Naftalofos (BAN, USAN, rINN) Niclosamide Monohydrate (BANM) Niclosamida Mono-hidratada; Niclosamida monohidrato; Bay-9002; E-9002; ENT-25567; Naftalofós; Naftalofosum; Naph- O thalophos; Phthalophos; S-940. Diethyl naphthalimido-oxyphos- Niclosamide monohydraté; Niclosamidum monohydricum; Nik- phonate. losamid monohydrát; Niklosamidimonohydraatti; Niklosamid- monohydrat; Niklozamidas monohidratas; Niklozamid-mono- S Нафталофос hidrát. O2NN C H NO P = 349.3. Никлозамид Моногидрат 16 16 6 Profile CAS — 1491-41-4. C13H8Cl2N2O4,H2O = 345.1. ATC — P02DA01. Nitroscanate is an isothiocyanate anthelmintic used in veterinary ATC Vet — QP52AB06. medicine. Pharmacopoeias. In Eur. (see p.vii). Int. permits the monohydrate or the anhydrous substance under the title Niclosamide. O Ph. Eur. 6.2 (Niclosamide Monohydrate). Yellowish, fine crys- Nitroxinil (BAN, rINN) CH O 3 tals. Practically insoluble in water; slightly soluble in dehydrated Nitroxinilo; Nitroxinilum; Nitroxynil. 4-Hydroxy-3-iodo-5-ni- alcohol; sparingly soluble in acetone. Protect from light. NOPO trobenzonitrile. Нитроксинил OCH3 Adverse Effects C7H3IN2O3 = 290.0. O Gastrointestinal disturbances may occur occasionally CAS — 1689-89-0 (nitroxinil); 27917-82-4 (nitroxinil eg- with niclosamide. Lightheadedness and pruritus have lumine). ATC Vet — QP52AG08. Profile been reported less frequently. Naftalofos is an organophosphorus compound (see Organophos- phorus Insecticides, p.2047) used as an anthelmintic in veteri- Pharmacokinetics OH nary medicine. Niclosamide is not significantly absorbed from the gastrointestinal tract. INO2 Uses and Administration Netobimin (BAN, USAN, rINN) Niclosamide is an anthelmintic which is active against Netobimina; Nétobimine; Netobiminum; Sch-32481. 2-{3-Meth- most tapeworms, including the beef tapeworm (Taenia CN oxycarbonyl-2-[2-nitro-5-(propylthio)phenyl]guanidi- saginata), the pork tapeworm (T. solium), the fish tape- no}ethanesulphonic acid. worm (Diphyllobothrium latum) and the dog tape- Pharmacopoeias. In BP(Vet). Also in Fr. for veterinary use only. Нетобимин worm (Dipylidium caninum); it has also been given for BP(Vet) 2008 (Nitroxinil). A yellow to yellowish brown pow- infections with the dwarf tapeworm, Hymenolepis C14H20N4O7S2 = 420.5. der. Practically insoluble in water; slightly soluble in alcohol; CAS — 88255-01-0. nana. For discussions of the treatment of tapeworm in- sparingly soluble in ether; it dissolves in solutions of alkali hy- fections, see Diphyllobothriasis, p.136, Hymenolepia- droxides. Protect from light. ATC Vet — QP52AC06. sis, p.136, and Taeniasis, p.139. The activity of niclosa- Profile mide against these worms appears to be due to Nitroxinil is an anthelmintic used in veterinary medicine for the inhibition of mitochondrial oxidative phosphorylation; treatment of fascioliasis and some gastrointestinal roundworms HO OCH3 O anaerobic ATP production is also affected. in cattle and sheep. S O O Niclosamide is given as tablets, which must be chewed NH S thoroughly before swallowing and washed down with HN CH3 water. Oxamniquine (BAN, USAN, rINN) N For infections with pork tapeworm a single 2-g dose is Oxamniquina; Oxamniquinum; UK-4271. 1,2,3,4-Tetrahydro-2- given after a light breakfast. Niclosamide is not active isopropylaminomethyl-7-nitro-6-quinolylmethanol. Оксамнихин -O N+ against the larval form (cysticerci) and, although the risk of inducing cysticercosis appears to be theoretical, C14H21N3O3 = 279.3. O a laxative is given about 2 hours after the dose to expel CAS — 21738-42-1. the killed worms and minimise the possibility of the ATC — P02BA02. Profile ATC Vet — QP52AA02. Netobimin is an anthelmintic used in veterinary medicine. migration of ova of T. solium into the stomach; an an- tiemetic may also be given before treatment.
For infections with beef or fish tapeworms the 2-g dose O CH3 H of niclosamide may be divided, with 1 g taken after N+ N - (BAN, USAN, rINN) breakfast and 1 g an hour later. ONCH3 Niclosamide H In dwarf-tapeworm infections an initial dose of 2 g has HO Anhydrous Niclosamide; Bay-2353; Niclosamida; Niclosamida been given on the first day followed by 1 g daily for 6 Anidra; Niclosamide anhydre; Niclosamidum; Niclosamidum an- days. hydricum; Niklosamid; Niklosamid, vattenfri; Niklosamidi; Niklos- Pharmacopoeias. In Fr. and Int. amidi, vedetön; Niklozamid; Niklozamid bezwodny; Niklozami- Children aged 2 to 6 years are given half the above dos- das, bevandenis; Phenasale; Vízmentes niklozamid. 2′,5-Dichloro- es and those under 2 years of age are given one-quarter Adverse Effects 4′-nitrosalicylanilide; 5-Chloro-N-(2-chloro-4-nitrophenyl)-2-hy- the above doses. Oxamniquine causes severe pain at the injection site droxybenzamide. Unless expulsion of the worm is aided by a laxative, when given intramuscularly and is no longer given by Никлозамид portions are voided in a partially digested form after this route. treatment with niclosamide; the scolex is rarely identi- C13H8Cl2N2O4 = 327.1. It is generally well tolerated after oral doses, although fiable. dizziness with or without drowsiness occurs in at least CAS — 50-65-7. In schistosomiasis (p.138), niclosamide is used as a a third of patients, beginning up to 3 hours after a dose ATC — P02DA01. molluscicide in water-treatment control programmes. and usually lasting for up to 6 hours. Headache and ATC Vet — QP52AG03. Preparations gastrointestinal effects such as nausea, vomiting, and BP 2008: Niclosamide Tablets. diarrhoea are also common. Proprietary Preparations (details are given in Part 3) Allergic-type reactions including urticaria, pruritic OH Belg.: Yomesan; Braz.: Atenase†; Cz.: Yomesan†; Denm.: Yomesan†; Cl Fin.: Kontal; Fr.: Tredemine; Ger.: Yo m e s a n ; Gr.: Tredemine; Yomesan; In- skin rashes, and fever may occur. Liver enzyme values H dia: Niclosan; Israel: Yo m e s a n ; Ital.: Yo m e s a n ; Mex.: Overoid; Neth.: have been raised transiently in some patients. Epilepti- N Yo m e s a n ; S.Afr.: Yo m e s a n ; Swed.: Yo m e sa n ; Thai.: Manozide; Niclosan†; Cl Telmitin; Unicide; Yomesan; Turk.: Yo m e s a n ; UK: Yo m e s a n . form convulsions have been reported, especially in pa- Multi-ingredient: Thai.: Zenda†. tients with a history of convulsive disorders. Hallucina- O tions and excitement have occurred rarely. NO2 A reddish discoloration of urine, probably due to a me- Nitroscanate (BAN, USAN, rINN) Pharmacopoeias. In Chin. and Eur. (see p.vii). tabolite of oxamniquine, has been reported. Int. permits the anhydrous substance or the monohydrate under CGA-23654; Nitroscanato; Nitroscanatum; Nitroskanaatti; Ni- Effects on body temperature. A review1 in 1987 noted that the title Niclosamide. troskanat. 4-(4-Nitrophenoxy)phenyl isothiocyanate. although a modest post-treatment rise in temperature had been Ph. Eur. 6.2 (Niclosamide, Anhydrous). Yellowish-white to yel- Нитросканат reported occasionally, fever was not a common adverse effect of lowish, fine crystals. Practically insoluble in water; slightly solu- C13H8N2O3S = 272.3. oxamniquine, except in Egypt where it appeared to be character- ble in dehydrated alcohol; sparingly soluble in acetone. Store in CAS — 19881-18-6. istic. The cause was not known. Increased immune complexes airtight containers. Protect from light. ATC Vet — QP52AX01. and excretion of antigens occurred in only half the cases, there The symbol † denotes a preparation no longer actively marketed The symbol ⊗ denotes a substance whose use may be restricted in certain sports (see p.vii)