70-30-4Oc1c(Cl)cc(Cl)c(Cl)c1Cc1c(O)c(Cl)cc(Cl)c1ClACGUYXCXAPNIKK-UHFFFAOYSA-NHexachlorophene appears as a white free-flowing odorless powder. Insoluble in water and denser than water. Contact may irritate skin, eyes and mucous membranes. May be toxic by ingestion. Used to make other chemicals.
70-30-4DTXSID6020690CHEMBL496CHEBI:5693Pharmaceuticals
Pharmaceuticals -> Listed in ZINC15
Pesticide -> EPA IRIS
Fungicides
Active substance -> EU Pesticides database: Not approved
log Kow = 7.54
6.3
7.54 (calculated)
Crystals from benzene
Needles from benzene
WHITE TO LIGHT TAN, CRYSTALLINE POWDER
White, free-flowing powder
less than 1 mg/mL at 68 °F (NTP, 1992)
Soluble in chloroform, polyethylene glycols, propylene glycol, olive oil, cottonseed oil, dilute aqueous alkaline solutions.
Soluble at 1 in 3.5 parts of alcohol, 1 in less than 1 part of acetone, & 1 in less than 1 part of ether
안전 정보는 참고용이며, 공급업체의 물질안전보건자료(SDS), 관련 법규 및 전문가 평가를 대체하지 않습니다.
Danger
H301: Toxic if swallowed [Danger Acute toxicity, oral]
P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)
Danger
H301+H311 (34.5%): Toxic if swallowed or in contact with skin [Danger Acute toxicity, oral; acute toxicity, dermal]
P262, P264, P270, P273, P280, P301+P316, P302+P352, P316, P321, P330, P361+P364, P391, P405, and P501 (click each P-code to see the statement)
Chemical: Phenol, 2,2'-methylenebis[3,4,6-trichloro-
Hazard Traits - Neurotoxicity
SP - indicates a substance that is identified in a proposed Significant New Use Rule.
2002/2076
Hexachlorophene: Does not have an individual approval but may be used under an appropriate group standard
The New Jersey Worker and Community Right to Know Act requires public and private employers to provide information about hazardous substances at their workplaces. (N.J.S.A. 34:5A-1 et. seq.)
Special Hazards of Combustion Products: Contain toxic and irritating chloride fumes.
· Non-combustible, substance itself does not burn but may decompose upon heating to produce corrosive and/or toxic fumes.
Combustible. Gives off irritating or toxic fumes (or gases) in a fire.
Inhalation of dust is poisonous; irritating to mucous membranes. Eye and skin irritant. Poisonous if swallowed. Symptoms following ingestion include anorexia, nausea, vomiting, abdominal cramps, and diarrhea. Dehydration may be severe and may be associated with shock. (USCG, 1999)
D - Dermatologicals
QD - Dermatologicals
QP - Antiparasitic products, insecticides and repellents
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.
The primary mechanism of action of hexachlorophene, based on studies with <i>Bacillus megatherium</i>, 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.
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), uncompetitive inhibition at 0.65 mM (= IC50), and mixed-type inhibition at 0.8 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.
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.
The half life is 24 hours (range, 6 to 44 hours).
In newborn infants exposed to soap containing hexachlorophene, its half-life ranged from 6-44 hr ... .
불러오는 중…
SOL IN DILUTE SOLUTIONS OF FIXED ALKALI HYDROXIDES
About 100 mg/mL in dimethyl sulfoxide at 20 °C
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
· Highly toxic, may be fatal if inhaled, ingested or absorbed through skin.
Hexachlorophene was removed from the over-the-counter market in the 1970s after neurotoxic effects were reported. Studies showed that between 0.3% and 6% of photo patch tested patients were allergic to this substance. [Marks, p. 232-3] Asthma reported in hospital employee; [Malo] In high-dose animal studies, hexachlorophene causes testicular damage and birth defects. [Frazier, p. 271-2] Acute exposure may cause CNS effects; A skin sensitizer; May cause asthma; [ICSC]
The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including hexachlorophene, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
POWELL HC, LAMPERT PW; HEXACHLOROPHENE TOXICITY; HANDB CLIN NEUROL 37 (PART II): 479-509 (1979). REVIEW: TOXICITY OF HEXACHLOROPHENE WITH PARTICULAR REFERENCE TO ITS EFFECTS ON MYELIN SHEATH.
MENNUTI MT; DRUG AND CHEMICAL RISKS TO THE FETUS: OCCUPATIONAL HAZARDS FOR MEDICAL PERSONNEL; PROG CLIN BIOL RES 36: 41-7 (1980). POSSIBLE TERATOGENIC HAZARDS FROM VOLUNTARY USE OR OCCUPATIONAL EXPOSURE TO HEXACHLOROPHENE ARE DISCUSSED. POSSIBLE ABSORPTION & NEUROTOXICITY TO NEWBORNS ARE REVIEWED.
PLUECKHAHN VD ET AL; HEXACHLOROPHENE PREPARATIONS IN INFANT ANTISEPTIC SKIN CARE--BENEFITS, RISKS, AND THE FUTURE; MED J AUST 2 (DEC 2): 555-60 (1978). REVIEW: USE OF HEXACHLOROPHENE PREPN IN EMULSIONS & POWDER FORM IS ASSESSED AT EXPTL & REVIEW LEVEL & IS DISCUSSED IN RELATION TO EFFICACY, TOXICITY & STRENGTH OF PREPN, & ITS SUITABILITY AS AN ANTIBACTERIAL AGENT AGAINST STAPHYLOCOCCAL SKIN DISEASES IN NEWBORN INFANTS & MOTHERS IN MATERNITY HOSPITALS.
O'Donoghue JL; Neurotox Ind Commer Chem 2: 139-53 (1985). A review with 157 references on the neurotoxicity of phenol, pentachlorophenol, hexachlorophene, and 2,4-dichlorophenoxyacetic acid.
For more Special Reports (Complete) data for HEXACHLOROPHENE (7 total), please visit the HSDB record page.
Excerpt from ERG Guide 151 [Substances - Toxic (Non-Combustible)]:
Use water spray, powder, foam, carbon dioxide.
Fresh air, rest.
Remove contaminated clothes. Rinse and then wash skin with water and soap. Refer for medical attention .
Rinse with plenty of water (remove contact lenses if easily possible).
Rinse mouth. Rest. Give a slurry of activated charcoal in water to drink. Refer immediately for medical attention.
· CALL 911. Then call emergency response telephone number on shipping paper. If shipping paper not available or no answer, refer to appropriate telephone number listed on the inside back cover.
· Do not touch damaged containers or spilled material unless wearing appropriate protective clothing.
EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.
General First Aid:
If material on fire or involved in fire: Extinguish fire using agent suitable for type of surrounding fire. (Material itself does not burn or burns with difficulty.) Use water in flooding quantities as fog. Use foam, dry chemical or carbon dioxide. Keep run-off waste out of sewers and water sources.
Generators of waste (equal to or greater than 100 kg/mo) containing this contaminant, EPA hazardous waste number U132, must conform with USEPA regulations in storage, transportation, treatment and disposal of waste.[
SRP: Wastewater from contaminant suppression, cleaning of protective clothing/equipment, or contaminated sites should be contained and evaluated for subject chemical or decomposition product concentrations. Concentrations shall be lower than applicable environmental discharge or disposal criteria. Alternatively, pretreatment and/or discharge to a permitted wastewater treatment facility is acceptable only after review by the governing authority and assurance that "pass through" violations will not occur. Due consideration shall be given to remediation worker exposure (inhalation, dermal and ingestion) as well as fate during treatment, transfer and disposal. If it is not practicable to manage the chemical in this fashion, it must be evaluated in accordance with EPA 40 CFR Part 261, specifically Subpart B, in order to determine the appropriate local, state and federal requirements for disposal.
The following wastewater treatment technologies have been investigated for chlorinated pesticides (unspecified): Resin adsorption.
A potential candidate for rotary kiln incineration at a temperature range of 820 to 1,600 °C and residence times of seconds for liquids and gases, and hours for solids. A potential candidate for fluidized bed incineration at a temperature range of 450 to 980 °C and residence times of seconds for liquids and gases, and longer for solids.
Incineration, preferably after mixing with another combustible fuel. Care must be exercised to assure complete combustion to prevent the formation of phosgene. An acid scrubber is necessary to remove the halo acids produced. Recommendable method: Incineration.
Personal protection: particulate filter respirator adapted to the airborne concentration of the substance. Do NOT let this chemical enter the environment. Sweep spilled substance into covered sealable containers. If appropriate, moisten first to prevent dusting. Carefully collect remainder. Then store and dispose of according to local regulations.
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
... All protective clothing (suits, gloves, footwear, headgear) should be clean, available each day and put on before work. ... Employees should wash immediately with soap when skin is wet or contaminated.
Personnel protection: Keep upwind. Avoid breathing vapors. ... Do not handle broken packages unless wearing appropriate personal protective equipment. If contact with the material anticipated, wear appropriate chemical protective clothing.
SRP: Contaminated protective clothing should be segregated in such a manner so that there is no direct personal contact by personnel who handle, dispose, or clean the clothing. The completeness of the cleaning procedures should be considered before the decontaminated protective clothing is returned for reuse by the workers. Contaminated clothing should not be taken home at the end of shift, but should remain at employee's place of work for cleaning.
If material not on fire and not involved in fire: Keep sparks, flames, and other sources of ignition away. Keep material out of water sources and sewers. Build dikes to contain flow as necessary. Attempt to stop leak if without undue personnel hazard.
Hexachlorophene has been detected in human milk at levels of 0-9 ug/L; conditions not specified(1). The average concentration of hexachlorophene in mother's milk (whole) after its application to disinfect the nipples (prior to FDA recommendation on stopping usage of hexachlorophene for this purpose in 1972) was 5.7 ppb (6 samples; range, <2-9.5 ppb). In 5 milk samples taken two years later, 20% were positive for hexachlorophene with an average concentration of 8.3 ppb(2).
In a study of the use of 3% hexachlorophene solution as body and hand soap, blood levels ranged from less than 0.005-0.38 mg/L blood, compared with mean baseline concn in 30 control people of 0.02 mg/L blood. After prolonged use of soap containing 0.75% hexachlorophene, levels ranged from 0.02-0.14 mg/L blood. In a study of randomly selected hospital patients, hexachlorophene blood levels ranged from 0 to 0.12 mg/L, with mean level of 0.03 mg/L(1).
Samples of adipose tissue obtained from neck during routine surgery contained mean concn of 0.01 mg/kg tissue; abdominal fat obtained at autopsy contained 0.04 mg/kg tissue. In another study, hexachlorophene was detected at levels of 0-80 ug/kg adipose tissue(1).
Whole Blood Reference Ranges: Normal - less than 0.03 mg/ cu ml; Exposed - People using mouthwash containing 0.5% hexachlorophene for 3 weeks, avg concentration 0.06 mg/cu mL; Toxic - level of 0.78 mg/mL was found in a child who died, however adults with levels as high as 2.16 mg/mL have been asymptomatic.
For more Body Burden (Complete) data for HEXACHLOROPHENE (6 total), please visit the HSDB record page.
LD50; Species: Colinus virginianus (bobwhite quail) oral 575 mg/kg /Isobac/
LD50; Species: Anas platyrhynchos (mallard duck) female oral 1450 mg/kg /Isobac/
EC50; Species: Daphnia magna (Water Flea) age <24 hr neonate; Conditions: freshwater, static, 21 °C, pH 7.6; Concentration: 0.000487 mM for 24 hr; Effect: intoxication, immobilization
LC50; Species: Pimephales promelas (Fathead minnow) age 30 days, length 20.1 mm, weight 0.103 g; Conditions: freshwater, flow through, 24.3 °C, pH 7.30, hardness 51.1 mg/L CaCO3, alkalinity 45.8 mg/L CaCO3, dissolved oxygen 5.8 mg/L; Concentration: 21 ug/L for 96 hr (95% confidence interval: 19-23 ug/L) /99% purity/
TERRESTRIAL FATE: Based on a classification scheme(1), a reported Koc value of 91,000(2), indicates that hexachlorophene is expected to be immobile in soil(SRC). The pKa of hexachlorophene is 4.95(3), indicating that this compound will partially exist in anion form in the environment and anions generally do not adsorb more strongly to soils containing organic carbon and clay than their neutral counterparts(4). Volatilization of hexachlorophene from moist soil surfaces is not expected to be an important fate process(SRC) given an estimated Henry's Law constant of 5.5X10-13 atm-cu m/mole(SRC), using a fragment constant estimation method(5) and the pKa(3). Hexachlorophene is not expected to volatilize from dry soil surfaces(SRC) based upon an estimated vapor pressure of 8.3X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(6). A 0% of theoretical BOD using activated sludge in the Japanese MITI test(7), suggests that biodegradation is not an important environmental fate process in soil(SRC).
AQUATIC FATE: Based on a classification scheme(1), a reported Koc value of 91,000(2), indicates that hexachlorophene is expected to adsorb to suspended solids and sediment(SRC). A pKa of 4.95(3) indicates hexachlorophene will exist partially in the anion form at pH values of 5 to 9 and therefore volatilization of the anion from water surfaces is not expected to be an important fate process(SRC). Volatilization of the neutral species from water surfaces is not expected(4) based upon an estimated Henry's Law constant of 5.5X10-13 atm-cu m/mole(SRC), developed using a fragment constant estimation method(5). Hexachlorophene is not expected to undergo hydrolysis in the environment due to the lack of functional groups that hydrolyze under environmental conditions(4). According to a classification scheme(6), BCFs of 82-153 in carp (Cyprinus carpio)(7) and 278 in mosquito fish (Gambusia affinis)(8) suggest bioconcentration in aquatic organisms is moderate to high(SRC). Radio-labeled C14-hexachlorophene was not biodegraded in surface water from the Skidaway River, GA(9). Hexachlorophene contains chromophores that absorb at wavelengths of 302 and 312 nm at pH 7 and 8, respectively(10-11), and therefore may be susceptible to aqueous photolysis by sunlight(SRC).
ATMOSPHERIC FATE: According to a model of gas/particle partitioning of semivolatile organic compounds in the atmosphere(1), hexachlorophene, which has an estimated vapor pressure of 8.3X10-11 mm Hg at 25 °C(SRC), determined from a fragment constant method(2), is expected to exist solely in the particulate phase in the ambient atmosphere. Particulate-phase hexachlorophene may be removed from the air by wet or dry deposition(SRC). Hexachlorophene has an atmospheric half-life of 4.9 days based upon average atmospheric reaction rates with hydroxyl radicals and ozone(3).
MAY BE ABSORBED! See Ingestion.
Redness.
Nausea. Vomiting. Diarrhoea. Drowsiness. Fall in blood pressure. Convulsions. See Effects of short-term exposure Symptoms may be delayed.
The following link will take the user to the National Toxicology Program (NTP) Test Agent Search Results page, which tabulates all of the "Standard Toxicology & Carcinogenesis Studies", "Developmental Studies", and "Genetic Toxicity Studies" performed with this chemical. Clicking on the "Testing Status" link will take the user to the status (i.e., in review, in progress, in preparation, on test, completed, etc.) and results of all the studies that the NTP has done on this chemical.[Available from: http://ntp-apps.niehs.nih.gov/ntp_tox/index.cfm?fuseaction=ntpsearch.searchresults&searchterm=70-30-4]
Hexachlorophene was detected in all 35 sewage sludge samples from 25 different treatment plants across Canada; concentrations were 22.6 to 1190 ng/g and concentrations were higher in digested sludge. The samples were collected from 1994 to 2000(1).
Hexachlorophene concentrations and removal for 7 consecutive days were tracked from Sept 24-30, 1969 at a Corvallis, OR sewage treatment plant(1).[Table#847]
Concentrations of hexachlorophene in 24-Hour composite samples from sewage treatment plants located in Oregon; samples were collected Nov 13, 1969(1).[Table#848]
The substance is very toxic to aquatic organisms. Bioaccumulation of this chemical may occur along the food chain, for example in aquatic organisms. The substance may cause long-term effects in the aquatic environment. It is strongly advised not to let the chemical enter into the environment.
Hexachlorophene
Gastrointestinal
3 x 10 ^-4 mg/kg-day
The Approved Drug Products with Therapeutic Equivalence Evaluations identifies currently marketed prescription drug products, including hexachlorophene, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.
U132; As stipulated in 40 CFR 261.33, when hexachlorophene, as a commercial chemical product or manufacturing chemical intermediate or an off-specification commercial chemical product or a manufacturing chemical intermediate, becomes a waste, it must be managed according to Federal and/or State hazardous waste regulations. Also defined as a hazardous waste is any residue, contaminated soil, water, or other debris resulting from the cleanup of a spill, into water or on dry land, of this waste. Generators of small quantities of this waste may qualify for partial exclusion from hazardous waste regulations (40 CFR 261.5).
Persons in charge of vessels or facilities are required to notify the National Response Center (NRC) immediately, when there is a release of this designated hazardous substance, in an amount equal to or greater than its reportable quantity of 100 lb or 45.4 kg. The toll free number of the NRC is (800) 424-8802. The rule for determining when notification is required is stated in 40 CFR 302.4 (section IV.D.3.b).
(ME) MAINE 2 ug/L
(FL) FLORIDA 6 ug/L
IWW5FV6NK2
HEXACHLOROPHENE
Established Pharmacologic Class [EPC] - Antiseptic
Hexachlorophene is an Antiseptic.
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.
Compounds that interfere with FATTY ACID SYNTHASE resulting in a reduction of FATTY ACIDS. This is a target mechanism in humans of some ANTINEOPLASTIC AGENTS and ANTI-OBESITY AGENTS and of some ANTI-INFECTIVE AGENTS which interfere with CELL WALL and CELL MEMBRANE formation.
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.
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.
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.
Hexachlorophene was administered intraperitoneally to rats and rabbits. Excretion of this chemical was slow, most (48-83%) excreted unchanged in the feces.
For more Absorption, Distribution and Excretion (Complete) data for HEXACHLOROPHENE (14 total), please visit the HSDB record page.
Used as an antibacterial agent, disinfectant, fungicide, and acaricide; [HSDB]
Using Disinfectants or Biocides [Category: Clean]
For hexachlorophene (USEPA/OPP Pesticide Code: 044901) there are 0 labels match. /SRP: Not registered for current use in the U.S., but approved pesticide uses may change periodically and so federal, state and local authorities must be consulted for currently approved uses./
Chiefly in the manufacture of germicidal soaps
Topical antiinfective (restricted), veterinary medicine
Primarily in consumer products, including cosmetics and germicidal preparations.
USEPA/OPP Pesticide Code 044901; Trade Names: G 11, Acigena, Almederm, AT 7, AT 17, Dermadex, Exofene, Fomac, Fostril, Hexide, Hexophene, Nabac, Septisol, Phisohex, Hexosan, Steral, Surofene, Trichlorophene, Turgex, Eleven. /SRP: Former/
Topical: Emulsion (Hexachlorophene Cleansing Emulsion) 3% w/w pHisoHex (Sanofi-Aventis).
Nabac, 25% emulsifiable concentrate. /SRP: Former/
Isobac (Seribak) (discontinued 1987 by Kalo, Inc) is the monosodium salt of 2,2-methylene bis(3,4,6-trichlorophenol). It was formulated as a 20% emulsifiable concentrate. Compex, a compatibility agent, (principal functioning agents: alcohol sulfates, sodium alkyl butanediamate, polyesters of sodium thio butanedioate) has been suggested for addition to isobac when it was incompatible with other herbicides, fungicides or insecticides. /SRP: Former/
For more Formulations/Preparations (Complete) data for HEXACHLOROPHENE (12 total), please visit the HSDB record page.
Phenol, 2,2'-methylenebis[3,4,6-trichloro-: ACTIVE
Isobac /discontinued in 1987/ is a broad spectrum contact soil, foliar fungicide. /Isobac/