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Dimesna

Uroprotective agent CAS# 16208-51-8

Dimesna

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Chemical structure

Dimesna

3D structure

Chemical Properties of Dimesna

Cas No. 16208-51-8 SDF Download SDF
PubChem ID 65625 Appearance Powder
Formula C4H8Na2O6S4 M.Wt 326.34
Type of Compound N/A Storage Desiccate at -20°C
Synonyms Sodium 2,2'-disulfanediyldiethanesulfonate;Tavocept;CCRIS 5852;BNP 7787;NSC 716976;Ethanesulfonic acid, 2,2'-dithiobis-, disodium salt
Solubility DMSO : 68 mg/mL (208.37 mM; Need ultrasonic and warming)
Chemical Name disodium;2-(2-sulfonatoethyldisulfanyl)ethanesulfonate
SMILES [Na+].[Na+].[O-][S](=O)(=O)CCSSCC[S]([O-])(=O)=O
Standard InChIKey KQYGMURBTJPBPQ-UHFFFAOYSA-L
Standard 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
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Biological Activity of Dimesna

DescriptionDimesna is a kidney selective prodrug of Mesna with Km value of 636, 390 and 590 μM for OAT1, OAT3 and OAT4, resepectively.
TargetsOAT1OAT3OAT4   
IC50636 μM (Km)390 μM (Km)590 μM (Km)    

Dimesna Dilution Calculator

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Dimesna Molarity Calculator

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Preparing Stock Solutions of Dimesna

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 3.0643 mL 15.3214 mL 30.6429 mL 61.2858 mL 76.6072 mL
5 mM 0.6129 mL 3.0643 mL 6.1286 mL 12.2572 mL 15.3214 mL
10 mM 0.3064 mL 1.5321 mL 3.0643 mL 6.1286 mL 7.6607 mL
50 mM 0.0613 mL 0.3064 mL 0.6129 mL 1.2257 mL 1.5321 mL
100 mM 0.0306 mL 0.1532 mL 0.3064 mL 0.6129 mL 0.7661 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Dimesna

Dimesna is an inhibitor of OAT family with IC50 value of 636 μM, 390 μM, and 590 μM for OAT1, OAT3, and OAT4, respectively [1].
OATs (organic anion transporters) involve in many life processes, like elimination of a variety of endogenous substances, xenobiotics and their metabolites from the body. It has been shown that OATs play an important role in mediating the renal and hepatic elimination of organic anions using molecular cloning method [2].
Dimesna is an OAT inhibitor and often used as an uroprotective drug. When tested with renal tubular cell line LLC-PK1, in combination with IF metabolites, dimesna treatment exerted uroprotective action [3]. When tested with human renal proximal tubule HK-2 cells, dimesna was detected to accumulate in cells and played an important role in reducing chemotherapy-induced toxicities [4].
References:
[1].Cutler, M.J., 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): p. 530-42.
[2].Roth, M., A. Obaidat, and B. Hagenbuch, OATPs, OATs and OCTs: the organic anion and cation transporters of the SLCO and SLC22A gene superfamilies. Br J Pharmacol, 2012. 165(5): p. 1260-87.
[3].Mohrmann, M., et al., Dithio-bis-mercaptoethanesulphonate (DIMESNA) does not prevent cellular damage by metabolites of ifosfamide and cyclophosphamide in LLC-PK1 cells. Pediatr Nephrol, 1994. 8(4): p. 458-65.
[4].Hausheer, F.H., et al., Accumulation of BNP7787 in human renal proximal tubule cells. J Pharm Sci, 2011. 100(9): p. 3977-84.

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References on Dimesna

Vibrational spectroscopic studies of mesna and dimesna.[Pubmed:12736065]

Spectrochim Acta A Mol Biomol Spectrosc. 2003 Jun;59(8):1791-8.

Raman, and infrared spectra of mesna and Dimesna have been collected in the present spectroscopic studies. Based on the group frequencies, relative intensities and Raman depolarization measurements, some vibrational assignments have been suggested. For both mesna and Dimesna, at least two rotational conformers have been identified. Adsorption behavior was investigated from the recorded surface-enhanced Raman scattering (SERS) spectra. It was found that both mesna and Dimesna adsorbed as thiolate on silver sol particles with the cleavage of the S-H bond in mesna and the S-S bond in Dimesna. For the adsorbed thiolate, two conformers existed in the adsorption state.

Quantification of BNP7787 (dimesna) and its metabolite mesna in human plasma and urine by high-performance liquid chromatography with electrochemical detection.[Pubmed:11334343]

J Chromatogr B Biomed Sci Appl. 2001 Apr 5;753(2):293-302.

A sensitive and accurate assay was developed and validated to determine BNP7787 (Dimesna), a new protector against cisplatin-induced toxicities, and its metabolite mesna in plasma and urine of patients. Both analytes were measured as mesna in deproteinized plasma or in urine diluted with mobile phase using high-performance liquid chromatography with an electrochemical detector provided with a wall-jet gold electrode. The assays for BNP7787 and mesna in deproteinized plasma were linear over the range of 1.6-500 microM and 0.63-320 microM, respectively. In plasma, the mean recovery of BNP7787 over the whole concentration range was 100.6% and of mesna 94.6%. The lower limits of quantitation (LLQs) of BNP7787 and mesna in deproteinized plasma were 1.6 microM and 0.63 microM, respectively. For both compounds the within- and between-day accuracy and precision of the assay was better than 12%. The assays for BNP7787 and mesna in urine were linear over the range of 0.8-1200 microM and 0.63-250 microM, respectively. In urine, the mean recovery of BNP7787 over the whole concentration range was 94.1% and of mesna 93.1%. The LLQ of BNP7787 in urine was 0.8 microM and of mesna 1.6 microM. The within- and between-day accuracy and precision of the assay for BNP7787 and mesna was lower than 15%. The stability of mesna in urine increased with an increasing concentration of mesna, lower temperature and addition of EDTA (1 g/l) and hydrochloric acid (0.2 M). BNP7787 in urine was stable for at least 24 h at temperatures in the range of -20 degrees C up to 37 degrees C and independent of the concentration. The developed assays are currently applied for samples of patients with solid tumors participating in a phase I trial of BNP7787 in combination with cisplatin.

Enzymatic and non-enzymatic mechanisms of dimesna metabolism.[Pubmed:25488427]

Amino Acids. 2015 Mar;47(3):511-23.

The chemical reduction of the disulfide homodimer Dimesna to its constituent mesna moieties is essential for its mitigation of nephrotoxicity associated with cisplatin and ifosfamide anticancer therapies and enhancement of dialytic clearance of the cardiovascular risk factor homocysteine. The objective of this study was to investigate potential enzymatic and non-enzymatic mechanisms of intracellular Dimesna reduction. Similar to endogenous intracellular disulfides, Dimesna undergoes thiol-disulfide exchange with thiolate anion-forming sulfhydryl groups via the two-step SN2 reaction. Determination of equilibrium constants of Dimesna reduction when mixed with cysteine or glutathione provided a mechanistic explanation for dramatic cysteine and homocysteine depletion, but sparing of the endogenous antioxidant glutathione, previously observed during mesna therapy. Dimesna was reduced by recombinant enzymes of the thioredoxin system; however, oxidation of NADPH by the glutaredoxin system was only observed in the presence of combined Dimesna and reduced glutathione, suggesting formation of oxidized glutathione following an initial non-enzymatic reduction of Dimesna. Production of mesna by enzymatic and non-enzymatic mechanisms in HeLa cell lysate following Dimesna incubation was demonstrated by a loss in mesna production following protein denaturation and prediction of residual non-enzymatic mesna production by mathematical modeling of thiol-disulfide exchange reactions. Reaction modeling also revealed that mixed disulfides make up a significant proportion of intracellular thiols, supporting their role in providing additional nephroprotection, independent of direct platinum conjugation.

In vitro and in vivo assessment of renal drug transporters in the disposition of mesna and dimesna.[Pubmed:21505084]

J Clin Pharmacol. 2012 Apr;52(4):530-42.

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.

Description

Dimesna is an protective agent used to decrease urotoxicity.

Keywords:

Dimesna,16208-51-8,Sodium 2,2'-disulfanediyldiethanesulfonate;Tavocept;CCRIS 5852;BNP 7787;NSC 716976;Ethanesulfonic acid, 2,2'-dithiobis-, disodium salt,Natural Products,Others, buy Dimesna , Dimesna supplier , purchase Dimesna , Dimesna cost , Dimesna manufacturer , order Dimesna , high purity Dimesna

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