4-Hydroperoxy cyclophosphamide, active metabolite form of the proagent Cyclophosphamide. 4-Hydroperoxy cyclophosphamide induces T cell apoptosis and forms crosslinks in DNA without requiring the activation of death receptors; however, it triggers the pathways leading to mitochondrial death by generating reactive oxygen species (ROS). 4-Autoimmune diseases and lymphomas may be brought on by 4-hydroxycyclophosphamide.

Physicochemical Properties

Molecular Formula	C7H15CL2N2O4P
Molecular Weight	293.085
Exact Mass	292.015
Elemental Analysis	C, 28.69; H, 5.16; Cl, 24.19; N, 9.56; O, 21.84; P, 10.57
CAS #	39800-16-3
Related CAS #	4-Hydroperoxy Cyclophosphamide-d4;1246816-71-6
PubChem CID	38347
Appearance	White to yellow solid powder
Density	1.465g/cm3
Boiling Point	419.946ºC at 760 mmHg
Melting Point	100-103ºC
Flash Point	207.776ºC
Index of Refraction	1.525
LogP	2.028
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	6
Rotatable Bond Count	6
Heavy Atom Count	16
Complexity	253
Defined Atom Stereocenter Count	0
SMILES	ClCCN(P1(OCCC(OO)N1)=O)CCCl
InChi Key	VPAWVRUHMJVRHU-UHFFFAOYSA-N
InChi Code	InChI=1S/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)
Chemical Name	N,N-bis(2-chloroethyl)-4-hydroperoxy-2-oxo-1,3,2lambda5-oxazaphosphinan-2-amine
Synonyms	ASTA-6496; 4-OOH-CY; ASTA 6496; ASTA6496; 4-hydroperoxy Cyclophosphamide
HS Tariff Code	2934.99.9001
Storage	Powder-20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture.
Shipping Condition	Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)

Biological Activity

References

[1]. 4-hydroperoxy-cyclophosphamide mediates caspase-independent T-cell apoptosis involving oxidative stress-induced nuclear relocation of mitochondrial apoptogenic factors AIF and EndoG.

Additional Infomation

4-hydroperoxycyclophosphamide is a phosphorodiamide that is the active metabolite of the nitrogen mustard cyclophosphamide. It has potent antineoplastic and immunosuppressive properties. It has a role as an antineoplastic agent, an immunosuppressive agent, an alkylating agent, a metabolite and a drug allergen. It is a phosphorodiamide, a nitrogen mustard, a peroxol and an organochlorine compound. See also: Perfosfamide (annotation moved to).

Solubility Data

Solubility (In Vitro)

DMSO : ~50 mg/mL (~170.6 mM)

Solubility (In Vivo)

Solubility in Formulation 1: 2.5 mg/mL (8.53 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 400 μL PEG300 and mix evenly; then add 50 μL Tween-80 to the above solution and mix evenly; then add 450 μL normal saline to adjust the volume to 1 mL. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (8.53 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 3: ≥ 2.5 mg/mL (8.53 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.4119 mL	17.0596 mL	34.1192 mL
	5 mM	0.6824 mL	3.4119 mL	6.8238 mL
	10 mM	0.3412 mL	1.7060 mL	3.4119 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.