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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2022-03-07 02:51:53 UTC
HMDB IDHMDB0015156
Secondary Accession Numbers
  • HMDB15156
Metabolite Identification
Common NameTrichlormethiazide
DescriptionTrichlormethiazide is only found in individuals that have used or taken this drug. It is a thiazide diuretic with properties similar to those of hydrochlorothiazide. (From Martindale, The Extra Pharmacopoeia, 30th ed, p830)Trichlormethiazide appears to block the active reabsorption of chloride and possibly sodium in the ascending loop of Henle, altering electrolyte transfer in the proximal tubule. This results in excretion of sodium, chloride, and water and, hence, diuresis. As a diuretic, Trichloromethiazide 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 Trichloromethiazide 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 Trichloromethiazide 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.
Structure
Data?1582753265
Synonyms
ValueSource
HydrotrichlorothiazideChEBI
TrichlormethiazidumChEBI
TriclormetiazidaChEBI
NaquaKegg
Schering brand OF trichlormethiazideMeSH, HMDB
American urologicals brand OF trichloromethiazideMeSH, HMDB
AquazideMeSH, HMDB
DiureseMeSH, HMDB
TriazideMeSH, HMDB
TrichloromethiazideMeSH, HMDB
Jones brand OF trichloromethiazideMeSH, HMDB
Chemical FormulaC8H8Cl3N3O4S2
Average Molecular Weight380.656
Monoisotopic Molecular Weight378.90218026
IUPAC Name6-chloro-3-(dichloromethyl)-1,1-dioxo-3,4-dihydro-2H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide
Traditional Nametrichlormethiazide
CAS Registry Number133-67-5
SMILES
NS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C(Cl)Cl
InChI Identifier
InChI=1S/C8H8Cl3N3O4S2/c9-3-1-4-6(2-5(3)19(12,15)16)20(17,18)14-8(13-4)7(10)11/h1-2,7-8,13-14H,(H2,12,15,16)
InChI KeyLMJSLTNSBFUCMU-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
  • Alkyl chloride
  • Organopnictogen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Amine
  • Hydrocarbon derivative
  • Alkyl halide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Ontology
Physiological effectNot Available
Disposition
Process
RoleNot Available
Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.42 g/LNot Available
LogP0.7Not Available
Experimental Chromatographic PropertiesNot Available
Predicted Molecular Properties
PropertyValueSource
Water Solubility0.42 g/LALOGPS
logP0.86ALOGPS
logP0.97ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)8.32ChemAxon
pKa (Strongest Basic)-4.1ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area118.36 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity77.44 m³·mol⁻¹ChemAxon
Polarizability31.97 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+166.530932474
DeepCCS[M-H]-164.14230932474
DeepCCS[M-2H]-198.40830932474
DeepCCS[M+Na]+173.55530932474
AllCCS[M+H]+172.032859911
AllCCS[M+H-H2O]+169.232859911
AllCCS[M+NH4]+174.532859911
AllCCS[M+Na]+175.232859911
AllCCS[M-H]-163.132859911
AllCCS[M+Na-2H]-163.232859911
AllCCS[M+HCOO]-163.432859911

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
TrichlormethiazideNS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C(Cl)Cl4459.4Standard polar33892256
TrichlormethiazideNS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C(Cl)Cl2759.5Standard non polar33892256
TrichlormethiazideNS(=O)(=O)C1=C(Cl)C=C2NC(NS(=O)(=O)C2=C1)C(Cl)Cl3360.9Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Trichlormethiazide,1TMS,isomer #1C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)NS2(=O)=O3051.7Semi standard non polar33892256
Trichlormethiazide,1TMS,isomer #1C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)NS2(=O)=O3175.2Standard non polar33892256
Trichlormethiazide,1TMS,isomer #1C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)NS2(=O)=O4740.7Standard polar33892256
Trichlormethiazide,1TMS,isomer #2C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C(Cl)Cl2993.8Semi standard non polar33892256
Trichlormethiazide,1TMS,isomer #2C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C(Cl)Cl3221.0Standard non polar33892256
Trichlormethiazide,1TMS,isomer #2C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C(Cl)Cl4781.9Standard polar33892256
Trichlormethiazide,1TMS,isomer #3C[Si](C)(C)N1C(C(Cl)Cl)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O2987.5Semi standard non polar33892256
Trichlormethiazide,1TMS,isomer #3C[Si](C)(C)N1C(C(Cl)Cl)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O3201.8Standard non polar33892256
Trichlormethiazide,1TMS,isomer #3C[Si](C)(C)N1C(C(Cl)Cl)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O4903.1Standard polar33892256
Trichlormethiazide,2TMS,isomer #1C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)NS2(=O)=O2967.7Semi standard non polar33892256
Trichlormethiazide,2TMS,isomer #1C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)NS2(=O)=O3379.4Standard non polar33892256
Trichlormethiazide,2TMS,isomer #1C[Si](C)(C)N([Si](C)(C)C)S(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)NS2(=O)=O4571.9Standard polar33892256
Trichlormethiazide,2TMS,isomer #2C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C(Cl)Cl)NS2(=O)=O2962.1Semi standard non polar33892256
Trichlormethiazide,2TMS,isomer #2C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C(Cl)Cl)NS2(=O)=O3328.0Standard non polar33892256
Trichlormethiazide,2TMS,isomer #2C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C(Cl)Cl)NS2(=O)=O4028.3Standard polar33892256
Trichlormethiazide,2TMS,isomer #3C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)N([Si](C)(C)C)S2(=O)=O3001.9Semi standard non polar33892256
Trichlormethiazide,2TMS,isomer #3C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)N([Si](C)(C)C)S2(=O)=O3338.8Standard non polar33892256
Trichlormethiazide,2TMS,isomer #3C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)N([Si](C)(C)C)S2(=O)=O4313.1Standard polar33892256
Trichlormethiazide,2TMS,isomer #4C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C)C1C(Cl)Cl2983.5Semi standard non polar33892256
Trichlormethiazide,2TMS,isomer #4C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C)C1C(Cl)Cl3325.3Standard non polar33892256
Trichlormethiazide,2TMS,isomer #4C[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)N([Si](C)(C)C)C1C(Cl)Cl4450.0Standard polar33892256
Trichlormethiazide,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)NC1C(Cl)Cl2959.0Semi standard non polar33892256
Trichlormethiazide,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)NC1C(Cl)Cl3508.6Standard non polar33892256
Trichlormethiazide,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)NC1C(Cl)Cl3889.8Standard polar33892256
Trichlormethiazide,3TMS,isomer #2C[Si](C)(C)N1C(C(Cl)Cl)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S1(=O)=O2972.1Semi standard non polar33892256
Trichlormethiazide,3TMS,isomer #2C[Si](C)(C)N1C(C(Cl)Cl)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S1(=O)=O3535.1Standard non polar33892256
Trichlormethiazide,3TMS,isomer #2C[Si](C)(C)N1C(C(Cl)Cl)NC2=CC(Cl)=C(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)C=C2S1(=O)=O4220.8Standard polar33892256
Trichlormethiazide,3TMS,isomer #3C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C(Cl)Cl)N([Si](C)(C)C)S2(=O)=O2962.2Semi standard non polar33892256
Trichlormethiazide,3TMS,isomer #3C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C(Cl)Cl)N([Si](C)(C)C)S2(=O)=O3459.3Standard non polar33892256
Trichlormethiazide,3TMS,isomer #3C[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)N([Si](C)(C)C)C(C(Cl)Cl)N([Si](C)(C)C)S2(=O)=O3861.2Standard polar33892256
Trichlormethiazide,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)C1C(Cl)Cl2993.7Semi standard non polar33892256
Trichlormethiazide,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)C1C(Cl)Cl3679.3Standard non polar33892256
Trichlormethiazide,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)C1C(Cl)Cl3822.7Standard polar33892256
Trichlormethiazide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)NS2(=O)=O3314.5Semi standard non polar33892256
Trichlormethiazide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)NS2(=O)=O3423.5Standard non polar33892256
Trichlormethiazide,1TBDMS,isomer #1CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)NS2(=O)=O4724.1Standard polar33892256
Trichlormethiazide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C(Cl)Cl3274.6Semi standard non polar33892256
Trichlormethiazide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C(Cl)Cl3457.3Standard non polar33892256
Trichlormethiazide,1TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C2=CC(Cl)=C(S(N)(=O)=O)C=C2S(=O)(=O)NC1C(Cl)Cl4844.5Standard polar33892256
Trichlormethiazide,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(C(Cl)Cl)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O3290.0Semi standard non polar33892256
Trichlormethiazide,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(C(Cl)Cl)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O3437.3Standard non polar33892256
Trichlormethiazide,1TBDMS,isomer #3CC(C)(C)[Si](C)(C)N1C(C(Cl)Cl)NC2=CC(Cl)=C(S(N)(=O)=O)C=C2S1(=O)=O4977.0Standard polar33892256
Trichlormethiazide,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(C(Cl)Cl)NS2(=O)=O3514.2Semi standard non polar33892256
Trichlormethiazide,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(C(Cl)Cl)NS2(=O)=O3836.8Standard non polar33892256
Trichlormethiazide,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(C(Cl)Cl)NS2(=O)=O4476.5Standard polar33892256
Trichlormethiazide,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(C(Cl)Cl)NS2(=O)=O3472.0Semi standard non polar33892256
Trichlormethiazide,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(C(Cl)Cl)NS2(=O)=O3819.0Standard non polar33892256
Trichlormethiazide,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(C(Cl)Cl)NS2(=O)=O4028.6Standard polar33892256
Trichlormethiazide,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)N([Si](C)(C)C(C)(C)C)S2(=O)=O3475.1Semi standard non polar33892256
Trichlormethiazide,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)N([Si](C)(C)C(C)(C)C)S2(=O)=O3809.0Standard non polar33892256
Trichlormethiazide,2TBDMS,isomer #3CC(C)(C)[Si](C)(C)NS(=O)(=O)C1=CC2=C(C=C1Cl)NC(C(Cl)Cl)N([Si](C)(C)C(C)(C)C)S2(=O)=O4325.3Standard polar33892256
Trichlormethiazide,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)C1C(Cl)Cl3495.1Semi standard non polar33892256
Trichlormethiazide,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)C1C(Cl)Cl3829.2Standard non polar33892256
Trichlormethiazide,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)C1C(Cl)Cl4500.7Standard polar33892256
Trichlormethiazide,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)NC1C(Cl)Cl3708.8Semi standard non polar33892256
Trichlormethiazide,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)NC1C(Cl)Cl4209.4Standard non polar33892256
Trichlormethiazide,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)NC1C(Cl)Cl3932.8Standard polar33892256
Trichlormethiazide,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(C(Cl)Cl)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)=O3679.0Semi standard non polar33892256
Trichlormethiazide,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(C(Cl)Cl)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)=O4225.7Standard non polar33892256
Trichlormethiazide,3TBDMS,isomer #2CC(C)(C)[Si](C)(C)N1C(C(Cl)Cl)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)=O4227.9Standard polar33892256
Trichlormethiazide,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(C(Cl)Cl)N([Si](C)(C)C(C)(C)C)S2(=O)=O3669.2Semi standard non polar33892256
Trichlormethiazide,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(C(Cl)Cl)N([Si](C)(C)C(C)(C)C)S2(=O)=O4225.3Standard non polar33892256
Trichlormethiazide,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(C(Cl)Cl)N([Si](C)(C)C(C)(C)C)S2(=O)=O3968.8Standard polar33892256
Trichlormethiazide,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)C1C(Cl)Cl3900.9Semi standard non polar33892256
Trichlormethiazide,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)C1C(Cl)Cl4656.5Standard non polar33892256
Trichlormethiazide,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)C1C(Cl)Cl3964.2Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Trichlormethiazide GC-MS (Non-derivatized) - 70eV, Positivesplash10-016r-5190000000-adca0c41d4316946e8e72017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trichlormethiazide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Trichlormethiazide GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental LC-MS/MSLC-MS/MS Spectrum - Trichlormethiazide LC-ESI-qTof , Positive-QTOFsplash10-01p2-2950000000-2584307bcbe6b5fd0ba02017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Trichlormethiazide , positive-QTOFsplash10-01p2-2950000000-2584307bcbe6b5fd0ba02017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlormethiazide 10V, Positive-QTOFsplash10-004i-0009000000-157fc9a854cac50342732016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlormethiazide 20V, Positive-QTOFsplash10-014i-0193000000-19681cc56851e71306812016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlormethiazide 40V, Positive-QTOFsplash10-01q9-9240000000-495a697e32278834571e2016-08-01Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlormethiazide 10V, Negative-QTOFsplash10-002b-1098000000-d57f49d3da33c6ee42152016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlormethiazide 20V, Negative-QTOFsplash10-004i-8229000000-aa6c1dcaba15bbab0ac52016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlormethiazide 40V, Negative-QTOFsplash10-0a6r-7900000000-7232d73fcd73c28a33022016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlormethiazide 10V, Negative-QTOFsplash10-004i-0009000000-22a9e371f9df589420dc2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlormethiazide 20V, Negative-QTOFsplash10-004i-1009000000-9c0808e171bb412a558c2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlormethiazide 40V, Negative-QTOFsplash10-0fa9-9680000000-64ed1ff15d1871a3564e2021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlormethiazide 10V, Positive-QTOFsplash10-004i-0009000000-97cf46653736791faa852021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlormethiazide 20V, Positive-QTOFsplash10-004i-0009000000-8fb17fc3e2dfa5f4a0f42021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Trichlormethiazide 40V, Positive-QTOFsplash10-0gx1-3392000000-87a4644ddc894296eb202021-10-11Wishart 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 DB01021 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB01021 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB01021
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5359
KEGG Compound IDC07767
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTrichlormethiazide
METLIN IDNot Available
PubChem CompoundNot Available
PDB IDNot Available
ChEBI ID9683
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Download (PDF)
General ReferencesNot Available

Enzymes

General function:
Involved in ATP binding
Specific function:
This is the catalytic component of the active enzyme, which catalyzes the hydrolysis of ATP coupled with the exchange of sodium and potassium ions across the plasma membrane. This action creates the electrochemical gradient of sodium and potassium ions, providing the energy for active transport of various nutrients.
Gene Name:
ATP1A1
Uniprot ID:
P05023
Molecular weight:
112895.01
References
  1. Takahashi N, Kondo Y, Fujiwara I, Ito O, Igarashi Y, Abe K: Characterization of Na+ transport across the cell membranes of the ascending thin limb of Henle's loop. Kidney Int. 1995 Mar;47(3):789-94. [PubMed:7752578 ]
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. 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 ]
  3. Temperini C, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem. 2009 Feb 1;17(3):1214-21. doi: 10.1016/j.bmc.2008.12.023. Epub 2008 Dec 24. [PubMed:19119014 ]
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. 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 ]
  3. Temperini C, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem. 2009 Feb 1;17(3):1214-21. doi: 10.1016/j.bmc.2008.12.023. Epub 2008 Dec 24. [PubMed:19119014 ]
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 ]
  3. Temperini C, Cecchi A, Scozzafava A, Supuran CT: Carbonic anhydrase inhibitors. Comparison of chlorthalidone, indapamide, trichloromethiazide, and furosemide X-ray crystal structures in adducts with isozyme II, when several water molecules make the difference. Bioorg Med Chem. 2009 Feb 1;17(3):1214-21. doi: 10.1016/j.bmc.2008.12.023. Epub 2008 Dec 24. [PubMed:19119014 ]

Transporters

General function:
Involved in transport
Specific function:
Electrically silent transporter system. Mediates sodium and chloride reabsorption. Plays a vital role in the regulation of ionic balance and cell volume
Gene Name:
SLC12A1
Uniprot ID:
Q13621
Molecular weight:
121449.1
References
  1. Li J, Wang DH: Function and regulation of epithelial sodium transporters in the kidney of a salt-sensitive hypertensive rat model. J Hypertens. 2007 May;25(5):1065-72. [PubMed:17414671 ]
  2. Hasannejad H, Takeda M, Taki K, Shin HJ, Babu E, Jutabha P, Khamdang S, Aleboyeh M, Onozato ML, Tojo A, Enomoto A, Anzai N, Narikawa S, Huang XL, Niwa T, Endou H: Interactions of human organic anion transporters with diuretics. J Pharmacol Exp Ther. 2004 Mar;308(3):1021-9. Epub 2003 Nov 10. [PubMed:14610216 ]
  3. Smith SM: Thiazide diuretics. N Engl J Med. 2010 Feb 18;362(7):659-60; author reply 660. [PubMed:20187262 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]