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=CC(=C(Cl)C=C2O)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 1447
renal sodium excretion 4 Target ID: GO:0035812 Sources: http://www.ncbi.nlm.nih.gov/pubmed/15727159	Activator 1447

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: http://www.who.int/selection_medicines/committees/expert/17/application/thiazides.pdf	Primary		Approved 8583	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 8583	DIUREXAN Approved Use To treat edemas.

C_max

Value	Dose	Co-administered	Analyte	Population
3 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6734710/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		XIPAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
690 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6734710/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		XIPAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
943 μg × min/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6734710/	20 mg single, intravenous dose: 20 mg route of administration: Intravenous experiment type: SINGLE co-administered:		XIPAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN

T_1/2

Value	Dose	Co-administered	Analyte	Population
7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/6734710/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		XIPAMIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
10.031 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/22197154/	20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered:		XIPAMIDE urine	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

Doses

Dose	Population	Adverse events
40 mg 1 times / day steady-state, oral Highest studied dose Dose: 40 mg, 1 times / day Route: oral Route: steady-state Dose: 40 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7006620/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7006620/	Other AEs: hypokalaemia, hypercalcaemia... Other AEs: hypokalaemia (1 pt) hypercalcaemia (1 pt) Sources: https://pubmed.ncbi.nlm.nih.gov/7006620/
20 mg 1 times / day steady-state, oral Studied dose Dose: 20 mg, 1 times / day Route: oral Route: steady-state Dose: 20 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/1832291/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: M Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/1832291/	Sources: https://pubmed.ncbi.nlm.nih.gov/1832291/
40 mg 1 times / day steady-state, oral Studied dose Dose: 40 mg, 1 times / day Route: oral Route: steady-state Dose: 40 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/6987114/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/6987114/	Sources: https://pubmed.ncbi.nlm.nih.gov/6987114/

AEs

AE	Significance	Dose	Population
hypercalcaemia	1 pt	40 mg 1 times / day steady-state, oral Highest studied dose Dose: 40 mg, 1 times / day Route: oral Route: steady-state Dose: 40 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7006620/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7006620/
hypokalaemia	1 pt	40 mg 1 times / day steady-state, oral Highest studied dose Dose: 40 mg, 1 times / day Route: oral Route: steady-state Dose: 40 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7006620/	healthy, ADULT Health Status: healthy Age Group: ADULT Sex: unknown Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7006620/

PubMed

Title	Date	PubMed
Spectrophotometric and spectrodensitometric determination of triamterene and xipamide in pure form and in pharmaceutical formulation.	2010-03	20878892
Combined effect of solvent content, temperature and pH on the chromatographic behaviour of ionisable compounds.	2007-09-07	17585924
Trough levels of mycophenolic acid and its glucuronidated metabolite in renal transplant recipients.	2005-08	16119513
Screening procedure for detection of diuretics and uricosurics and/or their metabolites in human urine using gas chromatography-mass spectrometry after extractive methylation.	2005-08	16044110
[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
Experimental design optimization of a capillary zone electrophoresis method for the screening of several diuretics and ACE inhibitors.	2004-02	15023259
Effects of pH and the presence of micelles on the resolution of diuretics by reversed-phase liquid chromatography.	2004-01-02	14753771
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
[Proven in the practice. Follow up of the use confirms high trial value].	2003-12-18	14974328
[What did the ALLHAT study bring? To do the one without foregoing the other].	2003-12-18	14974327
[Thiazide analogs. Also can be used in renal failure].	2003-08-21	14526580
Can xipamide or tacrolimus inhibit the glucuronidation of mycophenolic acid in rat liver slices?	2003-06	12877348
Effect of the location of hydrogen abstraction on the fragmentation of diuretics in negative electrospray ionization mass spectrometry.	2003-06	12781467
Severe electrolyte disturbances and renal failure in elderly patients with combined diuretic therapy including xipamid.	2002-11-30	12528327
Liver carbonic anhydrase and urea synthesis. The effect of diuretics.	1986-10-01	3094538
Ventricular fibrillation induced by xipamide.	1982-05-08	6804002
Hypokalaemia and xipamide.	1982-03-27	6802373
Hypotensive effects of xipamide in essential hypertension. Crossover comparison with hydrochlorothiazide.	1981-07	7021608

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 `Mon Mar 31 17:56:46 GMT 2025` Edited by `admin` on `Mon Mar 31 17:56:46 GMT 2025`
Record UNII	4S9EY0NUEC
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

BE-1293

Preferred Name

English

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

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