Metolazone (CHEM018174)

IdentificationTaxonomyBiological PropertiesPhysical PropertiesToxicity ProfileSpectraConcentrationsLinksReferencesXML
Record Information
Version1.0
Creation Date2016-05-22 05:02:39 UTC
Update Date2016-11-09 01:15:45 UTC
Accession NumberCHEM018174
Identification
Common NameMetolazone
ClassSmall Molecule
DescriptionA quinazoline that consists of 1,2,3,4-tetrahydroquinazolin-4-one bearing additional methyl, 2-tolyl, sulfamyl and chloro substituents at positions 2, 3, 6 and 7 respectively. A quinazoline diuretic, with properties similar to thiazide diuretics.
Contaminant Sources
  • HMDB Contaminants - Urine
  • STOFF IDENT Compounds
  • ToxCast & Tox21 Chemicals
Contaminant TypeNot Available
Chemical Structure
Thumb
MOLSDF3D-SDFPDBSMILESInChI View 3D 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
PathwaysNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot 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
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8j-3597000000-ad3d0d3d7130fb037587Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, PositiveNot AvailableSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0aor-1494000000-aae5f0a5c86e9d0828e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-qTof , Positivesplash10-0bvi-2960000000-1eed022b28a6bb140f60Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0aor-1494000000-aae5f0a5c86e9d0828e2Spectrum
LC-MS/MSLC-MS/MS Spectrum - , positivesplash10-0bvi-2960000000-1eed022b28a6bb140f60Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-a2ec696223204fee136fSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0279000000-4b5932a93a7777aa9293Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0zfr-2492000000-e56f6f011b99c12fe90eSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-c969b7886e22277846edSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-01t9-8119000000-fb2264110d55cdd31ad4Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004i-9110000000-7cb0633c91fcbb9b8881Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-03di-0009000000-1e4f596ff037e4c41189Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-03di-2009000000-2d6cdb71493d37e99073Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-003r-9321000000-3e5878b7c7d017a45529Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-014i-0009000000-6789fa47262c2e6bd71aSpectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-014i-0009000000-eb6980c64348c1d78ad9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kai-4892000000-6b2c2e53c19f2fd5f60dSpectrum
Toxicity Profile
Route of ExposureNot Available
Mechanism of ToxicityNot Available
MetabolismNot Available
Toxicity ValuesNot Available
Lethal DoseNot Available
Carcinogenicity (IARC Classification)Not Available
Uses/SourcesNot Available
Minimum Risk LevelNot Available
Health EffectsNot Available
SymptomsNot Available
TreatmentNot Available
Concentrations
Not Available
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.