ARGIMESNA

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C6H14N4O2.C2H6O3S2
Molecular Weight	316.398
Optical Activity	UNSPECIFIED
Defined Stereocenters	1 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS(=O)(=O)CCS.N[C@@H](CCCNC(N)=N)C(O)=O

InChI

InChIKey=MZDDDSNBRVMDIH-WCCKRBBISA-N

InChI=1S/C6H14N4O2.C2H6O3S2/c7-4(5(11)12)2-1-3-10-6(8)9;3-7(4,5)2-1-6/h4H,1-3,7H2,(H,11,12)(H4,8,9,10);6H,1-2H2,(H,3,4,5)/t4-;/m0./s1

HIDE SMILES / InChI

Molecular Formula	C6H14N4O2
Molecular Weight	174.201
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	1 / 1
E/Z Centers	0
Optical Activity	UNSPECIFIED

Molecular Formula	C2H6O3S2
Molecular Weight	142.197
Charge	0
Count

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1622852

Argimesna (also known as arginine 2-mercaptoethanesulfonate) is a sulfhydryl group-containing molecule, which has no effect on glutathione status or on the total thiol pool, but is an uroprotective agent. Argimesna was investigated for the prevention of haemorrhagic cystitis from ifosfamide (IFO), but these studies were discontinued

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Hemorragic cystitis 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/1622852	Secondary		Phase II 1144	Unknown Approved Use Unknown

AUC

Value	Dose	Co-administered	Analyte	Population
217.72 mg × h/L EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/1508821/	920 mg single, oral dose: 920 mg route of administration: Oral experiment type: SINGLE co-administered:		MESNA plasma	Homo sapiens population: HEALTHY age: ADULT sex: MALE food status: UNKNOWN

PubMed

Title	Date	PubMed
Arginine 2-mercaptoethane sulfonate and sodium 2-mercaptoethane sulfonate: a comparative study of their effects upon tumour cells.	1988	3149236
Serum concentrations of sodium 2-mercaptoethanesulfonate (MESNA) and its metabolite, disulfide form (DIMESNA), in volunteers after oral dosing: a comparison between MESNA and ARGIMESNA.	1992 Feb-Mar	1508821

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Oral

In Vitro Use Guide

It was evaluated the effectiveness of L-arginine mono(2-mercaptoethanesulfonate) (argimesna) to limit the extent of myocardial damage resulting from 60 minutes of severe ischemia followed by 30 minutes of reperfusion in the Langendorff-perfused rabbit heart. The effects of 10(-6) M argimesna were compared with those of 10(-6) M L-arginine and of 10(-6) M sodium salt of 2-mercaptoethanesulfonate (mesna). Pretreatment of the hearts with 10(-6) M argimesna resulted in marked myocardial protection, measured in terms of improved recovery of developed pressure (p less than 0.01), reduced release of creatine kinase (p less than 0.01), maintenance of mitochondrial function and increased stores of ATP on reperfusion (p less than 0.01).

Substance Class	Chemical Created by `admin` on `Wed Jul 05 23:03:39 UTC 2023` Edited by `admin` on `Wed Jul 05 23:03:39 UTC 2023`
Record UNII	62V6QH821R
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ARGIMESNA

Official Name

English

argimesna [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C2082