39800-16-3

Basic information

• Product Name: 4-HYDROPEROXY CYCLOPHOSPHAMIDE
• Synonyms: 4-HYDROPEROXY CYCLOPHOSPHAMIDE;,2-oxide;2-(bis(2-chloroethyl)amino)-4-hydroperoxytetrahydro-2h-1,3,2-oxazaphosphorin;2-oxazophosphorine,2-(bis(2-chloroethyl)amino)-4-hydroperoxytetrahydro-2h-3;4-hydroperoxyphosphamide;4-oohcyclophosphamide;4-peroxy-cpa;asta6496
• CAS NO: 39800-16-3
• Molecular Formula: C₇H₁₅Cl₂N₂O₄P
• Molecular Weight: 293.08
• Product Categories: Various Metabolites and Impurities;Intermediates & Fine Chemicals;Metabolites & Impurities;Pharmaceuticals;Phosphorylating and Phosphitylating Agents
• Mol File: 39800-16-3.mol
• Article Data: 7

Chemical Properties

• Melting Point: 100-103°C
• Boiling Point: 419.9 °C at 760 mmHg
• Flash Point: 207.8 °C
• Appearance: /
• Density: 1.46 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.525
• Storage Temp.: Hygroscopic, -86°C Freezer, Under Inert Atmosphere
• Solubility: Acetone (Slightly), Chloroform (Slightly), Methanol (Slightly), DCM
• Stability: Hygroscopic, Temperature Sensitive
• CAS DataBase Reference: 4-HYDROPEROXY CYCLOPHOSPHAMIDE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-HYDROPEROXY CYCLOPHOSPHAMIDE(39800-16-3)
• EPA Substance Registry System: 4-HYDROPEROXY CYCLOPHOSPHAMIDE(39800-16-3)

Safety Data

• Hazardous Substances Data: 39800-16-3(Hazardous Substances Data)

Usage

Description

4-HYDROPEROXY CYCLOPHOSPHAMIDE is the active metabolite of the nitrogen mustard cyclophosphamide, characterized by its potent antineoplastic and immunosuppressive properties. It is a white solid substance that plays a significant role in cancer treatment and bone marrow purging.

Uses

Used in Oncology:
4-HYDROPEROXY CYCLOPHOSPHAMIDE is used as an antineoplastic agent for the treatment of various types of cancer. It is particularly effective due to its ability to inhibit the growth and spread of cancer cells, making it a crucial component in cancer therapy.
Used in Bone Marrow Purging:
In the field of hematology, 4-HYDROPEROXY CYCLOPHOSPHAMIDE is used as a bone marrow purging agent. It helps in the removal of cancerous cells from the bone marrow, thus facilitating the process of bone marrow transplantation and improving the success rate of such procedures.
Used in Immunosuppression:
4-HYDROPEROXY CYCLOPHOSPHAMIDE is also utilized as an immunosuppressive agent in the treatment of autoimmune diseases and organ transplants. Its immunosuppressive properties help in reducing the risk of organ rejection and managing the immune response in patients with autoimmune conditions.

InChI:InChI=1/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(13)10-7(15-12)1-6-14-16/h7,12H,1-6H2,(H,10,13)/t7-,16-/m1/s1

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 
• 593-56-6 N-methoxylamine hydrochloride 
• 51274-71-6 4-peroxycyclophosphamide 
• 50-18-0 cyclophosphamide 

Downstream Products

• 61903-30-8 trans-4-hydroxycyclophosphamide 
• 343967-21-5 aldophosphamide O-methyloxime 
• 82084-80-8 (E)-aldophosphamide O-methyl oxime 
• 35144-64-0 aldophosphamide 
• 40277-05-2 4-hydroxycyclophosphamide 
• 65882-95-3 4-(S-ethanol)-sulfido-cyclophosphamide 
• 71310-25-3 4-{2-[bis-(2-chloro-ethyl)-amino]-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-ylsulfanylmethyl}-benzoic acid 
• 70396-87-1 3-{2-[bis-(2-chloro-ethyl)-amino]-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-ylsulfanyl}-propionic acid 
• 70396-85-9 6-{2-[bis-(2-chloro-ethyl)-amino]-2-oxo-2λ⁵-[1,3,2]oxazaphosphinan-4-ylsulfanyl}-hexan-1-ol 
• 107961-75-1 4-(benzyloxy)cyclophosphamide 
• 84489-09-8 iminocyclophosphamide 
• 61903-29-5 cis-4-hydroxycyclophosphamide 
• 10159-53-2 phosphoramide mustard 
• 88802-97-5 C₄H₁₁N₂O₈PS₄^(2-)*2Na⁽¹⁺⁾ 

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.

O-Methylhydroxylamine as a new trapping reagent for quantitative studies of 4-hydroxycyclophosphamide and aldophosphamide

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