Phosphoramide mustard cyclohexanamine is the active metabolite of cyclophosphamide and has anti-tumor activity. Phosphoramide mustard cyclohexanamine can causes damage to DNA.

Physicochemical Properties

Molecular Formula	C10H24CL2N3O2P
Molecular Weight	320.20
Exact Mass	319.098
Elemental Analysis	C, 37.51; H, 7.56; Cl, 22.14; N, 13.12; O, 9.99; P, 9.67
CAS #	1566-15-0
Related CAS #	Phosphoramide mustard;10159-53-2
PubChem CID	96355
Appearance	White to off-white solid powder
Boiling Point	363.5ºC at 760mmHg
Melting Point	100-103 °C
Flash Point	173.6ºC
Vapour Pressure	2.84E-06mmHg at 25°C
LogP	3.503
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	5
Rotatable Bond Count	5
Heavy Atom Count	18
Complexity	197
Defined Atom Stereocenter Count	0
SMILES	C1(N)CCCCC1.ClCCN(CCCl)P(N)(=O)O
InChi Key	BGTIPRUDEMNRIP-UHFFFAOYSA-N
InChi Code	InChI=1S/C6H13N.C4H11Cl2N2O2P/c7-6-4-2-1-3-5-6;5-1-3-8(4-2-6)11(7,9)10/h6H,1-5,7H2;1-4H2,(H3,7,9,10)
Chemical Name	amino-[bis(2-chloroethyl)amino]phosphinic acid;cyclohexanamine
Synonyms	PMC; NSC-69945; NSC 69945; NSC69945; Phosphoramide Mustard cyclohexylammonium salt
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: (1). This product requires protection from light (avoid light exposure) during transportation and storage.(2). 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

ln Vitro	In order to prevent DNA strand separation during replication, phosphoramide mustard cyclohexanamine forms cross-linked DNA adducts, which are cytotoxic[1]. For a 48-hour period, rat spontaneously immortalized granulosa cells (SIGCs) exposed to phosphoramide mustard cyclohexanamine (3-6 μM) lose viability. Damage to ovarian DNA and the production of DNA adducts are caused by phosphoamide mustard cyclohexanamine (3-6 μM; 24-48 hours). The expression of DNA damage response (DDR) gene mRNA and DDR proteins are increased by phosphoamide mustard cyclohexanamine (3-6 μM; 24-48 hours)[1].
ln Vivo	Rats' subcutaneous tumor growth is inhibited by phosphoramide mustard cyclohexanamine (2.1-20.7 mg/kg; ip; daily; for 5 days)[2]. After intravenous injection (rat 59.4 mg/kg), phosphoramide mustard cyclohexanamine shows terminal elimination half-lives (rat 15.1 min)[2].
Cell Assay	Cell Viability Assay[1] Cell Types: SIGCs Tested Concentrations: 0.5 μM, 1 μM, 3 μM, 6 μM Incubation Duration: 48 hrs (hours) Experimental Results: decreased cell viability at concentrations of 3 μM and higher. RT-PCR[1] Cell Types: SIGCs Tested Concentrations: 3 μM, 6 μM Incubation Duration: 24 hrs (hours), 48 hrs (hours) Experimental Results: Increased DDR gene mRNA expression levels. Western Blot Analysis[1] Cell Types: SIGCs Tested Concentrations: 3 μM, 6 μM Incubation Duration: 24 hrs (hours), 48 hrs (hours) Experimental Results: Generally increased DDR proteins.
Animal Protocol	Animal/Disease Models: Rat, subcutaneously (sc) implanted Walker 256 carcinosarcoma tumor[2] Doses: 2.1 mg/kg, 4.8 mg/kg , 10.4 mg/kg, 20.7 mg/kg Route of Administration: intraperitoneal (ip)injection, one time/day, for 5 days Experimental Results: Required to produce 50% inhibition of subcutaneous (sc)tumor growth with dose of 12 mg/kg. Animal/Disease Models: Rats[2] Doses: 86.0 mg/kg (pharmacokinetic/PK Analysis) Route of Administration: intravenous (iv)injection Experimental Results: T1/2 (15.1 min).
References	[1]. Phosphoramide mustard exposure induces DNA adduct formation and the DNA damage repair response in rat ovarian granulosa cells. Toxicol Appl Pharmacol. 2015 Feb 1; 282(3): 252–258. [2]. Brain and plasma pharmacokinetics and anticancer activities of cyclophosphamide and phosphoramide mustard in the rat. Cancer Chemother Pharmacol. 1990;27(1):1-7.

Solubility Data

Solubility (In Vitro)	H2O : ~100 mg/mL (~312.3 mM)
Solubility (In Vivo)	Solubility in Formulation 1: 100 mg/mL (312.30 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.  (Please use freshly prepared in vivo formulations for optimal results.)

Preparing Stock Solutions		1 mg	5 mg	10 mg
	1 mM	3.1230 mL	15.6152 mL	31.2305 mL
	5 mM	0.6246 mL	3.1230 mL	6.2461 mL
	10 mM	0.3123 mL	1.5615 mL	3.1230 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.