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Mesna (INN) /ˈmɛznə/ is an organosulfur compound used as an adjuvant in cancer chemotherapy involving cyclophosphamide and ifosfamide. It is marketed by Baxter as Uromitexan and Mesnex. The name of the substance is an acronym for 2-mercaptoethane sulfonate Na (Na being the chemical symbol for sodium). It is on the World Health Organization's List of Essential Medicines, a list of the most important medication needed in a basic health system.^[1]

Medical uses

Chemotherapy adjuvant

Mesna is used therapeutically to reduce the incidence of haemorrhagic cystitis and haematuria when a patient receives ifosfamide or cyclophosphamide for cancer chemotherapy. These two anticancer agents, in vivo, may be converted to urotoxic metabolites, such as acrolein.

Mesna assists to detoxify these metabolites by reaction of its sulfhydryl group with the vinyl group. It also increases urinary excretion of cysteine.

Other

Outside North America, mesna is also used as a mucolytic agent, working in the same way as acetylcysteine; it is sold for this indication as Mistabron^[2] and Mistabronco.

Administration

It is administered intravenously or orally (per mouth).^[3] The IV mesna infusions would be given with IV ifosfamide, while oral mesna would be given with oral cyclophosphamide. The oral doses must be double the intravenous (IV) mesna dose due to bioavailability issues. The oral preparation allows patients to leave the hospital sooner, instead of staying four to five days for all the IV mesna infusions.

Mechanism

It is believed to act as an antioxidant.^[4]

References

^ "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014.
^ "Mistabron Ampoules". South African Electronic Package Inserts. August 1973. Retrieved 2008-08-12.
^ Mace JR, Keohan ML, Bernardy H, et al. (December 2003). "Crossover randomized comparison of intravenous versus intravenous/oral mesna in soft tissue sarcoma treated with high-dose ifosfamide". Clin. Cancer Res. 9 (16 Pt 1): 5829–34. PMID 14676103.
^ Mashiach E, Sela S, Weinstein T, Cohen HI, Shasha SM, Kristal B (March 2001). "Mesna: a novel renoprotective antioxidant in ischaemic acute renal failure". Nephrol. Dial. Transplant. 16 (3): 542–51. doi:10.1093/ndt/16.3.542. PMID 11239029.

External links

BC Cancer Agency
NIH/MedlinePlus patient information

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UpToDate Contents

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1. 癌患者における膀胱炎 cystitis in patients with cancer
2. イホスファミドの腎毒性 ifosfamide nephrotoxicity
3. 軟部肉腫および骨肉腫の治療プロトコル treatment protocols for soft tissue and bone sarcoma
4. リウマチ性疾患および腎疾患におけるシクロホスファミドの使用の一般原則 general principles of the use of cyclophosphamide in rheumatic and renal disease
5. 炎症性疾患におけるシクロホスファミドおよびクロラムブシルの全身毒性 general toxicity of cyclophosphamide and chlorambucil in inflammatory diseases

English Journal

The protective effect of 2-mercaptoethane sulfonate (MESNA) against traumatic brain injury in rats.

Yilmaz ER, Kertmen H, Gürer B, Kanat MA, Arikok AT, Ergüder BI, Hasturk AE, Ergil J, Sekerci Z.SourceNeurosurgery Clinic, Diskapi Yildirim Beyazit Education and Research Hospital, Ministry of Health, Ankara, Turkey.
Acta neurochirurgica.Acta Neurochir (Wien).2013 Jan;155(1):141-9. doi: 10.1007/s00701-012-1501-3. Epub 2012 Sep 29.
BACKGROUND: The agent, 2-mercaptoethane sulfonate (MESNA), is a synthetic small molecule, widely used as a systemic protective agent against chemotherapy toxicity, but is primarily used to reduce hemorrhagic cystitis induced by cyclophosphamide. Because MESNA has potential antioxidant and cytoprotec
PMID 23053276

Acrolein and chloroacetaldehyde: An examination of the cell and cell-free biomarkers of toxicity.

Macallister SL, Martin-Brisac N, Lau V, Yang K, O'Brien PJ.SourceDepartment of Pharmaceutical Science, Faculty of Pharmacy, University of Toronto, 144 College St., Toronto, Canada M5S 3M2.
Chemico-biological interactions.Chem Biol Interact.2012 Dec 7. pii: S0009-2797(12)00261-X. doi: 10.1016/j.cbi.2012.11.017. [Epub ahead of print]
Cyclophosphamide and ifosfamide are two commonly used DNA-alkylating agents in cancer chemotherapy that undergo biotransformation to several toxic and non-toxic metabolites, including acrolein and chloroacetaldehyde (CAA). Acrolein and CAA toxicities occur by several different mechanisms, including
PMID 23220588

Japanese Journal

症例メスナ,アドリアマイシン,イホスファマイドおよびダカルバジン併用療法が奏効した再発性後腹膜平滑筋肉腫

松浦朋彦,加藤廉平,小原航 [他]
臨床泌尿器科 64(6), 433-437, 2010-05
NAID 40017090907

血管肉腫に対する国立がんセンターの治療戦略

山崎直也
Skin cancer : official organ of the Japanese Society for Skin Cancer = 皮膚悪性腫瘍研究会機関誌 24(3), 385-391, 2010-02-18
… 遠隔転移に対しては全身化学療法が治療の主体となり，抗がん剤単剤ではpaclitaxel，docetaxelが，多剤併用療法ではMAID（Mesna＋Doxorubicin＋Ifosfamide＋Dacarbazine）療法が高い奏効率を示す。 …
NAID 10027902410

Related Pictures

★リンクテーブル★

リンク元	「シクロホスファミド」「メスナ」
関連記事	「mes」

「シクロホスファミド」

Mesna
Systematic (IUPAC) name
	sodium 2-sulfanylethanesulfonate
Clinical data
AHFS/Drugs.com	monograph
Pregnancy cat.	AU: B1; US: B;
Legal status	AU: Prescription Only (S4); UK: POM; US: ℞-only;
Routes	Oral, intravenous
Pharmacokinetic data
Bioavailability	45–79% (Oral)
Metabolism	Oxidised in circulation
Half-life	0.36–8.3 hours
Excretion	Renal
Identifiers
CAS number	19767-45-4
ATC code	R05CB05 V03AF01
PubChem	CID 29769
ChemSpider	27663
UNII	NR7O1405Q9
KEGG	D01459
ChEMBL	CHEMBL975
Chemical data
Formula	C2H5NaO3S2
Molecular mass	164.181 g/mol
	SMILES [Na+].[O-]S(=O)(=O)CCS;
	InChI InChI=1S/C2H6O3S2.Na/c3-7(4,5)2-1-6;/h6H,1-2H2,(H,3,4,5);/q;+1/p-1 ; Key:XOGTZOOQQBDUSI-UHFFFAOYSA-M ;
(what is this?) (verify)

　　[★]

英: cyclophosphamide, CPA CPM
ラ: cyclophosphamidum
商: Cytoxan, Neosar、エンドキサン
関

first aid step1 2006 p.207,257,309,324,326,386

抗悪性腫瘍薬

アルキル化薬

免疫抑制薬

特徴

プロドラッグであり、肝臓で加水分解を受けて薬効を及ぼす

構造

作用機序

薬理作用

抗菌スペクトル

動態

適応

non-Hodgkin’s lymphoma, breast and ovarian carcinomas
immunosuppressants

注意

禁忌

副作用

出血性膀胱炎、骨髄抑制
myelosuppression; hemorrhagic cystitis, which can be partially prevented with mesna

副作用(再評価結果より)

再評価結果時の自覚的並びに他覚的症状緩和における安全性評価対象例5021例（経口投与を含む）中，主なものは，白血球減少1903例（37.90％），悪心・嘔吐1041例（20.73％），脱毛1221例（24.32％）等であった。また，急性白血病等の造血幹細胞移植の前治療における本剤の第2相臨床試験の安全性評価対象例67例中，主なものは悪心・嘔吐61例（91％），下痢，口内炎各42例（各63％），脱毛38例（57％）であった。

重大な副作用

ショック，アナフィラキシー様症状
骨髄抑制
出血性膀胱炎，排尿障害
イレウス，胃腸出血
間質性肺炎，肺線維症
心筋障害，心不全（5％未満），心タンポナーデ，心膜炎
抗利尿ホルモン不適合分泌症候群（SIADH)
皮膚粘膜眼症候群（Stevens-Johnson症候群），中毒性表皮壊死症（Lyell症候群）
肝機能障害，黄疸
急性腎不全

再評価結果における安全性評価例の集計

種類＼頻度	5%以上	5%未満	頻度不明
肝臓		肝機能異常，黄疸	コリンエステラーゼ低下
腎臓		蛋白尿，浮腫	食欲不振，味覚異常，胸やけ，おくび，腹部膨満感
消化器	悪心・嘔吐	口渇，潰瘍性口内炎，腹痛，便秘，下痢
過敏症		発疹
皮膚	脱毛	皮膚炎，色素沈着，爪の変形・変色
精神神経系		頭痛，眩暈，不眠，運動失調	倦怠感
呼吸器			肺水腫
循環器		心電図異常，心悸亢進，低血圧
内分泌系		副腎皮質機能不全	甲状腺機能亢進
性腺		無月経	無精子症，卵巣機能不全
その他		発熱，注射時熱感，局所痛，CK（CPK）上昇	創傷の治癒遅延，高血糖

添付文書

注射用エンドキサン100mg／注射用エンドキサン500mg

http://www.info.pmda.go.jp/go/pack/4211401D1033_1_10/4211401D1033_1_10?view=body

「メスナ」

　　[★]

英: mesna
商: ウロミテキサン、Mesnex

「mes」

　　[★]

comb form.

中央、中間、中位

ex.

mesonephros 中腎

[1] "WHO Model List of EssentialMedicines". World Health Organization. October 2013. Retrieved 22 April 2014.

[2] "Mistabron Ampoules". South African Electronic Package Inserts. August 1973. Retrieved 2008-08-12.

[pmid14676103-3] Mace JR, Keohan ML, Bernardy H, et al. (December 2003). "Crossover randomized comparison of intravenous versus intravenous/oral mesna in soft tissue sarcoma treated with high-dose ifosfamide". Clin. Cancer Res. 9 (16 Pt 1): 5829–34. PMID 14676103.

[pmid11239029-4] Mashiach E, Sela S, Weinstein T, Cohen HI, Shasha SM, Kristal B (March 2001). "Mesna: a novel renoprotective antioxidant in ischaemic acute renal failure". Nephrol. Dial. Transplant. 16 (3): 542–51. doi:10.1093/ndt/16.3.542. PMID 11239029.

匿名

検索

案内

案内

mesna