66-75-1

IARC Cancer Review: Group 2B IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man 7 (1987),p. 370.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; Animal Sufficient Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man 9 (1975),p. 235.(World Health Organization, Internation Agency for Research on Cancer,Lyon, France.: ) (Single copies can be ordered from WHO Publications Centre U.S.A., 49 Sheridan Avenue, Albany, NY 12210) ; NCI Carcinogenesis Studies (ipr); Clear Evidence: mouse, rat RRCRBU    Recent Results in Cancer Research. 52 (1975),1. . EPA Genetic Toxicology Program.

The IUPAC name of 5-(Bis(2-chloroethyl)amino)uracil is 5-[bis(2-chloroethyl)amino]-1H-pyrimidine-2,4-dione. With the CAS registry number 66-75-1 and EINECS 200-631-3, it is also named as Uracil mustard. The classification codes are Alkylating Agents; Antineoplastic; Antineoplastic Agents; Antineoplastic agents, alkylating; Drug / Therapeutic Agent; Mutation data; Noxae; Tumor data. It is creamy white crystals or off-white powder which is slightly soluble in water. It is also highly toxic and flammable. The storage environment should be well-ventilated, low-temperature and dry. Keep 5-(Bis(2-chloroethyl)amino)uracil separate from raw materials of food.

The other characteristics of this product can be summarized as: (1)ACD/LogP: 1.13; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.13; (4)ACD/LogD (pH 7.4): 1.13; (5)ACD/BCF (pH 5.5): 4.28; (6)ACD/BCF (pH 7.4): 4.28; (7)ACD/KOC (pH 5.5): 98.6; (8)ACD/KOC (pH 7.4): 98.57; (9)#H bond acceptors: 5; (10)#H bond donors: 2; (11)#Freely Rotating Bonds: 5; (12)Polar Surface Area: 43.86 Å²; (13)Index of Refraction: 1.574; (14)Molar Refractivity: 57.8 cm³; (15)Molar Volume: 174.9 cm³; (16)Polarizability: 22.91×10^-24 cm³; (17)Surface Tension: 54.6 dyne/cm; (18)Rotatable Bond Count: 5; (19)Tautomer Count: 9; (20)Exact Mass: 251.022832; (21)MonoIsotopic Mass: 251.022832; (22)Topological Polar Surface Area: 61.4; (23)Heavy Atom Count: 15; (24)Complexity: 288.

Uses of 5-(Bis(2-chloroethyl)amino)uracil: It is used in lymphatic malignancies, and causes mainly gastrointestinal and bone marrow damage. It works by damaging DNA, primarily in cancer cells that preferentially take up the uracil due to their need to make nucleic acids during their rapid cycles of cell division.

People can use the following data to convert to the molecule structure. 
1. SMILES:O=C1C(\N(CCCl)CCCl)=C/NC(=O)N1
2. InChI:InChI=1/C8H11Cl2N3O2/c9-1-3-13(4-2-10)6-5-11-8(15)12-7(6)14/h5H,1-4H2,(H2,11,12,14,15) 
3. InChIKey:IDPUKCWIGUEADI-UHFFFAOYAW

The following are the toxicity data which has been tested.