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
PubMed
| Title | Date | PubMed |
|---|---|---|
| BNP7787-mediated modulation of paclitaxel- and cisplatin-induced aberrant microtubule protein polymerization in vitro. | 2010-09 |
|
| Mechanistic study of BNP7787-mediated cisplatin nephroprotection: modulation of gamma-glutamyl transpeptidase. | 2010-04 |
|
| Efficient, chemoselective synthesis of immunomicelles using single-domain antibodies with a C-terminal thioester. | 2009-07-20 |
|
| Analysis of BNP7787 thiol-disulfide exchange reactions in phosphate buffer and human plasma using microscale electrochemical high performance liquid chromatography. | 2009-04-01 |
|
| One-step refolding and purification of disulfide-containing proteins with a C-terminal MESNA thioester. | 2008-10-01 |
|
| 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). | 2008-10 |
|
| Phase I and pharmacokinetic study of the novel chemoprotector BNP7787 in combination with cisplatin and attempt to eliminate the hydration schedule. | 2005-05-09 |
|
| Possible (enzymatic) routes and biological sites for metabolic reduction of BNP7787, a new protector against cisplatin-induced side-effects. | 2004-08-01 |
|
| Pharmacokinetic behaviour of the chemoprotectants BNP7787 and mesna after an i.v. bolus injection in rats. | 2004-04-19 |
|
| The effect of cytoprotective agents in platinum anticancer therapy. | 2004 |
|
| Pharmacokinetics and preliminary clinical data of the novel chemoprotectant BNP7787 and cisplatin and their metabolites. | 2003-08 |
|
| Pharmacokinetics of BNP7787 and its metabolite mesna in plasma and ascites: a case report. | 2003-06 |
|
| Vibrational spectroscopic studies of mesna and dimesna. | 2003-06 |
|
| 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. | 2003-06 |
|
| Simultaneous determination of BNP7787 and its metabolite mesna in plasma and tissue by micro-HPLC with a dual electrochemical detector. | 2003-05 |
|
| Modulation of plasma thiols and mixed disulfides by BNP7787 in patients receiving paclitaxel/cisplatin therapy. | 2003-05 |
|
| BNP7787, a novel protector against platinum-related toxicities, does not affect the efficacy of cisplatin or carboplatin in human tumour xenografts. | 2002-05 |
|
| Prevention of cyclophosphamide-induced carcinogenesis in the urinary bladder of rats by administration of mesna. | 1983-09 |
|
| 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). | 1983-02-15 |
|
| [Prevention of urotoxic actions of cyclophosphamide and ifosfamide by dimesna (preliminary communication) (author's transl)]. | 1982 |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 23:04:41 GMT 2025
by
admin
on
Mon Mar 31 23:04:41 GMT 2025
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| Record UNII |
6Q2L2H0POF
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| Record Status |
Validated (UNII)
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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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CHROMATOGRAPHIC PURITY (HPLC/UV)
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PARENT -> IMPURITY |
CHROMATOGRAPHIC PURITY (HPLC/UV)
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