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...

基本信息

化学结构

分子式

C₁₆H₁₆ClN₃O₃S

分子量

365.83454

精确质量

365.06009007

电荷

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

计算属性

JChem

Acid pKa

9.535759

质子受体

质子供体

LogD (pH = 5.5)

2.943545

LogD (pH = 7.4)

2.940775

Log P

2.9435806

摩尔折射率

94.5879

极化性

36.030464

极化表面积

92.5

可自由旋转的化学键

里宾斯基五规则

true

ALOGPS 2.1

Log P

3.21

LOG S

-3.95

溶解度

4.07e-02 g/l

数据来源

名称和标识

IUPAC标准名

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

别名

7-Chloro-1,2,3,4-tetrahydro-2-methyl-3-(2-methylphenyl)-4-oxo-6-quinazolinesulfonamideZaroxolynMetolazoneMetolazona [INN-Spanish]Metolazonum [INN-Latin]MetolazoneMykroxMetolazone(Zaroxolyn)Diulo7-Chloro-2-methyl-4-oxo-3-(o-tolyl)-1,2,3,4-tetrahydroquinazoline-6-sulfonamideXuretSR 720-22Metenix2-Methyl-3-(o-tolyl)-6-sulfamyl-7-chloro-1,2,3,4-tetrahydro-4-quinazolinoneNormelanMetozaloneOldren

IUPAC传统名

metolazone (product) metolazone

商标名

MetalozoneDiuloZaroxolynMykroxMicroxOldrenMetenixXuretMetalazone

名称和标识

数据登录号

CAS号

17560-51-9

EC号

241-539-3

PubChem SID

2472453216096386946509058

MDL号

MFCD00069304

PubChem CID

4170

数据登录号

化合物性质

产品相关信息

药理学性质

相关基因信息

human ... SLC12A1(6557)

化合物性质

分子相关蛋白质

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分子图谱

暂无数据

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描述信息

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.

描述信息

参考文献

PubChem文献

数据源提供

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

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

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

参考文献

生物活性

PubChem BioAssay

生物活性

名称和标识

IUPAC标准名

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

别名

IUPAC传统名

metolazone (product) metolazone

商标名

MetalozoneDiuloZaroxolynMykroxMicroxOldrenMetenixXuretMetalazone

数据登录号

CAS号

17560-51-9

EC号

241-539-3

PubChem SID

2472453216096386946509058

MDL号

MFCD00069304

PubChem CID

4170

描述信息

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]