TTD Target ID: TTDR01224

Target Information
Name	Carbonic anhydrase I
Type of target	Research target
Synonyms	CA-I
	Carbonate dehydratase I
	Carbonic anhydrase B
Disease	Glaucoma [ICD9: 365   ICD10: H40-H42]				[1]
	Hypertension [ICD9: 401   ICD10: I10, I11, I12, I13, I15]				[2]
	Pancreatic cancer [ICD9: 157   ICD10: C25]				[3]
BioChemical Class	Carbon-oxygen lyases
EC Number	EC 4.2.1.1
Pathway	Nitrogen metabolism
UniProt ID	P00915
PDB Structure	1AZM; 1BZM; 1CRM; 1CZM; 1HCB; 1HUG; 1HUH; 1J9W; 1JV0; 2CAB; 2FOY; 2FW4; 2IT4; 2NMX; 2NN1; 2NN7; 3LXE; 3W6H; 3W6I.
Function	Reversible hydration of carbon dioxide.
Sequence	MASPDWGYDDKNGPEQWSKLYPIANGNNQSPVDIKTSETKHDTSLKPISVSYNPATAKEI INVGHSFHVNFEDNDNRSVLKGGPFSDSYRLFQFHFHWGSTNEHGSEHTVDGVKYSAELH VAHWNSAKYSSLAEAASKADGLAVIGVLMKVGEANPKLQKVLDALQAIKTKGKRAPFTNF DPSTLLPSSLDFWTYPGSLTHPPLYESVTWIICKESISVSSEQLAQFRSLLSNVEGDNAV PMQHNNRPTQPLKGRTVRASF
Target Validation	Click to Find Target Validation Information.
QSAR Model	Click to Find Target QSAR Model.
Inhibitor	2,4-dichloro-5-sulfamoylbenzoic acid		[4]
	2- (biphenyl-4-yl)vinylboronic acid		[5]
	2-Hydroxycinnamic acid		[6]
	2-oxo-2H-thiochromene-3-carboxylic acid		[7]
	3-phenylprop-1-enylboronic acid		[5]
	4-azidobenzenesulfonamide		[8]
	4-bromophenylboronic acid		[5]
	4-butylphenylboronic acid		[5]
	4-ethynyl benzene sulfonamide		[9]
	4-methoxyphenylboronic acid		[5]
	4-methylstyrylboronic acid		[5]
	4-nitrophenyl phosphate		[10]
	4-phenoxyphenylboronic acid		[5]
	6-methoxy-2-oxo-2H-chromene-3-carboxylic acid		[7]
	Aminobenzolamide derivative		[11]
	Azide		[12]
	BENZENESULFONAMIDE		[13]
	BENZOLAMIDE		[14]
	CATECHIN		[6]
	CHLORIDE		[15]
	COUMARIN		[16]
	COUMATE		[17]
	CURCUMIN		[6]
	CYANATE		[12]
	Cynooxide anion		[18]
	Ditiocarb sodium		[19]
	ELLAGIC ACID		[20]
	EMATE		[21]
	FERULIC ACID		[20]
	GALLICACID		[20]
	HERNIARIN		[7]
	HYDROSULFIDE		[12]
	INDISULAM		[22]
	IODIDE		[15]
	Indan-5-sulfonic acid amide		[23]
	N- (prop-2-ynyl)-4-sulfamoylbenzamide		[24]
	N-hydroxysulfamide		[25]
	N-hydroxysulfonamides		[26]
	N-unsubstituted carbamate esters		[27]
	NITRATE		[15]
	NSC-654077		[28]
	PARABEN		[20]
	PARAOXON		[10]
	PHENOL		[6]
	PHENYLDIFLUOROMETHANESULFONAMIDE		[21]
	PHENYLMETHANESULFONAMIDE		[21]
	PHENYLSULFAMATE		[21]
	Phenyl Boronic acid		[15]
	SACCHARIN		[29]
	SALICYLATE		[30]
	SULFAMATE		[15]
	SULFAMIDE		[15]
	SULFATE		[15]
	Sulfenamido-sulfonamides		[31]
	Syringic Acid		[20]
	Thioureido sulfonamide		[32]
	Thioureido sulfonamide		[32]
	Thioureido sulfonamide		[32]
	[Au (CN)2]-		[33]
	[Cu (CN)2]-		[33]
	beta-naphthylboronic acid		[5]
	biphenylboronic acid		[5]
	decyl sulfamate		[34]
	hexane-1,6-diamine		[35]
octyl sulfamate		[34]
p-Coumaric Acid		[20]
pentane-1,5-diamine		[35]
phenethylboronic acid		[5]
phenoxyarsonous acid		[15]
prop-2-ynyl 4-sulfamoylbenzoate		[24]
sodium trithiocarbonate		[19]
styrylboronic acid		[5]
sulfanilamide derivative		[36]
Cross References	3D Structure Related Literature On-Line Medical Dictionary
Ref 1	Carbonic anhydrase inhibitors: synthesis and inhibition against isozymes I, II and IV of topically acting antiglaucoma sulfonamides incorporating cis-5-norbornene-endo-3-carboxy-2-carboxamido moieties. J Enzyme Inhib. 2001;16(2):113-23. To Reference
Ref 2	Calcium channel blockers reduce blood pressure in part by inhibiting vascular smooth muscle carbonic anhydrase I. Cardiovasc Drugs Ther. 2000 Oct;14(5):523-8. To Reference
Ref 3	Immunohistochemical demonstration of the carbonic anhydrase isoenzymes I and II in pancreatic tumours. Histochem J. 1995 Feb;27(2):133-8. To Reference
Ref 4	Bioorg 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. To Reference
Ref 5	Bioorg 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 6	Bioorg 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 7	J Med Chem. 2010 Jan 14;53(1):335-44.Deciphering the mechanism of carbonic anhydrase inhibition with coumarins and thiocoumarins. To Reference
Ref 8	Bioorg 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 9	J Med Chem. 2008 Mar 27;51(6):1945-53. Epub 2008 Feb 29.Inhibition of carbonic anhydrases with glycosyltriazole benzene sulfonamides. To Reference
Ref 10	Bioorg Med Chem Lett. 2010 Nov 1;20(21):6208-12. Epub 2010 Aug 26.Paraoxon, 4-nitrophenyl phosphate and acetate are substrates of ¦Á- but not of ¦Â-, ¦Ã- and ¦Æ-carbonic anhydrases. To Reference
Ref 11	Bioorg 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. To Reference
Ref 12	Bioorg Med Chem Lett. 2004 Dec 6;14(23):5769-73.Carbonic anhydrase inhibitors: inhibition of the membrane-bound human isozyme IV with anions. To Reference
Ref 13	Nat Chem Biol. 2009 May;5(5):341-3. Epub 2009 Mar 29.Ligand-directed tosyl chemistry for protein labeling in vivo. To Reference
Ref 14	Bioorg 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 15	Bioorg Med Chem Lett. 2004 Nov 1;14(21):5435-9.Carbonic anhydrase inhibitors. Inhibition of the newly isolated murine isozyme XIII with anions. To Reference
Ref 16	Bioorg 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. To Reference
Ref 17	Bioorg 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 18	Bioorg 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. To Reference
Ref 19	Bioorg Med Chem Lett. 2009 Apr 1;19(7):1855-7. Epub 2009 Feb 26.Carbonic anhydrase inhibitors. Inhibition of cytosolic isoforms I, II, III, VII and XIII with less investigated inorganic anions. To Reference
Ref 20	Bioorg 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 21	Bioorg 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 22	Eur 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. To Reference
Ref 23	Bioorg Med Chem Lett. 2004 Dec 6;14(23):5781-6.Carbonic anhydrase inhibitors. Design of anticonvulsant sulfonamides incorporating indane moieties. To Reference
Ref 24	J Med Chem. 2006 Nov 2;49(22):6539-48.A novel class of carbonic anhydrase inhibitors: glycoconjugate benzene sulfonamides prepared by "click-tailing". To Reference
Ref 25	Bioorg 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 26	Carbonic anhydrase inhibitors: inhibition of isozymes I, II and IV with N-hydroxysulfonamides--a novel class of intraocular pressure lowering agents. J Enzyme Inhib. 1998 Jul;13(4):267-84. To Reference
Ref 27	Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50. To Reference
Ref 28	J Med Chem. 2008 Jun 12;51(11):3051-6. Epub 2008 Mar 19.Recent developments of carbonic anhydrase inhibitors as potential anticancer drugs. To Reference
Ref 29	Bioorg 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. To Reference
Ref 30	Bioorg 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 31	Sulfenamido-sulfonamides as inhibitors of carbonic anhydrase isozymes I, II and IV. J Enzyme Inhib. 1997 Aug;12(3):175-90. To Reference
Ref 32	Bioorg Med Chem Lett. 2005 Sep 1;15(17):3821-7.Carbonic anhydrase inhibitors: design of thioureido sulfonamides with potent isozyme II and XII inhibitory properties and intraocular pressure lowering activity in a rabbit model of glaucoma. To Reference
Ref 33	Bioorg Med Chem Lett. 2005 Apr 1;15(7):1909-13.Carbonic anhydrase inhibitors. Inhibition of isozymes I, II, IV, V and IX with complex fluorides, chlorides and cyanides. To Reference
Ref 34	J 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 35	J Med Chem. 2010 Aug 12;53(15):5511-22.Polyamines inhibit carbonic anhydrases by anchoring to the zinc-coordinated water molecule. To Reference
Ref 36	Bioorg Med Chem Lett. 2005 Jun 15;15(12):3096-101.Carbonic anhydrase inhibitors. Inhibition of cytosolic/tumor-associated carbonic anhydrase isozymes I, II, IX, and XII with Schiff's bases incorporating chromone and aromatic sulfonamide moieties, and their zinc complexes. To Reference

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Professor in Department of Pharmacy
National University of Singapore, Singapore

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