2,4-Pyrimidinediamine,5-(4-chlorophenyl)-6-ethyl-

IARC Cancer Review: Group 3 IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 7 ,1987,p. 56.(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 Limited Evidence IMEMDT    IARC Monographs on the Evaluation of Carcinogenic Risk of Chemicals to Man . 13 ,1977,p. 233.(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 Bioassay (feed); Inadequate Studies: mouse NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-77 ,1978. ; (feed); No Evidence: rat NCITR*    National Cancer Institute Carcinogenesis Technical Report Series. (Bethesda, MD 20014) No. NCI-CG-TR-77 ,1978. . EPA Genetic Toxicology Program.

The Pyrimethamine, with the CAS registry number 58-14-0 and EINECS registry number 200-364-2, has the systematic name of 5-(4-chlorophenyl)-6-ethylpyrimidine-2,4-diamine. It is also called Daraprim, and the molecular formula of this chemical is C₁₂H₁₃ClN₄. It is a kind of white solid, and harmful if swallowed, so you had better be careful. It is sensitive to exposure to light, and insoluble in water. What's more, it should be stored at 0-6°C.

The physical properties of Pyrimethamine are as following: (1)ACD/LogP: 2.75; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): 1.49; (4)ACD/LogD (pH 7.4): 2.66; (5)ACD/BCF (pH 5.5): 3.95; (6)ACD/BCF (pH 7.4): 58.84; (7)ACD/KOC (pH 5.5): 40.66; (8)ACD/KOC (pH 7.4): 606.32; (9)#H bond acceptors: 4; (10)#H bond donors: 4; (11)#Freely Rotating Bonds: 2; (12)Polar Surface Area: 32.26 Å²; (13)Index of Refraction: 1.655; (14)Molar Refractivity: 69.94 cm³; (15)Molar Volume: 190.4 cm³; (16)Polarizability: 27.72×10^-24cm³; (17)Surface Tension: 61.3 dyne/cm; (18)Density: 1.305 g/cm³; (19)Flash Point: 251 °C; (20)Enthalpy of Vaporization: 75.82 kJ/mol; (21)Boiling Point: 491.5 °C at 760 mmHg; (22)Vapour Pressure: 8.34E-10 mmHg at 25°C.

Applications of Pyrimethamine: It is a medication used for protozoal infections,. It is commonly used as an antimalarial drug (for both treatment and prevention of malaria). and combined with sulfadiazine, it can be used in the treatment of Toxoplasma gondii infections in immunocompromised patients, such as HIV-positive individuals. What's more, it is one of the folic acid antagonists that is used as an antimalarial or with a sulfonamide to treat toxoplasmosis.

Uses of Pyrimethamine: It can react with butyric acid anhydride to produce N-[2-butyrylamino-5-(4-chloro-phenyl)-6-ethyl-pyrimidin-4-yl]-butyramide. This reaction will need heating, and the yield is about 77%.

You can still convert the following datas into molecular structure:
(1)SMILES: Clc2ccc(c1c(nc(nc1CC)N)N)cc2
(2)InChI: InChI=1/C12H13ClN4/c1-2-9-10(11(14)17-12(15)16-9)7-3-5-8(13)6-4-7/h3-6H,2H2,1H3,(H4,14,15,16,17)
(3)InChIKey: WKSAUQYGYAYLPV-UHFFFAOYAW

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
chicken	LDLo	intraperitoneal	75mg/kg (75mg/kg)		United States Patent Document. Vol. #3919229,
hamster	LDLo	oral	250mg/kg (250mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD	Teratology, The International Journal of Abnormal Development. Vol. 4, Pg. 205, 1971.
infant	TDLo	unreported	19mg/kg/31D-I (19mg/kg)	BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: COMA BLOOD: NORMOCYTIC ANEMIA	Journal of Analytical Toxicology. Vol. 17, Pg. 248, 1993.
mouse	LD50	intraperitoneal	74mg/kg (74mg/kg)		European Journal of Medicinal Chemistry--Chimie Therapeutique. Vol. 9, Pg. 658, 1974.
mouse	LD50	oral	92mg/kg (92mg/kg)		British Journal of Pharmacology and Chemotherapy. Vol. 6, Pg. 185, 1951.
mouse	LDLo	subcutaneous	160mg/kg (160mg/kg)		Journal of Medicinal Chemistry. Vol. 16, Pg. 1399, 1973.
rat	LD50	intraperitoneal	70mg/kg (70mg/kg)		"International Congress of Chemotherapy, Proceedings of the 3rd Congress, 1963," Kuemmerle, H.P., and Prezios, P., Stuttgart, Fed. Rep. Ger., Georg Thieme Verlag, 1964Vol. -, Pg. 367, 1964.
rat	LD50	oral	440mg/kg (440mg/kg)	BEHAVIORAL: TREMOR BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ATAXIA	Journal of Chemotherapy. Vol. 5, Pg. 400, 1993.