Mesna

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

MedKoo CAT#: 100600

CAS#: 19767-45-4

Description: Mesna is a sulfhydryl compound that is used to reduce the incidence of hemorrhagic cystitis associated with certain chemotherapeutic agents. Mesna is converted to a free thiol compound in the kidney, where it binds to and inactivates acrolein and other urotoxic metabolites of ifosfamide and cyclophosphamide, thereby reducing their toxic effects on the urinary tract during urinary excretion. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus). Mesnex is indicated as a prophylactic agent in reducing the incidence of ifosfamide-induced hemorrhagic cystitis.

Chemical Structure

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Mesna
CAS# 19767-45-4
Instruction

Theoretical Analysis

MedKoo Cat#: 100600
Name: Mesna
CAS#: 19767-45-4
Chemical Formula: C2H5NaO3S2
Exact Mass: 0.00
Molecular Weight: 164.180
Elemental Analysis: C, 14.63; H, 3.07; Na, 14.00; O, 29.24; S, 39.06

Price and Availability

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Synonym: mercaptoethane sulfonate; Mesnum. US brand name: Mesnex. Foreign brand names: Ausobronc; Filesna; Mesnil; Mexan; Mistabron; Mistabronco; Mitexan; Mucofluid; Mucolene; Uromitexan; Ziken. Abbreviation: MSA. Code names: D7093; UCB 3983.

IUPAC/Chemical Name: sodium 2-mercaptoethanesulfonate

InChi Key: XOGTZOOQQBDUSI-UHFFFAOYSA-M

InChi Code: InChI=1S/C2H6O3S2.Na/c3-7(4,5)2-1-6;/h6H,1-2H2,(H,3,4,5);/q;+1/p-1

SMILES Code: SCCS(=O)([O-])=O.[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: >2 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

More Info:   DRUG DESCRIPTION Mesnex® (mesna) is a detoxifying agent to inhibit the hemorrhagic cystitis induced by ifosfamide (IFEX®).The active ingredient mesna is a synthetic sulfhydryl compound designated as sodium-2-mercaptoethane sulfonate with a molecular formula of C2H5NaO3S2 and a molecular weight of 164.18. Mesnex Injection is a sterile, nonpyrogenic, aqueous solution of clear and colorless appearance in clear glass multi-dose vials for intravenous administration.Mesnex Injection contains 100 mg/mL mesna, 0.25 mg/mL edetate disodium and sodium hydroxide for pH adjustment.Mesnex Injection multidose vials also contain 10.4 mg of benzyl alcohol as a preservative. The solution has a pH range of 7.5-8.5.  Mesnex Tablets are white, oblong, scored biconvex film coated tablets with the imprint M4. They contain 400 mg mesna. Excipients include lactose, microcrystalline cellulose, calcium phosphate, cornstarch, povidone, magnesium stearate, hydroxypropylmethylcellulose, polyethylene glycol, titanium dioxide, and simethicone.   Mechanism of Action Mesnex was developed as a prophylactic agent to reduce the risk of hemorrhagic cystitis induced by ifosfamide. Analogous to the physiological cysteine-cystine system, mesna is rapidly oxidized to its major metabolite, mesna disulfide (dimesna).Mesna disulfide remains in the intravascular compartment and is rapidly eliminated by the kidneys.  In the kidney, the mesna disulfide is reduced to the free thiol compound, mesna, which reacts chemically with the urotoxic ifosfamide metabolites (acrolein and 4-hydroxy-ifosfamide) resulting in their detoxification. The first step in the detoxification process is the binding of mesna to 4-hydroxy-ifosfamide forming a nonurotoxic 4-sul-foethylthioifosfamide. Mesna also binds to the double bonds of acrolein and to other urotoxic metabolites.  In multiple human xenograft or rodent tumor model studies of limited scope, using IV or IP routes of administration, mesna in combination with ifosfamide (at dose ratios of up to 20-fold as single or multiple courses) failed to demonstrate interference with antitumor efficacy.   

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 164.18 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.

Recalculate based on batch purity %
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
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Casale M, Di Martino A, Salvinelli F, Trombetta M, Denaro V. MESNA for chemically assisted tissue dissection. Expert Opin Investig Drugs. 2010 Jun;19(6):699-707. doi: 10.1517/13543784.2010.485192. Review. PubMed PMID: 20433403.

2: Khaw SL, Downie PA, Waters KD, Ashley DM, Heath JA. Adverse hypersensitivity reactions to mesna as adjunctive therapy for cyclophosphamide. Pediatr Blood Cancer. 2007 Sep;49(3):341-3. Review. PubMed PMID: 16333822.

3: Siu LL, Moore MJ. Use of mesna to prevent ifosfamide-induced urotoxicity. Support Care Cancer. 1998 Mar;6(2):144-54. Review. PubMed PMID: 9540174.

4: Goren MP. Oral administration of mesna with ifosfamide. Semin Oncol. 1996 Jun;23(3 Suppl 6):91-6. Review. PubMed PMID: 8677457.

5: Haselberger MB, Schwinghammer TL. Efficacy of mesna for prevention of hemorrhagic cystitis after high-dose cyclophosphamide therapy. Ann Pharmacother. 1995 Sep;29(9):918-21. Review. PubMed PMID: 8547741.

6: Sutton G. Ifosfamide and mesna in epithelial ovarian carcinoma. Gynecol Oncol. 1993 Oct;51(1):104-8. Review. PubMed PMID: 8244163.

7: Skinner R, Sharkey IM, Pearson AD, Craft AW. Ifosfamide, mesna, and nephrotoxicity in children. J Clin Oncol. 1993 Jan;11(1):173-90. Review. PubMed PMID: 8418231.

8: Goren MP. Oral mesna: a review. Semin Oncol. 1992 Dec;19(6 Suppl 12):65-71. Review. PubMed PMID: 1485175.

9: Dechant KL, Brogden RN, Pilkington T, Faulds D. Ifosfamide/mesna. A review of its antineoplastic activity, pharmacokinetic properties and therapeutic efficacy in cancer. Drugs. 1991 Sep;42(3):428-67. Review. PubMed PMID: 1720382.

10: Brade WP, Herdrich K, Kachel-Fischer U, Araujo CE. Dosing and side-effects of ifosfamide plus mesna. J Cancer Res Clin Oncol. 1991;117 Suppl 4:S164-86. Review. PubMed PMID: 1795007.