XIPAMIDE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H15ClN2O4S
Molecular Weight	354.809
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CC=CC(C)=C1NC(=O)C2=C(O)C=C(Cl)C(=C2)S(N)(=O)=O

InChI

InChIKey=MTZBBNMLMNBNJL-UHFFFAOYSA-N

InChI=1S/C15H15ClN2O4S/c1-8-4-3-5-9(2)14(8)18-15(20)10-6-13(23(17,21)22)11(16)7-12(10)19/h3-7,19H,1-2H3,(H,18,20)(H2,17,21,22)

HIDE SMILES / InChI

Molecular Formula	C15H15ClN2O4S
Molecular Weight	354.809
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.sciencedirect.com/science/article/pii/S1658365513000903

Xipamide is a diuretic of thiazide class. It is used for the treatment of hypertension and edema. The diuretic effect of the drug is due to reduction of sodium reabsorption and increase in potassium excretion.

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
renal potassium excretion 1 Target ID: GO:0036359 Sources: http://www.ncbi.nlm.nih.gov/pubmed/15727159	Activator 1430
renal sodium excretion 4 Target ID: GO:0035812 Sources: http://www.ncbi.nlm.nih.gov/pubmed/15727159	Activator 1430

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 567 Sources: http://www.who.int/selection_medicines/committees/expert/17/application/thiazides.pdf	Primary		Approved 8429	DIUREXAN Approved Use For the treatment of hypertension, either alone or as an adjunct to treatment with anti-hypertensive drugs.
Oedema 7 Sources: http://www.who.int/selection_medicines/committees/expert/17/application/thiazides.pdf	Primary		Approved 8429	DIUREXAN Approved Use To treat edemas.

PubMed

Title	Date	PubMed
Hypotensive effects of xipamide in essential hypertension. Crossover comparison with hydrochlorothiazide.	1981 Jul	7021608
Hypokalaemia and xipamide.	1982 Mar 27	6802373
Ventricular fibrillation induced by xipamide.	1982 May 8	6804002
Liver carbonic anhydrase and urea synthesis. The effect of diuretics.	1986 Oct 1	3094538
Severe electrolyte disturbances and renal failure in elderly patients with combined diuretic therapy including xipamid.	2002 Nov 30	12528327
[Thiazide analogs. Also can be used in renal failure].	2003 Aug 21	14526580
[Proven in the practice. Follow up of the use confirms high trial value].	2003 Dec 18	14974328
[What did the ALLHAT study bring? To do the one without foregoing the other].	2003 Dec 18	14974327
Can xipamide or tacrolimus inhibit the glucuronidation of mycophenolic acid in rat liver slices?	2003 Jun	12877348
Effect of the location of hydrogen abstraction on the fragmentation of diuretics in negative electrospray ionization mass spectrometry.	2003 Jun	12781467
Determination of Xipamide metabolite in human urine by high-performance liquid chromatography/diode-array detection, high-performance liquid chromatography/electrospray ionization mass spectrometry and gas chromatography/mass spectrometry.	2004	15384135
Experimental design optimization of a capillary zone electrophoresis method for the screening of several diuretics and ACE inhibitors.	2004 Feb	15023259
Effects of pH and the presence of micelles on the resolution of diuretics by reversed-phase liquid chromatography.	2004 Jan 2	14753771
[Mechanism of action of xipamide and its classification as a "low ceiling diuretic". Pharmacodynamic-pharmacokinetic studies in healthy volunteers and in kidney and liver patients].	2005	15727159
Trough levels of mycophenolic acid and its glucuronidated metabolite in renal transplant recipients.	2005 Aug	16119513
Screening procedure for detection of diuretics and uricosurics and/or their metabolites in human urine using gas chromatography-mass spectrometry after extractive methylation.	2005 Aug	16044110
Combined effect of solvent content, temperature and pH on the chromatographic behaviour of ionisable compounds.	2007 Sep 7	17585924
Spectrophotometric and spectrodensitometric determination of triamterene and xipamide in pure form and in pharmaceutical formulation.	2010 Mar	20878892

Patents

Sample Use Guides

In Vivo Use Guide

Oedema, initially 40 mg daily by mouth, subsequently reduced to 20 mg daily according to response. Hypertension, 20 mg daily as a single morning dose, either alone or with other antihypertensives.

Route of Administration: Oral

In Vitro Use Guide

The in vitro effects of xipamide in a concentration range of 10(-8) to 10(-2) M were investigated on various Na+ and K+ transport systems in human red blood cells. Xipamide inhibited the anion carrier or DIDS-sensitive LiCO3- -influx starting from a concentration of 10(-5) M.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:24:37 GMT 2023` Edited by `admin` on `Fri Dec 15 15:24:37 GMT 2023`
Record UNII	4S9EY0NUEC
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

XIPAMIDE

Official Name

English

MJF-10938

Code

English

BENZAMIDE, 5-(AMINOSULFONYL)-4-CHLORO-N-(2,6-DIMETHYLPHENYL)-2-HYDROXY-

Systematic Name

English

XIPAMIDE [MART.]

Common Name

English

BE-1293

Code

English

xipamide [INN]

Common Name

English

Xipamide [WHO-DD]

Common Name

English

XIPAMIDE [USAN]

Common Name

English

MJF 10,938

Code

English

4-CHLORO-5-SULFAMOYL-2',6'-SALICYLOXYLIDIDE

Systematic Name

English

XIPAMIDE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C448