Hexachlorophene

FromWikipedia,thefreeencyclopedia

Hexachlorophene,alsoknownas
Nabac,isanorganochlorinecompound
Hexachlorophene
thatwasoncewidelyusedasa
disinfectant.Thecompoundoccursasa
whiteodorlesssolid,although
commercialsamplescanbeoffwhiteand
possessaslightlyphenolicodor.Itis
insolubleinwaterbutdissolvesin
acetone,ethanol,diethylether,and
chloroform.Inmedicine,
hexachloropheneisausefulasatopical
antiinfective,antibacterialagent,often
usedinsoapsandtoothpaste.Itisalso
usedinagricultureasasoilfungicide,
Clinicaldata
plantbactericide,andacaricide.[1]
Trade pHisoHex,Gamophen,Septisol,
names Turgex,GermaMedica,
Hexachlorophane,Almederm
Contents ATCcode D08AE01(WHO(http://www.w
hocc.no/atc_ddd_index/?code=D
1 Commercialization
1.1 US,andremovalfrom 08AE01))QP52AG02(WHO(ht
market tp://www.whocc.no/atcvet/atcvet
1.2 Europe _index/?code=QP52AG02))
2 Production Legalstatus
3 Safety
Legalstatus US:onlyforhumanuse
4 Tradenames
5 References Rxonlyforhumanuse
Identifiers
IUPACname
Commercialization CAS 70304(http://www.commonche
Number mistry.org/ChemicalDetail.aspx?
US,andremovalfrommarket ref=70304)
PubChem 3598(https://pubchem.ncbi.nlm.
CID nih.gov/compound/3598)
DrugBank
In1972,theU.S.FoodandDrug DB00756(https://www.drugban
Administration(FDA)haltedthe k.ca/drugs/DB00756)
productionanddistributionofproducts ChemSpider 3472(http://www.chemspider.co
containingmorethan1%of
m/ChemicalStructure.3472.htm
hexachlorophene.[2]Afterthatpoint, l)
mostproductsthatcontain
UNII IWW5FV6NK2(http://fdasis.nl
hexachlorophenewereavailableonlyby
m.nih.gov/srs/srsdirect.jsp?regno
prescriptionfromadoctor.[3]The
=IWW5FV6NK2)
restrictionswereenactedafter15deaths
intheUnitedStatesand39deathsin KEGG D00859(http://www.kegg.jp/entr
Francewerereportedfollowingbrain y/D00859)
damagecausedbyhexachlorophene.[4] ChEBI CHEBI:5693(https://www.ebi.a
c.uk/chebi/searchId.do?chebiId=
Atleasttwocompaniesmanufactured CHEBI:5693)
overthecounterpreparations
ChEMBL CHEMBL496(https://www.ebi.a
incorporatinghexachlorophene.One
c.uk/chembldb/index.php/compo
productwasBabyMagicBathbyThe
MennenCompany.Mennenrecalledthe und/inspect/CHEMBL496)
productin1971,anditwasremoved ECHA 100.000.667(https://echa.europa.eu/su
fromretaildistribution.Immediately InfoCard bstanceinformation//substanceinfo/1
afterthewithdrawal,therewasan 00.000.667)
outbreakofStaphylococcusinfectionsin Chemicalandphysicaldata
hospitalsacrosstheUSA.[5] Formula C13H6Cl6O2
Twocommercialpreparationsusing Molarmass 406.89gmol1
hexachlorophene,pHisoDermand
3Dmodel Interactiveimage(http://chemap
pHisoHex,werewidelyusedas (Jmol) ps.stolaf.edu/jmol/jmol.php?mod
antibacterialskincleansersinthe
treatmentofacne,withpHisoDerm el=C1%3DC%28C%28%3DC%
developedforthoseallergictotheactive 28C%28%3DC1Cl%29Cl%29C
ingredientsinpHisoHex.IntheUS C2%3DC%28C%28%3DCC%2
duringthe1960s,bothwereavailable 8%3DC2Cl%29Cl%29Cl%29
overthecounter.Afterthebanwas O%29O%29Cl)
enacted,pHisoDermwasreformulated Density 1.71g/cm3
withouthexachlorophene,andcontinued
tobesoldoverthecounter,while Melting 163to165C(325to329F)
point
pHisoHex,whichcontained3%
hexachlorophene(threetimesthelegal Boiling 471C(880F)
point
limitimposedin1972),[4]became
available(andremainsavailabletoday) SMILES
asaprescriptionbodywash.Inthe InChI
EuropeanCommunitycountriesduring
the1970sand1980s,pHisoHexwasavailableoverthecounter.Arelatedproduct,pHisoAc,
wasusedasaskinmasktodryandpeelawayacnelesions.Anotherpreparation,pHiso
Scrub,wasahexachloropheneimpregnatedspongeforscrubbing,hassincebeen
discontinued.Severalsubstituteproducts(includingtriclosan)weredeveloped,butnone
hadthegermkillingcapabilityofhexachlorophene.SanofiAventiswasthesole
manufacturerofpHisoHex,whileTheMentholatumCompanyownsthepHisoDermbrand
today.SanofiAventisdiscontinuedproductionofseveralformsofpHisoHexinAugust
2009anddiscontinuedallproductionofpHisoHexinSeptember2013.[6]

TheformulaforDialsoapwaschangedtoremovehexachloropheneaftertheFDAputan
endtooverthecounteravailabilityin1972.[3]

Europe

InGermany,cosmeticscontaininghexachlorophenehavebeenforbiddensince1985.In
Austria,saleofdrugscontainingthesubstancehasbeenforbiddensince1990.[7]

Production
Hexacholoropheneisproducedbyalkylationof2,4,5trichlorophenolwithformaldehyde.
Relatedantisepticsarepreparedsimilarly,e.g.,bromochloropheneanddichlorophene.[1]

Safety
TheLD50(oral,rat)is59mg/kg,indicatingthatthecompoundisrelativelytoxic.Itisnot
mutagenicnorteratogenicaccordingtoUllmann'sEncyclopaedia,[1]but"embryotoxicand
producessometeratogeniceffects"accordingtotheInternationalAgencyforResearchon
Cancer.[8]

Tradenames
Tradenamesforhexachloropheneinclude:Acigena,Almederm,AT7,AT17,Bilevon,
Exofene,Fostril,Gamophen,G11,GermaMedica,Hexosan,K34,Septisol,
Surofene.[9][10]
References
1.Fiege,H.Voges,H.M.Hamamoto,TUmemura,S.Iwata,T.Miki,H.Fujita,Y.Buysch,
H.J.Garbe,D.Paulus,W.(2000)."PhenolDerivatives".Ullmann'sEncyclopediaofIndustrial
Chemistry.Weinheim:WileyVCH.doi:10.1002/14356007.a19_313.ISBN3527306730.
2.GermicideLimitStirsConfusion,NewYorkTimes,September24,1972,pg.53.
3.TheMilwaukeeSentinel:"USOrderCurbsHexachlorophene"(UPI),September23,1972.From
GoogleNews.(https://news.google.com/newspapers?id=hHRQAAAAIBAJ&sjid=YhEEAAAA
IBAJ&pg=3621,2685761&dq=dial+hexachlorophene&hl=en)
4.OcalaStarBanner,"15DeathsCitedInUseofGermKiller,Hexachlorophene"(AP),March21,
1973.FromGoogleNews.(https://news.google.com/newspapers?nid=1356&dat=19730321&id
=dI5PAAAAIBAJ&sjid=fQUEAAAAIBAJ&pg=7064,4239653&hl=en)
5.Dixon,REKaslow,RAMallison,GFBennett,JV(1973)."Staphylococcaldiseaseoutbreaks
inhospitalnurseriesintheUnitedStatesDecember1971throughMarch1972".Pediatrics.51
(2):4137.PMID4700144.
6.http://www.ashp.org/menu/DrugShortages/DrugsNoLongerAvailable/Bulletin.aspx?id=1059.
7.RechtsinformationssystemdessterreichischenBundeskanzleramtes(http://www.ris.bka.gv.at/D
okumente/Bundesnormen/NOR12134873/NOR12134873.html)(German)
8."Hexachlorophene".InternationalAgencyforResearchonCancer(IARC)Summaries&
Evaluations.IPCSInchem.20:241.1998[1979].
9."Hexachlorophene".PharmGKB.Retrieved20121228.
10.Dept.ofHealth,Education,andWelfare(1972)."Consumernews".OfficeofConsumerAffairs.
2(21):10.

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Categories: Teratogens Chloroarenes Antiseptics Phenols

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