MEFRUSIDE

Possibly Marketed Outside US

Details

Stereochemistry	RACEMIC
Molecular Formula	C13H19ClN2O5S2
Molecular Weight	382.883
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CN(CC1(C)CCCO1)S(=O)(=O)C2=CC=C(Cl)C(=C2)S(N)(=O)=O

InChI

InChIKey=SMNOERSLNYGGOU-UHFFFAOYSA-N

InChI=1S/C13H19ClN2O5S2/c1-13(6-3-7-21-13)9-16(2)23(19,20)10-4-5-11(14)12(8-10)22(15,17)18/h4-5,8H,3,6-7,9H2,1-2H3,(H2,15,17,18)

HIDE SMILES / InChI

Molecular Formula	C13H19ClN2O5S2
Molecular Weight	382.883
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: http://druginfosys.com/Drug.aspx?drugCode=445&drugName=&type=1
Curator's Comment: Description was created based on several sources, including http://www.ncbi.nlm.nih.gov/pubmed/7371701 and https://www.ncbi.nlm.nih.gov/pubmed/4779251

Mefruside is a benzene disulfonamide derivative related to the benzothiadiazine or thiazide diuretics. Mefruside is adminisered orally, it is indicated for the treatment of edema and hypertension. It was developed by Bayer A.G. and is sold under the tradename Baycaron.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Urea synthesis 1 Target ID: Urea synthesis Sources: http://www.ncbi.nlm.nih.gov/pubmed/3094538	Inhibitor 8504
Carbonic anhydrase 6 Target ID: CHEMBL2095180 Sources: http://www.ncbi.nlm.nih.gov/pubmed/5459063	Inhibitor 8504		0.73 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hypertension 575 Sources: http://druginfosys.com/Drug.aspx?drugCode=445&drugName=&type=1	Primary		Approved 8583	Baycaron Approved Use Mefruside is primarily indicated in conditions like Edema, Hypertension, Oedema.

C_max

Value	Dose	Co-administered	Analyte	Population
861 ng/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/530169_2135001F1136_1_009_1F.pdf#page=15	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		MEFRUSIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
5929 ng × h/mL OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/530169_2135001F1136_1_009_1F.pdf#page=15	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		MEFRUSIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.85 h OTHER GOV'T https://www.info.pmda.go.jp/go/interview/1/530169_2135001F1136_1_009_1F.pdf#page=15	25 mg single, oral dose: 25 mg route of administration: Oral experiment type: SINGLE co-administered:		MEFRUSIDE plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: FASTED

Doses

Dose	Population	Adverse events
25 mg 1 times / day multiple, oral Recommended Dose: 25 mg, 1 times / day Route: oral Route: multiple Dose: 25 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/5135250/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/5135250/	Sources: https://pubmed.ncbi.nlm.nih.gov/5135250/
50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=33877	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=33877	Disc. AE: Hyponatremia, Hypokalemia... AEs leading to discontinuation/dose reduction: Hyponatremia Hypokalemia Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=33877

AEs

AE	Significance	Dose	Population
Hypokalemia	Disc. AE	50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=33877	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=33877
Hyponatremia	Disc. AE	50 mg 1 times / day multiple, oral Recommended Dose: 50 mg, 1 times / day Route: oral Route: multiple Dose: 50 mg, 1 times / day Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=33877	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://www.rad-ar.or.jp/siori/english/kekka.cgi?n=33877

PubMed

Title	Date	PubMed
Development of a list of potentially inappropriate drugs for the korean elderly using the delphi method.	2010-12	21818443
A novel study of screening and confirmation of modafinil, adrafinil and their metabolite modafinilic acid under EI-GC-MS and ESI-LC-MS-MS ionization.	2009-12	20407560
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
Transport of anionic drugs across the basolateral membrane of proximal S2 segments of the rabbit kidney. Inverse relationship between the affinity to the p-aminohippurate transport system and the transport rate.	2002	12572530

Patents

Sample Use Guides

In Vivo Use Guide

Oral Oedema Adult: 25-50 mg daily, increase if necessary to 75-100 mg. For long-term therapy: 25-50 mg every 2nd or 3rd day. Oral Hypertension Adult: 25-50 mg daily alone or in combination with other antihypertensives, alternate-day maintenance dosage may be used.

Route of Administration: Oral

In Vitro Use Guide

Mefruside (0.3 mM) resulted in 34% Inhibition of urea synthesis from NH4Cl by isolated perfused rat liver

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:33:58 GMT 2025` Edited by `admin` on `Mon Mar 31 18:33:58 GMT 2025`
Record UNII	X1NS9SNS92
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

MEFRUSIDE

Official Name

English

BAYCARON

Preferred Name

English

4-CHLORO-N(SUP 1)-METHYL-N(SUP 1)-(TETRAHYDRO-2-METHYLFURFURYL)-M-BENZENEDISULFONAMIDE

Common Name

English

MEFRUSIDE [MART.]

Common Name

English

MEFRUSIDE [USAN]

Common Name

English

MEFRUSIDE [MI]

Common Name

English

MEFRUSIDE [JAN]

Common Name

English

mefruside [INN]

Common Name

English

Mefruside [WHO-DD]

Common Name

English

BAY 1500

Code

English

1,3-BENZENEDISULFONAMIDE, 4-CHLORO-N(SUP 1)-METHYL-N(SUP 1)-((TETRAHYDRO-2-METHYL-2-FURANYL)METHYL)-

Common Name

English

BAY-1500

Code

English

Classification Tree Code System Code

WHO-VATC

QC03BB05