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

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
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
Analysis of BNP7787 thiol-disulfide exchange reactions in phosphate buffer and human plasma using microscale electrochemical high performance liquid chromatography.
2009 Apr 1
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

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