Details of the Drug

General Information of Drug (ID: DMJ4AWC)

Drug Name

Cyclothiazide

Synonyms

Anhydron; Aquirel; Ciclotiazida; Ciclotiazide; Cyclothiazidum; Doburil; Fluidil; Renazide; Valmiran; Ciclotiazide [DCIT]; C 9847; MDi 193; Anhydron (TN); Ciclotiazida [INN-Spanish]; Cyclothiazidum [INN-Latin]; Lilly 35,483; Cyclothiazide [USAN:INN:BAN]; Cyclothiazide (JAN/USAN/INN); 2H-1,2,4-Benzothiadiazine-7-sulfonamide, 3,4-dihydro-6-chloro-3-(5-norbornen-2-yl)-, 1,1-dioxide; 2H-1,2,4-Benzothiadiazine-7-sulfonamide, 3,4-dihydro-6-chloro-3-(5-norbornen-2-yl)-,1,1-dioxide; 2H-1,2,4-Benzothiadiazine-7-sulfonamide, 3-bicyclo(2.2.1)hept-5-en-2-yl-6-chloro-3,4-dihydro-, 1,1-dioxide; 2H-1,2,4-Benzothiadiazine-7-sulfonamide, 3-bicyclo[2.2.1]hept-5-en-2-yl-6-chloro-3,4-dihydro-, 1,1-dioxide; 2H-1,2,4-Benzothiadiazine-7-sulfonamide, 6-chloro-3,4-dihydro-3-(5-norbornen-2-yl)-, 1,1-dioxide; 3-(bicyclo[2.2.1]hept-5-en-2-yl)-6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; 3-Bicyclo(2.2.1)hept-5-en-2-yl-6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; 3-Bicyclo[2.2.1]hept-5-en-2-yl-6-chloro-3,4-dihydro-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; 6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; 6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-2H-1,2-4-benzothiadiazine-7-sulfonamide 1,1-dioxide; 6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-7-sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxide; 6-Chloro-3,4-dihydro-3-(5-norbornen-2-yl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; 6-Chloro-3,4-dihydro-3-(norbornen-2-yl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide; 6-Chloro-3-(2-norbornen-5-yl)-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxide; 6-chloro-3,4-dihydro-3-(norbornen-2-yl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide

Indication

Disease Entry	ICD 11	Status	REF
Congestive heart failure	BD10	Approved	[1], [2], [3]

Therapeutic Class

Antihypertensive Agents

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

389.9

Topological Polar Surface Area (xlogp)

2

Rotatable Bond Count (rotbonds)

2

Hydrogen Bond Donor Count (hbonddonor)

3

Hydrogen Bond Acceptor Count (hbondacc)

7

Chemical Identifiers

Formula: C14H16ClN3O4S2
IUPAC Name: 3-(2-bicyclo[2.2.1]hept-5-enyl)-6-chloro-1,1-dioxo-3,4-dihydro-2H-1lambda6,2,4-benzothiadiazine-7-sulfonamide
Canonical SMILES: C1C2CC(C1C=C2)C3NC4=CC(=C(C=C4S(=O)(=O)N3)S(=O)(=O)N)Cl
InChI: InChI=1S/C14H16ClN3O4S2/c15-10-5-11-13(6-12(10)23(16,19)20)24(21,22)18-14(17-11)9-4-7-1-2-8(9)3-7/h1-2,5-9,14,17-18H,3-4H2,(H2,16,19,20)
InChIKey: BOCUKUHCLICSIY-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 2910
ChEBI ID: CHEBI:31448
CAS Number: 2259-96-3
DrugBank ID: DB00606
TTD ID: D03CNS
VARIDT ID: DR00511

Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Carbonic anhydrase II (CA-II)	TTANPDJ	CAH2_HUMAN	Inhibitor	[4]

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Molecular Interaction Atlas (MIA)

MIA Detail

Jump to Detail Molecular Interaction Atlas of This Drug

Molecular Expression Atlas of This Drug

The Studied Disease

Congestive heart failure

ICD Disease Classification

BD10

Molecule Name	Molecule Type	Gene Name	p-value	Fold-Change	Z-score
Carbonic anhydrase II (CA-II)	DTT	CA2	7.95E-08	0.52	0.33

Molecular Expression Atlas (MEA)

MEA Detail

Jump to Detail Molecular Expression Atlas of This Drug

References

1	URL: 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: 4167).
2	Drugs@FDA. U.S. Food and Drug Administration. U.S. Department of Health & Human Services. 2015
3	FDA Approved Drug Products from FDA Official Website. 2009. Application Number: (NDA) 013157.
4	Selective effect of thiazides on the human osteoblast-like cell line MG-63. Kidney Int. 1996 Nov;50(5):1476-82.
5	Carbonic anhydrase inhibitors: inhibition of mammalian isoforms I-XIV with a series of substituted phenols including paracetamol and salicylic acid. Bioorg Med Chem. 2008 Aug 1;16(15):7424-8.
6	Sulfonamide linked neoglycoconjugates--a new class of inhibitors for cancer-associated carbonic anhydrases. J Med Chem. 2010 Apr 8;53(7):2913-26.
7	Carbonic anhydrase inhibitors. Inhibition studies of a coral secretory isoform by sulfonamides. Bioorg Med Chem. 2009 Jul 15;17(14):5054-8.
8	Localization of diuretic effects along the loop of Henle: an in vivo microperfusion study in rats. Clin Sci (Lond). 2000 Apr;98(4):481-8.
9	The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42.
10	Inhibition of carbonic anhydrases I and II by N-unsubstituted carbamate esters. J Biol Chem. 1992 Dec 15;267(35):25044-50.
11	Nature of the inhibition of carbonic anhydrase by acetazolamide and benzthiazide. J Pharmacol Exp Ther. 1961 Mar;131:271-4.
12	Carbonic anhydrase inhibitors. Antioxidant polyphenols effectively inhibit mammalian isoforms I-XV. Bioorg Med Chem Lett. 2010 Sep 1;20(17):5050-3.
13	Carbonic anhydrase inhibitors. Inhibition of mammalian isoforms I-XIV with a series of natural product polyphenols and phenolic acids. Bioorg Med Chem. 2010 Mar 15;18(6):2159-2164.