Dimesna

• CAT Number: I002083
• CAS Number: 16208-51-8
• Molecular Formula: C4H8Na2O6S4
• Molecular Weight: 326.34
• Purity: ≥95%
• Synonyms: mesna disulfide. US brand name: Tavocept. Abbreviation: DIM. Code name: BNP7787. Chemical structure name: 22dithiobisethanesulfonate disodium salt
• Solubility: 10 mM in DMSO
• Storage: <label class=
• InChI: 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
• InChIKey: KQYGMURBTJPBPQ-UHFFFAOYSA-L
• SMILES: O=S(CCSSCCS(=O)([O-])=O)([O-])=O.[Na+].[Na+]

Dimesna(CAT: I002083), also known as mesna, is a synthetic compound that is used as a protective agent against the toxic effects of certain chemotherapy drugs, particularly cyclophosphamide, and ifosfamide. These drugs can cause bladder toxicity by producing a reactive metabolite, acrolein, that damages the lining of the bladder. Dimesna works by binding to and detoxifying acrolein, thereby reducing the risk of bladder toxicity. Dimesna is usually administered intravenously before and after chemotherapy treatment, and it has been shown to be effective in preventing bladder toxicity in clinical studies. While it is generally well-tolerated, common side effects may include nausea, vomiting, and headache.

Reference

1. J Clin Pharmacol. 2012 Apr;52(4):530-42. doi: 10.1177/0091270011400414. Epub 2011
Apr 19.

In vitro and in vivo assessment of renal drug transporters in the disposition of
mesna and dimesna.

Cutler MJ(1), Urquhart BL, Velenosi TJ, Meyer Zu Schwabedissen HE, Dresser GK,
Leake BF, Tirona RG, Kim RB, Freeman DJ.

Author information:
(1)Department of Medicine, Division of Clinical Pharmacology, The University of
Western Ontario, London, Ontario, Canada.

Mesna and its dimer, dimesna, are coadministered for mitigation of ifosfamide-
and cisplatin-induced toxicities, respectively. Dimesna is selectively reduced to
mesna in the kidney, producing its protective effects. In vitro screens of uptake
and efflux transporters revealed saturable uptake by renal organic anion
transporters OAT1, OAT3, and OAT4. Efflux transporters breast cancer resistance
protein; multidrug and toxin extrusion 1 (MATE1); multidrug resistance proteins
MRP1, MRP2, MRP4, and MRP5; and P-glycoprotein (Pgp) significantly reduced
dimesna accumulation. Further investigation demonstrated that renal apical efflux
transporters MATE1, MRP2, and Pgp were also capable of mesna efflux.
Administration of OAT inhibitor probenecid to healthy subjects significantly
increased combined mesna and dimesna plasma exposure (91% ± 34%) while decreasing
the renal clearance due to net secretion (67.0% ± 12.7%) and steady-state volume
of distribution (45.2% ± 13.4%). Thus, the kidney represents a significant sink
of total mesna, whereas function of renal drug transporters facilitates clearance
in excess of glomerular filtration rate and likely the presence of active mesna
in the urine. Loss of renal transporter function due to genetic variability or
drug-drug interactions may decrease the efficacy of chemoprotectants, increasing
the risk of ifosfamide- and cisplatin-induced toxicities.

2. Arzneimittelforschung. 1982;32(5):486-7.

[Prevention of urotoxic actions of cyclophosphamide and ifosfamide by dimesna
(preliminary communication) (author/’s transl)].

Brock N, Stekar J.

Sodium 2-mercaptoethane sulfonate (mesna, Uromitexan) is oxidized in the organism
of rats to 2,2/’-dithiodi-(ethane sodium sulfonate) (dimesna). Dimesna is
partially reduced to the mercapto compound mesna (kidneys); both compounds are
eliminated via the urine. Even after administration of dimesna mesna can be
detected in the urine. Accordingly dimesna also proved to be an effective
antidote against the urotoxic actions of cyclophosphamide and ifosfamide.