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Details

Stereochemistry ACHIRAL
Molecular Formula C4H8O6S4.2Na
Molecular Weight 326.342
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIMESNA

SMILES

[Na+].[Na+].[O-]S(=O)(=O)CCSSCCS([O-])(=O)=O

InChI

InChIKey=KQYGMURBTJPBPQ-UHFFFAOYSA-L
InChI=1S/C4H10O6S4.2Na/c5-13(6,7)3-1-11-12-2-4-14(8,9)10;;/h1-4H2,(H,5,6,7)(H,8,9,10);;/q;2*+1/p-2

HIDE SMILES / InChI

Molecular Formula C4H8O6S4
Molecular Weight 280.363
Charge -2
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
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
Vibrational spectroscopic studies of mesna and dimesna.
2003 Jun
The effect of cytoprotective agents in platinum anticancer therapy.
2004
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
One-step refolding and purification of disulfide-containing proteins with a C-terminal MESNA thioester.
2008 Oct 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 Fri Dec 15 15:26:51 GMT 2023
Edited
by admin
on Fri Dec 15 15:26:51 GMT 2023
Record UNII
230R951Y4D
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIMESNA
INN   MART.   MI  
INN   USAN  
Official Name English
dimesna [INN]
Common Name English
Disodium 2,2′-dithiodiethanesulfonate
Systematic Name English
DIMESNA [MI]
Common Name English
TAVOCEPT
Brand Name English
Ethanesulfonic acid, 2,2′-dithiobis-, sodium salt (1:2)
Systematic Name English
NSC-760345
Code English
NSC-716976
Code English
BNP-7787
Code English
DISODIUM 2,2'-DITHIODIETHANESULPHONATE
Systematic Name English
DIMESNA [MART.]
Common Name English
BNP7787
Code English
Dimesna [WHO-DD]
Common Name English
DIMESNA [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2082
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
Code System Code Type Description
EVMPD
SUB07166MIG
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
FDA UNII
230R951Y4D
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
NSC
716976
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
CAS
16208-51-8
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
ChEMBL
CHEMBL2009034
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
SMS_ID
100000082639
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
USAN
NN-30
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
MESH
C027032
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
NSC
760345
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
MERCK INDEX
m4503
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY Merck Index
NCI_THESAURUS
C1365
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
ECHA (EC/EINECS)
240-337-2
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
INN
4888
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
EPA CompTox
DTXSID6066024
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
PUBCHEM
65625
Created by admin on Fri Dec 15 15:26:51 GMT 2023 , Edited by admin on Fri Dec 15 15:26:51 GMT 2023
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE