CAS 17560-51-9|7-chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2,3,4-tetrahydroquinazoline-6-sulfonamide|7-Chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-6-quinazolinesulfonamide|metolazon...

General Information

Structure

Molecular Formula

C₁₆H₁₆ClN₃O₃S

Molecular Mass

365.83454

Exact Mass

365.06009007

Charge

InChI

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)

InChIKey

AQCHWTWZEMGIFD-UHFFFAOYSA-N

Canonic Smiles

CC1Nc2cc(Cl)c(cc2C(=O)N1c1ccccc1C)S(=O)(=O)N

Isomeric Smiles

Clc1cc2NC(N(C(=O)c2cc1S(=O)(=O)N)c1c(cccc1)C)C

Calculated Properties

JChem

Acid pKa

9.535759

H Acceptors

H Donor

LogD (pH = 5.5)

2.943545

LogD (pH = 7.4)

2.940775

Log P

2.9435806

Molar Refractivity

94.5879

Polarizability

36.030464

Polar Surface Area

92.5

Rotatable Bonds

Lipinski's Rule of Five

true

ALOGPS 2.1

Log P

3.21

LOG S

-3.95

Solubility (Water)

4.07e-02 g/l

Data Source

Names and Identifiers

IUPAC name

7-chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2,3,4-tetrahydroquinazoline-6-sulfonamide

Synonyms

MetolazoneZaroxolyn7-Chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-6-quinazolinesulfonamideMetolazona [INN-Spanish]Metolazonum [INN-Latin]MetolazoneMykroxMetolazone(Zaroxolyn)Diulo7-Chloro-2-methyl-4-oxo-3-(o-tolyl)-1,2,3,4-tetrahydroquinazoline-6-sulfonamideMetenix2-Methyl-3-(o-tolyl)-6-sulfamyl-7-chloro-1,2,3,4-tetrahydro-4-quinazolinoneNormelanXuretMetozaloneSR 720-22Oldren

IUPAC Traditional name

metolazone (product) metolazone

Brand Name

MicroxMetenixMetalozoneMykroxOldrenXuretMetalazoneZaroxolynDiulo

Names and Identifiers

Registration numbers

CAS Number

17560-51-9

EC Number

241-539-3

PubChem SID

2472453216096386946509058

MDL Number

MFCD00069304

PubChem CID

4170

Registration numbers

Properties

Product Information

Pharmacology Properties

Gene Information

human ... SLC12A1(6557)

Properties

Related Proteins

No Data Available

Click here to submit data

Molecular Spectra

Molecule Details

DrugBank

DB00524

Drug Groups

approved

Description

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]

Indication

For the treatment of hypertension, alone or in combination with other antihypertensive drugs of a different class.

Pharmacology

Metolazone is a quinazoline diuretic, with properties generally similar to the thiazide diuretics. A proximal action of metolazone has been shown in humans by increased excretion of phosphate and magnesium ions and by a markedly increased fractional excretion of sodium in patients with severely compromised glomerular filtration. This action has been demonstrated in animals by micropuncture studies.

Toxicity

Symptoms of overdose include difficulty breathing, dizziness, dizziness on standing up, drowsiness, fainting, irritation of the stomach and intestines, and lethargy leading to coma.

Affected Organisms

Humans and other mammals

Biotransformation

Not substantially metabolized. 70-95% is excreted unchanged in urine via glomerular filtration and active tubular secretion. Undergoes enterohepatic recycling.

Absorption

Peak blood levels are obtained within 2 to 4 hours of oral administration. The rate and extent of absorption are formulation dependent.

Half Life

Approximately 14 hours.

Protein Binding

50-70% bound to erythrocytes, up to 33% bound to plasma proteins, 2-5% of the drug in circulation is unbound

Elimination

Most of the drug is excreted in the unconverted form in the urine.

References

• 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]

External Links

• [Wikipedia]

• [RxList]

• [PDRhealth]

• [Drugs.com]

Selleck Chemicals

S1610

Research Area: Cardiovascular Disease
Biological Activity:
Metolazone(Zaroxolyn) is primarily used to treat congestive heart failure and high blood pressure. Metolazone indirectly decreases the amount of water reabsorbed into the bloodstream by the kidney, which results in the decreases of blood volume and the increases of urine volume. Metolazone and the other thiazide diuretics inhibit the function of the sodium-chloride symporter and prevent sodium and chloride, water as well, from leaving the lumen to enter the tubule cell. [1]

MP Biomedicals

02153617

Diuretic; anti-hypertensive

Sigma Aldrich

M1195

Biochem/physiol Actions
Inhibitor of thiazide-sensitive Na+-Cl- cotransporter; antihypertensive; moderate "loop" diuretic.
Other Notes
Tandem Mass Spectrometry data independently generated by Scripps Center for Metabolomics is available to view or download in PDF. M1195.pdf Tested metabolites are featured on Scripps Center for Metabolomics METLIN Metabolite Database. To learn more, visit sigma.com/metlin.

TRC

M338750

A diruetic. An antihypertensive.

Molecule Details

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Metolazone

• Kiyingi, A., et al.: Lancet, 335, 29 (1990)

• Curry, C.L., et al.: Clin. Ther., 9, 47 (1986)

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC name

7-chloro-2-methyl-3-(2-methylphenyl)-4-oxo-1,2,3,4-tetrahydroquinazoline-6-sulfonamide

Synonyms

IUPAC Traditional name

metolazone (product) metolazone

Brand Name

MicroxMetenixMetalozoneMykroxOldrenXuretMetalazoneZaroxolynDiulo

Registration numbers

CAS Number

17560-51-9

EC Number

241-539-3

PubChem SID

2472453216096386946509058

MDL Number

MFCD00069304

PubChem CID

4170

References

PubChem Literature

From Data Sources

• http://en.wikipedia.org/wiki/Metolazone

• Kiyingi, A., et al.: Lancet, 335, 29 (1990)

• Curry, C.L., et al.: Clin. Ther., 9, 47 (1986)

Bioactivity

PubChem BioAssay

Properties

Product Information

Pharmacology Properties

Gene Information

human ... SLC12A1(6557)

Molecule Details

DrugBank

DB00524

Drug Groups

approved

Description

Indication

For the treatment of hypertension, alone or in combination with other antihypertensive drugs of a different class.

Pharmacology

Toxicity

Symptoms of overdose include difficulty breathing, dizziness, dizziness on standing up, drowsiness, fainting, irritation of the stomach and intestines, and lethargy leading to coma.

Affected Organisms

Humans and other mammals

Biotransformation

Not substantially metabolized. 70-95% is excreted unchanged in urine via glomerular filtration and active tubular secretion. Undergoes enterohepatic recycling.

Absorption

Peak blood levels are obtained within 2 to 4 hours of oral administration. The rate and extent of absorption are formulation dependent.

Half Life

Approximately 14 hours.

Protein Binding

50-70% bound to erythrocytes, up to 33% bound to plasma proteins, 2-5% of the drug in circulation is unbound

Elimination

Most of the drug is excreted in the unconverted form in the urine.

References

External Links

• [Wikipedia]

• [RxList]