Chlorguanide
Title: Chlorguanide
CAS Registry Number: 500-92-5
CAS Name: N-(4-Chlorophenyl)-N¢-(1-methylethyl)imidodicarbonimidic diamide
Additional Names: 1-(p-chlorophenyl)-5-isopropylbiguanide; N1-p-chlorophenyl-N5-isopropyldiguanide; chloroguanide; proguanil
Molecular Formula: C11H16ClN5
Molecular Weight: 253.73
Percent Composition: C 52.07%, H 6.36%, Cl 13.97%, N 27.60%
Literature 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 Rhône-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°.
Melting point: mp 129°
 
Derivative Type: Acetate
Molecular Formula: C11H16ClN5.C2H4O2
Molecular Weight: 313.78
Percent Composition: C 49.76%, H 6.42%, Cl 11.30%, N 22.32%, O 10.20%
Properties: Crystals from acetone, mp 189-190°.
Melting point: mp 189-190°
 
Derivative Type: Hydrochloride
CAS Registry Number: 637-32-1
Manufacturers' Codes: M-4888; RP-3359; SN-12837
Trademarks: Paludrine (AstraZeneca)
Molecular Formula: C11H16ClN5.HCl
Molecular Weight: 290.19
Percent Composition: 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).
Melting point: mp 243-244°
Absorption maximum: uv max (alc): 259 nm
Toxicity data: LD50 orally in rats: 200 mg/kg (Schmidt)
 
Therap-Cat: Antimalarial.
Keywords: Antimalarial.

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