Drug Info Approved Glaucoma [7], [8]
SALICYLATE Drug Info Phase 4 Discovery agent [9]
CG-100649 Drug Info Phase 3 Arthritis [10], [11]
Curcumin Drug Info Phase 3 Cancer [12], [13]
PARABEN Drug Info Phase 3 Discovery agent [14]
PHENOL Drug Info Phase 2/3 Discovery agent [15]
COUMATE Drug Info Phase 2 Breast cancer [16]
SULFAMIDE Drug Info Phase 1 Discovery agent [17]
Inhibitor (2-bromophenyl)difluoromethanesulfonamide Drug Info [18]
(4-bromophenyl)difluoromethanesulfonamide Drug Info [18]
1,4-Dihydro-1-methyl-4-oxo-3-pyridinesulfonamide Drug Info [19]
1-acetamido-5-sulfonamidoindane Drug Info [20]
1-Benzyl-1,4-dihydro-4-oxo-3-pyridinesulfonamide Drug Info [19]
1-cyclohexylamido-5-sulfonamidoindane Drug Info [21]
1-pentafluorophenylamido-5-sulfonamidoindane Drug Info [21]
1-valproylamido-5-sulfonamidoindane Drug Info [21]
2,2,2-Trifluoro-N-(4-sulfamoyl-phenyl)-acetamide Drug Info [22]
2,3-dihydro-1H-indene-5-sulfonamide Drug Info [20]
2,4-dichloro-5-sulfamoylbenzoic acid Drug Info [23]
2,4-Disulfamyltrifluoromethylaniline Drug Info [24]
2-(4-chlorobenzyloxyamino)-N-hydroxyacetamide Drug Info [25]
2-(4-chlorobenzyloxyamino)-N-hydroxyhexanamide Drug Info [25]
2-(4-chlorobenzyloxyamino)-N-hydroxypropanamide Drug Info [25]
2-(biphenyl-4-yl)vinylboronic acid Drug Info [26]
2-acetamido-5-sulfonamidoindane Drug Info [21]
2-Acetylamino-indan-5-sulfonic acid hydrate Drug Info [20]
2-Amino-indan-5-sulfonic acid Drug Info [20]
2-butylamido-5-sulfonamidoindane Drug Info [21]
2-cyclohexylamido-5-sulfonamidoindane Drug Info [21]
2-ethylamido-5-sulfonamidoindane Drug Info [21]
2-Hydroxycinnamic acid Drug Info [27]
2-Mercapto-N-(4-sulfamoyl-phenyl)-benzamide Drug Info [28]
2-Morpholin-4-yl-N-(4-sulfamoyl-phenyl)-acetamide Drug Info [29]
2-nonylamido-5-sulfonamidoindane Drug Info [21]
2-oxo-2H-chromene-3-carboxylic acid Drug Info [30]
2-oxo-2H-thiochromene-3-carboxylic acid Drug Info [30]
2-pentafluorophenylamido-5-sulfonamidoindane Drug Info [21]
2-propylamido-5-sulfonamidoindane Drug Info [21]
2-valproylamido-5-sulfonamidoindane Drug Info [21]
3-(3-Phenyl-ureido)-benzenesulfonamide Drug Info [22]
3-(4-sulfamoylphenyl)propanoic acid Drug Info [24]
3-bromophenyl-difluoromethanesulfonamide Drug Info [18]
3-Chloro-4-hydrazino-benzenesulfonamide Drug Info [31]
3-Fluoro-4-hydrazino-benzenesulfonamide Drug Info [31]
3-mercapto-N-(4-sulfamoyl-phenyl)-propionamide Drug Info [32]
3-phenyl-5-sulfamoyl-1H-indole-2-carboxamide Drug Info [33]
3-phenylprop-1-enylboronic acid Drug Info [26]
3-[4-(AMINOSULFONYL)PHENYL]PROPANOIC ACID Drug Info [34]
4,4'-thiodipyridine-3-sulfonamide Drug Info [35]
4,6-Dinitro salicylic acid Drug Info [36]
4-(2-Amino-ethyl)-benzenesulfonamide Drug Info [37]
4-(2-aminopyrimidin-4-ylamino)benzenesulfonamide Drug Info [24]
4-(2-Methyl-8-quinolinoxy)-3-pyridinesulfonamide Drug Info [35]
4-(2-Phenylacetamido)-3-bromobenzenesulfonamide Drug Info [38]
4-(2-Phenylacetamido)-3-chlorobenzenesulfonamide Drug Info [38]
4-(2-Phenylacetamido)-3-fluorobenzenesulfonamide Drug Info [38]
4-(2-Phenylacetamido)benzenesulfonamide Drug Info [38]
4-(2-Phenylacetamidoethyl)benzenesulfonamide Drug Info [38]
4-(2-Phenylacetamidomethyl)benzenesulfonamide Drug Info [38]
4-(2-Propynylthio)pyridine-3-sulfonamide Drug Info [35]
4-(2-Pyridin-2-ylacetamido)benzenesulfonamide Drug Info [38]
4-(2-Pyridin-4-ylacetamido)benzenesulfonamide Drug Info [38]
4-(4-Cyanophenoxy)-3-pyridinesulfonamide Drug Info [35]
4-(4-Fluorophenoxy)-3-pyridinesulfonamide Drug Info [35]
4-(5-Methyl-2-pirazolino)-3-pyridinesulfonamide Drug Info [35]
4-(Allylamino)-3-pyridinesulfonamide Drug Info [35]
4-(Carbamolymethylthio)pyridine-3-sulfonamide Drug Info [35]
4-(Cyanomethylthio)pyridine-3-sulfonamide Drug Info [35]
4-(hydroxymethyl)benzenesulfonamide Drug Info [24]
4-(Methylhydrazino)-3-pyridinesulfonamide Drug Info [35]
4-(N-Oxide-2-pyridylthio)pyridine-3-sulfonamide Drug Info [35]
4-(Quinolinoxy)-3-pyridinesulfonamide Drug Info [35]
4-Amino-3-bromo-benzenesulfonamide Drug Info [24]
4-Amino-3-chloro-benzenesulfonamide Drug Info [24]
4-Amino-3-fluoro-benzenesulfonamide Drug Info [39]
4-Amino-3-iodo-benzenesulfonamide Drug Info [24]
4-amino-6-chlorobenzene-1,3-disulfonamide Drug Info [39]
4-amino-N-(4-sulfamoylbenzyl)benzenesulfonamide Drug Info [24]
4-azidobenzenesulfonamide Drug Info [40]
4-Benzenesulfonylamino-benzenesulfonamide Drug Info [22]
4-Benzythiopyridine-3-sulfonamide Drug Info [35]
4-bromophenylboronic acid Drug Info [26]
4-butylphenylboronic acid Drug Info [26]
4-Chloro-N-(5-sulfamoyl-indan-2-yl)-benzamide Drug Info [20]
4-Ethoxy-3-pyridinesulfonamide Drug Info [35]
4-ethynyl benzene sulfonamide Drug Info [41]
4-fluoro-N-(4-sulfamoylbenzyl)benzenesulfonamide Drug Info [42]
4-Hydrazino-3-pyridinesulfonamide Drug Info [35]
4-Hydrazino-benzenesulfonamide Drug Info [31]
4-Hydrazinocarbonyl-benzenesulfonamide Drug Info [31]
4-isothiocyanatobenzenesulfonamide Drug Info [43]
4-Methanesulfonylamino-benzenesulfonamide Drug Info [22]
4-Methoxy-3-pyridinesulfonamide Drug Info [35]
4-methoxyphenylboronic acid Drug Info [26]
4-methylphenyl-difluoromethanesulfonamide Drug Info [18]
4-methylstyrylboronic acid Drug Info [26]
4-Methylthiopyridine-3-sulfonamide Drug Info [35]
4-nitrophenyl phosphate Drug Info [44]
4-nitrophenyl-difluoromethanesulfonamide Drug Info [18]
4-phenoxyphenylboronic acid Drug Info [26]
4-[2-(2-Thienyl)acetamidoethyl]benzenesulfonamide Drug Info [38]
4-[2-(2-Thienyl)acetamido]benzenesulfonamide Drug Info [38]
4-[2-(3-Phenyl-ureido)-ethyl]-benzenesulfonamide Drug Info [22]
5-amino-1,3,4-thiadiazole-2-sulfonamide Drug Info [45]
5-Amino-[1,3,4]thiadiazole-2-thiol Drug Info [46]
5-Chlorosalicylic Acid Drug Info [36]
5-hydroxy-1-tosyl-1H-pyrrol-2(5H)-one Drug Info [47]
5-oxo-1-tosyl-2,5-dihydro-1Hpyrrol-2-yl acetate Drug Info [47]
6-(aminomethyl)-2H-chromen-2-one Drug Info [30]
6-Amino-benzothiazole-2-sulfonic acid amide Drug Info [48]
6-Hydroxy-benzothiazole-2-sulfonic acid amide Drug Info [49]
6-methoxy-2-oxo-2H-chromene-3-carboxylic acid Drug Info [30]
6-methyl-2-oxo-2H-chromene-3-carboxylic acid Drug Info [30]
7-methoxy-2-oxo-2H-chromene-4-carboxylic acid Drug Info [30]
8-methoxy-2-oxo-2H-chromene-3-carboxylic acid Drug Info [30]
Aminobenzolamide derivative Drug Info [50]
Azide Drug Info [51]
BENZENESULFONAMIDE Drug Info [52]
BENZOLAMIDE Drug Info [24]
Benzothiazole-2-sulfonic acid amide Drug Info [53]
Beta-naphthylboronic acid Drug Info [26]
Biphenyl-4-ylboronic acid Drug Info [26]
Carbamoyl phosphate disodium Drug Info [54]
Carzenide Drug Info [52]
CATECHIN Drug Info [27]
CG-100649 Drug Info [55]
CL-5343 Drug Info [56]
COUMARIN Drug Info [57]
COUMATE Drug Info [58]
Curcumin Drug Info [27]
CYANATE Drug Info [51]
Cynooxide anion Drug Info [59]
Decane-1,10-diyl disulfamate Drug Info [60]
Decyl sulfamate Drug Info [60]
ELLAGIC ACID Drug Info [61]
ETHYL 3-[4-(AMINOSULFONYL)PHENYL]PROPANOATE Drug Info [34]
FERULIC ACID Drug Info [61]
GALLICACID Drug Info [61]
HERNIARIN Drug Info [30]
Hexane-1,6-diamine Drug Info [62]
HYDROSULFIDE Drug Info [51]
IODIDE Drug Info [63]
N-(4-cyanophenyl)sulfamide Drug Info [64]
N-(4-Sulfamoyl-phenyl)-benzamide Drug Info [22]
N-(4-Sulfamoyl-phenyl)-butyramide Drug Info [22]
N-(4-Sulfamoyl-phenyl)-propionamide Drug Info [22]
N-(4-sulfamoylphenylethyl)-4-sulfamoylbenzamide Drug Info [65]
N-(5-ethyl-1,3,4-thiadiazol-2-yl)sulfamide Drug Info [66]
N-(5-Mercapto-[1,3,4]thiadiazol-2-yl)-acetamide Drug Info [46]
N-(5-phenyl-1,3,4-thiadiazol-2-yl)sulfamide Drug Info [66]
N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)sulfamide Drug Info [66]
N-(pentafluorophenyl)sulfamide Drug Info [64]
N-1,3,4-thiadiazol-2-ylsulfamide Drug Info [66]
N-hydroxysulfamide Drug Info [67]
N-hydroxysulfonamides Drug Info [68]
N-propynyl amidebenzenesulphonide Drug Info [69]
N-unsubstituted carbamate esters Drug Info [70]
N-[4-(trifluoromethyl)phenyl]sulfamide Drug Info [64]
N-[5-(ethylthio)-1,3,4-thiadiazol-2-yl]sulfamide Drug Info [66]
N-[5-(methylthio)-1,3,4-thiadiazol-2-yl]sulfamide Drug Info [66]
N-{2-[4-(AMINOSULFONYL)PHENYL]ETHYL}ACETAMIDE Drug Info [34]
NITRATE Drug Info [63]
NSC-654077 Drug Info [28]
Octane-1,8-diyl disulfamate Drug Info [60]
Octyl sulfamate Drug Info [60]
P-Coumaric Acid Drug Info [61]
PARABEN Drug Info [61]
PARAOXON Drug Info [44]
Pentane-1,5-diamine Drug Info [62]
Pentanoic acid (4-sulfamoyl-phenyl)-amide Drug Info [22]
Phenethylboronic acid Drug Info [26]
PHENOL Drug Info [27]
Phenoxyarsonous acid Drug Info [63]
Phenyl Boronic acid Drug Info [63]
PHENYLDIFLUOROMETHANESULFONAMIDE Drug Info [18]
PHENYLMETHANESULFONAMIDE Drug Info [18]
PHENYLSULFAMATE Drug Info [18]
Prop-2-ynyl 4-sulfamoylbenzoate Drug Info [69]
SACCHARIN Drug Info [39]
SALICYLATE Drug Info [71]
Sodium trithiocarbonate Drug Info [72]
Styrylboronic acid Drug Info [26]
SULFAMATE Drug Info [63]
Sulfamic acid 12-sulfamoyloxy-dodecyl ester Drug Info [73]
Sulfamic acid 16-sulfamoyloxy-hexadecyl ester Drug Info [73]
Sulfamic acid 3-sulfamoyloxy-phenyl ester Drug Info [73]
Sulfamic acid 4-sulfamoyloxy-butyl ester Drug Info [73]
Sulfamic acid 6-sulfamoyloxy-hexyl ester Drug Info [73]
Sulfamic acid 7-sulfamoyloxy-heptyl ester Drug Info [73]
SULFAMIDE Drug Info [63]
Sulfanilamide derivative Drug Info [74]
SULFATE Drug Info [63]
Sulfenamido-sulfonamides Drug Info [75]
Syringic Acid Drug Info [61]
Thioureido sulfonamide Drug Info [76]
[Au(CN)2]- Drug Info [77]
[Cu(CN)2]- Drug Info [77]
Modulator Acetazolamide Drug Info [78]
Dichlorphenamide Drug Info [78]
Ethoxzolamide Drug Info [78]
L-693612 Drug Info [79], [80]
Methazolamide Drug Info [56]
Target Expression Profile (TEP) and Drug Resistance Mutation (DRM)
TEP EXP Info
Pathways
KEGG Pathway Nitrogen metabolism
Pathway Interaction Database C-MYB transcription factor network
PathWhiz Pathway Gastric Acid Production
Reactome Erythrocytes take up carbon dioxide and release oxygen
Erythrocytes take up oxygen and release carbon dioxide
Reversible hydration of carbon dioxide
WikiPathways Reversible Hydration of Carbon Dioxide
Uptake of Carbon Dioxide and Release of Oxygen by Erythrocytes
Uptake of Oxygen and Release of Carbon Dioxide by Erythrocytes
References
REF 1FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (ANDA) 040195.
REF 2(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: 6792).
REF 3FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 011366.
REF 4(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: 6807).
REF 5FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 011047.
REF 6(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: 6814).
REF 7ClinicalTrials.gov (NCT02463357) Three New Ideas to Protect Special Forces From the Stress of High Altitude.
REF 8(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: 6828).
REF 9ClinicalTrials.gov (NCT01712295) 17% Salicylate Versus 17% Salicylate-Ethyl Pyruvate for Plantar Foot Warts. U.S. National Institutes of Health.
REF 10ClinicalTrials.gov (NCT01765296) Phase III Study of CG100649 in Osteoarthritis Patients. U.S. National Institutes of Health.
REF 11(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: 8316).
REF 12Nanocurcumin: a promising therapeutic advancement over native curcumin. Crit Rev Ther Drug Carrier Syst. 2013;30(4):331-68.
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REF 14ClinicalTrials.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 15ClinicalTrials.gov (NCT02527187) Determination of the Sensitivity and Specificity of Prick Test Betula Verrucosa.
REF 16Irosustat: a first-generation steroid sulfatase inhibitor in breast cancer. Expert Rev Anticancer Ther. 2011 Feb;11(2):179-83.
REF 17ClinicalTrials.gov (NCT02216669) Trial to Determine Optimal Phase II Dose of the Oral Dual CAIX Inhibitor/ Radiosensitizer. U.S. National Institutes of Health.
REF 18Bioorg 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 19Eur J Med Chem. 2010 Sep;45(9):3656-61. Epub 2010 May 12.Carbonic anhydrase inhibitors. Regioselective synthesis of novel 1-substituted 1,4-dihydro-4-oxo-3-pyridinesulfonamides and their inhibition of the human cytosolic isozymes I and II and transmembrane cancer-associated isozymes IX and XII.
REF 20Bioorg Med Chem Lett. 2004 Dec 6;14(23):5781-6.Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties.
REF 21J Med Chem. 2006 May 4;49(9):2743-9.Indanesulfonamides as carbonic anhydrase inhibitors. Toward structure-based design of selective inhibitors of the tumor-associated isozyme CA IX.
REF 22Bioorg Med Chem Lett. 2005 Nov 1;15(21):4862-6.Carbonic anhydrase inhibitors: inhibition of the tumor-associated isozymes IX and XII with a library of aromatic and heteroaromatic sulfonamides.
REF 23Bioorg Med Chem. 2010 Jan 15;18(2):930-8. Epub 2009 Nov 20.Synthesis, characterization and antiglaucoma activity of a novel proton transfer compound and a mixed-ligand Zn(II) complex.
REF 24Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Bioorg Med Chem. 2009 Jul 15;17(14):5054-8. Epub 2009 May 30.
REF 25Bioorg Med Chem. 2007 Mar 15;15(6):2298-311. Epub 2007 Jan 19.Carbonic anhydrase and matrix metalloproteinase inhibitors. Inhibition of human tumor-associated isozymes IX and cytosolic isozyme I andII with sulfonylated hydroxamates.
REF 26Bioorg 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 27Bioorg 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 28J Med Chem. 2008 Jun 12;51(11):3051-6. Epub 2008 Mar 19.Recent developments of carbonic anhydrase inhibitors as potential anticancer drugs.
REF 29Bioorg Med Chem Lett. 2005 Jan 17;15(2):367-72.Carbonic anhydrase inhibitors. Novel sulfanilamide/acetazolamide derivatives obtained by the tail approach and their interaction with the cytosolic isozymes I and II, and the tumor-associated isozyme IX.
REF 30J Med Chem. 2010 Jan 14;53(1):335-44.Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins.
REF 31J Med Chem. 2005 Mar 24;48(6):2121-5.Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/membrane-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides incorporatinghydrazino moieties.
REF 32J Med Chem. 2006 Sep 7;49(18):5544-51.Carbonic anhydrase inhibitors: Hypoxia-activatable sulfonamides incorporating disulfide bonds that target the tumor-associated isoform IX.
REF 33J Med Chem. 2009 Jul 9;52(13):4063-7.Discovery of low nanomolar and subnanomolar inhibitors of the mycobacterial beta-carbonic anhydrases Rv1284 and Rv3273.
REF 34The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
REF 35Eur J Med Chem. 2010 Jun;45(6):2396-404. Epub 2010 Feb 12.Carbonic anhydrase inhibitors: synthesis and inhibition of the human cytosolic isozymes I and II and transmembrane isozymes IX, XII (cancer-associated) and XIV with 4-substituted 3-pyridinesulfonamides.
REF 36Bioorg Med Chem. 2008 Oct 15;16(20):9101-5. Epub 2008 Sep 13.In vitro inhibition of salicylic acid derivatives on human cytosolic carbonic anhydrase isozymes I and II.
REF 37J Med Chem. 2005 Jul 28;48(15):4834-41.Carbonic anhydrase inhibitors. Design of fluorescent sulfonamides as probes of tumor-associated carbonic anhydrase IX that inhibit isozyme IX-mediated acidification of hypoxic tumors.
REF 38Bioorg 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 39Bioorg Med Chem. 2010 Aug 1;18(15):5498-503. Epub 2010 Jun 22.Mutation of Phe91 to Asn in human carbonic anhydrase I unexpectedly enhanced both catalytic activity and affinity for sulfonamide inhibitors.
REF 40Bioorg 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 41J Med Chem. 2008 Mar 27;51(6):1945-53. Epub 2008 Feb 29.Inhibition of carbonic anhydrases with glycosyltriazole benzene sulfonamides.
REF 42Bioorg Med Chem. 2009 Jan 15;17(2):553-7. Epub 2008 Dec 6.Ligand-based and structure-based virtual screening to identify carbonic anhydrase IX inhibitors.
REF 43J Med Chem. 2004 Oct 7;47(21):5224-9.Carbonic anhydrase inhibitors: the first on-resin screening of a 4-sulfamoylphenylthiourea library.
REF 44Bioorg 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 45Eur J Med Chem. 2010 Nov;45(11):4769-73. Epub 2010 Jul 24.Synthesis, characterization and antiglaucoma activity of some novel pyrazole derivatives of 5-amino-1,3,4-thiadiazole-2-sulfonamide.
REF 46Bioorg Med Chem Lett. 2005 May 2;15(9):2347-52.Carbonic anhydrase inhibitors. Inhibition of the cytosolic and tumor-associated carbonic anhydrase isozymes I, II, and IX with a series of 1,3,4-thiadiazole- and 1,2,4-triazole-thiols.
REF 47Bioorg Med Chem. 2010 Jun 15;18(12):4468-74. Epub 2010 May 28.A novel and one-pot synthesis of new 1-tosyl pyrrol-2-one derivatives and analysis of carbonic anhydrase inhibitory potencies.
REF 48J Med Chem. 1999 Jul 15;42(14):2641-50.Carbonic anhydrase inhibitors. Synthesis of water-soluble, topically effective, intraocular pressure-lowering aromatic/heterocyclic sulfonamides containing cationic or anionic moieties: is the tail more important than the ring?.
REF 49J 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 50Bioorg Med Chem Lett. 2004 Dec 6;14(23):5775-80.Carbonic anhydrase inhibitors: synthesis and inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, and IX with sulfonamides derived from 4-isothiocyanato-benzolamide.
REF 51Bioorg Med Chem Lett. 2004 Dec 6;14(23):5769-73.Carbonic anhydrase inhibitors: inhibition of the membrane-bound human isozyme IV with anions.
REF 52Nat Chem Biol. 2009 May;5(5):341-3. Epub 2009 Mar 29.Ligand-directed tosyl chemistry for protein labeling in vivo.
REF 53Bioorg 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 54Bioorg Med Chem Lett. 2004 Dec 6;14(23):5763-7.Carbonic anhydrase inhibitors. Interaction of isozymes I, II, IV, V, and IX with phosphates, carbamoyl phosphate, and the phosphonate antiviral drug foscarnet.
REF 55Understanding the Dual Inhibition of COX-2 and Carbonic Anhydrase-II by Celecoxib and CG100649 Using Density Functional Theory Calculations and other Molecular Modelling Approaches. Protein Pept Lett. 2015;22(10):903-12.
REF 56(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. (Target id: 2597).
REF 57Bioorg Med Chem Lett. 2010 Dec 15;20(24):7255-8. Epub 2010 Oct 25.7,8-disubstituted- but not 6,7-disubstituted coumarins selectively inhibit the transmembrane, tumor-associated carbonic anhydrase isoforms IX and XII over the cytosolic ones I and II in the low nanomolar/subnanomolar range.
REF 58Bioorg 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 59Bioorg Med Chem Lett. 2004 Sep 6;14(17):4563-7.Carbonic anhydrase inhibitors. Inhibition of the beta-class enzyme from the methanoarchaeon Methanobacterium thermoautotrophicum (Cab) with anions.
REF 60J 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.
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