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Cat. No. Name Size Price Add Cart
KI1103Dimesna100 mg$112
Dimesna200 mg$192

Chemical Characteristic

Product NameDimesna
SynonymsBNP7787
CAS No.16208-51-8
Molecular Weight 326.34
FormulaC4H8Na2O6S4
Chemical Name2-(2-sulfonatoethyldisulfanyl)ethanesulfonate
Smiles[Na] [Na] S(SCCS(=O)(=O)O)CCS(=O)(=O)O
Chemical Structure

Biological activities

Dimesna is a chemoprotective agent used to protect against cisplatin-induced nephrotoxicity and neurotoxicity. The degradation half-lives of cisplatin with 17.2 mM dimesna are 124 minutes. [1] The selective protection of dimesna appears to arise from the preferential uptake of dimesna in the kidneys, where dimesna would undergo intracellular conversion into mesna, which in turn can prevent cisplatin induced toxicities.[2] The only metabolite of dimesna is mesna, which is selectively formed in the kidneys, intestines and probably in the bone marrow by enzymatic reduction.[3] Dimesna-derived mesna in the kidneys can locally inactivate cisplatin by forming non-toxic platinum complexes and thereby preventing cisplatin-induced nephrotoxicity without interfering with the antitumor activity of cisplatin.[4] Saturable, kidney-specific uptake of dimesna has been observed in experiments using perfused organs and isolated epithelial cells.[3] In vitro, from a screen of 12 human uptake transporters, only the predominantly renally expressed OAT1 , OAT3, and OAT4 significantly increases dimesna accumulation in transfected HeLa cells.[5] In nude mice bearing well-established OVCAR-3 xenografts, dimesna co-administered with carboplatin is significantly more effective in inhibition of tumour growth than carboplatin alone.[6]

Protocols

In vivo: Dimesna is dissolved in water.[6]

References

[1] Verschraagen M, et al. 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. Cancer Chemother Pharmacol. 2003, 51(6): 499-504.
[2] Verschraagen M, et al. Possible (enzymatic) routes and biological sites for metabolic reduction of BNP7787, a new protector against cisplatin-induced side-effects. Biochem Pharmacol. 2004, 68(3): 493-502.
[3] Ormstad K, et al. Pharmacokinetics and metabolism of sodium 2-mercaptoethanesulfonate in the rat. Cancer Res. 1983, 43(1): 333-338.
[4] Verschraagen M, et al. Quantification of BNP7787 (dimesna) and its metabolite mesna in human plasma and urine by high-performance liquid chromatography with electrochemical detection. J Chromatogr B Biomed Sci Appl. 2001, 753(2): 293-302.
[5] Cutler MJ, et al. In vitro and in vivo assessment of renal drug transporters in the disposition of mesna and dimesna. J Clin Pharmacol. 2012, 52(4): 530-542.
[6] Boven E, et al. BNP7787, a novel protector against platinum-related toxicities, does not affect the efficacy of cisplatin or carboplatin in human tumour xenografts. Eur J Cancer. 2002, 38(8): 1148-1156.

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