U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ARGIMESNA

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

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

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
Unknown

Approved Use

Unknown
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
217.72 mg × h/L
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

PubMed

TitleDatePubMed
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
Patents

Patents

Sample Use Guides

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 Fri Dec 15 15:34:18 GMT 2023
Edited
by admin
on Fri Dec 15 15:34:18 GMT 2023
Record UNII
62V6QH821R
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ARGIMESNA
INN  
INN  
Official Name English
argimesna [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2082
Created by admin on Fri Dec 15 15:34:18 GMT 2023 , Edited by admin on Fri Dec 15 15:34:18 GMT 2023
Code System Code Type Description
CAS
106854-46-0
Created by admin on Fri Dec 15 15:34:18 GMT 2023 , Edited by admin on Fri Dec 15 15:34:18 GMT 2023
PRIMARY
MESH
C059083
Created by admin on Fri Dec 15 15:34:18 GMT 2023 , Edited by admin on Fri Dec 15 15:34:18 GMT 2023
PRIMARY
SMS_ID
300000036862
Created by admin on Fri Dec 15 15:34:18 GMT 2023 , Edited by admin on Fri Dec 15 15:34:18 GMT 2023
PRIMARY
NCI_THESAURUS
C77395
Created by admin on Fri Dec 15 15:34:18 GMT 2023 , Edited by admin on Fri Dec 15 15:34:18 GMT 2023
PRIMARY
FDA UNII
62V6QH821R
Created by admin on Fri Dec 15 15:34:18 GMT 2023 , Edited by admin on Fri Dec 15 15:34:18 GMT 2023
PRIMARY
PUBCHEM
65897
Created by admin on Fri Dec 15 15:34:18 GMT 2023 , Edited by admin on Fri Dec 15 15:34:18 GMT 2023
PRIMARY
EPA CompTox
DTXSID60910136
Created by admin on Fri Dec 15 15:34:18 GMT 2023 , Edited by admin on Fri Dec 15 15:34:18 GMT 2023
PRIMARY
INN
6336
Created by admin on Fri Dec 15 15:34:18 GMT 2023 , Edited by admin on Fri Dec 15 15:34:18 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
PARENT -> SALT/SOLVATE