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Substance Name: Hexachlorophene [USP:INN:BAN]
RN: 70-30-4
UNII: IWW5FV6NK2
InChIKey: ACGUYXCXAPNIKK-UHFFFAOYSA-N

Note

  • 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)

Molecular Formula

  • C13-H6-Cl6-O2

Molecular Weight

  • 406.906
 

Classification Codes

Classification Codes

  • Acaricide
  • Agricultural Chemical
  • Anti-Infective Agents
  • Anti-Infective Agents, Local
  • Anti-Infective, Topical
  • Detergent
  • Drug / Therapeutic Agent
  • Fungicide, Bactericide, Wood Preservative
  • Germicide, Bactericide, Disinfectant
  • Human Data
  • Reproductive Effect
  • Skin / Eye Irritant
  • TSCA Flag SP (Substance is Identified in a Proposed Significant New Use Rule)
  • Tumor Data

Superlist Classification Codes

  • Overall Carcinogenic Evaluation: Group 3
  • Reportable Quantity (RQ) = 100 lb

Names and Synonyms

Name of Substance

  • 2,2'-Methylenebis(3,4,6-trichlorophenol)
  • Bis(3,5,6-trichloro-2-hydroxyphenyl)-methane
  • Hexachlorophene
  • Hexachlorophene [USP:INN:BAN]
  • Phenol, 2,2'-methylenebis(3,4,6-trichloro-

MeSH Heading

  • Hexachlorophene

Synonyms

  • 2,2',3,3',5,5'-Hexachloro-6,6'-dihydroxydiphenylmethane
  • 2,2'-Dihydroxy-3,3',5,5',6,6'-hexachlorodiphenylmethane
  • 2,2'-Dihydroxy-3,5,6,3',5',6'-hexachlorodiphenylmethane
  • 2,2'-Methylenebis(3,4,6-trichlorophenol)
  • 4-06-00-06659 (Beilstein Handbook Reference)
  • Acigena
  • AI3-02372
  • Almederm
  • Armohex
  • AT 7
  • At-17
  • B & b Flea Kontroller for Dogs Only
  • B 32 (VAN)
  • B32
  • Bilevon
  • Bis(2-hydroxy-3,5,6-trichlorophenyl)methane
  • Bis(3,5,6-trichloro-2-hydroxyphenyl)methane
  • Bis-2,3,5-trichloro-6-hydroxyfenylmethan
  • Bis-2,3,5-trichloro-6-hydroxyfenylmethan [Czech]
  • Blockade Anti Bacterial Finish
  • Brevity Blue Liquid Bacteriostatic Scouring Cream
  • Brevity Blue Liquid Sanitizing Scouring Cream
  • BRN 2064407
  • Caswell No. 566
  • CCRIS 331
  • Compound G-11
  • Cotofilm
  • Dermadex
  • Dial
  • Distodin
  • E-Z Scrub
  • EINECS 200-733-8
  • En-Viron D Concentrated Phenolic Disinfectant
  • Enditch Pet Shampoo
  • EPA Pesticide Chemical Code 044901
  • Esaclorofene
  • Esaclorofene [DCIT]
  • Exofene
  • Fesia-sin
  • Fomac
  • Fostril
  • G-11
  • G-Eleven
  • G-II
  • Gamophen
  • Gamophene
  • Germa-medica
  • HCP
  • Hexa-Germ
  • Hexabalm
  • Hexachlorofen
  • Hexachlorofen [Czech]
  • Hexachlorophen
  • Hexachlorophene
  • Hexachlorophenum
  • Hexachlorophenum [INN-Latin]
  • Hexaclorofeno
  • Hexaclorofeno [INN-Spanish]
  • Hexafen
  • Hexaphene-LV
  • Hexascrub
  • Hexide
  • Hexophene
  • Hexosan
  • Hilo Cat Flea Powder
  • Hilo Flea Powder
  • HSDB 224
  • Methane, bis(2,3,5-trichloro-6-hydroxyphenyl)-
  • Nabac
  • Nabac 25 EC
  • NCI-C02653
  • Neosept V
  • NSC 49115
  • Pedigree Dog Shampoo Bar
  • Phenol, 2,2'-methylenebis(3,4,6-trichloro)-
  • Phenol, 2,2'-methylenebis(3,4,6-trichloro-
  • Phenol, 2,2'-methylenebis(3,5,6-trichloro-
  • Phiso-Scrub
  • Phisodan
  • pHisoHex
  • Pre-OP
  • Pre-OP II
  • RCRA waste number U132
  • Ritosept
  • Scrubteam Surgical Spongebrush
  • Septi-Soft
  • Septisol
  • Septofen
  • Solu-Heks
  • Soy-Dome
  • Staphene O
  • Ster-Zac
  • Steral
  • Steraskin
  • Surgi-Cen
  • Surgi-cin
  • Surofene
  • Tersaseptic
  • Thera-Groom Pet Shampoo for Dogs for Veterinary Use Only
  • Trichlorophene
  • Trisophen
  • Turgex
  • UNII-IWW5FV6NK2

Systematic Names

  • Hexachlorophene
  • Phenol, 2,2'-methylenebis(3,4,6-trichloro-

Superlist Names

  • 2,2'-Methylenebis(3,4,6-trichlorophenol)
  • Hexachlorophene
  • Hexachlorophene [UN2875] [Poison]
  • Phenol, 2,2'-methylenebis(3,4,6-trichloro-
  • RCRA waste no. U132
  • UN2875

Mixture Names

  • pHisoHex
  • Soy-Dome

Registry Numbers

CAS Registry Number

  • 70-30-4

FDA UNII

  • IWW5FV6NK2

Other Registry Numbers

  • 1195388-85-2
  • 139411-96-4
  • 8054-98-6

System Generated Number

  • 0000070304

Structure Descriptors

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

InChIKey

ACGUYXCXAPNIKK-UHFFFAOYSA-N

Smiles

c1(Cc2c(c(cc(c2Cl)Cl)Cl)O)c(c(cc(c1Cl)Cl)Cl)O

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child LDLo oral 250mg/kg (250mg/kg) LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

LUNGS, THORAX, OR RESPIRATION: CYANOSIS

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Medical Journal of Australia. Vol. 1, Pg. 737, 1963.
dog LDLo intravenous 5mg/kg (5mg/kg) BLOOD: CHANGE IN CLOTTING FACTORS

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Surgery. Vol. 24, Pg. 542, 1948.
dog LDLo oral 40mg/kg (40mg/kg)   Veterinarski Arhiv. Veterinary Archives. Vol. 35, Pg. 35, 1965.
domestic animals - goat/sheep LD50 oral 30mg/kg (30mg/kg)   Annals of the New York Academy of Sciences. Vol. 320, Pg. 426, 1979.
guinea pig LD50 oral 60mg/kg (60mg/kg)   Drugs in Japan Vol. 6, Pg. 742, 1982.
guinea pig LD50 skin 1100mg/kg (1100mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 47(10), Pg. 26, 1982.
guinea pig LDLo intraperitoneal 25mg/kg (25mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 163, Pg. 210, 1966.
infant TDLo oral 257mg/kg/7D-I (257mg/kg) VASCULAR: SHOCK

GASTROINTESTINAL: NAUSEA OR VOMITING

GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"
American Journal of Diseases of Children. Vol. 111, Pg. 333, 1966.
mouse LC50 inhalation 290mg/m3 (290mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 49(8), Pg. 25, 1984.
mouse LD50 intraperitoneal 20mg/kg (20mg/kg)   Zentralblatt fuer Bakteriologie, Parasitenkunde, Infektionskrankheiten und Hygiene, Abteilung 1: Originale, Reihe A: Medizinische Mikrobiologie und Parasitologie. Vol. 234, Pg. 110, 1976.
mouse LD50 oral 67mg/kg (67mg/kg) LUNGS, THORAX, OR RESPIRATION: CHRONIC PULMONARY EDEMA

KIDNEY, URETER, AND BLADDER: OTHER CHANGES

LIVER: FATTY LIVER DEGERATION
Chinese Medical Journal Vol. 82, Pg. 691, 1963.
mouse LD50 skin 270mg/kg (270mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 47(10), Pg. 26, 1982.
mouse LD50 subcutaneous 46mg/kg (46mg/kg)   Nippon Eiseigaku Zasshi. Japanese Journal of Hygiene. Vol. 16, Pg. 13, 1961.
rabbit LD50 intravenous 8500ug/kg (8.5mg/kg)   Journal of the Society of Cosmetic Chemists. Vol. 20, Pg. 173, 1969.
rabbit LD50 oral 40690ug/kg (40.69mg/kg)   Teratology, The International Journal of Abnormal Development. Vol. 20, Pg. 413, 1979.
rat LC50 inhalation 340mg/m3 (340mg/m3)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 49(8), Pg. 25, 1984.
rat LD50 intraperitoneal 22mg/kg (22mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE)
Toxicology and Applied Pharmacology. Vol. 24, Pg. 239, 1973.
rat LD50 intravenous 7500ug/kg (7.5mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toxicology and Applied Pharmacology. Vol. 25, Pg. 332, 1973.
rat LD50 oral 56mg/kg (56mg/kg) GASTROINTESTINAL: "HYPERMOTILITY, DIARRHEA"

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Toxicology and Applied Pharmacology. Vol. 25, Pg. 332, 1973.
rat LD50 skin 1840mg/kg (1840mg/kg)   Gigiena i Sanitariya. For English translation, see HYSAAV. Vol. 47(10), Pg. 26, 1982.
rat LD50 subcutaneous 7650ug/kg (7.65mg/kg)   Industrial Medicine and Surgery. Vol. 38, Pg. 64, 1969.
women TDLo oral 600mg/kg (600mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION
JAMA, Journal of the American Medical Association. Vol. 181, Pg. 587, 1962.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 166.5 deg C   EXP
Boiling Point 479 deg C   EXP
pKa Dissociation Constant 4.95 (none)   EXP
log P (octanol-water) 7.54 (none)   EXP
Water Solubility 140 mg/L 25 EXP
Vapor Pressure 1.03E-10 mm Hg 25 EST
Henry's Law Constant 5.48E-13 atm-m3/mole 25 EST
Atmospheric OH Rate Constant 2.18E-12 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.