Dimesna

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 201030

CAS#: 16208-51-8

Description: Dimesna reacts with acrolein and other urotoxic metabolites of oxazaphosphorines (cyclophosphamide or ifosfamide) to form stable, non-urotoxic compounds. Mesna does not have any antitumour activity, nor does it appear to interfere with the antitumour activity of antineoplastic drugs. This medication is used to protect the bladder wall from the harmful effects of some cancer-fighting drugs.


Chemical Structure

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Dimesna
CAS# 16208-51-8

Theoretical Analysis

MedKoo Cat#: 201030
Name: Dimesna
CAS#: 16208-51-8
Chemical Formula: C4H8Na2O6S4
Exact Mass:
Molecular Weight: 326.34
Elemental Analysis: C, 14.72; H, 2.47; Na, 14.09; O, 29.42; S, 39.30

Size Price Shipping out time Quantity
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Pricing updated 2021-03-09. Prices are subject to change without notice.

Dimesna is not in stock, but may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.

Synonym: mesna disulfide. US brand name: Tavocept. Abbreviation: DIM. Code name: BNP7787. Chemical structure name: 22dithiobisethanesulfonate disodium salt

IUPAC/Chemical Name: sodium 2,2'-disulfanediyldiethanesulfonate

InChi Key: KQYGMURBTJPBPQ-UHFFFAOYSA-L

InChi Code: 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

SMILES Code: O=S(CCSSCCS(=O)([O-])=O)([O-])=O.[Na+].[Na+]

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>5 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001

Handling Instructions:

Preparing Stock Solutions

The following data is based on the product molecular weight 326.34 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Hausheer FH, Parker AR, Petluru PN, Jair KW, Chen S, Huang Q, Chen X, Ayala PY, Shanmugarajah D, Kochat H. Mechanistic study of BNP7787-mediated cisplatin nephroprotection: modulation of human aminopeptidase N. Cancer Chemother Pharmacol. 2010 May 4. [Epub ahead of print] PubMed PMID: 20440617.

2: Hausheer FH, Shanmugarajah D, Leverett BD, Chen X, Huang Q, Kochat H, Petluru PN, Parker AR. Mechanistic study of BNP7787-mediated cisplatin nephroprotection: modulation of gamma-glutamyl transpeptidase. Cancer Chemother Pharmacol. 2010 Apr;65(5):941-51. Epub 2009 Aug 28. PubMed PMID: 19714332.

3: Shanmugarajah D, Ding D, Huang Q, Chen X, Kochat H, Petluru PN, Ayala PY, Parker AR, Hausheer FH. Analysis of BNP7787 thiol-disulfide exchange reactions in phosphate buffer and human plasma using microscale electrochemical high performance liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2009 Apr 1;877(10):857-66. Epub 2009 Feb 28. PubMed PMID: 19278906.

4: Głowacki R, Gryglik D, Kuśmierek K, Bald E. Urinary mesna and total mesna measurement by high performance liquid chromatography with ultraviolet detection. Talanta. 2005 Apr 30;66(3):534-9. Epub 2005 Jan 1. PubMed PMID: 18970018.

5: Bastings MM, van Baal I, Meijer EW, Merkx M. One-step refolding and purification of disulfide-containing proteins with a C-terminal MESNA thioester. BMC Biotechnol. 2008 Oct 1;8:76. PubMed PMID: 18828922; PubMed Central PMCID: PMC2570673.

6: Miller AA, Wang XF, Gu L, Hoffman P, Khatri J, Dunphy F, Edelman MJ, Bolger M, Vokes EE, Green MR; Cancer and Leukemia Group B (CALGB). 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). J Thorac Oncol. 2008 Oct;3(10):1159-65. PubMed PMID: 18827613.

7: Wang And X, Guo Z. The role of sulfur in platinum anticancer chemotherapy. Anticancer Agents Med Chem. 2007 Jan;7(1):19-34. Review. PubMed PMID: 17266503.

8: Patzer L, Hernando N, Ziegler U, Beck-Schimmer B, Biber J, Murer H. Ifosfamide metabolites CAA, 4-OH-Ifo and Ifo-mustard reduce apical phosphate transport by changing NaPi-IIa in OK cells. Kidney Int. 2006 Nov;70(10):1725-34. Epub 2006 Sep 27. PubMed PMID: 17003823.

9: Boven E, Westerman M, van Groeningen CJ, Verschraagen M, Ruijter R, Zegers I, van der Vijgh WJ, Giaccone G. Phase I and pharmacokinetic study of the novel chemoprotector BNP7787 in combination with cisplatin and attempt to eliminate the hydration schedule. Br J Cancer. 2005 May 9;92(9):1636-43. PubMed PMID: 15841080; PubMed Central PMCID: PMC2362054.

10: Verschraagen M, Boven E, Torun E, Hausheer FH, Bast A, van der Vijgh WJ. Possible (enzymatic) routes and biological sites for metabolic reduction of BNP7787, a new protector against cisplatin-induced side-effects. Biochem Pharmacol. 2004 Aug 1;68(3):493-502. PubMed PMID: 15242815.



Additional Information

Dimesna is a synthetic derivative of dithio-ethane sulfonate with uroprotective properties. In the kidney, dimesna undergoes reduction to the free thiol compound, mesna, which reacts chemically with the urotoxic ifosfamide metabolites acrolein and 4-hydroxy-ifosfamide, resulting in their detoxification. This agent also inhibits cyclophosphamide-induced hemorrhagic cystitis. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus).
 
Current developer:    Takeda Pharmaceutical Company Limited.