62435-42-1

Basic information

• Product Name: Perfosfamide
• Synonyms: Hydroperoxide,(2R,4R)-2-[bis(2-chloroethyl)amino]tetrahydro-2-oxido-2H-1,3,2-oxazaphosphorin-4-yl,rel- (9CI); Hydroperoxide,2-[bis(2-chloroethyl)amino]tetrahydro-2H-1,3,2-oxazaphosphorin-4-yl, P-oxide,cis-(?à)-; 2H-1,3,2-Oxazaphosphorine,hydroperoxide deriv.; 4-HC; 4-Hydroperoxycyclophosphamide; Hydroperoxide,2-[bis(2-chloroethyl)amino]tetrahydro-2-oxido-2H-1,3,2-oxazaphosphorin-4-yl,cis-; Hydroperoxycyclofosfamide; NSC 181815; Perfosfamide; Pergamid;cis-4-Hydroperoxycyclophosphamide
• CAS NO: 62435-42-1
• Molecular Formula: C₇H₁₅Cl₂N₂O₄P
• Molecular Weight: 293.086
• Mol File: 62435-42-1.mol
• Article Data: 5

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Perfosfamide(CAS DataBase Reference)
• NIST Chemistry Reference: Perfosfamide(62435-42-1)
• EPA Substance Registry System: Perfosfamide(62435-42-1)

Safety Data

• Hazardous Substances Data: 62435-42-1(Hazardous Substances Data)

Upstream product

• 84489-09-8 iminocyclophosphamide 
• 74307-83-8 2-bis(2-chloroethyl)aminotetrahydro-2H-3,4-epoxy<1,3,2>oxazaphosphorine 2-oxide 
• 19767-45-4 mesna 
• 61903-29-5 cis-4-hydroxycyclophosphamide 
• 39800-29-8 O-3-buten-1-yl N,N-bis(2-chloroethyl)phosphorodiamidate 

Downstream Products

• 61903-30-8 trans-4-hydroxycyclophosphamide 
• 82084-80-8 (E)-aldophosphamide O-methyl oxime 
• 343967-21-5 aldophosphamide O-methyloxime 
• 107961-75-1 4-(benzyloxy)cyclophosphamide 
• 65882-95-3 4-(S-ethanol)-sulfido-cyclophosphamide 
• 84489-09-8 iminocyclophosphamide 
• 35144-64-0 aldophosphamide 
• 61903-29-5 cis-4-hydroxycyclophosphamide 
• 10159-53-2 phosphoramide mustard 
• 88802-97-5 C₄H₁₁N₂O₈PS₄^(2-)*2Na⁽¹⁺⁾ 
• 88685-78-3 aldophosphamide hydrate 

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.

Base-catalyzed hydrolysis of 4-hydroperoxycyclophosphamide: Evidence for iminocyclophosphamide as an intermediate

cis-4-Hydroperoxycyclophosphamide (5) undergoes facile reaction with acqueous phosphate or Tris buffers at pH 7-8 and 30 °C. The kinetics of 5 are complex,and the trans-4-hydroperoxy isomer 6 is produced and subsequently disappears over the course of the reaction. Addition of hydrogen peroxide to the reaction mixture retards the disappearance rate of 5 and increases the amount of 6 generated. Rate constants for the reversible disappearance of 5 and appearance of 6 and 4-hydrocyclophosphamide (2) have been determined by nonlinear least-squares methods. The reaction is catalyzed by hydroxide ion, Tris free base, and HPO42-, with catalytic constants of 0.032 min-1 (pH 8.0), 0.052, and 0.115 M-1, respectively. The major product in the presence of Tris is the oxazolidine arising from the addition of Tris to aldophosphamide, not 2 as assumed previously. These results are consistent with a mechanism involving general-base-catalyzed elimination to produce iminocyclophosphamide as a transient intermediate; the imine can react with the hydrogen peroxide evolved in the reaction to give 5 and 6, with water to give 2, or, in general, by addition of a nucleophile to C-4. The significance of these findings with respect to other 4-substituted cyclophosphamides is discussed.

A new oxidized derivative of cyclophosphamide obtained from ozonolysis of O-3-butenyl N,N-bis(2-chloroethyl)phosphorodiamidate

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