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
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
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 |
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Target ID: GO:0046785 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20807779 |
PubMed
Title | Date | PubMed |
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Prevention of cyclophosphamide-induced carcinogenesis in the urinary bladder of rats by administration of mesna. | 1983 Sep |
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BNP7787, a novel protector against platinum-related toxicities, does not affect the efficacy of cisplatin or carboplatin in human tumour xenografts. | 2002 May |
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Pharmacokinetics and preliminary clinical data of the novel chemoprotectant BNP7787 and cisplatin and their metabolites. | 2003 Aug |
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Vibrational spectroscopic studies of mesna and dimesna. | 2003 Jun |
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Simultaneous determination of BNP7787 and its metabolite mesna in plasma and tissue by micro-HPLC with a dual electrochemical detector. | 2003 May |
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Modulation of plasma thiols and mixed disulfides by BNP7787 in patients receiving paclitaxel/cisplatin therapy. | 2003 May |
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Pharmacokinetic behaviour of the chemoprotectants BNP7787 and mesna after an i.v. bolus injection in rats. | 2004 Apr 19 |
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One-step refolding and purification of disulfide-containing proteins with a C-terminal MESNA thioester. | 2008 Oct 1 |
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Analysis of BNP7787 thiol-disulfide exchange reactions in phosphate buffer and human plasma using microscale electrochemical high performance liquid chromatography. | 2009 Apr 1 |
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Mechanistic study of BNP7787-mediated cisplatin nephroprotection: modulation of gamma-glutamyl transpeptidase. | 2010 Apr |
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C2082
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PARENT (SALT/SOLVATE)
SUBSTANCE RECORD