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Details

Stereochemistry ACHIRAL
Molecular Formula C4H10O6S4
Molecular Weight 282.379
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 2,2'-DITHIODIETHANESULFONIC ACID

SMILES

OS(=O)(=O)CCSSCCS(O)(=O)=O

InChI

InChIKey=BYUKOOOZTSTOOH-UHFFFAOYSA-N
InChI=1S/C4H10O6S4/c5-13(6,7)3-1-11-12-2-4-14(8,9)10/h1-4H2,(H,5,6,7)(H,8,9,10)

HIDE SMILES / InChI
Dimesna is a prodrug of mesna (dimer of mesna). Dimesna is reduced to mesna in the kidneys. Dimesna does not prevent cellular damage by metabolites of ifosfamide and cyclophosphamide in the renal tubular cell line LLC-PK1. Dimesna is a mucolytic agent used to alleviate toxic side effects of antitumor drugs. The organic acid transporter OAT4 on the luminal side of the proximal renal tubule facilitates the reabsorption of dimesna, and therefore its reduction to mesna, whereas the multidrug and toxin extrusion protein MATE1, the multidrug resistance protein MRP2, and P glycoprotein facilitate the efflux of mesna and/or dimesna back into the lumen; dimesna may also be excreted unchanged by MRP4. It has therefore been suggested that polymorphism of these renal transport proteins or transporter-mediated drug-drug interactions may reduce the efficacy of mesna and dimesna.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Prevention of cyclophosphamide-induced carcinogenesis in the urinary bladder of rats by administration of mesna.
1983 Sep
Pharmacokinetics and preliminary clinical data of the novel chemoprotectant BNP7787 and cisplatin and their metabolites.
2003 Aug
Pharmacokinetics of BNP7787 and its metabolite mesna in plasma and ascites: a case report.
2003 Jun
Vibrational spectroscopic studies of mesna and dimesna.
2003 Jun
Possible (enzymatic) routes and biological sites for metabolic reduction of BNP7787, a new protector against cisplatin-induced side-effects.
2004 Aug 1
Patents

Patents

Name Type Language
MESNA RELATED COMPOUND B
USP-RS  
Preferred Name English
2,2'-DITHIODIETHANESULFONIC ACID
Systematic Name English
MESNA IMPURITY D [EP IMPURITY]
Common Name English
DIMESNA FREE ACID
Common Name English
BIS(2-SULFOETHYL)DISULFIDE
Systematic Name English
MESNA RELATED COMPOUND B [USP IMPURITY]
Common Name English
ETHANESULFONIC ACID, 2,2'-DITHIOBIS-
Systematic Name English
MESNA RELATED COMPOUND B [USP-RS]
Common Name English
.OMEGA.,.OMEGA.'-ETHANEDISULFIDEDISULFONIC ACID
Common Name English
Code System Code Type Description
FDA UNII
6Q2L2H0POF
Created by admin on Mon Mar 31 23:04:41 GMT 2025 , Edited by admin on Mon Mar 31 23:04:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID40196395
Created by admin on Mon Mar 31 23:04:41 GMT 2025 , Edited by admin on Mon Mar 31 23:04:41 GMT 2025
PRIMARY
PUBCHEM
65626
Created by admin on Mon Mar 31 23:04:41 GMT 2025 , Edited by admin on Mon Mar 31 23:04:41 GMT 2025
PRIMARY
RS_ITEM_NUM
1392829
Created by admin on Mon Mar 31 23:04:41 GMT 2025 , Edited by admin on Mon Mar 31 23:04:41 GMT 2025
PRIMARY
CAS
45127-11-5
Created by admin on Mon Mar 31 23:04:41 GMT 2025 , Edited by admin on Mon Mar 31 23:04:41 GMT 2025
PRIMARY