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142 Anthelmintics

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142 Anthelmintics 142 Anthelmintics Antimony sodium tartrate was formerly used as an emetic. The Bithionol (BAN, rINN) Profile sodium tartrate and potassium tartrate have also been used as ex- Cambendazole is a benzimidazole carbamate anthelmintic struc- Bithionololum; Bithionolum; Bitionol; Bitionolol; Bitionololi. 2,2′- pectorants. turally related to tiabendazole (p.156). It is used in the treatment Thiobis(4,6-dichlorophenol). of strongyloidiasis. Preparations Битионол Preparations Proprietary Preparations (details are given in Part 3) C12H6Cl4O2S = 356.1. CAS — 97-18-7. Proprietary Preparations (details are given in Part 3) Multi-ingredient: Thai.: Brown Mixture. ATC — D10AB01; P02BX01. Braz.: Cambem†. ATC Vet — QD10AB01; QP52AG07. Multi-ingredient: Braz.: Exelmin†. Ascaridole Cl Cl Chenopodium Oil Ascaridol. 1-Isopropyl-4-methyl-2,3-dioxabicyclo[2.2.2]oct-5- ene. OH Aceite de quenopodio; Aetheroleum Chenopodii; Esencia de Quenopodio Vermifuga; Oil of American Wormseed; Wurmsa- Аскаридол menöl. C10H16O2 = 168.2. Cl S Cl Амброзиевое Масло; Маревое Масло CAS — 512-85-6. CAS — 8006-99-3. OH Profile Pharmacopoeias. Fr. includes bithionol oxide for veterinary Chenopodium oil is distilled with steam from the fresh flowering use. and fruiting plants, excluding roots, of Chenopodium ambrosio- CH3 ides var. anthelminticum. It contains ascaridole. It was formerly H3C Adverse Effects used as an anthelmintic for the expulsion of roundworms (As- OO Adverse effects in patients taking bithionol by mouth include an- caris) and hookworms. It is toxic and has caused numerous fatal- CH3 orexia, nausea, vomiting, abdominal discomfort, diarrhoea, sali- ities. vation, dizziness, headache, and skin rashes. Handling. Chenopodium oil may explode when heated. Profile Photosensitivity reactions have occurred in persons using soap Ascaridole is the active principle of chenopodium oil (p.142) and containing bithionol. Cross-sensitisation with other halogenated has the same actions. disinfectants has also occurred. Uses and Administration Clorsulon (BAN, USAN, rINN) Handling. Ascaridole is an unstable liquid which is liable to ex- Bithionol is a chlorinated bis-phenol with bactericidal and an- plode when heated or when treated with organic acids. Clorsulón; Clorsulone; Clorsulonum; MK-401. 4-Amino-6- thelmintic properties. It is active against most trematodes (trichlorovinyl)benzene-1,3-disulphonamide. (flukes). Bithionol is used in preference to praziquantel in fasci- Клорсулон oliasis (see Liver Fluke Infections, p.137) and is also used in paragonimiasis (see Lung Fluke Infections, p.137) as an alterna- C8H8Cl3N3O4S2 = 380.7. Bephenium Hydroxynaphthoate (BAN, rINN) tive to praziquantel. It may be given in an oral dose of 30 to CAS — 60200-06-8. Bephenii Hydroxynaphthoas; Béphénium, Hydroxynaphtoate de; 50 mg/kg on alternate days for 10 to 15 doses. Alternatively, for Hidroxinaftoato de befenio; Naphthammonum. Benzyldime- fascioliasis, WHO recommends a regimen of 30 mg/kg daily for 5 days. H N thyl(2-phenoxyethyl)ammonium 3-hydroxy-2-naphthoate. 2 O Bithionol was formerly used topically as a bactericide but this S Бефения Гидроксинафтоат use has declined because of photosensitivity reactions. O Cl O C28H29NO4 = 443.5. Preparations S NH CAS — 7181-73-9 (bephenium); 3818-50-6 (bephenium Proprietary Preparations (details are given in Part 3) 2 hydroxynaphthoate). Multi-ingredient: Arg.: Fonergine. Cl O ATC — P02CX02. Cl NH2 CH3 Bromofenofos (rINN) Pharmacopoeias. In US for veterinary use only. USP 31 (Clorsulon). A white to off-white powder. Slightly sol- O COO Bromfenofos; Bromofénofos; Bromofenofós; Bromofenofosum; N uble in water; freely soluble in acetonitrile and in methyl alcohol; Bromophenophos; Bromphenphos. 3,3′,5,5′-Tetrabromo-2,2′- very slightly soluble in dichloromethane. CH3 OH biphenyldiolmono(dihydrogen phosphate). Бромофенофос Profile Clorsulon is an anthelmintic used in veterinary medicine for the Pharmacopoeias. In Int. C12H7Br4O5P = 581.8. treatment of liver fluke infections. CAS — 21466-07-9. Profile ATC Vet — QP52AB02. Bephenium hydroxynaphthoate is an anthelmintic formerly used in the treatment of hookworm infections, ascariasis, and tricho- strongyliasis. Closantel (BAN, USAN, rINN) Br Closantelum; R-31520. 5′-Chloro-4′-(4-chloro-α-cyanobenzyl)- 3,5-di-iodosalicyl-o-toluidide. OH Клозантел Betanaphthol Br C22H14Cl2I2N2O2 = 663.1. β-Naftol; 2-Naftol; Naphthol. Naphth-2-ol. Br CAS — 57808-65-8. HO ATC Vet — QP52AG09. Бета-нафтол O C H O = 144.2. P 10 8 O CAS — 135-19-3. OH Br Cl I Profile O CH OH Bromofenofos is an organophosphorus compound (see Organo- 3 phosphorus Insecticides, p.2047) used as an anthelmintic in vet- erinary medicine for the treatment of fluke infections. HN IOH Pharmacopoeias. In Pol. and Swiss. Cl N Cambendazole (BAN, USAN, rINN) Profile Betanaphthol was formerly used as an anthelmintic in hook- Cambendazol; Cambendazolum; MK-905. Isopropyl 2-(thiazol-4- worm and tapeworm infections, but it has been superseded by yl)-1H-benzimidazol-5-ylcarbamate. Closantel Sodium (BANM, rINNM) less toxic and more efficient drugs. Камбендазол Closantel sódico; Closantel sodique; Closantelum natricum; Klosanteelinatrium; Klosantel sodná sůl; Klosantelnatrium; Natrii Betanaphthol has a potent parasiticidal effect and has been used C14H14N4O2S = 302.4. topically in the treatment of scabies, ringworm, and other skin CAS — 26097-80-3. Closantelum; R-34828. diseases. ATC Vet — QP52AC08. Натрий Клозантел Betanaphthyl benzoate has been used in preparations for the C22H14Cl2I2N2O2Na = 686.1. treatment of gastrointestinal disorders. H Pharmacopoeias. In Eur. (see p.vii) as the dihydrate for veter- N inary use. Preparations CH3 O S Ph. Eur. 6.2 (Closantel Sodium Dihydrate for Veterinary Use; Proprietary Preparations (details are given in Part 3) Closantel Sodium Dihydrate BP(Vet) 2008). A yellow, slightly N N hygroscopic, powder. It exhibits polymorphism. Very slightly Multi-ingredient: Arg.: Hekabetol; Austria: Salvyl. H3C O N H soluble in water; freely soluble in alcohol; soluble in methyl al- cohol. Store in airtight containers. Protect from light. Ascaridole/Diethylcarbamazine Citrate 143 Profile Pharmacopoeias. In Chin., Eur. (see p.vii), Int., Jpn, and US. normally excluded when diethylcarbamazine is used in Closantel is an anthelmintic used in veterinary medicine for the Ph. Eur. 6.2 (Diethylcarbamazine Citrate). A white or almost mass treatment schedules. treatment of fluke and nematode infections. white, crystalline, slightly hygroscopic powder. Very soluble in Effects on the eyes. Loss of eyesight was reported in 11 wom- water; soluble in alcohol; practically insoluble in acetone. Store Pregnancy. Pregnant women are normally excluded when di- en who received closantel (Flukiver) in mistake for a gynaeco- in airtight containers. ethylcarbamazine is used in mass treatment schedules. logical product.1 Sight was restored after closantel was stopped USP 31 (Diethylcarbamazine Citrate). A white, crystalline, Animal studies1 suggest that the uterine hypermotility induced by but incapacitating eye pain remained. slightly hygroscopic powder, odourless or has a slight odour. diethylcarbamazine is mediated via prostaglandin synthesis; this 1. ’t Hoen E, et al. Harmful human use of donated veterinary drug. Very soluble in water; sparingly soluble in alcohol; practically in- might explain the mechanism of the abortifacient action previ- Lancet 1993; 342: 308–9. soluble in acetone, in chloroform, and in ether. Store in airtight ously reported.2 containers. 1. Joseph CA, Dixon PAF. Possible prostaglandin-mediated effect of diethylcarbamazine on rat uterine contractility. J Pharm Phar- Diamfenetide (BAN, rINN) Adverse Effects macol 1984; 36: 281–2. Adverse effects directly attributable to diethylcar- 2. Subbu VSV, Biswas AR. Ecbolic effect of diethyl carbamazine. Diamfenetida; Diamfénétide; Diamfenetidum; Diamphenethide. Indian J Med Res 1971; 59: 646–7. β,β′-Oxybis(aceto-p-phenetidide). bamazine include nausea and vomiting. Headache, diz- Диамфенетид ziness, and drowsiness may occur. Renal impairment. For a study on the effects of renal impair- C H N O = 372.4. ment on the pharmacokinetics of diethylcarbamazine, see under 20 24 2 5 Hypersensitivity reactions arise from the death of the Pharmacokinetics, below. CAS — 36141-82-9. microfilariae. These can be serious, especially in on- chocerciasis where there may also be sight-threatening Pharmacokinetics O O O O O ocular toxicity; fatalities have been reported. Encepha- Diethylcarbamazine is readily absorbed from the gas- litis may be exacerbated in patients with loiasis and fa- trointestinal tract and also through the skin and con- HC N N CH talities have occurred. H H junctiva. It is widely distributed in tissues and is mainly ◊ Reactions occurring during diethylcarbamazine treatment of excreted in the urine unchanged and as the N-oxide Profile lymphatic filariasis are basically of 2 types: pharmacological metabolite. Urinary excretion and hence plasma half- Diamfenetide is an anthelmintic that has been used in veterinary dose-dependent responses and a response of the infected host to medicine for the control of fascioliasis in sheep. 1 life is dependent on urinary pH. About 5% of a dose is the destruction and death of parasites. eliminated in the faeces. • Reactions of the first type include weakness, dizziness, lethar- gy, anorexia, and nausea. They begin within 1 to 2 hours of Disposition. A pharmacokinetic study in 6 patients with Dichlorophen (BAN, rINN) taking diethylcarbamazine, and persist for a
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