2090. Chlorguanide
Nomenclature
CAS number: 500-92-5
N-(4-Chlorophenyl)-N′-(1-methylethyl)imidodicarbonimidic
diamide; 1-(p-chlorophenyl)-5-isopropylbiguanide; N1-p-chlorophenyl-N5-isopropyldiguanide; chloroguanide; proguanil. C11H16ClN5; mol wt 253.73.
C 52.07%, H 6.36%, Cl 13.97%, N 27.60%.
Description and references
Prepn: Curd, Rose, J. Chem. Soc. 1946, 729; Curd et al., ibid. 1948, 1630; Ainley et al., ibid. 1949, 98. Manuf of acetate: Gailliot, FR 1001548 (1952 to Rh^one-Poulenc), C.A. 51, 7411e (1957). Toxicity study: Schmidt et al., J. Pharmacol. Exp. Ther. 90, 233 (1947).
Properties
Rectangular plates from toluene, mp 129°.Derivative
Acetate.C11H16ClN5.C2H4O2; mol wt 313.78.
C 49.76%, H 6.42%, Cl 11.30%, N 22.32%, O 10.20%.
Properties
Crystals from acetone, mp 189-190°.Derivative
Hydrochloride.Nomenclature
CAS number: 637-32-1
M-4888; RP-3359; SN-12837; Paludrine (AstraZeneca). C11H16ClN5.HCl; mol wt 290.19.
C 45.53%, H 5.90%, Cl 24.43%, N 24.13%.
Properties
Crystals from water or aq ethanol, mp 243-244°. uv max (alc): 259 nm. Sol in alc; slightly sol in water. Practically insol in chloroform and ether. pH of satd aq soln 5.8-6.3. LD50 orally in rats: 200 mg/kg (Schmidt).Therapeutic Category
Antimalarial.
Keywords
Antimalarial