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
PubMed
| Title | Date | PubMed |
|---|---|---|
| [Prevention of urotoxic actions of cyclophosphamide and ifosfamide by dimesna (preliminary communication) (author's transl)]. | 1982 |
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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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| 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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| 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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| 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 |
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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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| 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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| Possible (enzymatic) routes and biological sites for metabolic reduction of BNP7787, a new protector against cisplatin-induced side-effects. | 2004 Aug 1 |
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| Phase I and pharmacokinetic study of the novel chemoprotector BNP7787 in combination with cisplatin and attempt to eliminate the hydration schedule. | 2005 May 9 |
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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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| 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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| Efficient, chemoselective synthesis of immunomicelles using single-domain antibodies with a C-terminal thioester. | 2009 Jul 20 |
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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
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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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