Chlorothiazide (CED0005152)

Record Information
Version1.0
Creation Date2016-05-22 03:38:47 UTC
Update Date2026-08-24 04:38:48 UTC
Accession NumberCHEM016626
Identification
Common NameChlorothiazide
ClassSmall Molecule
Description
Chlorothiazide is an organic compound with the formula C7H6ClN3O4S2 and an average molecular weight of 295.72 g/mol. Chlorothiazide belongs to the benzothiadiazines, a subclass of thiadiazines within the organic compounds. It is categorized under the superclass of organoheterocyclic compounds. The compound is found in or released from 18 recorded sources. Within healthcare, pharmaceuticals, and veterinary products, it is used in gynecologicals and diuretics. In the category of food, food processing, and cookware, it is associated with food preservation and the preparation of wort, wine, or sparkling wine. It is also found in household cleaning and consumer products, including soap detergents, perfumes within detergents and soaps, cigar cigarettes, non-electric simulated smoking devices, and other smoking requisites. Additionally, it is linked to electrical and electronic equipment, such as electrodes, discharge lamps, antennas, conductors or conductive bodies characterised by the conductive materials, and electrically stimulated smoking devices. At the molecular level, chlorothiazide interacts with three recorded protein targets. It acts as an inhibitor of Solute carrier family 12 member 3 (SLC12A3), Carbonic anhydrase 1 (CA1), and Carbonic anhydrase 2 (CA2). Recorded exposure routes for this compound include oral and intravenous administration.
Contaminant Type
  • Human Neurotoxin
Chemical Structure
Synonyms
ValueSource
6-Chloro-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[1,2,4]thiadiazine-7-sulfonic acid amideChEBI
6-Chloro-7-sulfamoyl-2H-1,2,4-benzothiadiazine 1,1-dioxideChEBI
ChlorothiazidumChEBI
ClorotiazidaChEBI
DiurilKegg
6-Chloro-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[1,2,4]thiadiazine-7-sulfonate amideGenerator
6-Chloro-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[1,2,4]thiadiazine-7-sulphonate amideGenerator
6-Chloro-1,1-dioxo-1,2-dihydro-1lambda*6*-benzo[1,2,4]thiadiazine-7-sulphonic acid amideGenerator
6-Chloro-7-sulphamoyl-2H-1,2,4-benzothiadiazine 1,1-dioxideGenerator
ChlorothiazidHMDB
ChlorthiazideHMDB
ChlortiazidHMDB
Chemical FormulaC7H6ClN3O4S2
Average Molecular Mass295.723 g/mol
Monoisotopic Mass294.949 g/mol
CAS Registry Number58-94-6
IUPAC Name6-chloro-1,1-dioxo-4H-1λ⁶,2,4-benzothiadiazine-7-sulfonamide
Traditional Namemicrozide
SMILESNS(=O)(=O)C1=C(Cl)C=C2NC=NS(=O)(=O)C2=C1
InChI IdentifierInChI=1S/C7H6ClN3O4S2/c8-4-1-5-7(2-6(4)16(9,12)13)17(14,15)11-3-10-5/h1-3H,(H,10,11)(H2,9,12,13)
InChI KeyJBMKAUGHUNFTOL-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
  • Aryl chloride
  • Aryl halide
  • Organosulfonic acid amide
  • Benzenoid
  • Organic sulfonic acid or derivatives
  • Organosulfonic acid or derivatives
  • Sulfonyl
  • Aminosulfonyl compound
  • Propargyl-type 1,3-dipolar organic compound
  • Formamidine
  • Amidine
  • Organic 1,3-dipolar compound
  • Azacycle
  • Organopnictogen compound
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organosulfur compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Hydrocarbon derivative
  • Organic oxide
  • Aromatic heteropolycyclic compound
Molecular FrameworkAromatic heteropolycyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility0.4 g/LALOGPS
logP0.41ALOGPS
logP-0.44ChemAxon
logS-2.9ALOGPS
pKa (Strongest Acidic)9.1ChemAxon
pKa (Strongest Basic)1.15ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area118.69 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity62.51 m³·mol⁻¹ChemAxon
Polarizability24.55 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0fvi-3390000000-4907b28333e017912f33Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0090000000-e74dd6446e0284a7f0aaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0090000000-baf93e639a13c39dc1d6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ox-0090000000-473477518be3f6c8ddcdNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0290000000-0e599c26917ade291ca0Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0890000000-ad270ef1247ce9a114adNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0920000000-3c4bb920bb8316022718Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-2900000000-eca13dbca70054de3470Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-02vr-9700000000-9261e1bf4e212aee7d84Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0i09-9100000000-491baf01fc6ef9ca39e1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0090000000-388cb4ff11dc0a41ad99Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002b-0090000000-5645eee512f78cd689a7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0390000000-a39ffe78224ed4cacc13Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0pbl-0920000000-eb979e3c4ecd1f12fb71Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-059f-2900000000-4c2eb27958fba0102431Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05tk-5900000000-b42b446bc2b9f6216af1Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-00kk-9400000000-b4b975e3c1fabe09f4a7Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-9100000000-f8f80586b12a43c2a667Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-9000000000-9d41a0f061f998097c17Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0190000000-b4aa6830cd5272c0d44bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-01ox-0090000000-f73f1d2095131e09a83fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0890000000-3b5907d8f80aafef9a69Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-004i-0920000000-f852932de45c2b61abcfNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-05tk-5900000000-ccf8264076d5dc2acd5bNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0090000000-baf93e639a13c39dc1d6Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-002b-0090000000-3c04a662f104fe3a7f25Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0udi-0390000000-3f9a099e5ae7e51c01e4Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-059f-2900000000-a6ef74cc8e465a77e610Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0pbl-0920000000-221694a896352e407c75Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-0090000000-e74dd6446e0284a7f0aaNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0002-0090000000-3b060103ddcb70b2913fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-6500ac39cf672b42f75dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0090000000-80ebd93be346579a63b3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0uxr-0790000000-2156a2679d57dbda9635Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0090000000-d2924827db1564ab2598Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1090000000-5218745f5848fdcbeb08Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9020000000-8cc5eabcbcc35fa29dbcNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-f44b565690ae504c95e1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0002-0090000000-f44b565690ae504c95e1Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-1910000000-d2ae219607c94768a101Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0090000000-fd6c56746e26ea4f9d6dNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-0090000000-31eea24951d4fbd1201eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0udi-2920000000-b45192ca13e809448210Not AvailableView Spectrum
1D NMR13C NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
1D NMR1H NMR Spectrum (1D, D2O, predicted)Not AvailableNot AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
5779.0Log mg/kg[3200:10000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
233BrushesPersonal care & cosmeticsNot Available
290DiureticsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
540X Ray TubesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
549Preparation Of Wine Or Sparkling WineFood, food processing & cookwareNot Available
550Preparation Of WortFood, food processing & cookwareNot Available
556Cigar CigarettesHousehold cleaning & consumer productsNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
560Other Smoking RequisitesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
581Paper Making MachinesIndustrial manufacturing & chemical processingNot Available
596AcaricidesAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
634BucklesTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
657Surface Finishing Of LeatherTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
Pathways
4 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)47.9551
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)43.2842
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)70.6871
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)45.8532
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)69.2858
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)22.5763
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)32.3074
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)33.6309
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)30.0498
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)34.7208
Click to view 3D structureCarbonate dehydrataseB2V8E3Sulfurihydrogenibium sp. (strain YO3AOP1)Predicted (SEA)15.5698
Click to view 3D structureAstrosclerin-3A6YCJ1Astrosclera willeyanaPredicted (SEA)16.504
Click to view 3D structureCarbonic anhydrase, alpha familyQ31FD6Thiomicrospira crunogenaPredicted (SEA)15.5698
Click to view 3D structureDelta carbonic anhydraseQ5U9J1Conticribra weissflogiiPredicted (SEA)12.5337
Click to view 3D structureAGAP002992-PAQ5TU56Anopheles gambiaePredicted (SEA)12.1445
Click to view 3D structureCarbonic anhydrase 13Q9D6N1Mus musculusPredicted (SEA)23.0434
Carbonic anhydrase 3 structureClick to view 3D structureCarbonic anhydrase 3P07451HumansPredicted (SEA)23.1212
Carbonic anhydrase 13 structureClick to view 3D structureCarbonic anhydrase 13Q8N1Q1HumansPredicted (SEA)54.4166
Click to view 3D structureCarbonic anhydrase 4Q95323Bos taurusPredicted (SEA)85.167
Click to view 3D structureCarbonic anhydraseO24855Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)Predicted (SEA)41.1044
Click to view 3D structureCarbonic anhydraseQ6FTL6Candida glabrata CBS 138Predicted (SEA)65.4712
Click to view 3D structureAlpha carbonic anhydraseB5SU02Stylophora pistillataPredicted (SEA)39.236
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)56.9078
Click to view 3D structureCarbonic anhydraseP53615Saccharomyces cerevisiae S288cPredicted (SEA)34.3315
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)67.7288
Concentrations
Not Available
External Links
DrugBank IDDB00880
HMDB IDHMDB0015018
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkChlorothiazide
Chemspider ID2619
ChEBI ID3640
PubChem Compound ID2720
Kegg Compound IDC07461
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=10891117
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=2160536
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=28166217
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=29438107
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=3712385