88859-04-5

Basic information

• Product Name: Mafosfamide
• Synonyms: Mafosfamide;(+-)-2-((2-(Bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl)thio)ethanesulfonic acid p-cis-oxide;Ethanesulfonic acid, 2-(((2R,4R)-2-(bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl)thio)-, rel-;Ethanesulfonic acid, 2-((2-(bis(2-chloroethyl)amino)tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl)thio)-, p-oxide, cis-(+-)-;Mafosfamid;Mafosfamida;Mafosfamida [spanish];Mafosfamidum
• CAS NO: 88859-04-5
• Molecular Formula: C9H19Cl2N2O5PS2
• Molecular Weight: 401.27
• Product Categories: API
• Mol File: 88859-04-5.mol
• Article Data: 2

Chemical Properties

• Appearance: /
• Density: 1.54 g/cm³
• Refractive Index: 1.573
• CAS DataBase Reference: Mafosfamide(CAS DataBase Reference)
• NIST Chemistry Reference: Mafosfamide(88859-04-5)
• EPA Substance Registry System: Mafosfamide(88859-04-5)

Safety Data

• Hazardous Substances Data: 88859-04-5(Hazardous Substances Data)

Usage

General Description

Mafosfamide is a prodrug of the alkylating chemotherapeutic agent ifosfamide, which is used to treat various types of cancer. It is converted into ifosfamide in the body and exerts its cytotoxic effects by alkylating DNA and inhibiting cell division. Mafosfamide is particularly effective against cancers of the bladder, breast, lung, and soft tissue sarcomas. It is often used in combination with other chemotherapy drugs to enhance its antitumor activity. Despite its effectiveness, mafosfamide can cause side effects such as nausea, vomiting, and myelosuppression, and it should be administered under the supervision of a healthcare professional.

InChI:InChI=1/C9H19Cl2N2O5PS2/c10-2-4-13(5-3-11)19(14)12-9(1-6-18-19)20-7-8-21(15,16)17/h9H,1-8H2,(H,12,14)(H,15,16,17)

Upstream product

• 84210-72-0 cis-Mosfosfamide 
• 19767-45-4 mesna 
• 61903-29-5 cis-4-hydroxycyclophosphamide 

Relevant articles and documents

Activation Mechanisms of Mafosfamide and the Role of Thiols in Cyclophosphamide Metabolism

cis-Mafosfamide (cis-5) (ASTA Z7557), a stable analogue of cis-4-hydroxycyclophosphamide (cis-2), undergoes rapid decomposition in aqueous phosphate buffer or plasma at pH 7.4 and 37 deg C.The reaction kinetics of cis-5 are complex, and trans-mafosfamide (trans-5) and cis-2 are produced and subsequently disappear over the course of the reaction.The rates of decomposition of cis-5 as well as cis-2 were much faster in plasma than in buffer.The cis-trans isomerization of cis-5 occured by a specific-base-catalyzed process via iminocyclophosphamide (8) as a transient intermediate.In contrast, formation of cis- and trans-mafosfamide (5) from cis-2 and MESNA (sodium 2-mercaptoethanesulfonate) proceeded by an acid-catalyzed process via the hemithioacetal intermediate (6).The significance of these findings with respect to cyclophosphamide metabolism is discussed.