Finished Dosage Form (FDF) import of Niclosamide obtained from Indian Custom Trade Statistics

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Chemistry

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Also known as: 50-65-7, 5-chloro-n-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide, Niclocide, Bayluscid, Phenasal, Tredemine
Molecular Formula
C13H8Cl2N2O4
Molecular Weight
327.12  g/mol
InChI Key
RJMUSRYZPJIFPJ-UHFFFAOYSA-N
FDA UNII
8KK8CQ2K8G

Niclosamide
An antihelmintic that is active against most tapeworms. (From Martindale, The Extra Pharmacopoeia, 30th ed, p48)
1 2D Structure

Niclosamide

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-chloro-N-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide
2.1.2 InChI
InChI=1S/C13H8Cl2N2O4/c14-7-1-4-12(18)9(5-7)13(19)16-11-3-2-8(17(20)21)6-10(11)15/h1-6,18H,(H,16,19)
2.1.3 InChI Key
RJMUSRYZPJIFPJ-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=CC(=C(C=C1[N+](=O)[O-])Cl)NC(=O)C2=C(C=CC(=C2)Cl)O
2.2 Other Identifiers
2.2.1 UNII
8KK8CQ2K8G
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Bayer 2353

2. Bayer 73

3. Bayluscide

4. Clonitralide

5. Fenasal

6. Niclocide

7. Niclosamide, 2-aminoethanol (1:1)

8. Phenasal

9. Radewerm

10. Trdmine

11. Yomesan

2.3.2 Depositor-Supplied Synonyms

1. 50-65-7

2. 5-chloro-n-(2-chloro-4-nitrophenyl)-2-hydroxybenzamide

3. Niclocide

4. Bayluscid

5. Phenasal

6. Tredemine

7. Fenasal

8. Yomesan

9. Dichlosale

10. Helmiantin

11. Atenase

12. Cestocid

13. Devermin

14. Devermine

15. Iomesan

16. Iomezan

17. Mansonil

18. Radeverm

19. Sagimid

20. Vermitid

21. Lintex

22. Nasemo

23. Sulqui

24. 2',5-dichloro-4'-nitrosalicylanilide

25. Mato

26. Fedal-telmin

27. Bayer 73

28. Zestocarp

29. Bayer 2353

30. Bay 2353

31. Chemagro 2353

32. Benzamide, 5-chloro-n-(2-chloro-4-nitrophenyl)-2-hydroxy-

33. Wr 46234

34. 5-chloro-2'-chloro-4'-nitrosalicylanilide

35. Nicolsamide

36. Niclosamide (anhydrous)

37. Hl 2447

38. Ent 25823

39. 2-hydroxy-5-chloro-n-(2-chloro-4-nitrophenyl)benzamide

40. N-(2-chloro-4-nitrophenyl)-5-chlorosalicylamide

41. Niclosamide Anhydrous

42. 2-chloro-4-nitrophenylamide-6-chlorosalicylic Acid

43. Niclosamide, Anhydrous

44. Salicylanilide, 2',5-dichloro-4'-nitro-

45. 2',5-dichlor-4'-nitro-salizylsaeureanilid

46. Nsc-178296

47. 5-chloro-n-(2'-chloro-4'-nitrophenyl)salicylamide

48. 8kk8cq2k8g

49. Sr 73

50. Radewerm

51. N-(2'-chlor-4'-nitrophenyl)-5-chlorsalicylamid

52. Bay-2353

53. Cas-50-65-7

54. Ncgc00015735-07

55. Niclosamide 100 Microg/ml In Acetonitrile

56. C13h8cl2n2o4

57. Dsstox_cid_20362

58. Dsstox_rid_79485

59. Dsstox_gsid_40362

60. N-(2'-chloro-4'-nitrophenyl)-5-chlorosalicylamide

61. Niclosamida

62. Niclosamidum

63. Cestocide

64. Niclosamidum [inn-latin]

65. Niclosamida [inn-spanish]

66. Nitrophenyl Chlorsalicylamide

67. Niclosamide [iso]

68. Niclosamide [usan:inn:ban]

69. Ccris 3437

70. Hsdb 1572

71. Sr-01000076024

72. Niclosamide [bsi:iso]

73. Einecs 200-056-8

74. Unii-8kk8cq2k8g

75. Nsc 178296

76. Brn 2820605

77. Yomensan

78. Niclo-samide

79. Ai3-25823

80. 5-chlorosalicyloyl-(o-chloro-p-nitranilide)

81. B 2353

82. Niclocide (tn)

83. Prestwick_354

84. 2',5-dichlor-4'-nitro-salizylsaeureanilid [german]

85. Mfcd00057597

86. Niclosamidum Anhydrous

87. Mollutox (salt/mix)

88. N-(2'-chlor-4'-nitrophenyl)-5-chlorsalicylamid [german]

89. Spectrum_000239

90. Niclosamide (niclocide)

91. Clonitralid (salt/mix)

92. Clonitralide (salt/mix)

93. Niclosamide [mi]

94. Prestwick0_000040

95. Prestwick1_000040

96. Prestwick2_000040

97. Prestwick3_000040

98. Spectrum2_001183

99. Spectrum3_000667

100. Spectrum4_000196

101. Spectrum5_001083

102. Lopac-n-3510

103. Niclosamide [inn]

104. Niclosamide (usan/inn)

105. Niclosamide [hsdb]

106. Niclosamide [usan]

107. Niclosamide [vandf]

108. Chembl1448

109. Niclosamide [mart.]

110. Lopac0_000866

111. Oprea1_259151

112. Schembl67182

113. Bspbio_000139

114. Bspbio_002333

115. Kbiogr_000771

116. Kbioss_000719

117. Niclosamide [who-dd]

118. Mls002154181

119. Divk1c_000709

120. Spectrum1503265

121. Spbio_001225

122. Spbio_002060

123. Bpbio1_000153

124. Chebi:7553

125. Gtpl8494

126. Dtxsid7040362

127. Niclosamide [green Book]

128. Schembl18563900

129. Wln: Wnr Cg Dmvr Bq Eg

130. Bdbm11242

131. Hms502d11

132. Kbio1_000709

133. Kbio2_000719

134. Kbio2_003287

135. Kbio2_005855

136. Kbio3_001553

137. 5-chloro-n-(2-chloro-4-nitro-phenyl)-2-hydroxy-benzamide

138. Niclosamide - Cas 50-65-7

139. Niclosamide [orange Book]

140. Ninds_000709

141. Bdbm513089

142. Hms1568g21

143. Hms2093a21

144. Hms2095g21

145. Hms2231h06

146. Hms3262n13

147. Hms3373p08

148. Hms3712g21

149. Kuc107299n

150. Niclosamide [ep Monograph]

151. Pharmakon1600-01503265

152. Bcp22958

153. Hy-b0497

154. Zinc3874496

155. Tox21_110209

156. Tox21_300749

157. Tox21_500866

158. Bbl004110

159. Ccg-39641

160. Nsc178296

161. Nsc758440

162. S3030

163. Salicylanilide,5-dichloro-4'-nitro-

164. Stk396676

165. 2,5-dichloro-4-nitrosalicylanilide ?

166. Akos003589004

167. Niclosamide Anhydrous [who-ip]

168. Tox21_110209_1

169. At15436

170. Bcp9000068

171. Db06803

172. Ks-5210

173. Lp00866

174. Nsc-758440

175. Sb19414

176. Sdccgsbi-0050841.p004

177. 2',5'-dichloro-4'-nitrosalicylanilide

178. Idi1_000709

179. Smp2_000228

180. 5-chloro-n-(2-chloro-4-nitrophenyl)-

181. Ncgc00015735-01

182. Ncgc00015735-02

183. Ncgc00015735-03

184. Ncgc00015735-04

185. Ncgc00015735-05

186. Ncgc00015735-06

187. Ncgc00015735-08

188. Ncgc00015735-09

189. Ncgc00015735-11

190. Ncgc00015735-12

191. Ncgc00015735-24

192. Ncgc00094190-01

193. Ncgc00094190-02

194. Ncgc00094190-03

195. Ncgc00094190-04

196. Ncgc00254654-01

197. Ncgc00261551-01

198. Ksc-18-157-2

199. Smr000058390

200. Sbi-0050841.p003

201. Db-051812

202. Vu0243604

203. Ab00052340

204. Eu-0100866

205. Ft-0603220

206. Niclosamide, Anhydrous [ep Impurity]

207. Niclosamidum Anhydrous [who-ip Latin]

208. En300-92958

209. D00436

210. N 3510

211. Ab00052340_08

212. Ab00052340_09

213. A828227

214. Q418523

215. Q-201469

216. Sr-01000076024-1

217. Sr-01000076024-3

218. Sr-01000076024-6

219. Brd-k35960502-001-06-9

220. Brd-k35960502-001-11-9

221. Z57902203

222. 5-chloro-n-(2-chloro-4-nitrophenyl) -2-hydroxybenzamide

223. 5-chloranyl-n-(2-chloranyl-4-nitro-phenyl)-2-oxidanyl-benzamide

224. Niclosamide (anhydrous), European Pharmacopoeia (ep) Reference Standard

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 327.12 g/mol
Molecular Formula C13H8Cl2N2O4
XLogP34
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count4
Rotatable Bond Count2
Exact Mass325.9861121 g/mol
Monoisotopic Mass325.9861121 g/mol
Topological Polar Surface Area95.2 Ų
Heavy Atom Count21
Formal Charge0
Complexity404
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Therapeutic Uses

Anticestodal Agents; Antinematodal Agents; Molluscacides

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)


THERE ARE NO CONTRAINDICATIONS TO THE USE OF NICLOSAMIDE AS A TENIACIDE.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 965


MEDICATION (VET): Niclosamide can also be used to treat tapeworm infections of lab animals /eg mice, rabbits, monkeys, or reptiles/. ... Niclosamide is admin orally in tablet form to dogs and cats ... It is usually admin to ruminants /eg cattle, sheep and goats/ ... as a drench ...

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 857


Therapeutic Use Niclosamide in the free-base form only is used primarily as a cestocide and to a lesser extent as a trematocide. The drug is formulated as a chewable tablet containing 500 mg of niclosamide. It is very effective against tapeworrn infections caused by Taenia saginata, Taenia solium, and Diphyllobothrium latum; tapeworms such as Hymenolepis diminuta, Hymenolepis nana, and Dipylidium caninum are somewhat more recalcitrant. For infections of Taenia saginata, Taenia solium, and Diphyllobothrium latum, single oral dosages of 2 gm (adult), 1.5 gm (child > 34 kg), and 1.0 gm (child 11-34 kg) are recommended. 0ther tapeworms may require repeated treatment for example, 2 gm/day in single daily doses for 7 days (adults), 1.5 gm given in a single dose on the first day followed by 1 gm/day for the next 6 days (child > 34 kg), and 1 gm given in a single dose on the first day followed by 500 mg/day for next 6 days (child 11-34 kg). Safety for use in children under 2 years of age has not been established. Since niclosamide is active only against intestinal cestodes, it is not effective for treatment of cysticercosis. As a trematocide, niclosamide is active mainly against flukes such as Fasciolopsis buski in the intestines.

Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 3. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 1498


For more Therapeutic Uses (Complete) data for NICLOSAMIDE (10 total), please visit the HSDB record page.


4.2 Drug Warning

SINCE TAPEWORM INFECTIONS GENERALLY ARE NOT LIFE THREATENING, IT IS RECOMMENDED THAT TREATMENT OF PREGNANT WOMEN BE POSTPONED UNTIL AFTER DELIVERY.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 1753


VET: DO NOT TREAT LACTATING ANIMALS.

Rossoff, I.S. Handbook of Veterinary Drugs. New York: Springer Publishing Company, 1974., p. 384


... It is important to note that the lethal action of the drug against the adult worn does not extend to the ova. Thus, use of niclosamide in Taenia solium infections may expose the patient to the risk of cysticercosis, since, following digestion of the dead segments, viable ova will be liberated into the lumen of the gut. It is desirable to give an adequate purge within 3 to 4 hours after the drug has been given, to clear the bowel of all dead segments before they can be digested.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 965


The drug causes segments to disintegrate, releasing viable eggs; hence, if used against pork tapeworm, a purge should be given 1 or 2 hr after treatment. Untoward effects occur only occasionally; nausea and abdominal pain have been reported.

Osol, A. (ed.). Remington's Pharmaceutical Sciences. 16th ed. Easton, Pennsylvania: Mack Publishing Co., 1980., p. 1182


For more Drug Warnings (Complete) data for NICLOSAMIDE (7 total), please visit the HSDB record page.


4.3 Drug Indication

For the treatment of tapeworm and intestinal fluke infections: Taenia saginata (Beef Tapeworm), Taenia solium (Pork Tapeworm), Diphyllobothrium latum (Fish Tapeworm), Fasciolopsis buski (large intestinal fluke). Niclosamide is also used as a molluscicide in the control of schistosomiasis.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Niclosamide is an antihelminth used against tapeworm infections. It may act by the uncoupling of the electron transport chain to ATP synthase. The disturbance of this crucial metabolic pathway prevents creation of adenosine tri-phosphate (ATP), an essential molecule that supplies energy for metabolism.


5.2 MeSH Pharmacological Classification

Antinematodal Agents

Substances used in the treatment or control of nematode infestations. They are used also in veterinary practice. (See all compounds classified as Antinematodal Agents.)


Molluscacides

Agents destructive to snails and other mollusks. (See all compounds classified as Molluscacides.)


Anticestodal Agents

Agents used to treat tapeworm infestations in man or animals. (See all compounds classified as Anticestodal Agents.)


5.3 ATC Code

P02DA01

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


P - Antiparasitic products, insecticides and repellents

P02 - Anthelmintics

P02D - Anticestodals

P02DA - Salicylic acid derivatives

P02DA01 - Niclosamide


5.4 Absorption, Distribution and Excretion

Absorption

Niclosamide appears to be minimally absorbed from the gastrointestinal tractneither the drug nor its metabolites have been recovered from the blood or urine.


VERY LITTLE IS ABSORBED FROM THE GI TRACT ... .

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 965


EXPOSING RAINBOW TROUT TO (14)C-BAYER 73 CAUSED BILE TO WATER (14)C RATIO OF 10,000:1. AFTER 24 HR OF EXPOSURE, THIN LAYER CHROMATOGRAPHY OF UNFRACTIONATED BILE FROM FISH SHOWED 1 MAJOR RADIOACTIVE PEAK. UNCHANGED BAYER 73 WAS FOUND IN BILE.

STATHAM CN ET AL; PHARMACOLOGIST 16 (2): 327 (1974)


Niclosamide is excreted in feces.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 95. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1995 (Plus Supplements 1995)., p. 44


When male and female volunteers each were treated orally with 2000 mg of radiocarbon-labeled niclosamide, between 2 and 25% of the dose was eliminated in the urine over a 4-day period; the remainder was found in the feces. Elimination of niclosamide equivalents was essentially complete after 1-2 days. Maximal niclosamide equivalents in serum ranged from 0.25 to 6.0 ppm; the variation associated with this parameter was attrributed to differential rates of absorption among the individual.

Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 3. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 1499


For more Absorption, Distribution and Excretion (Complete) data for NICLOSAMIDE (6 total), please visit the HSDB record page.


5.5 Metabolism/Metabolites

ANTHELMINTIC NICLOSAMIDE...REDUCED TO CORRESPONDING AMINO DERIVATIVE BY BOTH MOUSE- & SHEEP-LIVER ENZYME PREPARATIONS & BY ENZYMES FROM CESTODES & NEMATODES. ...NICLOSAMIDE WAS NOT HYDROLYZED EITHER BY MAMMALIAN & HELMINTH ENZYME PREPN OR BY WHOLE HELMINTHS.

The Chemical Society. Foreign Compound Metabolism in Mammals. Volume 5: A Review of the Literature Published during 1976 and 1977. London: The Chemical Society, 1979., p. 372


In warm-blooded organisms, the nitro group is reduced to an amino group (5,2'-dichloro-4-aminosalicylanilide).

Hartley, D. and H. Kidd (eds.). The Agrochemicals Handbook. Old Woking, Surrey, United Kingdom: Royal Society of Chemistry/Unwin Brothers Ltd., 1983., p. A297/Oct 83


Pregnant rats were treated orally with niclosamide at 1000 mg/kg on day 13, 19, or 20 of gestation, and rats were sacrificed at 4, 8, 16, or 24 hr posttreatment. Highest concentrations of niclosamide and 2,5'-dichloro-4'-aminosalicylanilide were detected in liver and kidney 8 hr after treatment. Niclosamide, but not its amino metabolite, was present in fetuses from rats treated on day 13, whereas both compounds were found in fetuses from rats treated on day 19 or 20. It was suggested that 19- and 20-day-old fetuses, but not 13-day-old fetuses, were able to metabolize niclosamide.

Hayes, W.J., Jr., E.R. Laws, Jr., (eds.). Handbook of Pesticide Toxicology. Volume 3. Classes of Pesticides. New York, NY: Academic Press, Inc., 1991., p. 1497


Niclosamide ... is absorbed from the gastrointestinal tract, and mutagenic metabolites are excreted in the free form and as conjugated glucuronides. as in the case of other secondary amides, phase I metabolism of niclosamide may result in hydrolytic cleavage of the amide bond, giving rise to 5-chlorosalicylic acid and 2-chloro-4-nitroaniline. ...

PMID:1944396 Espinosa-Aguirre JJ et al; Mutat Res 264 (3): 139-45 (1991)


5.6 Mechanism of Action

Niclosamide works by killing tapeworms on contact. Adult worms (but not ova) are rapidly killed, presumably due to uncoupling of oxidative phosphorylation or stimulation of ATPase activity. The killed worms are then passed in the stool or sometimes destroyed in the intestine. Niclosamide may work as a molluscicide by binding to and damaging DNA.


Niclosamide has prominent activity against most of the cestodes that infect man; Enterobius (Oxyuris) vermicularis is also susceptible. At low concn, niclosamide stimulates oxygen uptake by Hymenolepis diminuta, but at higher concn respiration is inhibited and glucose uptake is blocked. The principal action of the drug may be to inhibit anaerobic phosphorylation of adenosine diphosphate (ADP) by the mitochondria of the parasite, an energy producing process that is dependent on CO2 fixation ... .

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 965


Cestocidal activity is due to inhibition of absorption of glucose by the tapeworm and uncoupling of the oxidative phosphorylation process in the mitochondria of cestodes. Resultant blocking of the Krebs cycle leads to accumulation of lactic acid, which kills the tapeworm. ... overstimulation of adenosine triphosphatase (ATPase) activity of the mitochondria may be related to cestodal action of niclosamide.

Booth, N.H., L.E. McDonald (eds.). Veterinary Pharmacology and Therapeutics. 5th ed. Ames, Iowa: Iowa State University Press, 1982., p. 857


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04-Jan-2021
20-Aug-2024
KGS
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