DIMESNA

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7524598 | Elks, J. (2014) The Dictionary of Drugs: Chemical Data, page 461, retrieved from: https://books.google.ru/books?id=0vXTBwAAQBAJ | Aronson, J.K. (2015) Meyler's Side Effects of Drugs, page 854, retrieved from: https://books.google.ru/books?id=NOKoBAAAQBAJ

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

Primary Target	Pharmacology	Condition	Potency
microtubule polymerization 20 Target ID: GO:0046785 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20807779	Inhibitor 8297

PubMed

Title	Date	PubMed
[Prevention of urotoxic actions of cyclophosphamide and ifosfamide by dimesna (preliminary communication) (author's transl)].	1982	6809014
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	6401591
Prevention of cyclophosphamide-induced carcinogenesis in the urinary bladder of rats by administration of mesna.	1983 Sep	6414697
BNP7787, a novel protector against platinum-related toxicities, does not affect the efficacy of cisplatin or carboplatin in human tumour xenografts.	2002 May	12008205
Pharmacokinetics and preliminary clinical data of the novel chemoprotectant BNP7787 and cisplatin and their metabolites.	2003 Aug	12891226
Pharmacokinetics of BNP7787 and its metabolite mesna in plasma and ascites: a case report.	2003 Jun	12750838
Vibrational spectroscopic studies of mesna and dimesna.	2003 Jun	12736065
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	12715205
Simultaneous determination of BNP7787 and its metabolite mesna in plasma and tissue by micro-HPLC with a dual electrochemical detector.	2003 May	12712424
Modulation of plasma thiols and mixed disulfides by BNP7787 in patients receiving paclitaxel/cisplatin therapy.	2003 May	12682786
The effect of cytoprotective agents in platinum anticancer therapy.	2004	15206103
Possible (enzymatic) routes and biological sites for metabolic reduction of BNP7787, a new protector against cisplatin-induced side-effects.	2004 Aug 1	15242815
Phase I and pharmacokinetic study of the novel chemoprotector BNP7787 in combination with cisplatin and attempt to eliminate the hydration schedule.	2005 May 9	15841080
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	18827613
One-step refolding and purification of disulfide-containing proteins with a C-terminal MESNA thioester.	2008 Oct 1	18828922
Analysis of BNP7787 thiol-disulfide exchange reactions in phosphate buffer and human plasma using microscale electrochemical high performance liquid chromatography.	2009 Apr 1	19278906
Efficient, chemoselective synthesis of immunomicelles using single-domain antibodies with a C-terminal thioester.	2009 Jul 20	19619333
Mechanistic study of BNP7787-mediated cisplatin nephroprotection: modulation of gamma-glutamyl transpeptidase.	2010 Apr	19714332

Patents

Name

Type

Language

DIMESNA

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