Emetine Hydrochloride

(BANM)
Emetine Hydrochloride Chemical formula
Synonyms: Cloridrato de Emetina; Emet. Hydrochlor.; Emetiinihydrokloridi; Emetina, hidrocloruro de; Emetin-dihydrochlorid; Émétine, chlorhydrate d’; Emetine Dihydrochloride; Emetin-hidroklorid; Emetinhydroklorid; Emetini Chloridum; Emetini Dihydrochloridum; Emetini hydrochloridum; Emetino hidrochloridas; Emetyny dichlorowodorek; Ipecine Hydrochloride; Methylcephaëline Hydrochloride. 6′,7′,10,11-Tetramethoxyemetan dihydrochloride heptahydrate; (2S,3R,11bS)-3-Ethyl-1,3,4,6,7,11b-hexahydro9,10-dimethoxy-2-[(1R)-1,2,3,4-tetrahydro-6,7-dimethoxy-1isoquinolylmethyl]-2H-benzo[a]quinolizine dihydrochloride heptahydrate.
Cyrillic synonym: Эметина Гидрохлорид.

💊 Chemical information

Chemical formula: C29H40N2O4,2HCl,7H2O = 679.7.
CAS — 483-18-1 (emetine); 316-42-7 (anhydrous emetine hydrochloride); 7083-71-8 (emetine hydrochloride, hydrate); 79300-08-6 (emetine hydrochloride, heptahydrate).
ATC — P01AX02.

Pharmacopoeias.

In Chin., Eur., and Viet. Eur. also has a monograph for Emetine Hydrochloride Pentahydrate; Int. permits the heptahydrate or pentahydrate in the same monograph. US has a monograph for the anhydrous salt.

Ph. Eur. 6.2 (Emetine Hydrochloride Heptahydrate; Emetine Hydrochloride BP 2008). A white or slightly yellow crystalline powder. Freely soluble in water and in alcohol. A 2% solution in water has a pH of 4.0 to 6.0. Protect from light.

Ph. Eur. 6.2 (Emetine Hydrochloride Pentahydrate ). A white or slightly yellow crystalline powder. Freely soluble in water and in alcohol. A 2% solution in water has a pH of 4.0 to 6.0. Protect from light.

USP 31

(Emetine Hydrochloride). The hydrochloride of an alkaloid obtained from ipecacuanha, or prepared by methylation of cephaëline, or prepared synthetically. Anhydrous emetine hydrochloride is a white or slightly yellowish, odourless, crystalline powder. Freely soluble in water and in alcohol. Store in airtight containers at a temperature of 25°, excursions permitted between 15° and 30°. Protect from light.

💊 Adverse Effects

Emetine hydrochloride is commonly associated with aching, tenderness, stiffness, and weakness of the muscles in the area of the injection site; there may be necrosis and abscess formation. After injection, diarrhoea and nausea and vomiting, sometimes with dizziness and headache, are common. There may be generalised muscle weakness and muscular pain, especially in the neck and limbs, and, more rarely, mild sensory disturbances. Eczematous, urticarial, and purpuric skin lesions have been reported. Cardiovascular effects are considered the most serious and include precordial pain, dyspnoea, tachycardia, and hypotension. Changes in the ECG, particularly flattening or inversion of the Twave and prolongation of the QT interval, occur in many patients. Emetine accumulates in the body and large doses or prolonged use may cause lesions of the heart, gastrointestinal tract, kidneys, liver, and skeletal muscle. Severe acute degenerative myocarditis may occur and may give rise to sudden cardiac failure and death. In some patients cardiotoxic effects have appeared after the completion of treatment with therapeutic doses. Emetine hydrochloride is very irritant and contact with mucous membranes should be avoided.

💊 Precautions

Emetine is contra-indicated in cardiac, renal, or neuromuscular disease. Its use should be avoided during pregnancy and it should not be given to children, except in severe amoebic dysentery unresponsive to other drugs. It should be used with great caution in old or debilitated patients. Patients given emetine should be closely supervised; ECG monitoring is advisable during treatment.

💊 Pharmacokinetics

After injection emetine hydrochloride is concentrated in the liver, and to some extent in kidney, lung, and spleen. Excretion is slow and detectable amounts may persist in urine 40 to 60 days after treatment has been stopped.

💊 Uses and Administration

Emetine, an alkaloid of ipecacuanha, is a tissue amoebicide acting principally in the bowel wall and in the liver. It has been given by deep subcutaneous or intramuscular injection in the treatment of severe invasive amoebiasis, including hepatic amoebiasis in patients who do not respond to metronidazole, although dehydroemetine has tended to replace it. Emetine was formerly given orally as emetine and bismuth iodide. Emetine has also been included in combination preparations for the symptomatic relief of cough.

💊 Preparations

USP 31: Emetine Hydrochloride Injection. Proprietary PreparationsMulti-ingredient: Austria: Spirbon; Cz.: Ipecarin†; Kodynal†; Hung.: Radipon; Switz.: Ipeca†; Sano Tuss.
Published November 14, 2018.