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Chemistry

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Also known as: 70-30-4, Hexachlorofen, Hexachlorophen, Nabac, Phisohex, Almederm
Molecular Formula
C13H6Cl6O2
Molecular Weight
406.9  g/mol
InChI Key
ACGUYXCXAPNIKK-UHFFFAOYSA-N
FDA UNII
IWW5FV6NK2

Hexachlorophene
A chlorinated bisphenol antiseptic with a bacteriostatic action against Gram-positive organisms, but much less effective against Gram-negative organisms. It is mainly used in soaps and creams and is an ingredient of various preparations used for skin disorders. (From Martindale, The Extra Pharmacopoeia, 30th ed, p797)
Hexachlorophene is an Antiseptic.
1 2D Structure

Hexachlorophene

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol
2.1.2 InChI
InChI=1S/C13H6Cl6O2/c14-6-2-8(16)12(20)4(10(6)18)1-5-11(19)7(15)3-9(17)13(5)21/h2-3,20-21H,1H2
2.1.3 InChI Key
ACGUYXCXAPNIKK-UHFFFAOYSA-N
2.1.4 Canonical SMILES
C1=C(C(=C(C(=C1Cl)Cl)CC2=C(C(=CC(=C2Cl)Cl)Cl)O)O)Cl
2.2 Other Identifiers
2.2.1 UNII
IWW5FV6NK2
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Hexachlorophane

2.3.2 Depositor-Supplied Synonyms

1. 70-30-4

2. Hexachlorofen

3. Hexachlorophen

4. Nabac

5. Phisohex

6. Almederm

7. Gamophen

8. Septisol

9. Exofene

10. Fostril

11. Turgex

12. Germa-medica

13. Gamophene

14. Hexophene

15. Steraskin

16. Tersaseptic

17. Acigena

18. Dermadex

19. Distodin

20. Hexabalm

21. Hexafen

22. Phisodan

23. Septofen

24. Surofene

25. Hexide

26. Steral

27. Soy-dome

28. Surgi-cen

29. Surgi-cin

30. Hexachlorophane

31. Cotofilm

32. Hexascrub

33. Ritosept

34. Hexosan

35. Fomac

36. Fesia-sin

37. Phiso-scrub

38. Septi-soft

39. Ster-zac

40. Hexa-germ

41. Neosept V

42. G-eleven

43. Bilevon

44. Hexaclorofeno

45. Pre-op

46. Armohex

47. Hexachlorophenum

48. E-z Scrub

49. Compound G-11

50. 6,6'-methylenebis(2,4,5-trichlorophenol)

51. Nabac 25 Ec

52. Staphene O

53. Solu-heks

54. Esaclorofene

55. G-ii

56. 2,2'-methylenebis(3,4,6-trichlorophenol)

57. Scrubteam Surgical Spongebrush

58. At-17

59. Rcra Waste Number U132

60. 2,2'-methanediylbis(3,4,6-trichlorophenol)

61. At-7

62. Bis(2-hydroxy-3,5,6-trichlorophenyl)methane

63. Bis(3,5,6-trichloro-2-hydroxyphenyl)methane

64. Nci-c02653

65. G-11

66. 3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol

67. 2,2',3,3',5,5'-hexachloro-6,6'-dihydroxydiphenylmethane

68. 2,2'-dihydroxy-3,5,6,3',5',6'-hexachlorodiphenylmethane

69. 2,2'-dihydroxy-3,3',5,5',6,6'-hexachlorodiphenylmethane

70. Mls000028433

71. Smr000058356

72. Phenol, 2,2'-methylenebis(3,4,6-trichloro-

73. Phenol, 2,2'-methylenebis[3,4,6-trichloro-

74. Iww5fv6nk2

75. B 32

76. Mls002152906

77. Chebi:5693

78. 2,2'-methylenebis[3,4,6-trichlorophenol]

79. Bivelon

80. Trisophen

81. Hexaphene-lv

82. Hilo Flea Powder

83. Nsc-49115

84. Enditch Pet Shampoo

85. Ncgc00091195-04

86. Fascol

87. 6,6-methylenebis(2,4,5-trichlorophenol)

88. Esaclorofene [dcit]

89. Hexachlorofen [czech]

90. Hilo Cat Flea Powder

91. Dsstox_cid_690

92. Hexachlorophene [inn]

93. 2,4,6-trichlorophenol]

94. 2,5,6-trichlorophenol)

95. Pre-op Ii

96. Pedigree Dog Shampoo Bar

97. Dsstox_rid_75738

98. Dsstox_gsid_20690

99. Hexaclorofeno [inn-spanish]

100. Hexachlorophenum [inn-latin]

101. Caswell No. 566

102. Blockade Anti Bacterial Finish

103. At 7

104. B 32 (van)

105. Bis-2,5-trichlor-6-hydroxyfenylmethan

106. Cas-70-30-4

107. Methane,3,5-trichloro-6-hydroxyphenyl)

108. B & B Flea Kontroller For Dogs Only

109. Ccris 331

110. Bis(2-hydroxy-3,6-trichlorophenyl)methane

111. Bis(3,6-trichloro-2-hydroxyphenyl)methane

112. Phenol,2'-methylenebis[3,4,6-trichloro-

113. Phenol,2'-methylenebis[3,5,6-trichloro-

114. Wln: Qr Bg Dg Eg F1r Bq Cg Eg Fg

115. Hsdb 224

116. 2,3',5,5',6,6'-hexachlorodiphenylmethane

117. 2,5,6,3',5',6'-hexachlorodiphenylmethane

118. Sr-01000721924

119. Brevity Blue Liquid Sanitizing Scouring Cream

120. En-viron D Concentrated Phenolic Disinfectant

121. Einecs 200-733-8

122. Unii-iww5fv6nk2

123. Nsc 49115

124. Un2875

125. Hexachlorophene [un2875] [poison]

126. Phenol, 2,2'-methylenebis(3,4,6-trichloro)-

127. Rcra Waste No. U132

128. Brevity Blue Liquid Bacteriostatic Scouring Cream

129. 2,3,3',5,5'-hexachloro-6,6'-dihydroxydiphenylmethane

130. Epa Pesticide Chemical Code 044901

131. Bis-2,3,5-trichloro-6-hydroxyfenylmethan [czech]

132. Hexachlorophene (usp/inn)

133. Brn 2064407

134. Bis-2,3,5-trichloro-6-hydroxyfenylmethan

135. Ai3-02372

136. Hexachlorophenone

137. Thera-groom Pet Shampoo For Dogs For Veterinary Use Only

138. 2,2'-methylene Bis(3,4,6-trichlorophenol)

139. Hexachlorophene [usp:inn:ban]

140. Bis(3,5,6-trichloro-2-hydroxyphenyl)-methane

141. Methane, Bis(2,3,5-trichloro-6-hydroxyphenyl)

142. Kuc106447n

143. Methane, Bis(2,3,5-trichloro-6-hydroxyphenyl)-

144. Phisohex (tn)

145. Mfcd00002171

146. Ksc-19-051

147. Spectrum_000867

148. Bis-2,3,5-trichlor-6-hydroxyfenylmethan

149. Opera_id_504

150. Spectrum2_001105

151. Spectrum3_000450

152. Spectrum4_000573

153. Spectrum5_000792

154. M0219

155. Chembl496

156. Cid_3598

157. Hexachlorophene [mi]

158. Regid_for_cid_3598

159. Schembl15579

160. Bspbio_002100

161. Kbiogr_001006

162. Kbioss_001347

163. Mls001148404

164. Bidd:er0608

165. Bidd:gt0722

166. Divk1c_000630

167. Hexachlorophene [hsdb]

168. Hexachlorophene [iarc]

169. Hexachlorophene [inci]

170. Spectrum1500328

171. Spbio_001210

172. Hexachlorophene [vandf]

173. Amy389

174. Hexachlorophene [mart.]

175. Dtxsid6020690

176. Hexachlorophene [usp-rs]

177. Hexachlorophene [who-dd]

178. Bdbm31712

179. Gtpl11069

180. Hms501p12

181. Kbio1_000630

182. Kbio2_001347

183. Kbio2_003915

184. Kbio2_006483

185. Kbio3_001320

186. Nsc9887

187. Ninds_000630

188. 3,3',5,5',6,6'-hexachloro-2,2'-dihydroxydiphenylmethane

189. Hms1920d07

190. Hms2091j13

191. Hms3259c19

192. Hms3715p21

193. Kuc112427n

194. Pharmakon1600-01500328

195. Nsc-9887

196. Nsc49115

197. Zinc1530968

198. Tox21_111099

199. Tox21_201350

200. Tox21_302741

201. 3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxy-phenyl)methyl]phenol

202. Ccg-39768

203. Hexachlorophene [orange Book]

204. Nsc757055

205. S4632

206. Stk377478

207. Akos005449243

208. Tox21_111099_1

209. Cs-3866

210. Db00756

211. Hexachlorophene [usp Monograph]

212. Nc00512

213. Nsc-757055

214. Un 2875

215. Idi1_000630

216. Ncgc00091195-01

217. Ncgc00091195-02

218. Ncgc00091195-03

219. Ncgc00091195-05

220. Ncgc00091195-06

221. Ncgc00091195-07

222. Ncgc00091195-08

223. Ncgc00256580-01

224. Ncgc00258902-01

225. As-10068

226. Bp-30177

227. H3p

228. Hy-12637

229. Inh 1 [pmid: 32284327]

230. Ksc-285-117-1

231. Sbi-0051403.p003

232. Ft-0626955

233. Bis(3,5,6-trichloro-2-hydroxy Phenyl)methane

234. Bis-(2-hydroxy-3,5,6-trichlorophenyl)methane

235. C08039

236. D00859

237. Mls-0072923.0001

238. Ab00052010_17

239. Bis[3,4,6-trichlorophenol], 2,2'-methylene-

240. Hexachlorophene, Pestanal(r), Analytical Standard

241. Q425362

242. Sr-01000721924-2

243. Sr-01000721924-5

244. Sr-01000721924-6

245. Brd-k99792991-001-02-6

246. Brd-k99792991-001-18-2

247. Hexachlorophene, United States Pharmacopeia (usp) Reference Standard

248. 139411-96-4

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 406.9 g/mol
Molecular Formula C13H6Cl6O2
XLogP37.5
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count2
Rotatable Bond Count2
Exact Mass405.846945 g/mol
Monoisotopic Mass403.849896 g/mol
Topological Polar Surface Area40.5 Ų
Heavy Atom Count21
Formal Charge0
Complexity328
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 Drug Information
1 of 6  
Drug NamePhisohex
PubMed HealthHexachlorophene (Topical application route)
Drug ClassesAntibacterial Cleansing Agent
Active IngredientHexachlorophene
Dosage FormEmulsion
RouteTopical
Strength3%
Market StatusPrescription
CompanySanofi Aventis Us

2 of 6  
Drug NamePre-op
Active IngredientHexachlorophene
Dosage FormSponge
RouteTopical
Strength480mg
Market StatusPrescription
CompanyDavis And Geck

3 of 6  
Drug NamePre-op ii
Active IngredientHexachlorophene
Dosage FormSponge
RouteTopical
Strength480mg
Market StatusPrescription
CompanyDavis And Geck

4 of 6  
Drug NamePhisohex
PubMed HealthHexachlorophene (Topical application route)
Drug ClassesAntibacterial Cleansing Agent
Active IngredientHexachlorophene
Dosage FormEmulsion
RouteTopical
Strength3%
Market StatusPrescription
CompanySanofi Aventis Us

5 of 6  
Drug NamePre-op
Active IngredientHexachlorophene
Dosage FormSponge
RouteTopical
Strength480mg
Market StatusPrescription
CompanyDavis And Geck

6 of 6  
Drug NamePre-op ii
Active IngredientHexachlorophene
Dosage FormSponge
RouteTopical
Strength480mg
Market StatusPrescription
CompanyDavis And Geck

4.2 Therapeutic Uses

Anti-Infective Agents, Local

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


Hexachlorophene is used as a surgical hand scrub and a bacteriostatic skin cleanser. Topical preparations containing hexachlorophene have been used by physicians, dentists, food handlers, pediatric nurses, and other individuals who are in a position to spread contaminants from their hands. Efficacy of hexachlorophene as a topical antiseptic depends on residual amounts of the drug being adsorbed onto the skin. Hexachlorophene is most effective after repeated daily application and may be ineffective in reducing cutaneous flora if used in a single, brief application.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3535


Hexachlorophene has been used topically to suppress staphylococcal infections in patients with acne vulgaris. However, hexachlorophene is not active against Propionibacterium acnes and is of no additional benefit in individuals using topical benzoyl peroxide or topical tetracycline, clindamycin, or erythromycin.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3535


/SRP: Former use/ The use of hexachlorophene in the nursery has diminished sharply since discovery that daily bathing of neonates with 3% hexachlorophene emulsion could result in serious neurotoxicity. In hospitals in which ... /it/ is still used, the practice is to employ low concn (0.25%), which is less effective than 3%, or delay hexachlorophene bath until the 3rd day. Sometimes only the umbilical stump ... is bathed. The practice of subsequently rinsing off hexachlorophene residue with an alcohol or bathing the neonate with nonmedicated soap, in order to prevent absorption of hexachlorophene through the skin, defeats original purpose of use of antiseptic. ... Chlorhexidine ... is a more rational choice of antiseptic ... .

Gilman, A.G., L.S.Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 7th ed. New York: Macmillan Publishing Co., Inc., 1985., p. 969


For more Therapeutic Uses (Complete) data for HEXACHLOROPHENE (8 total), please visit the HSDB record page.


4.3 Drug Warning

Food and Environmental Agents: Effect on Breast-Feeding: Hexachlorophene: None; possible contamination of milk from nipple washing. /from Table 7/

PMID:8265310 Committee on Drugs of the American Academy of Pediatrics: The Transfer of Drugs and Other Chemicals into Human Milk; Pediatrics 93 (1): 137-150 (1994)


Hexachlorophene should not be used routinely for prophylactic total body bathing. After use of hexachlorophene, the area, especially sensitive areas such as the scrotum and perineum, should be rinsed thoroughly. If hexachlorophene inadvertently gets into the eyes, the eyes should be flushed promptly and thoroughly with water.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3535


Because of the possibility of rapid and extensive absorption of hexachlorophene, preparations containing the drug should not be used on burned or denuded skin or mucous membranes and should not be used as and/or with occlusive dressings, wet packs, lotions, vaginal packs, or tampons. In addition, hexachlorophene preparations should not be applied to generalized dermatologic conditions (e.g., lesions of ichthyosis congenita, dermatitis of Letterer-Siwe's syndrome).

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3535


Hexachlorophene should not be used in individuals sensitive to the drug or any ingredient in the formulation. Because of the possibility of cross-sensitivity, hexachlorophene should not be used in individuals who have demonstrated primary light sensitivity to halogenated phenol derivatives.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3535


For more Drug Warnings (Complete) data for HEXACHLOROPHENE (14 total), please visit the HSDB record page.


4.4 Minimum/Potential Fatal Human Dose

The lethal dose in adults after acute ingestion or repeated skin application is not well defined but is estimated to be 43 mg/kg or 1 to 10 g.

Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 1251


4.5 Drug Indication

For use as a surgical scrub and a bacteriostatic skin cleanser. It may also be used to control an outbreak of gram-positive infection where other infection control procedures have been unsuccessful.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Hexachlorophene, a detergent cleanser, is an antibacterial sudsing emulsion for topical administration. It is a bacteriostatic cleansing agent. It cleanses the skin thoroughly and has bacteriostatic action against staphylococci and other gram-positive bacteria. Cumulative antibacterial action develops with repeated use. Cleansing with alcohol or soaps containing alcohol removes the antibacterial residue.


5.2 MeSH Pharmacological Classification

Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
HEXACHLOROPHENE
5.3.2 FDA UNII
IWW5FV6NK2
5.3.3 Pharmacological Classes
Established Pharmacologic Class [EPC] - Antiseptic
5.4 ATC Code

D - Dermatologicals

D08 - Antiseptics and disinfectants

D08A - Antiseptics and disinfectants

D08AE - Phenol and derivatives

D08AE01 - Hexachlorophene


5.5 Absorption, Distribution and Excretion

Absorption

Detectable blood levels of hexachlorophene following absorption through intact skin have been found in subjects who regularly scrubbed with hexachlorophene.


Hexachlorophene is absorbed systemically (percutaneously) following topical application to the skin. In one study, approximately 3% of a dose of hexachlorophene (in acetone) applied to the skin was absorbed systemically. Serum concentrations of hexachlorophene ranging from 0.009-4.35ug/mL have been reported in neonates bathed daily in hexachlorophene preparations for 1-56 days; highest concentrations occurred in low birthweight infants and infants with abraded or erythematous skin. In adults, 3-4 weeks of daily total body bathing with a 3% hexachlorophene preparation reportedly results in serum concentrations of the drug as high as 1.42 ug/mL. Hexachlorophene serum concentrations of 0.5 mcg/mL or higher have been reported following use of a 3% hexachlorophene preparation as a surgical scrub for hands and forearms 5 times daily for 10 days. In animals, characteristic changes in the CNS associated with hexachlorophene toxicity occur at serum drug concentrations of about 1 ug/mL or greater.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3536


Following topical application to intact skin, hexachlorophene is adsorbed onto the outer layers of skin. Repeated daily application of hexachlorophene results in a residual of the drug being retained on the skin for several days. One study using radiolabeled hexachlorophene indicated that the drug accumulates on the skin during the first 3 or 4 days of repeated use, but the concentration on skin remains relatively constant thereafter. Residual hexachlorophene is retained on the skin for several days after discontinuance of the drug or may be removed by cleansing with non-hexachlorophene-containing soaps or detergents or ethanol or isopropyl alcohol.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3536


Hexachlorophene is absorbed from the GI tract and from intact and denuded skin. Rapid absorption of hexachlorophene may occur following topical application to burned or inflamed skin.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3536


Hexachlorophene was administered intraperitoneally to rats and rabbits. Excretion of this chemical was slow, most (48-83%) excreted unchanged in the feces.

Menzie, C.M. Metabolism of Pesticides-Update III. Special Scientific Report- Wildlife No. 232. Washington, DC: U.S.Department of the Interior, Fish and Wildlife Service, 1980., p. 323


For more Absorption, Distribution and Excretion (Complete) data for HEXACHLOROPHENE (14 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Hexachlorophene is metabolized in the liver, although it apparently displays first-order (linear) kinetics.

Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 1251


5.7 Biological Half-Life

The half life is 24 hours (range, 6 to 44 hours).

Dart, R.C. (ed). Medical Toxicology. Third Edition, Lippincott Williams & Wilkins. Philadelphia, PA. 2004., p. 1251


In newborn infants exposed to soap containing hexachlorophene, its half-life ranged from 6-44 hr ... .

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V20 250 (1979)


5.8 Mechanism of Action

The primary mechanism of action of hexachlorophene, based on studies with Bacillus megatherium, is to inhibit the membrane-bound part of the electron transport chain, respiratory D-lactate dehydrogenase. It induces leakage, causes protoplast lysis, and inhibits respiration.


Hexachlorophene ... /uncouples/ rat liver mitochondrial oxidative phosphorylation.

IARC. Monographs on the Evaluation of the Carcinogenic Risk of Chemicals to Humans. Geneva: World Health Organization, International Agency for Research on Cancer, 1972-PRESENT. (Multivolume work). Available at: https://monographs.iarc.fr/ENG/Classification/index.php, p. V20 248 (1979)


Brain succinate dehydrogenase (SDH) activity was inhibited by in vitro hexachlorophene (HCP) with a half inhibitory concentration (IC50) of 0.65 x 10(-3) M. The HCP exerted noncompetitive inhibition at 0.5 mM (IC50) on SDH activity. The brain SDH demands more energy of activation (deltaE) in the presence of HCP. The ionizable groups of SDH such as the sulfhydral group of cysteine and alpha-amino groups of cysteine were not altered qualitatively in the presence of HCP.

PMID:10487417 Lokanatha V et al; J Biochem Mol Toxicol 13 (6): 303-6 (1999)


Although the exact mechanism(s) of action has not been determined, at low concentrations, hexachlorophene appears to interrupt bacterial electron transport and to inhibit other membrane-bound enzymes. Higher concentrations rupture bacterial membranes.

American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011, p. 3536


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