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Chemistry

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Also known as: Dichlorophene, 97-23-4, 2,2'-methylenebis(4-chlorophenol), Didroxane, Anthiphen, Dichlorofen

Molecular Formula

C₁₃H₁₀Cl₂O₂

Molecular Weight

269.12 g/mol

InChI Key

MDNWOSOZYLHTCG-UHFFFAOYSA-N

FDA UNII

T1J0JOU64O

Nontoxic laxative vermicide effective for taenia infestation. It tends to produce colic and nausea. It is also used as a veterinary fungicide, anthelmintic, and antiprotozoan. (From Merck, 11th ed.)

1 2D Structure

Dichlorophen

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

4-chloro-2-[(5-chloro-2-hydroxyphenyl)methyl]phenol

2.1.2 InChI

InChI=1S/C13H10Cl2O2/c14-10-1-3-12(16)8(6-10)5-9-7-11(15)2-4-13(9)17/h1-4,6-7,16-17H,5H2

2.1.3 InChI Key

MDNWOSOZYLHTCG-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC(=C(C=C1Cl)CC2=C(C=CC(=C2)Cl)O)O

2.2 Other Identifiers

2.2.1 UNII

T1J0JOU64O

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Panacide

2.3.2 Depositor-Supplied Synonyms

1. Dichlorophene

2. 97-23-4

3. 2,2'-methylenebis(4-chlorophenol)

4. Didroxane

5. Anthiphen

6. Dichlorofen

7. Dichlorphen

8. Parabis

9. Dicestal

10. Didroxan

11. Trivex

12. Antiphen

13. Cordocel

14. Difentan

15. Embephen

16. Panacide

17. Prevental

18. Taeniatol

19. Teniathane

20. Teniatol

21. Teniotol

22. Vermithana

23. Antifen

24. Halenol

25. Hyosan

26. Korium

27. Palacel

28. Dichlorophen B

29. Dichlorophene 10

30. Dichloorfeen

31. Gingivit

32. Wespuril

33. Gefir

34. Phenol, 2,2'-methylenebis[4-chloro-

35. Fungicide M

36. Dddm

37. Plath-lyse

38. Bis(5-chloro-2-hydroxyphenyl)methane

39. Fungicide Gm

40. Preventol Gd

41. Preventol Gdc

42. Diphenthane 70

43. Sandocide

44. Super Mosstox

45. Di-phentane-70

46. 2,2'-dihydroxy-5,5'-dichlorodiphenylmethane

47. Bis(chlorohydroxyphenyl)methane

48. 1322-43-6

49. Bis(2-hydroxy-5-chlorophenyl)methane

50. Giv Gard G 4-40

51. Di-(5-chloro-2-hydroxyphenyl)methane

52. 5,5'-dichloro-2,2'-dihydroxydiphenylmethane

53. 4-chloro-2-[(5-chloro-2-hydroxyphenyl)methyl]phenol

54. Bis-2-hydroxy-5-chlorfenylmethan

55. Dichlorofen [czech]

56. Bis(5-chlor-2-hydroxyphenyl)-methan

57. 4,4'-dichloro-2,2'-methylenediphenol

58. Methanedichlorofen

59. O,o-metilen-bis(4-cloro-fenolo)

60. G-4 Technical

61. G-4 Pure

62. ((dihydroxydichloro)diphenyl)methane

63. Nsc-38642

64. 2,2'-methylenebis-(4-chlorophenol)

65. G-4

66. 2,2'-methylene-bis (4-chlorophenol)

67. Phenol, 2,2'-methylenebis(4-chloro-

68. T1j0jou64o

69. Chembl33845

70. Mls000069468

71. G 4

72. 2,2/'-methylenebis(4-chlorophenol)

73. 4-chloro-2-(5-chloro-2-hydroxybenzyl)phenol

74. Chebi:34689

75. Nsc38642

76. 2,2'-methylenebis[4-chlorophenol]

77. O,o-methyleen-bis-(4-chloorfenol)

78. 2,2'-methanediylbis(4-chlorophenol)

79. Dichlorofen (czech)

80. Ncgc00091325-05

81. Dichlorophenum

82. Diclorofeno

83. Smr000059095

84. Dsstox_cid_1824

85. Dsstox_rid_76351

86. Dsstox_gsid_21824

87. 2,5'-dichlorodiphenylmethane

88. 5,2'-dihydroxydiphenylmethane

89. Sindar G 4

90. Dichloorfeen [dutch]

91. Wln: Qr Dg B1r Bq Eg

92. Caswell No. 563

93. 4-chloranyl-2-[(5-chloranyl-2-oxidanyl-phenyl)methyl]phenol

94. Phenol,2'-methylenebis[4-chloro-

95. [(dihydroxydichloro)diphenyl]methane

96. Ddm (van)

97. Diclorofeno [inn-spanish]

98. Cas-97-23-4

99. Dichlorophene [inn-french]

100. Dichlorophene [iso-french]

101. Dichlorophenum [inn-latin]

102. Dichlorophen [inn:ban:dcf]

103. Dichlorophen [iso]

104. Ccris 6060

105. G 4 (van)

106. Hsdb 6033

107. Dichlorophen [bsi:iso]

108. Einecs 202-567-1

109. Nsc 38642

110. Unii-t1j0jou64o

111. Epa Pesticide Chemical Code 055001

112. Brn 1884514

113. Algafen

114. Anthipen

115. Nuophene

116. Westpuril

117. Bis-2-hydroxy-5-chlorfenylmethan [czech]

118. Fungicide Fx

119. Ai3-02370

120. O,o-methyleen-bis(4-chloorfenol) [dutch]

121. Difent*n

122. O,o-metilen-bis(4-cloro-fenolo) [italian]

123. Acticide Ddm

124. Bis(5-chlor-2-hydroxyphenyl)-methan [german]

125. Diphentane 70

126. O,o-methyleen-bis(4-chloorfenol)

127. Mfcd00002322

128. Cuniphen (salt/mix)

129. Spectrum_000762

130. Opera_id_1730

131. Spectrum2_001214

132. Spectrum3_001405

133. Spectrum4_000390

134. Spectrum5_001519

135. Dichlorophen [mi]

136. Dichlorophen [inn]

137. Dichlorophen [hsdb]

138. Dichlorophene [inci]

139. Schembl18052

140. Bspbio_003050

141. Dichlorophen [mart.]

142. Kbiogr_000919

143. Kbioss_001242

144. Mls001076530

145. Bidd:er0237

146. Dichlorophen [who-dd]

147. Divk1c_000460

148. Spectrum1500626

149. Spbio_001028

150. 4-chloro-2-[(5-chloro-2-hydroxy-phenyl)methyl]phenol

151. Dtxsid6021824

152. Ecco Mp 2004 (salt/mix)

153. Hms501g22

154. Kbio1_000460

155. Kbio2_001242

156. Kbio2_003810

157. Kbio2_006378

158. Kbio3_002270

159. Zinc56435

160. Ninds_000460

161. Dichlorophene [green Book]

162. Hms1921m03

163. Hms2230h06

164. Hms3373o17

165. Kuc106446n

166. Kuc112931n

167. Pharmakon1600-01500626

168. Nsc39467

169. Tox21_111112

170. Tox21_201429

171. Tox21_303013

172. Bdbm50303912

173. Ccg-39772

174. Nsc-39467

175. Nsc757391

176. S5724

177. 2,2''-methylenebis(4-chlorophenol)

178. Akos015917706

179. Bis(2-hydroxy-5-chlorophenyl)-methane

180. Tox21_111112_1

181. 2,2'-methylene-bis(4-chloro-phenol)

182. Cs-3867

183. Db11396

184. Ksc-19-050

185. Nsc-757391

186. Bis-(5-chloro-2-hydroxyphenyl)-methane

187. Idi1_000460

188. Qtl1_000030

189. Ncgc00091325-01

190. Ncgc00091325-03

191. Ncgc00091325-04

192. Ncgc00091325-06

193. Ncgc00091325-07

194. Ncgc00091325-09

195. Ncgc00256543-01

196. Ncgc00258980-01

197. Ac-10330

198. As-12817

199. Hy-12638

200. Ksc-336-005-1

201. Sbi-0051563.p002

202. Bis(5-chloro-2-hydroxyphenyl)methane, 95%

203. Ft-0609137

204. Ft-0739351

205. M0213

206. E79441

207. 3,3''-dichloro-6,6''-dihydroxydiphenylmethane

208. Ab00052130_15

209. Dichlorophene, Pestanal(r), Analytical Standard

210. A845699

211. Q377552

212. Sr-01000721928

213. Dichlorophene; Bis(5-chloro-2-hydroxyphenyl)methane

214. Sr-01000721928-3

215. W-100114

216. Bis(5-chloro-2-hydroxyphenyl)methane, Technical Grade, 90%

217. Jal

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₁₃H₁₀Cl₂O₂
Molecular Weight	269.12 g/mol
XLogP3	4.3
Hydrogen Bond Donor Count	2
Hydrogen Bond Acceptor Count	2
Rotatable Bond Count	2
Exact Mass	268.0057849 g/mol
Monoisotopic Mass	268.0057849 g/mol
Topological Polar Surface Area	40.5 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	226
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Therapeutic Uses

Anticestodal Agents; Antifungal Agents; Antiprotozoal Agents; Cathartics

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

/SRP/: Dichlorophen is primarily effective against the large tapeworms of man & domestic animals. ... Dichlorophen is effective in clearing a large proportion of infections by Taenia saginata. Taenia solium is also susceptible... Available data suggest it may be useful against Diphyllobothrium latum & Hymenolepis mana infections.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1014

Dichlorophen is given orally without preliminary fasting or other prior preparation of the patient. Satisfactory results have been obtained by giving 2-3 g every 8 hr for 3 doses (children, 1-2 g). Alternatively, single dose of 6 g (children, 2-4 g) may be given on each of 2 successive days.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1014

Medication (Vet): Antihelmintic. Targets Cestodes. ... antiprotozoal,... antifungal agent

Milne, G.W.A. Veterinary Drugs: Synonyms and Properties. Ashgate Publishing Limited, Aldershot, Hampshire, England 2002., p. 17

Anthelmintic agent for Tapeworms in human & vet medicine

SRI

4.2 Drug Warning

...Usually nothing recognizable or only partially disintegrated mature segments can be seen in the stool. This presents difficulty in diagnosing cure, &, therefore, careful follow-up of the patient is required.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1014

...There may be danger of cysticereosis from liberated ova.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 1014

4.3 Minimum/Potential Fatal Human Dose

3. 3= MODERATELY TOXIC: Probable oral lethal dose (human) 0.5-5 g/kg, between 1 oz & 1 pint (or 1 lb) for 70 kg person (150 lbs).

Gosselin, R.E., H.C. Hodge, R.P. Smith, and M.N. Gleason. Clinical Toxicology of Commercial Products. 4th ed. Baltimore: Williams and Wilkins, 1976., p. II-131

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

Anticestodal Agents

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

Antiprotozoal Agents

Substances that are destructive to protozoans. (See all compounds classified as Antiprotozoal Agents.)

5.2 ATC Code

P - Antiparasitic products, insecticides and repellents

P02 - Anthelmintics

P02D - Anticestodals

P02DX - Other anticestodals

P02DX02 - Dichlorophen

5.3 Absorption, Distribution and Excretion

Following oral administration to the rat, (14)C-dichlorophen was well absorbed with 78% of the dose excreted in the urine and 15% in the feces in 2 days.

Dixon PAF, Caldwell J; Eur J Drug Metab Pharmacokinet 3 (2): 95 (1978)

/Investigators/ dosed female Wistar albino rats (3/group) orally with 50 mg/kg [14C]-dichlorophene dissolved in propane-1,2-diol. One group of rats was bile-duct cannulated 1 hr after oral administration of [14C]-dichlorophene. An average of 95% [14C]-dichlorophene was excreted in the urine and feces 2 days after dosing. Most (78%) of the biocide was recovered in the urine, and 17% was recovered in the feces.

Cosmetic Ingredient Review; International Journal of Toxicology 23 (Suppl 1): 1-27 (2004)

5.4 Metabolism/Metabolites

/Investigators/ dosed female Wistar albino rats (3/group) orally with 50 mg/kg [14C]-dichlorophene dissolved in propane-1,2-diol. ... The following urinary metabolites were identified: 4% dichlorophene; 17% dichlorophene sulfate; 25% dichlorophene monoglucuronide; and 19% dichlorophene diglucuronide. Bile duct-cannulated rats excreted 36% of the dose of [14C]-dichlorophene 1 to 4 hr after dosing. The intestinal contents and the intestinal wall had 32% and 11% [14C]-dichlorophene, respectively, whereas 2% was found in the urine. Only the monoglucuronide metabolite of [14C]-dichlorophene was found in the bile. The investigators suggested that dichlorophene underwent enterohepatic circulation.

Cosmetic Ingredient Review; International Journal of Toxicology 23 (Suppl 1): 1-27 (2004)

/Investigators examined/ the metabolites of dichlorophene from enterohepatic circulation in female Vom strain rats. Female rats were dosed orally with 50 mg/kg [14C]-dichlorophene (5 uCi/kg) and were bile-duct cannulated 1 hr later. Bile and urine were collected for 3 hr. The bile was then infused into the duodenum of another set of cannulated rats, from which bile and urine were collected. This process was repeated with a third set of rats. Five rats were used in each experiment. The only biliary metabolite was the monoglucuronide in all three experiments. In the urine, dichlorophene sulfate and diglucuronide were the major metabolites. Blood from the hepatic portal vein in rats receiving bile contained free dichlorophene and its monoglucuronide.

Cosmetic Ingredient Review; International Journal of Toxicology 23 (Suppl 1): 1-27 (2004)

/After/ orally administered dichlorophene: (1) dichlorophene is absorbed from the gut, is conjugated to the sulfate and monoglucuronide in the gut wall, and passes to the liver where more of these metabolites can be formed; (2) the diglucuronide is formed in the liver or other organs perfused by systemic circulation; (3) the sulfate and diglucuronide are eliminated from the peripheral circulation via the kidneys; (4) the diglucuronide is too water soluble for biliary excretion; however, most of the monoglucuronide undergoes biliary excretion; (5) residual monoglucuronide is metabolized to sulfate and diglucuronide on subsequent passes through the enterohepatic cycle and these are eliminated via the kidneys.

Cosmetic Ingredient Review; International Journal of Toxicology 23 (Suppl 1): 1-27 (2004)

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