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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

Molecular Formula C4H10O6S4
Molecular Weight 282.379
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

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 urotoxic actions of cyclophosphamide and ifosfamide by dimesna (preliminary communication) (author's transl)].
1982
Prevention of urinary bladder tumors in cyclophosphamide-treated rats by additional medication with the uroprotectors sodium 2-mercaptoethane sulfonate (mesna) and disodium 2,2'-dithio-bis-ethane sulfonate (dimesna).
1983 Feb 15
Prevention of cyclophosphamide-induced carcinogenesis in the urinary bladder of rats by administration of mesna.
1983 Sep
BNP7787, a novel protector against platinum-related toxicities, does not affect the efficacy of cisplatin or carboplatin in human tumour xenografts.
2002 May
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
The chemical reactivity of BNP7787 and its metabolite mesna with the cytostatic agent cisplatin: comparison with the nucleophiles thiosulfate, DDTC, glutathione and its disulfide GSSG.
2003 Jun
Simultaneous determination of BNP7787 and its metabolite mesna in plasma and tissue by micro-HPLC with a dual electrochemical detector.
2003 May
Modulation of plasma thiols and mixed disulfides by BNP7787 in patients receiving paclitaxel/cisplatin therapy.
2003 May
The effect of cytoprotective agents in platinum anticancer therapy.
2004
Pharmacokinetic behaviour of the chemoprotectants BNP7787 and mesna after an i.v. bolus injection in rats.
2004 Apr 19
Possible (enzymatic) routes and biological sites for metabolic reduction of BNP7787, a new protector against cisplatin-induced side-effects.
2004 Aug 1
Phase I and pharmacokinetic study of the novel chemoprotector BNP7787 in combination with cisplatin and attempt to eliminate the hydration schedule.
2005 May 9
Phase II randomized study of dose-dense docetaxel and cisplatin every 2 weeks with pegfilgrastim and darbepoetin alfa with and without the chemoprotector BNP7787 in patients with advanced non-small cell lung cancer (CALGB 30303).
2008 Oct
One-step refolding and purification of disulfide-containing proteins with a C-terminal MESNA thioester.
2008 Oct 1
Analysis of BNP7787 thiol-disulfide exchange reactions in phosphate buffer and human plasma using microscale electrochemical high performance liquid chromatography.
2009 Apr 1
Efficient, chemoselective synthesis of immunomicelles using single-domain antibodies with a C-terminal thioester.
2009 Jul 20
Mechanistic study of BNP7787-mediated cisplatin nephroprotection: modulation of gamma-glutamyl transpeptidase.
2010 Apr
BNP7787-mediated modulation of paclitaxel- and cisplatin-induced aberrant microtubule protein polymerization in vitro.
2010 Sep
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Dec 16 10:08:41 GMT 2023
Edited
by admin
on Sat Dec 16 10:08:41 GMT 2023
Record UNII
6Q2L2H0POF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
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
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 Sat Dec 16 10:08:41 GMT 2023 , Edited by admin on Sat Dec 16 10:08:41 GMT 2023
PRIMARY
EPA CompTox
DTXSID40196395
Created by admin on Sat Dec 16 10:08:41 GMT 2023 , Edited by admin on Sat Dec 16 10:08:41 GMT 2023
PRIMARY
PUBCHEM
65626
Created by admin on Sat Dec 16 10:08:41 GMT 2023 , Edited by admin on Sat Dec 16 10:08:41 GMT 2023
PRIMARY
RS_ITEM_NUM
1392829
Created by admin on Sat Dec 16 10:08:41 GMT 2023 , Edited by admin on Sat Dec 16 10:08:41 GMT 2023
PRIMARY
CAS
45127-11-5
Created by admin on Sat Dec 16 10:08:41 GMT 2023 , Edited by admin on Sat Dec 16 10:08:41 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE INACTIVE
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP