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834 Antiprotozoals USP 31 (Emetine Hydrochloride)

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834 Antiprotozoals USP 31 (Emetine Hydrochloride). The hydrochloride of an alka- Profile 4. Molina J-M, et al. Potential efficacy of fumagillin in intestinal loid obtained from ipecacuanha, or prepared by methylation of Ethopabate is an antiprotozoal used in veterinary practice with microsporidiosis due to Enterocytozoon bieneusi in patients with other drugs, such as amprolium, for the control of coccidiosis in HIV infection: results of a drug screening study. AIDS 1997; 11: cephaëline, or prepared synthetically. Anhydrous emetine hydro- 1603–10. chloride is a white or slightly yellowish, odourless, crystalline poultry. 5. Molina J-M, et al. Trial of oral fumagillin for the treatment of powder. Freely soluble in water and in alcohol. Store in airtight intestinal microsporidiosis in patients with HIV infection. AIDS containers at a temperature of 25°, excursions permitted between 2000; 14: 1341–8. 15° and 30°. Protect from light. 6. Molina J-M, et al. Fumagillin treatment of intestinal micro- Etofamide (rINN) sporidiosis. N Engl J Med 2002; 346: 1963–9. Adverse Effects 7. Abramowicz M, ed. Drugs for parasitic infections. 1st ed. New Ethychlordiphene; Etofamida; Étofamide; Etofamidum; K-430. Emetine hydrochloride is commonly associated with aching, ten- Rochelle NY: The Medical Letter, 2007. 2,2-Dichloro-N-(2-ethoxyethyl)-N-[4-(4-nitrophenoxy)benzyl]- derness, stiffness, and weakness of the muscles in the area of the Preparations injection site; there may be necrosis and abscess formation. After acetamide. Proprietary Preparations (details are given in Part 3) injection, diarrhoea and nausea and vomiting, sometimes with Этофамид Fr.: Flisint. dizziness and headache, are common. There may be generalised C19H20Cl2N2O5 = 427.3. muscle weakness and muscular pain, especially in the neck and CAS — 25287-60-9. limbs, and, more rarely, mild sensory disturbances. Eczematous, ATC — P01AC03. urticarial, and purpuric skin lesions have been reported. Furazolidone (BAN, rINN) Cardiovascular effects are considered the most serious and in- Furatsolidoni; Furazolidon; Furazolidona; Furazolidonum; Nifura- clude precordial pain, dyspnoea, tachycardia, and hypotension. zolidonum. 3-(5-Nitrofurfurylideneamino)-2-oxazolidone. CH3 Changes in the ECG, particularly flattening or inversion of the T- Фуразолидон wave and prolongation of the QT interval, occur in many pa- O C8H7N3O5 = 225.2. tients. Emetine accumulates in the body and large doses or pro- CAS — 67-45-8. longed use may cause lesions of the heart, gastrointestinal tract, O ATC — G01AX06. kidneys, liver, and skeletal muscle. Severe acute degenerative ATC Vet — QG01AX06. myocarditis may occur and may give rise to sudden cardiac fail- ure and death. In some patients cardiotoxic effects have appeared -O ON N+ after the completion of treatment with therapeutic doses. O Emetine hydrochloride is very irritant and contact with mucous O membranes should be avoided. Cl Cl O2N O O N N Precautions Emetine is contra-indicated in cardiac, renal, or neuromuscular Profile disease. Its use should be avoided during pregnancy and it should Etofamide, a dichloroacetamide derivative, is a luminal amoebi- Pharmacopoeias. In Br., Fr., and US. not be given to children, except in severe amoebic dysentery un- cide with actions and uses similar to those of diloxanide furoate . A yellow odourless or almost odour- responsive to other drugs. It should be used with great caution in (p.832). BP 2008 (Furazolidone) less crystalline powder. Very slightly soluble in water and in al- old or debilitated patients. Patients given emetine should be Preparations closely supervised; ECG monitoring is advisable during treat- cohol; slightly soluble in chloroform; practically insoluble in (details are given in Part 3) ment. Proprietary Preparations ether. The filtrate from a 1% suspension in water has a pH of 4.5 Braz.: Kitnos; Mex.: Kitnos; Philipp.: Kitnos. to 7.0. Protect from light. Pharmacokinetics USP 31 (Furazolidone). A yellow, odourless, crystalline powder. After injection emetine hydrochloride is concentrated in the liv- Practically insoluble in water, in alcohol, and in carbon tetrachlo- er, and to some extent in kidney, lung, and spleen. Excretion is ride. Store in airtight containers. Protect from light and avoid ex- Fumagillin (BAN, rINN) slow and detectable amounts may persist in urine 40 to 60 days posure to direct sunlight. after treatment has been stopped. Fumagilina; Fumagilliini; Fumagilline; Fumagillinum. 4-(1,2-Epoxy- 1,6-dimethylhex-4-enyl)-5-methoxy-1-oxaspiro[2.5]oct-6-yl hy- Adverse Effects The most common adverse effects of furazolidone involve the Uses and Administration drogen deca-2,4,6,8-tetraenedioate. Emetine, an alkaloid of ipecacuanha (p.1562), is a tissue amoe- gastrointestinal tract and include nausea and vomiting. Dizzi- bicide acting principally in the bowel wall and in the liver. It has Фумагиллин ness, drowsiness, headache, and a general malaise have also been been given by deep subcutaneous or intramuscular injection in C26H34O7 = 458.5. reported. the treatment of severe invasive amoebiasis (p.822), including CAS — 23110-15-8. Allergic reactions, most commonly skin reactions such as rashes hepatic amoebiasis in patients who do not respond to metronida- ATC — P01AX10. or angioedema, may occur. There have been instances of acute zole, although dehydroemetine has tended to replace it. Emetine ATC Vet — QP51AX23. pulmonary reactions, similar to those seen with the structurally was formerly given orally as emetine and bismuth iodide. related drug nitrofurantoin, and of hepatotoxicity. Agranulocyto- Emetine has also been included in combination preparations for sis has been reported rarely. Haemolytic anaemia may occur in the symptomatic relief of cough. H3C patients with G6PD deficiency given furazolidone. CH3 Darkening of the urine has been attributed to the presence of me- Preparations tabolites. O USP 31: Emetine Hydrochloride Injection. OH Precautions O Proprietary Preparations (details are given in Part 3) Furazolidone should be used with caution in those with G6PD deficiency because of the risk of haemolytic anaemia. It should Multi-ingredient: Austria: Spirbon; Cz.: Ipecarin†; Kodynal†; Hung.: O O Radipon; Switz.: Ipeca†; Sano Tuss. H3C not be given to infants under 1 month of age since their enzyme O O systems are immature. H3C Interactions A disulfiram-like reaction has been reported in patients taking Ethopabate (BAN) Profile alcohol while on furazolidone therapy; alcohol should be avoid- Etopabato. Methyl 4-acetamido-2-ethoxybenzoate. Fumagillin is an alicyclic antibiotic produced by certain strains ed during, and for a short period after, treatment with furazo- of Aspergillus fumigatus. It has activity against Microsporidia lidone. C H NO = 237.3. 12 15 4 and is used in veterinary practice to control Nosema apis infec- Furazolidone is an MAOI and the cautions advised for these CAS — 59-06-3. tion in honeybees. Fumagillin is given in an oral dose of 20 mg drugs regarding use with other drugs, especially indirect-acting ATC Vet — QP51AX17. three times daily for 14 days in the treatment of diarrhoea due to sympathomimetic amines, and the consumption of food and intestinal microsporidial infection with Enterocytozoon bieneusi drink containing tyramine, should be observed (see Phenelzine in patients with HIV infection. It has also been tried in humans in Sulfate, p.417). However, there appear to be no reports of hyper- H C the topical treatment of microsporidial keratoconjunctivitis. It tensive crises in patients receiving furazolidone and it has been 3 was formerly given orally in the treatment of intestinal amoebia- suggested that, since furazolidone inhibits monoamine oxidase sis, but produced an unacceptably high frequency of adverse ef- gradually over several days, the risks are small if treatment is O fects. Analogues of fumagillin have been studied for effects on limited to a 5-day course. Toxic psychosis has been reported in a angiogenesis in solid tumours. patient receiving furazolidone and amitriptyline (see Antiproto- O zoals, under Interactions of Amitriptyline, p.380). Microsporidiosis. As discussed on p.826, topical treatment of NH microsporidial keratoconjunctivitis has been disappointing. Pharmacokinetics O O There have been several reports of successful treatment in indi- Although furazolidone has been considered to be largely unab- vidual patients using fumagillin topically,1-3 usually as a solution sorbed when given orally, the occurrence of systemic adverse ef- CH3 H3C of bicyclohexylammonium fumagillin containing the equivalent fects and coloured metabolites in the urine suggest that this may of fumagillin 70 micrograms/mL. not be the case. Rapid and extensive metabolism, possibly in the Pharmacopoeias. In US for veterinary use only. Also in Oral fumagillin has been effective in the treatment of diarrhoea intestine, has been proposed. BP(Vet). due to intestinal microsporidial infection with Enterocytozoon Uses and Administration BP(Vet) 2008 (Ethopabate). A white or pinkish-white powder. bieneusi in patients with HIV infection.4-7 Furazolidone is a nitrofuran derivative with antiprotozoal and an- Very slightly soluble in water; sparingly soluble in alcohol; solu- 1. Rosberger DF, et al. Successful treatment of microsporidial kera- tibacterial activity. It is active against the protozoan Giardia in- ble in chloroform and in methyl alcohol; slightly soluble in ether. toconjunctivitis with topical fumagillin in a patient with AIDS. testinalis (Giardia lamblia) and against
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