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)
Molecular Formula | C4H10O6S4 |
Molecular Weight | 282.379 |
Charge | 0 |
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
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 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 |
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Vibrational spectroscopic studies of mesna and dimesna. | 2003 Jun |
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The effect of cytoprotective agents in platinum anticancer therapy. | 2004 |
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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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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 |
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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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Mechanistic study of BNP7787-mediated cisplatin nephroprotection: modulation of gamma-glutamyl transpeptidase. | 2010 Apr |
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BNP7787-mediated modulation of paclitaxel- and cisplatin-induced aberrant microtubule protein polymerization in vitro. | 2010 Sep |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:08:41 UTC 2023
by
admin
on
Sat Dec 16 10:08:41 UTC 2023
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Record UNII |
6Q2L2H0POF
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Record Status |
Validated (UNII)
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Record Version |
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6Q2L2H0POF
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DTXSID40196395
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65626
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1392829
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45127-11-5
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PARENT -> METABOLITE INACTIVE |
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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