CYZ

CYCLOTHIAZIDE

Created: 2002-04-08
Last modified:  2020-06-05

Find related ligands:

Chemical Details

Formal Charge0
Atom Count40
Chiral Atom Count4
Bond Count43
Aromatic Bond Count6
2D diagram of CYZ

Chemical Component Summary

NameCYCLOTHIAZIDE
Synonyms3-BICYCLO[2.2.1]HEPT-5-EN-2-YL-6-CHLORO-3,4- DIHYDRO-2H-1,2,4-BENZOTHIADIAZINE-7-SULFONAMIDE 1,1 DIOXIDE
Systematic Name (OpenEye OEToolkits)(3S)-3-[(1S,4S,6S)-6-bicyclo[2.2.1]hept-2-enyl]-6-chloro-1,1-dioxo-3,4-dihydro-2H-benzo[e][1,2,4]thiadiazine-7-sulfonamide
FormulaC14 H16 Cl N3 O4 S2
Molecular Weight389.878
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESACDLabs10.04O=S(=O)(c1c(Cl)cc2c(c1)S(=O)(=O)NC(N2)C4C3C=CC(C3)C4)N
SMILESCACTVS3.341N[S](=O)(=O)c1cc2c(N[CH](N[S]2(=O)=O)[CH]3C[CH]4C[CH]3C=C4)cc1Cl
SMILESOpenEye OEToolkits1.5.0c1c2c(cc(c1Cl)S(=O)(=O)N)S(=O)(=O)NC(N2)C3CC4CC3C=C4
Canonical SMILESCACTVS3.341 N[S](=O)(=O)c1cc2c(N[C@@H](N[S]2(=O)=O)[C@H]3C[C@@H]4C[C@H]3C=C4)cc1Cl
Canonical SMILESOpenEye OEToolkits1.5.0 c1c2c(cc(c1Cl)S(=O)(=O)N)S(=O)(=O)N[C@H](N2)[C@H]3C[C@@H]4C[C@H]3C=C4
InChIInChI1.03 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)/t7-,8+,9-,14-/m0/s1
InChIKeyInChI1.03 BOCUKUHCLICSIY-KSCJFIISSA-N

Drug Info: DrugBank

DrugBank IDDB00606 
NameCyclothiazide
Groups approved
DescriptionAs a diuretic, cyclothiazide inhibits active chloride reabsorption at the early distal tubule via the Na-Cl cotransporter, resulting in an increase in the excretion of sodium, chloride, and water. Thiazides like cyclothiazide also inhibit sodium ion transport across the renal tubular epithelium through binding to the thiazide sensitive sodium-chloride transporter. This results in an increase in potassium excretion via the sodium-potassium exchange mechanism. The antihypertensive mechanism of cyclothiazide is less well understood although it may be mediated through its action on carbonic anhydrases in the smooth muscle or through its action on the large-conductance calcium-activated potassium (KCa) channel, also found in the smooth muscle. Cyclothiazide is indicated as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy. It is also indicated in the management of hypertension either as the sole therapeutic agent or to enhance the effectiveness of other antihypertensive drugs in the more severe forms of hypertension.
Synonyms
  • Cyclothiazidum
  • Cyclothiazide
  • 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-(2-norbornen-5-yl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxide
  • Ciclotiazida
IndicationCyclothiazide is indicated as adjunctive therapy in edema associated with congestive heart failure, hepatic cirrhosis, and corticosteroid and estrogen therapy. It is also indicated in the management of hypertension either as the sole therapeutic agent or to enhance the effectiveness of other antihypertensive drugs in the more severe forms of hypertension.
Categories
  • Antihypertensive Agents
  • Cardiovascular Agents
  • Diuretics
  • Genito Urinary System and Sex Hormones
  • Gynecological Antiinfectives and Antiseptics
ATC-Code
  • G01AE10
  • C03AB09
  • C03AA09
CAS number2259-96-3

Drug Targets

NameTarget SequencePharmacological ActionActions
Sodium/potassium-transporting ATPase subunit gammaMTGLSMDGGGSPKGDVDPFYYDYETVRNGGLIFAGLAFIVGLLILLSRRF...unknowninhibitor
Carbonic anhydraseMASPDWGYDDKNGPEQWSKLYPIANGNNQSPVDIKTSETKHDTSLKPISV...unknowninhibitor
Carbonic anhydrase 1MASPDWGYDDKNGPEQWSKLYPIANGNNQSPVDIKTSETKHDTSLKPISV...unknowninhibitor
Carbonic anhydrase 2MSHHWGYGKHNGPEHWHKDFPIAKGERQSPVDIDTHTAKYDPSLKPLSVS...unknowninhibitor
Secreted frizzled-related protein 4MFLSILVALCLWLHLALGVRGAPCEAVRIPMCRHMPWNITRMPNHLHHST...unknowninhibitor
View More
Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
PubChem 5288009