19767-45-4 Usage
Uses
Used in Pharmaceutical Industry:
Mesna is used as an adrenergic agonist, coronary vasodilator, and calcium channel blocker for the treatment of various cardiovascular conditions.
Used in Oncology:
Mesna is used as a protective agent for the bladder wall against the harmful effects of some cancer-fighting drugs, such as cyclophosphamide and ifosfamide. It reacts with urotoxic metabolites of these drugs, forming stable, non-urotoxic compounds, without interfering with their antitumor activity.
Used in Antioxidant and Cytoprotective Applications:
Mesna is used as an antioxidant and cytoprotective agent in a wide range of applications, from protecting against the toxicity of therapeutic agents like cyclophosphamide to preventing brain injury damage.
Used in Quality Control:
Mesna serves as a pharmaceutical secondary standard for application in quality control, providing a convenient and cost-effective alternative to the preparation of in-house working standards for pharmaceutical laboratories and manufacturers.
Chemical Properties:
Mesna is a white to off-white solid with various applications in the pharmaceutical and medical fields.
Brand Names:
Some of the brand names for Mesna include Ausobrone, Mexnex, Mistabronco, Mistalon, Mucofluid, Mucolene, Uromitexan, and Uronexitan.
Originator
Mistabronco,UCB,W. Germany,1973
Manufacturing Process
2,100 g of β-S-thiuronium ethanesulfonate were placed in a solution of 2,100 cc of concentrated aqueous ammonia and 400 cc of water. The mixture was carefully warmed on a steam bath and an exothermic reaction ensured, at which point the β-S-thiuronium ethanesulfonate passed into solution. After standing for two hours at room temperature, the solution was concentrated until all of the excess ammonia had been removed. The resultant clear solution from the ammonolysis reaction was processed through "Amberlite IR-120" ion exchange resin and converted into β-Smercaptoethanesulfonic acid in 93.7% yield (based on β-S-thiuronium ethanesulfonate). It is expedient not to heat the reaction mixture rapidly since this increases the loss of ammonia and effects an incomplete reaction. Heating the mixture too rapidly may retard the ammonolysis reaction entirely. The amount of ammonia used is considered to be a satisfactory minimum and larger quantities of ammonia are not found to have any beneficial effect on the reaction. It is also expedient to remove the excess ammonia before processing the guanidinium β-mercaptoethanesulfonate solution through the ion exchange resin since the resin will also remove the ammonia with the result that the capacity of the resin for the exchange of guanidinium ions will be reduced. Although the preparation of β-mercaptoethanesulfonic acid through the ammonolysis reaction is the preferred method, it is also possible to prepare the sulfonic acid by the sodium hydroxide hydrolysis of β-S-thiuronium ethanesulfonate followed by the ion exchange treatment. The resulting acid,
however, is generally not as satisfactory as that prepared by the ammonolysis
reaction.
Therapeutic Function
Mucolytic
World Health Organization (WHO)
Mesna, an antidote used to protect patients treated with
cyclophosphamide or ifosfamide from haemorrhagic vesiculitis, was introduced on
the market in 1984. Shortly afterwards, its use became associated with allergic
reactions, which occurred mainly in patients treated with the oral solution. This led
to the withdrawal of this formulation in Germany, the only country where it was
marketed. An oral liquid dosage form is still registered, but not marketed, in the
Netherlands and products for intravenous injection remain available elsewhere.
Contact allergens
Mesna is used as a mucolytic agent, and as an antidote to chloro-acetyl-aldehyde and acrolein (a bladder toxic metabolite of ifosfamide or cyclophosphamide). It hasbeen reported as a cause of occupational allergic (hand and airborne) dermatitis in nurses
Clinical Use
Prophylaxis of urothelial toxicity in patients treated with
ifosfamide or cyclophosphamide
Drug interactions
Potentially hazardous interactions with other drugs
None known
Metabolism
Rapidly metabolised in the liver to the disulfide, dimesna,
and is excreted in the urine as both metabolite and
unchanged drug; dimesna is reduced back to mesna,
which is the active form, in the kidney.
Purification Methods
It can be recrystallised from H2O and does not melt below 250o. It is purified further by converting to the free acid by passing a 2M solution through an ion-exchange (Amberlite IR-120) column in the acid form, evaporating the eluate in a vacuum to give the acid as a viscous oil (readily decomposes) which can be checked by acid and SH titration. It is then dissolved in H2O, carefully neutralised with aqueous NaOH, evaporated and the salt recrystallised from H2O [Schramm J Am Chem Soc 77 6231 1955]. [Beilstein 4 IV 85.]
Check Digit Verification of cas no
The CAS Registry Mumber 19767-45-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,7,6 and 7 respectively; the second part has 2 digits, 4 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 19767-45:
(7*1)+(6*9)+(5*7)+(4*6)+(3*7)+(2*4)+(1*5)=154
154 % 10 = 4
So 19767-45-4 is a valid CAS Registry Number.
InChI:InChI=1/C2H6O3S2.Na/c3-7(4,5)2-1-6;/h6H,1-2H2,(H,3,4,5);
19767-45-4Relevant articles and documents
Preparation method of high-purity mesna
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Paragraph 0037; 0038; 0041; 0042; 0043; 0048; 0049; 0054, (2017/10/22)
The invention belongs to the technical field of drug synthesis, and particularly relates to a preparation method of high-purity mesna. The invention provides a brand new synthetic thought of high-purity mesna. Since a sulfydryl compound is unstable, and a disulfide bond is likely to form, a main impurity (di-mesna) of mesna is firstly prepared, and finally the di-mesna is decomposed into mesna by virtue of conventional hydrogenation reduction, so that the process flow greatly reduces the content of the di-mesna in the mesna, the reaction raw materials are easy to obtain, the operation is simple, the yield and purity are greatly increased, and the preparation method is suitable for the industrialized production.
SULFANYL DERIVATIVES AND THEIR USE AS SYNTHESIS INTERMEDIATES
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Page/Page column 3-4, (2009/04/25)
The present application relates to sulfanyl derivatives of formula (I) and to their use as synthesis intermediates, especially for the preparation of the pharmaceutically active compound mesna. Formula (I), wherein X is O or N-C(NH)NH2; M + is hydrogen, sodium, disodium, potassium, dipotassium, ammonium (NH4)+, diammonium, quaternary ammonium, calcium or magnesium.
Process for synthesizing disulfides
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Page/Page column 4, (2008/06/13)
This invention relates to a process for producing a substantially pure disulfide compound of Formula II as disclosed herein, such as disodium 2,2′-dithiobis ethane sulfonate, by an efficient procedure from available, relatively inexpensive raw materials.
A New Method for Obtaining Isotopic Fractionation Data at Multiple Sites in Rapidly Exchanging Systems
Jarret, Ronald M.,Saunders, Martin
, p. 2648 - 2654 (2007/10/02)
A new method for rapidly and conveniently obtaining isotopic fractionation factors in dilute aqueous solutions of compounds containing rapidly exchanging OH, NH, and SH groups is described.Shifts in the positions of NMR peaks for spectroscopically observable nuclei induced by isotopic substitution are the basis of this procedure which has the unique capability of separately measuring the isotopic exchange constants simultaneously for several different groups in the same molecule.The results for a series of alcohols, amines, thiols, phenols, acids, and amides with use of 13C NMR spectroscopy are reported.Atypically low values of Kfrac are observed in several cases, indicating that there are strong internal hydrogen bonds in competition with those to water, yielding conformational information.
