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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2022-03-07 02:51:42 UTC
HMDB IDHMDB0014665
Secondary Accession Numbers
  • HMDB14665
Metabolite Identification
Common NameMetolazone
DescriptionMetolazone is only found in individuals that have used or taken this drug. It is a quinazoline-sulfonamide that is considered a thiazide-like diuretic which is long-acting so useful in chronic renal failure. It also tends to lower blood pressure and increase potassium loss. [PubChem]The actions of metolazone result from interference with the renal tubular mechanism of electrolyte reabsorption. Metolazone acts primarily to inhibit sodium reabsorption at the cortical diluting site and to a lesser extent in the proximal convoluted tubule. Sodium and chloride ions are excreted in approximately equivalent amounts. The increased delivery of sodium to the distal tubular exchange site results in increased potassium excretion. Metolazone does not inhibit carbonic anhydrase. The antihypertensive mechanism of action of metolazone is not fully understood but is presumed to be related to its saluretic and diuretic properties.
Structure
Data?1582753205
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 Weight365.835
Monoisotopic Molecular Weight365.06008979
IUPAC Name7-chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2,3,4-tetrahydroquinazoline-6-sulfonamide
Traditional Namemetolazone
CAS Registry Number17560-51-9
SMILES
CC1NC2=CC(Cl)=C(C=C2C(=O)N1C1=CC=CC=C1C)S(N)(=O)=O
InChI Identifier
InChI=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
Ontology
Disposition

Biological location

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting Point256 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility0.041 g/LNot Available
LogP2.5Not Available
Experimental Chromatographic Properties

Experimental Collision Cross Sections

Adduct TypeData SourceCCS Value (Å2)Reference
[M+H]+Not Available181.235http://allccs.zhulab.cn/database/detail?ID=AllCCS00001108
Predicted Molecular 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
Predicted Chromatographic Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DeepCCS[M+H]+179.52830932474
DeepCCS[M-H]-177.1730932474
DeepCCS[M-2H]-210.20130932474
DeepCCS[M+Na]+185.62130932474

Predicted Kovats Retention Indices

Underivatized

MetaboliteSMILESKovats RI ValueColumn TypeReference
MetolazoneCC1NC2=CC(Cl)=C(C=C2C(=O)N1C1=CC=CC=C1C)S(N)(=O)=O4482.6Standard polar33892256
MetolazoneCC1NC2=CC(Cl)=C(C=C2C(=O)N1C1=CC=CC=C1C)S(N)(=O)=O2895.3Standard non polar33892256
MetolazoneCC1NC2=CC(Cl)=C(C=C2C(=O)N1C1=CC=CC=C1C)S(N)(=O)=O3250.5Semi standard non polar33892256

Derivatized

Derivative Name / StructureSMILESKovats RI ValueColumn TypeReference
Metolazone,1TMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N[Si](C)(C)C)=C(Cl)C=C2NC1C3130.8Semi standard non polar33892256
Metolazone,1TMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N[Si](C)(C)C)=C(Cl)C=C2NC1C3198.8Standard non polar33892256
Metolazone,1TMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N[Si](C)(C)C)=C(Cl)C=C2NC1C4229.7Standard polar33892256
Metolazone,1TMS,isomer #2CC1=CC=CC=C1N1C(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C2N([Si](C)(C)C)C1C2979.5Semi standard non polar33892256
Metolazone,1TMS,isomer #2CC1=CC=CC=C1N1C(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C2N([Si](C)(C)C)C1C3270.2Standard non polar33892256
Metolazone,1TMS,isomer #2CC1=CC=CC=C1N1C(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C2N([Si](C)(C)C)C1C4426.1Standard polar33892256
Metolazone,2TMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C2NC1C3046.3Semi standard non polar33892256
Metolazone,2TMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C2NC1C3346.0Standard non polar33892256
Metolazone,2TMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C2NC1C4123.1Standard polar33892256
Metolazone,2TMS,isomer #2CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N[Si](C)(C)C)=C(Cl)C=C2N([Si](C)(C)C)C1C2963.9Semi standard non polar33892256
Metolazone,2TMS,isomer #2CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N[Si](C)(C)C)=C(Cl)C=C2N([Si](C)(C)C)C1C3329.3Standard non polar33892256
Metolazone,2TMS,isomer #2CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N[Si](C)(C)C)=C(Cl)C=C2N([Si](C)(C)C)C1C3823.9Standard polar33892256
Metolazone,3TMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C2N([Si](C)(C)C)C1C2995.4Semi standard non polar33892256
Metolazone,3TMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C2N([Si](C)(C)C)C1C3494.3Standard non polar33892256
Metolazone,3TMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C)[Si](C)(C)C)=C(Cl)C=C2N([Si](C)(C)C)C1C3776.4Standard polar33892256
Metolazone,1TBDMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C(Cl)C=C2NC1C3343.3Semi standard non polar33892256
Metolazone,1TBDMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C(Cl)C=C2NC1C3440.9Standard non polar33892256
Metolazone,1TBDMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C(Cl)C=C2NC1C4217.3Standard polar33892256
Metolazone,1TBDMS,isomer #2CC1=CC=CC=C1N1C(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C2N([Si](C)(C)C(C)(C)C)C1C3248.6Semi standard non polar33892256
Metolazone,1TBDMS,isomer #2CC1=CC=CC=C1N1C(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C2N([Si](C)(C)C(C)(C)C)C1C3475.5Standard non polar33892256
Metolazone,1TBDMS,isomer #2CC1=CC=CC=C1N1C(=O)C2=CC(S(N)(=O)=O)=C(Cl)C=C2N([Si](C)(C)C(C)(C)C)C1C4481.6Standard polar33892256
Metolazone,2TBDMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C2NC1C3524.7Semi standard non polar33892256
Metolazone,2TBDMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C2NC1C3828.2Standard non polar33892256
Metolazone,2TBDMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C2NC1C4120.2Standard polar33892256
Metolazone,2TBDMS,isomer #2CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C(Cl)C=C2N([Si](C)(C)C(C)(C)C)C1C3410.1Semi standard non polar33892256
Metolazone,2TBDMS,isomer #2CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C(Cl)C=C2N([Si](C)(C)C(C)(C)C)C1C3814.2Standard non polar33892256
Metolazone,2TBDMS,isomer #2CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N[Si](C)(C)C(C)(C)C)=C(Cl)C=C2N([Si](C)(C)C(C)(C)C)C1C3915.4Standard polar33892256
Metolazone,3TBDMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C2N([Si](C)(C)C(C)(C)C)C1C3656.1Semi standard non polar33892256
Metolazone,3TBDMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C2N([Si](C)(C)C(C)(C)C)C1C4204.7Standard non polar33892256
Metolazone,3TBDMS,isomer #1CC1=CC=CC=C1N1C(=O)C2=CC(S(=O)(=O)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)=C(Cl)C=C2N([Si](C)(C)C(C)(C)C)C1C3906.7Standard polar33892256
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted GC-MSPredicted GC-MS Spectrum - Metolazone GC-MS (Non-derivatized) - 70eV, Positivesplash10-0f8j-3597000000-ad3d0d3d7130fb0375872017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Metolazone 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 - Metolazone LC-ESI-qTof , Positive-QTOFsplash10-0aor-1494000000-aae5f0a5c86e9d0828e22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metolazone LC-ESI-qTof , Positive-QTOFsplash10-0bvi-2960000000-1eed022b28a6bb140f602017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metolazone , positive-QTOFsplash10-0aor-1494000000-aae5f0a5c86e9d0828e22017-09-14HMDB team, MONAView Spectrum
Experimental LC-MS/MSLC-MS/MS Spectrum - Metolazone , positive-QTOFsplash10-0bvi-2960000000-1eed022b28a6bb140f602017-09-14HMDB team, MONAView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metolazone 10V, Positive-QTOFsplash10-014i-0009000000-a2ec696223204fee136f2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metolazone 20V, Positive-QTOFsplash10-014i-0279000000-4b5932a93a7777aa92932016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metolazone 40V, Positive-QTOFsplash10-0zfr-2492000000-e56f6f011b99c12fe90e2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metolazone 10V, Negative-QTOFsplash10-03di-0009000000-c969b7886e22277846ed2016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metolazone 20V, Negative-QTOFsplash10-01t9-8119000000-fb2264110d55cdd31ad42016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metolazone 40V, Negative-QTOFsplash10-004i-9110000000-7cb0633c91fcbb9b88812016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metolazone 10V, Negative-QTOFsplash10-03di-0009000000-1e4f596ff037e4c411892021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metolazone 20V, Negative-QTOFsplash10-03di-2009000000-2d6cdb71493d37e990732021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metolazone 40V, Negative-QTOFsplash10-003r-9321000000-3e5878b7c7d017a455292021-09-23Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metolazone 10V, Positive-QTOFsplash10-014i-0009000000-6789fa47262c2e6bd71a2021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metolazone 20V, Positive-QTOFsplash10-014i-0009000000-eb6980c64348c1d78ad92021-09-24Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Metolazone 40V, Positive-QTOFsplash10-0kai-4892000000-6b2c2e53c19f2fd5f60d2021-09-24Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00524 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00524 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00524
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID4026
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkMetolazone
METLIN IDNot Available
PubChem Compound4170
PDB IDNot Available
ChEBI ID64354
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 References
  1. 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. [PubMed:16189620 ]

Enzymes

General function:
Involved in transport
Specific function:
Electrically silent transporter system. Mediates sodium and chloride reabsorption
Gene Name:
SLC12A3
Uniprot ID:
P55017
Molecular weight:
113124.0
References
  1. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]