13-02199. Chlorphenoxamide [Archived]

Nomenclature

CAS number: 3576-64-5
2,2-Dichloro-N-(2-hydroxyethyl)-N-[[4-(4-nitrophenoxy)phenyl]methyl]acetamide; N-(β-hydroxyethyl)-N-[p-(4-nitrophenoxy)benzyl]dichloroacetamide; N-(β-hydroxyethyl)-N-[p-phenoxy-(4′-nitro)benzyl]dichloroacetamide; dichloro-N-(β-hydroxyethyl)-N-[p-(4′-nitrophenoxy)benzyl]acetamide; clefamide; chlorophenoxamide; Mebinol (Erba).
C17H16Cl2N2O5; mol wt 399.23.
C 51.14%, H 4.04%, Cl 17.76%, N 7.02%, O 20.04%.

Description and references

Prepn: Logemann et al., Farmaco Ed. Sci. 13, 139 (1958); US 2824894 (1958 to Carlo Erba). Antiamebic activity and toxicity data: Carneri, G. Mal. Infett. Parassit. 10, 850 (1958), C.A. 53, 5519C (1959).

Chemical structure

Properties

Crystals from 95% ethanol, mp 136-137°. Practically insol in water (soly ≈3 γ/ml). Sol in ethanol, acetone, dioxane. LD50 in mice (mg/kg): >5000 orally, 2000 i.p. (Carneri).

Note

Do not confuse with chlorphenoxamine.

Therapeutic Category

Antiamebic.

Keywords

Antiamebic

Status

This monograph has been retired and is no longer subject to revision or update.