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+]
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.
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.
| 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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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.
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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.
