STILBAMIDINE ISETHIONATE

US Previously Marketed

First approved in 1953

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H16N4.2C2H6O4S
Molecular Weight	516.588
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OCCS(O)(=O)=O.OCCS(O)(=O)=O.NC(=N)C1=CC=C(C=C1)\C=C\C2=CC=C(C=C2)C(N)=N

InChI

InChIKey=DXBSRDIXJYTKNV-SEPHDYHBSA-N

InChI=1S/C16H16N4.2C2H6O4S/c17-15(18)13-7-3-11(4-8-13)1-2-12-5-9-14(10-6-12)16(19)20;2*3-1-2-7(4,5)6/h1-10H,(H3,17,18)(H3,19,20);2*3H,1-2H2,(H,4,5,6)/b2-1+;;

HIDE SMILES / InChI

Molecular Formula	C2H6O4S
Molecular Weight	126.132
Charge	0
Count

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

Molecular Formula	C16H16N4
Molecular Weight	264.325
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	1
Optical Activity	NONE

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13096366 | https://www.ncbi.nlm.nih.gov/pubmed/13263964 | https://www.ncbi.nlm.nih.gov/pubmed/29012015

Stilbamidine Isethionate is a salt of Stilbenedicarboxamidine and Hydroxyethanesulfonic acid produced by The Wm. S. Merrell Company and was tested clinically for the treatment of tropical trypano- somiasis and leishmaniasis. It was also reportedly used for tic douloureux. This drug was replaced by Hydroxystilbamidinr isethionate ampuls (Merrell) because this derivative is less toxic and is equally effective in the treatment of the systemic fungus infections, blastomycosis, leishmaniasis, and Indian kala-azar

Originator

Approval Year

C_max

Value	Dose	Co-administered	Analyte	Population
40 μg/mL EXPERIMENT http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.941.923&rep=rep1&type=pdf	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:		STILBAMIDINE serum	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
15 μg × h/mL EXPERIMENT http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.941.923&rep=rep1&type=pdf	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:		STILBAMIDINE serum	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
45 min EXPERIMENT http://citeseerx.ist.psu.edu/viewdoc/download?doi=10.1.1.941.923&rep=rep1&type=pdf	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:		STILBAMIDINE serum	Mus musculus population: HEALTHY age: ADULT sex: UNKNOWN food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
ABI Chem	AC1O5FPF
NovoSeek	6433163
PubChem	6433163	https://pubchem.ncbi.nlm.nih.gov/compound/6433163

PubMed

Title	Date	PubMed
The Effect of Quinine and Stilbamidine (M&B 744) on the Reticulo-Endothelial System as Measured by the Congo-Red Index.	1944-03	29012015

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:16:23 GMT 2025` Edited by `admin` on `Mon Mar 31 18:16:23 GMT 2025`
Record UNII	Y56ICS757E
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

STILBAMIDINE ISETIONATE

Preferred Name

English

STILBAMIDINE ISETHIONATE

Systematic Name

English

Stilbamidine isetionate [WHO-DD]

Common Name

English

NSC-41802

Code

English

4,4'-STILBENEDICARBOXAMIDINE BIS(2-HYDROXYETHANESULPHONATE)

Systematic Name

English

stilbamidine isetionate [INN]

Common Name

English

4,4'-STILBENEDICARBOXAMIDINE BIS(2-HYDROXYETHANESULFONATE)

Systematic Name

English

STILBAMIDINE ISETHIONATE [MI]

Common Name

English

Code System Code Type Description

CAS

140-59-0