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
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)
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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Pharmacokinetics and preliminary clinical data of the novel chemoprotectant BNP7787 and cisplatin and their metabolites. | 2003 Aug |
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Pharmacokinetics of BNP7787 and its metabolite mesna in plasma and ascites: a case report. | 2003 Jun |
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Vibrational spectroscopic studies of mesna and dimesna. | 2003 Jun |
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Possible (enzymatic) routes and biological sites for metabolic reduction of BNP7787, a new protector against cisplatin-induced side-effects. | 2004 Aug 1 |
Patents
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6Q2L2H0POF
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DTXSID40196395
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65626
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45127-11-5
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PARENT (METABOLITE INACTIVE)
SALT/SOLVATE (PARENT)
SUBSTANCE RECORD