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Chemistry

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Also known as: 4-chloro-3,5-dimethylphenol, 88-04-0, Dettol, 4-chloro-3,5-xylenol, Pcmx, P-chloro-m-xylenol
Molecular Formula
C8H9ClO
Molecular Weight
156.61  g/mol
InChI Key
OSDLLIBGSJNGJE-UHFFFAOYSA-N
FDA UNII
0F32U78V2Q

Chloroxylenol
Chloroxylenol, or para-chloro-meta-xylenol (PCMX), is an antiseptic and disinfectant agent used for skin disinfection and surgical instruments. It is found in antibacterial soaps, wound-cleansing applications, and household antiseptics. The halophenol is shown to be most effective against Gram positive bacteria where it disrupts the cell wall due to its phenolic nature. Chloroxylenol is on the World Health Organization's List of Essential Medicines.
1 2D Structure

Chloroxylenol

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-chloro-3,5-dimethylphenol
2.1.2 InChI
InChI=1S/C8H9ClO/c1-5-3-7(10)4-6(2)8(5)9/h3-4,10H,1-2H3
2.1.3 InChI Key
OSDLLIBGSJNGJE-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CC(=CC(=C1Cl)C)O
2.2 Other Identifiers
2.2.1 UNII
0F32U78V2Q
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 2-chloro-5-hydroxy-1,3-dimethylbenzene

2. 3,5-dimethyl-4-chlorophenol

3. 4-chloro-3,5-dimethylphenol

4. 4-chloro-3,5-dimethylphenol Sulfonate

5. Chloroxylenol, Potassium Salt

6. Chloroxylenol, Sodium Salt

7. Dettol

8. Ice-o-derm

9. Micro-guard

10. P-chloro-m-xylenol

11. Parachlorometaxylenol

12. Pcmx

13. Sween Prep

2.3.2 Depositor-Supplied Synonyms

1. 4-chloro-3,5-dimethylphenol

2. 88-04-0

3. Dettol

4. 4-chloro-3,5-xylenol

5. Pcmx

6. P-chloro-m-xylenol

7. Benzytol

8. 2-chloro-m-xylenol

9. 4-chloro-m-xylenol

10. Phenol, 4-chloro-3,5-dimethyl-

11. Ottasept

12. Desson

13. Espadol

14. Chloro-xylenol

15. Parachlorometaxylenol

16. Ottasept Extra

17. Husept Extra

18. P-chloro-3,5-xylenol

19. Willenol V

20. 3,5-dimethyl-4-chlorophenol

21. Septiderm-hydrochloride

22. Chloroxylenolum

23. Cloroxilenol

24. 2-chloro-5-hydroxy-m-xylene

25. Dettol, Liquid Antiseptic

26. Nipacide Mx

27. Parametaxylenol

28. Rba 777

29. 2-chloro-5-hydroxy-1,3-dimethylbenzene

30. 4-chloro-1-hydroxy-3,5-dimethylbenzene

31. 3,5-xylenol, 4-chloro-

32. Nsc 4971

33. Parachlorometoxylenol

34. 4-chloro-3,5-dimethyl-phenol

35. Nsc-4971

36. 4-chloro-3, 5-xylenol

37. Chlorxylenolum

38. Chebi:34393

39. Nsc4971

40. 0f32u78v2q

41. 4-chloro-3,5-dimethylphenol;pcmx

42. Ncgc00094614-03

43. Clorossilenolo

44. Dsstox_cid_12316

45. Dsstox_rid_78913

46. Dsstox_gsid_32316

47. Caswell No. 218

48. Clorossilenolo [dcit]

49. Vionexus

50. Cas-88-04-0

51. Cloroxilenol [inn-spanish]

52. Camel (pesticide)

53. Chloroxylenolum [inn-latin]

54. Hsdb 7427

55. Einecs 201-793-8

56. Epa Pesticide Chemical Code 086801

57. Brn 1862539

58. Ayrtol

59. Unii-0f32u78v2q

60. Ai3-08632

61. 5-dimethylphenol

62. Nipacide Px

63. Chloroxylenol(usan

64. Chloroxylenol [usan:usp:inn:ban]

65. Chloroxylenol-[d6]

66. Spectrum_000138

67. 3, 4-chloro-

68. M-xylenol, 4-chloro-

69. Para-chloro-meta-xylenol

70. Spectrum2_000136

71. Spectrum3_000344

72. Spectrum4_000281

73. Spectrum5_000713

74. Chloroxylenol (usp/inn)

75. Chloroxylenol [ii]

76. Chloroxylenol [mi]

77. Chloroxylenol [inn]

78. 4-chloro-3,5dimethylphenol

79. Chloroxylenol [hsdb]

80. Chloroxylenol [inci]

81. Chloroxylenol [usan]

82. Schembl34163

83. Bspbio_002007

84. Chloroxylenol [vandf]

85. Kbiogr_000802

86. Kbioss_000598

87. P-chloro-3,5-dimethylphenol

88. Mls000028592

89. Bidd:er0218

90. Chloroxylenol [mart.]

91. Divk1c_000801

92. Spectrum1500182

93. Spbio_000212

94. Wln: Qr Dg C1 E1

95. Chloroxylenol [usp-rs]

96. Chloroxylenol [who-dd]

97. 3, 5-dimethyl-4-chlorophenol

98. Chembl398440

99. Zinc1132

100. Dtxsid0032316

101. Hms502i03

102. Kbio1_000801

103. Kbio2_000598

104. Kbio2_003166

105. Kbio2_005734

106. Kbio3_001227

107. Ninds_000801

108. Hms1920k19

109. Hms2091c22

110. Hms2233n06

111. Hms3369i18

112. Para Chloro Meta Xylenol (pcmx)

113. Pharmakon1600-01500182

114. 4-chloro-3,5-dimethylphenol Purum

115. Hy-b1414

116. Parachlorometoxylenol [vandf]

117. Tox21_111305

118. Tox21_302047

119. Ac-265

120. Ccg-38943

121. Chloroxylenol [usp Monograph]

122. Mfcd00002324

123. Nsc756683

124. S4518

125. Stl183324

126. 4-chloro-3,5-dimethylphenol, 99%

127. Akos009159132

128. Tox21_111305_1

129. Cs-4912

130. Db11121

131. Nsc-756683

132. Idi1_000801

133. Ncgc00094614-01

134. Ncgc00094614-02

135. Ncgc00094614-04

136. Ncgc00094614-06

137. Ncgc00094614-07

138. Ncgc00255257-01

139. Ls-13415

140. Smr000059157

141. Sbi-0051310.p003

142. Db-028803

143. Ft-0618059

144. A16004

145. D03473

146. Ab00051942_07

147. A842444

148. Q426460

149. Sr-01000778359

150. Sr-01000778359-2

151. 4-chloro-3,5-dimethylphenol, Purum, >=98.0% (t)

152. 4-chloro-3,5-xylenol, 4-chloro-sym-m-xylenol, Pcmx

153. Brd-k17223896-001-02-7

154. Brd-k17223896-001-06-8

155. F0001-2183

156. Z1235963354

157. Chloroxylenol, British Pharmacopoeia (bp) Reference Standard

158. Chloroxylenol, United States Pharmacopeia (usp) Reference Standard

159. Chloroxylenol, Pharmaceutical Secondary Standard; Certified Reference Material

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 156.61 g/mol
Molecular Formula C8H9ClO
XLogP32
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count1
Rotatable Bond Count0
Exact Mass156.0341926 g/mol
Monoisotopic Mass156.0341926 g/mol
Topological Polar Surface Area20.2 Ų
Heavy Atom Count10
Formal Charge0
Complexity104
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

Antibacterial; antiseptic (topical and urinary).

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 375


(VET): Antiseptic (topical).

O'Neil, M.J. (ed.). The Merck Index - An Encyclopedia of Chemicals, Drugs, and Biologicals. 13th Edition, Whitehouse Station, NJ: Merck and Co., Inc., 2001., p. 375


4.2 Drug Indication

The predominant medical applications for which chloroxylenol is formally indicated for therapeutic use is as an application to the skin for use in cuts, bites, stings, abrasions, and for use as antiseptic hand cleaner.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Chloroxylenol is a substituted phenol which has been widely used for many years as an ingredient of antiseptic and disinfectant products intended for external use. It is known to be bactericidal in low concentration to a wide range of Gram positive and Gram negative bacteria.


5.2 MeSH Pharmacological Classification

Schistosomicides

Agents that act systemically to kill adult schistosomes. (See all compounds classified as Schistosomicides.)


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.)


Disinfectants

Substances used on inanimate objects that destroy harmful microorganisms or inhibit their activity. Disinfectants are classed as complete, destroying SPORES as well as vegetative forms of microorganisms, or incomplete, destroying only vegetative forms of the organisms. They are distinguished from ANTISEPTICS, which are local anti-infective agents used on humans and other animals. (From Hawley's Condensed Chemical Dictionary, 11th ed) (See all compounds classified as Disinfectants.)


5.3 ATC Code

D08AE05

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


D - Dermatologicals

D08 - Antiseptics and disinfectants

D08A - Antiseptics and disinfectants

D08AE - Phenol and derivatives

D08AE05 - Chloroxylenol


5.4 Absorption, Distribution and Excretion

Absorption

No chloroxylenol was detected in the blood following the dermal administration of 2 g of p-chloroxylenol in an ethanol/olive oil vehicle in human subjects. After a dose of 5 g, only traces were found, after 8 g, 1 mg % (1 mg/dL) was found in the blood after 3 hours, and 4 mg % (4 mg/dL) after 24 hours. After a dose of 20 g, 4 mg % (4 mg/dL) was measured after half an hour, and 1 mg % (1 mg/dL) was present at 72 hours. For antiseptic purposes, chloroxylenol is considered to be well-absorbed when applied to the skin.


Route of Elimination

The major route of excretion is likely in urine, although some amounts may be found in bile and traces in exhaled air.


Volume of Distribution

The only data available regarding the volume of distribution of chloroxylenol is the mean Vss of 22.45 L determined after 200 mg intravenous single dose of chloroxylenol was administered to healthy mongrel dog subjects.


Clearance

The only data available regarding the clearance of chloroxylenol is the mean clearance rate of 13.76 L/hr following a 200 mg intravenous single dose of the substance into healthy mongrel dog subjects. Moreover, in another study, when 8 g of chloroxylenol was administered dermal on a human subject in an alcohol/glycerin vehicle, 11% was excreted in 48 hours.


Mongrel dogs received iv and oral single doses of 200 and 2000 mg 4-chloro-3,5-xylenol, respectively. Low range of absorption was noted. Kidneys were not the major route for rapid elimination of unchanged 4-chloro-3,5-xylenol.

Sheftel, V.O.; Indirect Food Additives and Polymers. Migration and Toxicology. Lewis Publishers, Boca Raton, FL. 2000., p. 880


Tests of a 25 percent solution of chloroxylenol with Sprague-Dawley rats demonstrated the chemical was practically all eliminated in the first 24 hours, mostly in the urine, with small amounts in feces, after oral or dermal exposure. Following dermal exposure, about half of the material was not absorbed. High concentrations were found in the tissues of the kidney, which indicates excretion in urine. Concentrations in the lungs indicates some elimination in expired air.

USEPA; Reregistration Eligibility Decision (RED) Database for Chloroxylenol (88-04-0). EPA 738-R-94-032 (September 1994). Available from, as of January 31, 2006: https://www.epa.gov/pesticides/reregistration/status.htm


In a study /with/ beagle dogs dosed orally excreted virtually all of the chloroxylenol in their urine within 24 hours. A small amount was present in feces, but essentially none remained in any tissue.

USEPA; Reregistration Eligibility Decision (RED) Database for Chloroxylenol (88-04-0). EPA 738-R-94-032 (September 1994). Available from, as of January 31, 2006: https://www.epa.gov/pesticides/reregistration/status.htm


The pharmacokinetic and metabolic profile of p-chloro-m-xylenol (PCMX) was studied in healthy mongrel dogs after intravenous and oral administration of single doses of 200 and 2000 mg of PCMX, respectively. ... The mean half-life and mean residence time were 1.84 and 1.69 hr. respectively. The apparent volume of distribution at steady state was estimated to be 22.4 liters, and the plasma clearance was 14.6 liters/hr. The bioavailability of PCMX was 21%. ... PCMX's metabolite data show that a presystemic elimination process (first-pass effect) is also occurring. PCMX plasma concentrations after intravenous administration of 500-, 200-, and 100-mg doses were found to be proportional to the dose given.

Dorantes A, Stavchansky S; Pharm Res (NY) 9 (5): 677-682 (1992)


5.5 Metabolism/Metabolites

Certain animal studies have shown that following dermal application of chloroxylenol, that the absorption was rapid with a Cmax = 1-2 hours, and that the administered substance was excreted via the kidney with almost complete elimination within 24 hours. The primary metabolites discovered in the excreted urine were glucuronides and sulfates. Some chloroxylenol monographs liken its pharmacokinetic profile to that of another antiseptic - triclosan - which is rapidly excreted in the urine also as a glucuronide metabolite, as observed in the human model. Moreover, In one human subject administered 5 mg intragluteally, 14% was excreted with glucuronic acid and 17% with sulfuric acid at 3 days. Any chloroxylenol absorbed into the body is likely extensively metabolized by the liver and rapidly excreted, mainly in the urine, as sulphate and glucuronide conjugates.


Mongrel dogs received iv and oral single doses of 200 and 2000 mg 4-chloro-3,5-xylenol, respectively. ...Main metabolites found in the urine were glucuronides and sulfates.

Sheftel, V.O.; Indirect Food Additives and Polymers. Migration and Toxicology. Lewis Publishers, Boca Raton, FL. 2000., p. 880


5.6 Biological Half-Life

One study estimated the mean terminal half-life and mean residence time after a 200 mg intravenous single dose of chloroxylenol in healthy mongrel dog subjects to be 1.7 and 1.69 hours, respectively. Alternatively, some product monographs liken chloroxylenol to a similar liquid antiseptic, triclosan, whose calculated urinary excretion half-life in man is approximately 10 hours.


5.7 Mechanism of Action

As a phenol antiseptic, it is believed that the hydroxyl -OH groups of the chloroxylenol molecule binds to certain proteins on the cell membrane of bacteria, and disrupts the membrane so as to allow the contents of the bacterial cell to leak out. This allows chloroxylenol to enter the bacterial cell to bind further with more proteins and enzymes to disable the cell's functioning. At particularly high concentrations of chloroxylenol, the protein and nucleic acid content of targeted bacterial cells become coagulated and cease to function, leading to rapid cell death.


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04-Jan-2021
26-Aug-2024
KGS
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Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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