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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2021-09-14 14:58:05 UTC
HMDB IDHMDB0014744
Secondary Accession Numbers
  • HMDB14744
Metabolite Identification
Common NameCyclothiazide
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.
Structure
Data?1582753216
Synonyms
ValueSource
6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxideChEBI
6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-7-sulfamoyl-1,2,4-benzothiadiazine 1,1-dioxideChEBI
6-Chloro-3,4-dihydro-3-(5-norbornen-2-yl)-2H-1,2,4-benzothiadiazine-7-sulfonamide 1,1-dioxideChEBI
6-Chloro-3-(2-norbornen-5-yl)-7-sulfamyl-3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxideChEBI
CiclotiazidaChEBI
CyclothiazidumChEBI
AnhydronKegg
6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-2H-1,2,4-benzothiadiazine-7-sulphonamide 1,1-dioxideGenerator
6-Chloro-3,4-dihydro-3-(2-norbornen-5-yl)-7-sulphamoyl-1,2,4-benzothiadiazine 1,1-dioxideGenerator
6-Chloro-3,4-dihydro-3-(5-norbornen-2-yl)-2H-1,2,4-benzothiadiazine-7-sulphonamide 1,1-dioxideGenerator
6-Chloro-3-(2-norbornen-5-yl)-7-sulphamyl-3,4-dihydro-1,2,4-benzothiadiazine 1,1-dioxideGenerator
CiclotiazideHMDB
Chemical FormulaC14H16ClN3O4S2
Average Molecular Weight389.878
Monoisotopic Molecular Weight389.027075102
IUPAC Name3-{bicyclo[2.2.1]hept-5-en-2-yl}-6-chloro-1,1-dioxo-3,4-dihydro-2H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide
Traditional Namecyclothiazide
CAS Registry Number2259-96-3
SMILES
NS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C1CC2CC1C=C2
InChI Identifier
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)
InChI KeyBOCUKUHCLICSIY-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as 1,2,4-benzothiadiazine-1,1-dioxides. These are aromatic heterocyclic compounds containing a 1,2,4-benzothiadiazine ring system with two S=O bonds at the 1-position.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassThiadiazines
Sub ClassBenzothiadiazines
Direct Parent1,2,4-benzothiadiazine-1,1-dioxides
Alternative Parents
Substituents
  • 1,2,4-benzothiadiazine-1,1-dioxide
  • Secondary aliphatic/aromatic amine
  • Aryl chloride
  • Aryl halide
  • Organosulfonic acid amide
  • Benzenoid
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Aminosulfonyl compound
  • Sulfonyl
  • Secondary amine
  • Azacycle
  • Organic oxide
  • Amine
  • Organopnictogen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point227 - 228 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.28 g/LNot Available
LogP1.6Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.28 g/LALOGPS
logP10(1.32) g/LALOGPS
logP10(0.94) g/LChemAxon
logS10(-3.2) g/LALOGPS
pKa (Strongest Acidic)9.06ChemAxon
pKa (Strongest Basic)-2.5ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity92.65 m³·mol⁻¹ChemAxon
Polarizability37.1 ųChemAxon
Number of Rings4ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
CyclothiazideNS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C1CC2CC1C=C24918.5Standard polar33892256
CyclothiazideNS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C1CC2CC1C=C23242.8Standard non polar33892256
CyclothiazideNS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C1CC2CC1C=C23655.2Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Cyclothiazide,1TMS,isomer #1C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O3656.1Semi standard non polar33892256
Cyclothiazide,1TMS,isomer #1C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O3371.2Standard non polar33892256
Cyclothiazide,1TMS,isomer #1C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O4671.0Standard polar33892256
Cyclothiazide,1TMS,isomer #2C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C1CC2C=CC1C23548.1Semi standard non polar33892256
Cyclothiazide,1TMS,isomer #2C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C1CC2C=CC1C23429.8Standard non polar33892256
Cyclothiazide,1TMS,isomer #2C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C1CC2C=CC1C24851.3Standard polar33892256
Cyclothiazide,1TMS,isomer #3C[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O3497.1Semi standard non polar33892256
Cyclothiazide,1TMS,isomer #3C[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O3378.2Standard non polar33892256
Cyclothiazide,1TMS,isomer #3C[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O5022.9Standard polar33892256
Cyclothiazide,2TMS,isomer #1C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O3519.3Semi standard non polar33892256
Cyclothiazide,2TMS,isomer #1C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O3576.3Standard non polar33892256
Cyclothiazide,2TMS,isomer #1C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O4637.7Standard polar33892256
Cyclothiazide,2TMS,isomer #2C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C1CC3C=CC1C3)NS2(=O)=O3512.7Semi standard non polar33892256
Cyclothiazide,2TMS,isomer #2C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C1CC3C=CC1C3)NS2(=O)=O3505.8Standard non polar33892256
Cyclothiazide,2TMS,isomer #2C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C1CC3C=CC1C3)NS2(=O)=O4274.6Standard polar33892256
Cyclothiazide,2TMS,isomer #3C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)N([Si](C)(C)C)S2(=O)=O3496.5Semi standard non polar33892256
Cyclothiazide,2TMS,isomer #3C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)N([Si](C)(C)C)S2(=O)=O3487.4Standard non polar33892256
Cyclothiazide,2TMS,isomer #3C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)N([Si](C)(C)C)S2(=O)=O4588.4Standard polar33892256
Cyclothiazide,2TMS,isomer #4C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C)C1C1CC2C=CC1C23414.0Semi standard non polar33892256
Cyclothiazide,2TMS,isomer #4C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C)C1C1CC2C=CC1C23527.7Standard non polar33892256
Cyclothiazide,2TMS,isomer #4C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C)C1C1CC2C=CC1C24718.9Standard polar33892256
Cyclothiazide,3TMS,isomer #1C[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S(=O)(=O)NC1C1CC2C=CC1C23442.9Semi standard non polar33892256
Cyclothiazide,3TMS,isomer #1C[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S(=O)(=O)NC1C1CC2C=CC1C23708.5Standard non polar33892256
Cyclothiazide,3TMS,isomer #1C[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S(=O)(=O)NC1C1CC2C=CC1C24207.8Standard polar33892256
Cyclothiazide,3TMS,isomer #2C[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S1(=O)=O3485.7Semi standard non polar33892256
Cyclothiazide,3TMS,isomer #2C[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S1(=O)=O3706.6Standard non polar33892256
Cyclothiazide,3TMS,isomer #2C[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S1(=O)=O4538.0Standard polar33892256
Cyclothiazide,3TMS,isomer #3C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C1CC3C=CC1C3)N([Si](C)(C)C)S2(=O)=O3387.9Semi standard non polar33892256
Cyclothiazide,3TMS,isomer #3C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C1CC3C=CC1C3)N([Si](C)(C)C)S2(=O)=O3654.1Standard non polar33892256
Cyclothiazide,3TMS,isomer #3C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C1CC3C=CC1C3)N([Si](C)(C)C)S2(=O)=O4234.3Standard polar33892256
Cyclothiazide,4TMS,isomer #1C[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S(=O)(=O)N([Si](C)(C)C)C1C1CC2C=CC1C23420.4Semi standard non polar33892256
Cyclothiazide,4TMS,isomer #1C[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S(=O)(=O)N([Si](C)(C)C)C1C1CC2C=CC1C23875.1Standard non polar33892256
Cyclothiazide,4TMS,isomer #1C[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S(=O)(=O)N([Si](C)(C)C)C1C1CC2C=CC1C24213.2Standard polar33892256
Cyclothiazide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O3921.4Semi standard non polar33892256
Cyclothiazide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O3634.1Standard non polar33892256
Cyclothiazide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O4739.8Standard polar33892256
Cyclothiazide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C1CC2C=CC1C23835.8Semi standard non polar33892256
Cyclothiazide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C1CC2C=CC1C23662.0Standard non polar33892256
Cyclothiazide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C1CC2C=CC1C24956.9Standard polar33892256
Cyclothiazide,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O3756.9Semi standard non polar33892256
Cyclothiazide,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O3627.3Standard non polar33892256
Cyclothiazide,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O5121.7Standard polar33892256
Cyclothiazide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O4031.5Semi standard non polar33892256
Cyclothiazide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O4078.3Standard non polar33892256
Cyclothiazide,2TBDMS,isomer #1CC(C)(C)[Si](C)(C)N([Si](C)(C)C(C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)NS2(=O)=O4703.2Standard polar33892256
Cyclothiazide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(C1CC3C=CC1C3)NS2(=O)=O4019.4Semi standard non polar33892256
Cyclothiazide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(C1CC3C=CC1C3)NS2(=O)=O4015.2Standard non polar33892256
Cyclothiazide,2TBDMS,isomer #2CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(C1CC3C=CC1C3)NS2(=O)=O4349.7Standard polar33892256
Cyclothiazide,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)N([Si](C)(C)C(C)(C)C)S2(=O)=O3942.8Semi standard non polar33892256
Cyclothiazide,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)N([Si](C)(C)C(C)(C)C)S2(=O)=O4023.9Standard non polar33892256
Cyclothiazide,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C1CC3C=CC1C3)N([Si](C)(C)C(C)(C)C)S2(=O)=O4657.7Standard polar33892256
Cyclothiazide,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C(C)(C)C)C1C1CC2C=CC1C23906.6Semi standard non polar33892256
Cyclothiazide,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C(C)(C)C)C1C1CC2C=CC1C24041.5Standard non polar33892256
Cyclothiazide,2TBDMS,isomer #4CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C(C)(C)C)C1C1CC2C=CC1C24813.4Standard polar33892256
Cyclothiazide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S(=O)(=O)NC1C1CC2C=CC1C24165.8Semi standard non polar33892256
Cyclothiazide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S(=O)(=O)NC1C1CC2C=CC1C24470.5Standard non polar33892256
Cyclothiazide,3TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S(=O)(=O)NC1C1CC2C=CC1C24300.7Standard polar33892256
Cyclothiazide,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S1(=O)=O4128.8Semi standard non polar33892256
Cyclothiazide,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S1(=O)=O4490.8Standard non polar33892256
Cyclothiazide,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(C2CC3C=CC2C3)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S1(=O)=O4601.5Standard polar33892256
Cyclothiazide,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(C1CC3C=CC1C3)N([Si](C)(C)C(C)(C)C)S2(=O)=O4068.1Semi standard non polar33892256
Cyclothiazide,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(C1CC3C=CC1C3)N([Si](C)(C)C(C)(C)C)S2(=O)=O4453.6Standard non polar33892256
Cyclothiazide,3TBDMS,isomer #3CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C(C)(C)C)C(C1CC3C=CC1C3)N([Si](C)(C)C(C)(C)C)S2(=O)=O4364.0Standard polar33892256
Cyclothiazide,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S(=O)(=O)N([Si](C)(C)C(C)(C)C)C1C1CC2C=CC1C24299.9Semi standard non polar33892256
Cyclothiazide,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S(=O)(=O)N([Si](C)(C)C(C)(C)C)C1C1CC2C=CC1C24908.6Standard non polar33892256
Cyclothiazide,4TBDMS,isomer #1CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)C=C2S(=O)(=O)N([Si](C)(C)C(C)(C)C)C1C1CC2C=CC1C24357.6Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Cyclothiazide GC-MS (Non-derivatized) - 70eV, Positivesplash10-016u-9133000000-93e2b7d86e56b630140d2017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclothiazide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Cyclothiazide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclothiazide 10V, Positive-QTOFsplash10-0006-0009000000-a75423eac08147027ff02016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclothiazide 20V, Positive-QTOFsplash10-0596-0629000000-2e3acef52ea168edcc372016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclothiazide 40V, Positive-QTOFsplash10-0uei-3691000000-be00a0c434bc4cd8b71b2016-08-02Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclothiazide 10V, Negative-QTOFsplash10-059i-0009000000-be104b4d7d376f5e31662016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclothiazide 20V, Negative-QTOFsplash10-00fr-9707000000-ad653225ea24c021e3312016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclothiazide 40V, Negative-QTOFsplash10-004l-9000000000-2690cb233bbed98f36522016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclothiazide 10V, Positive-QTOFsplash10-0006-0009000000-64cd4a4b5b37d098a23a2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclothiazide 20V, Positive-QTOFsplash10-0006-0009000000-6253f7a477fe74bfc21d2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclothiazide 40V, Positive-QTOFsplash10-052f-9644000000-7357e78e11d940fc0f752021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclothiazide 10V, Negative-QTOFsplash10-000i-0009000000-733060bf4799a6320f932021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclothiazide 20V, Negative-QTOFsplash10-000i-2009000000-66e570b5f08162e4e5412021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Cyclothiazide 40V, Negative-QTOFsplash10-004i-9640000000-f157eafa7f76c2f8ea732021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Cytoplasm
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00606 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00606 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00606
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID2807
KEGG Compound IDC12685
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkCyclothiazide
METLIN IDNot Available
PubChem Compound2910
PDB IDNot Available
ChEBI ID31448
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. Can hydrates cyanamide to urea.
Gene Name:
CA1
Uniprot ID:
P00915
Molecular weight:
28870.0
References
  1. Rammes G, Zeilhofer HU, Collingridge GL, Parsons CG, Swandulla D: Expression of early hippocampal CA1 LTP does not lead to changes in AMPA-EPSC kinetics or sensitivity to cyclothiazide. Pflugers Arch. 1999 Jan;437(2):191-6. [PubMed:9929558 ]
  2. Rammes G, Swandulla D, Collingridge GL, Hartmann S, Parsons CG: Interactions of 2,3-benzodiazepines and cyclothiazide at AMPA receptors: patch clamp recordings in cultured neurones and area CA1 in hippocampal slices. Br J Pharmacol. 1996 Mar;117(6):1209-21. [PubMed:8882618 ]
  3. Fleck MW, Bahring R, Patneau DK, Mayer ML: AMPA receptor heterogeneity in rat hippocampal neurons revealed by differential sensitivity to cyclothiazide. J Neurophysiol. 1996 Jun;75(6):2322-33. [PubMed:8793745 ]
  4. Pirotte B, Podona T, Diouf O, de Tullio P, Lebrun P, Dupont L, Somers F, Delarge J, Morain P, Lestage P, Lepagnol J, Spedding M: 4H-1,2,4-Pyridothiadiazine 1,1-dioxides and 2,3-dihydro-4H-1,2, 4-pyridothiadiazine 1,1-dioxides chemically related to diazoxide and cyclothiazide as powerful positive allosteric modulators of (R/S)-2-amino-3-(3-hydroxy-5-methylisoxazol-4-yl)propionic acid receptors: design, synthesis, pharmacology, and structure-activity relationships. J Med Chem. 1998 Jul 30;41(16):2946-59. [PubMed:9685234 ]
  5. Larson J, Le TT, Hall RA, Lynch G: Effects of cyclothiazide on synaptic responses in slices of adult and neonatal rat hippocampus. Neuroreport. 1994 Jan 12;5(4):389-92. [PubMed:8003661 ]
General function:
Involved in carbonate dehydratase activity
Specific function:
Essential for bone resorption and osteoclast differentiation (By similarity). Reversible hydration of carbon dioxide. Can hydrate cyanamide to urea. Involved in the regulation of fluid secretion into the anterior chamber of the eye.
Gene Name:
CA2
Uniprot ID:
P00918
Molecular weight:
29245.895
References
  1. Liljequist S, Cebers G, Kalda A: Effects of decahydroisoquinoline-3-carboxylic acid monohydrate, a novel AMPA receptor antagonist, on glutamate-induced CA2+ responses and neurotoxicity in rat cortical and cerebellar granule neurons. Biochem Pharmacol. 1995 Nov 27;50(11):1761-74. [PubMed:8615854 ]
  2. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
General function:
Involved in carbonate dehydratase activity
Specific function:
Reversible hydration of carbon dioxide. May stimulate the sodium/bicarbonate transporter activity of SLC4A4 that acts in pH homeostasis. It is essential for acid overload removal from the retina and retina epithelium, and acid release in the choriocapillaris in the choroid.
Gene Name:
CA4
Uniprot ID:
P22748
Molecular weight:
35032.075
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
General function:
Involved in ion channel activity
Specific function:
May be involved in forming the receptor site for cardiac glycoside binding or may modulate the transport function of the sodium ATPase
Gene Name:
FXYD2
Uniprot ID:
P54710
Molecular weight:
7283.3
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]

Transporters

General function:
Involved in ion transmembrane transporter activity
Specific function:
Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one molecule of endogenous dicarboxylic acid (glutarate, ketoglutarate, etc). Mediates the sodium-independent uptake of 2,3-dimercapto-1-propanesulfonic acid (DMPS). Mediates the sodium-independent uptake of p- aminohippurate (PAH), ochratoxin (OTA), acyclovir (ACV), 3'-azido- 3-'deoxythymidine (AZT), cimetidine (CMD), 2,4-dichloro- phenoxyacetate (2,4-D), hippurate (HA), indoleacetate (IA), indoxyl sulfate (IS) and 3-carboxy-4-methyl-5-propyl-2- furanpropionate (CMPF), cidofovir, adefovir, 9-(2- phosphonylmethoxyethyl) guanine (PMEG), 9-(2- phosphonylmethoxyethyl) diaminopurine (PMEDAP) and edaravone sulfate. PAH uptake is inhibited by p- chloromercuribenzenesulphonate (PCMBS), diethyl pyrocarbonate (DEPC), sulindac, diclofenac, carprofen, glutarate and okadaic acid. PAH uptake is inhibited by benzothiazolylcysteine (BTC), S-chlorotrifluoroethylcysteine (CTFC), cysteine S-conjugates S-dichlorovinylcysteine (DCVC), furosemide, steviol, phorbol 12-myristate 13-acetate (PMA), calcium ionophore A23187, benzylpenicillin, furosemide, indomethacin, bumetamide, losartan, probenecid, phenol red, urate, and alpha-ketoglutarate
Gene Name:
SLC22A6
Uniprot ID:
Q4U2R8
Molecular weight:
61815.8
References
  1. Uwai Y, Saito H, Hashimoto Y, Inui KI: Interaction and transport of thiazide diuretics, loop diuretics, and acetazolamide via rat renal organic anion transporter rOAT1. J Pharmacol Exp Ther. 2000 Oct;295(1):261-5. [PubMed:10991988 ]