Metolazone (CED0007054)

Record Information
Version1.0
Creation Date2016-05-22 05:02:39 UTC
Update Date2026-08-19 15:19:45 UTC
Accession NumberCHEM018174
Identification
Common NameMetolazone
ClassSmall Molecule
Description
Metolazone is an organic compound with the chemical formula C16H16ClN3O3S and an average molecular weight of 365.83 g/mol. Metolazone belongs to the benzodiazines, a subclass of diazanaphthalenes within the organic compounds. In terms of its biological activity, the compound is a recorded inhibitor of the protein target Solute carrier family 12 member 3 (SLC12A3). The compound is associated with 15 recorded sources across several categories. Within healthcare, pharmaceuticals, and veterinary products, it is found in diuretics and gynecologicals. It is also used in food preservation within the food, food processing, and cookware sector. Additional sources include household cleaning and consumer products, such as soap dispensers, perfumes within detergents and soaps, cigar cigarettes, non electric simulated smoking devices, and other smoking requisites. Furthermore, it is released from electrical and electronic equipment, including antennas, amplifiers, electrodes, discharge lamps, and electrically stimulated smoking devices. The recorded route of exposure for metolazone is oral.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
2-Methyl-3-O-tolyl-6-sulfamyl-7-chloro-1,2,3,4-tetrahydro-4-quinazolinoneChEBI
7-Chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-6-quinazolinesulfonamideChEBI
7-Chloro-1,2,3,4-tetrahydro-2-methyl-4-oxo-3-O-tolyl-6-quinazolinesulfonamideChEBI
MetolazonaChEBI
MetolazonumChEBI
ZaroxolynChEBI
2-Methyl-3-O-tolyl-6-sulphamyl-7-chloro-1,2,3,4-tetrahydro-4-quinazolinoneGenerator
7-Chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-6-quinazolinesulphonamideGenerator
7-Chloro-1,2,3,4-tetrahydro-2-methyl-4-oxo-3-O-tolyl-6-quinazolinesulphonamideGenerator
MicroxHMDB
MykroxHMDB
Celltech pharmaceuticals brand OF metolzoneHMDB
DiuloHMDB
UCB pharma brand OF metolazoneHMDB
Chemical FormulaC16H16ClN3O3S
Average Molecular Mass365.835 g/mol
Monoisotopic Mass365.060 g/mol
CAS Registry Number17560-51-9
IUPAC Name7-chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2,3,4-tetrahydroquinazoline-6-sulfonamide
Traditional Namemetolazone
SMILESCC1NC2=CC(Cl)=C(C=C2C(=O)N1C1=CC=CC=C1C)S(N)(=O)=O
InChI IdentifierInChI=1S/C16H16ClN3O3S/c1-9-5-3-4-6-14(9)20-10(2)19-13-8-12(17)15(24(18,22)23)7-11(13)16(20)21/h3-8,10,19H,1-2H3,(H2,18,22,23)
InChI KeyAQCHWTWZEMGIFD-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as quinazolines. Quinazolines are compounds containing a quinazoline moiety, which is made up of two fused six-member aromatic rings, a benzene ring and a pyrimidine ring.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassDiazanaphthalenes
Sub ClassBenzodiazines
Direct ParentQuinazolines
Alternative Parents
Substituents
  • Quinazoline
  • Secondary aliphatic/aromatic amine
  • Toluene
  • Aryl chloride
  • Aryl halide
  • Monocyclic benzene moiety
  • Benzenoid
  • Organosulfonic acid amide
  • Organic sulfonic acid or derivatives
  • Vinylogous amide
  • Aminosulfonyl compound
  • Tertiary carboxylic acid amide
  • Sulfonyl
  • Organosulfonic acid or derivatives
  • Amino acid or derivatives
  • Carboxamide group
  • Lactam
  • Carboxylic acid derivative
  • Secondary amine
  • Azacycle
  • Organic oxide
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Amine
  • Organopnictogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Hydrocarbon derivative
  • 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 Solubility0.041 g/LALOGPS
logP3.21ALOGPS
logP2.94ChemAxon
logS-4ALOGPS
pKa (Strongest Acidic)9.54ChemAxon
pKa (Strongest Basic)-1.6ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area92.5 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity94.59 m³·mol⁻¹ChemAxon
Polarizability36.38 ųChemAxon
Number of Rings3ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0f8j-3597000000-ad3d0d3d7130fb037587Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aor-1494000000-aae5f0a5c86e9d0828e2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bvi-2960000000-1eed022b28a6bb140f60Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0aor-1494000000-aae5f0a5c86e9d0828e2Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0bvi-2960000000-1eed022b28a6bb140f60Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-a2ec696223204fee136fNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0279000000-4b5932a93a7777aa9293Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0zfr-2492000000-e56f6f011b99c12fe90eNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0009000000-c969b7886e22277846edNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-01t9-8119000000-fb2264110d55cdd31ad4Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004i-9110000000-7cb0633c91fcbb9b8881Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0009000000-1e4f596ff037e4c41189Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-2009000000-2d6cdb71493d37e99073Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-003r-9321000000-3e5878b7c7d017a45529Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-6789fa47262c2e6bd71aNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-014i-0009000000-eb6980c64348c1d78ad9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0kai-4892000000-6b2c2e53c19f2fd5f60dNot 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
6525.0Log mg/kg[3700:12000]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
290DiureticsHealthcare, pharmaceuticals & veterinary productsNot Available
316GynecologicalsHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
514Discharge LampsElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
529Power CablesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, 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
564Soap DispensersHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
592Marine Propulsion Or SteeringMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
604Pest AttractantsAgriculture & land managementNot 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
642FootwearTextiles, leather & furnishingsNot Available
659Transfer PrintingTextiles, leather & furnishingsNot Available
Pathways
3 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Carbonic anhydrase 2 structureClick to view 3D structureCarbonic anhydrase 2P00918HumansPredicted (SEA)200.072
Carbonic anhydrase 1 structureClick to view 3D structureCarbonic anhydrase 1P00915HumansPredicted (SEA)171.58
Carbonic anhydrase 9 structureClick to view 3D structureCarbonic anhydrase 9Q16790HumansPredicted (SEA)178.43
Carbonic anhydrase 7 structureClick to view 3D structureCarbonic anhydrase 7P43166HumansPredicted (SEA)107.665
Carbonic anhydrase 12 structureClick to view 3D structureCarbonic anhydrase 12O43570HumansPredicted (SEA)158.89
Carbonic anhydrase 6 structureClick to view 3D structureCarbonic anhydrase 6P23280HumansPredicted (SEA)62.8243
Carbonic anhydrase 14 structureClick to view 3D structureCarbonic anhydrase 14Q9ULX7HumansPredicted (SEA)82.8316
Click to view 3D structureCarbonic anhydrase 5B, mitochondrialQ9Y2D0HumansPredicted (SEA)67.2617
Carbonic anhydrase 4 structureClick to view 3D structureCarbonic anhydrase 4P22748HumansPredicted (SEA)77.2264
Click to view 3D structureCarbonic anhydrase 5A, mitochondrialP35218HumansPredicted (SEA)92.6406
Carbonic anhydrase 13 structureClick to view 3D structureCarbonic anhydrase 13Q8N1Q1HumansPredicted (SEA)42.5057
Carbonic anhydrase 3 structureClick to view 3D structureCarbonic anhydrase 3P07451HumansPredicted (SEA)30.984
Click to view 3D structureCarbonic anhydrase 13Q9D6N1Mus musculusPredicted (SEA)57.4527
Click to view 3D structureCarbonate dehydrataseB2V8E3Sulfurihydrogenibium sp. (strain YO3AOP1)Predicted (SEA)48.1887
Click to view 3D structureAstrosclerin-3A6YCJ1Astrosclera willeyanaPredicted (SEA)50.6798
Click to view 3D structureCarbonic anhydrase, alpha familyQ31FD6Thiomicrospira crunogenaPredicted (SEA)48.1887
Click to view 3D structureDelta carbonic anhydraseQ5U9J1Conticribra weissflogiiPredicted (SEA)54.1052
Click to view 3D structureAGAP002992-PAQ5TU56Anopheles gambiaePredicted (SEA)51.0691
Click to view 3D structureCarbonic anhydraseQ6FTL6Candida glabrata CBS 138Predicted (SEA)118.175
Click to view 3D structureCarbonic anhydraseQ5AJ71Candida albicans (strain SC5314 / ATCC MYA-2876) (Yeast)Predicted (SEA)149.237
Click to view 3D structureCarbonic anhydraseO24855Helicobacter pylori (strain ATCC 700392 / 26695) (Campylobacterpylori)Predicted (SEA)69.5194
Click to view 3D structureCarbonic anhydrase 15Q99N23Mus musculusPredicted (SEA)156.477
Click to view 3D structureCarbonic anhydrase 2Q3I4V7Cryptococcus neoformansPredicted (SEA)127.906
Click to view 3D structureCarbonic anhydraseP53615Saccharomyces cerevisiae S288cPredicted (SEA)58.854
Click to view 3D structureBeta-carbonic anhydrase 1P9WPJ7Mycobacterium tuberculosisPredicted (SEA)127.828
Concentrations
Not Available
External Links
DrugBank IDDB00524
HMDB IDHMDB0014665
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkMetolazone
Chemspider ID4026
ChEBI ID64354
PubChem Compound ID4170
Kegg Compound IDNot Available
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=12671341
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=15095363
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=1593359
4. https://www.ncbi.nlm.nih.gov/pubmed/?term=16189620
5. https://www.ncbi.nlm.nih.gov/pubmed/?term=16538931
6. https://www.ncbi.nlm.nih.gov/pubmed/?term=16717105
7. https://www.ncbi.nlm.nih.gov/pubmed/?term=16908225
8. https://www.ncbi.nlm.nih.gov/pubmed/?term=1886511
9. https://www.ncbi.nlm.nih.gov/pubmed/?term=1928234
10. https://www.ncbi.nlm.nih.gov/pubmed/?term=1946137
11. https://www.ncbi.nlm.nih.gov/pubmed/?term=2071258
12. https://www.ncbi.nlm.nih.gov/pubmed/?term=21387350
13. https://www.ncbi.nlm.nih.gov/pubmed/?term=21886902
14. https://www.ncbi.nlm.nih.gov/pubmed/?term=8199745
15. https://www.ncbi.nlm.nih.gov/pubmed/?term=8205244
16. https://www.ncbi.nlm.nih.gov/pubmed/?term=8870895
17. https://www.ncbi.nlm.nih.gov/pubmed/?term=9089428
18. Rosenberg J, Gustafsson F, Galatius S, Hildebrandt PR: Combination therapy with metolazone and loop diuretics in outpatients with refractory heart failure: an observational study and review of the literature. Cardiovasc Drugs Ther. 2005 Aug;19(4):301-6.