Structure via PubChem · Public domain (PubChem)
hexachlorophene
Sign in to saveAlso known as Septi-Soft, Pre-Op, Turgex, Hexa-Germ, Gamophen, Phiso-Scrub, Septisol, Soy-Dome
Hexachlorophene, also known as Nabac, is an organochlorine compound that was once widely used as a disinfectant. The compound occurs as a white odorless solid, although commercial samples can be off-white and possess a slightly phenolic odor. It is insoluble in water but dissolves in acetone, ethanol, diethyl ether, and chloroform. In medicine, hexachlorophene is useful as a topical anti-infective and anti-bacterial agent. It is also used in agriculture as a soil fungicide, plant bactericide, and acaricide. It has also been reported to bind tubulin, blocking its polymerization.
Key facts
- Drug.IUPAC_name
- 2,2'-methylenebis(3,4,6-trichlorophenol)-3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol
- Drug.image
- Hexachlorophen horizontal.svg
- Drug.image_class
- skin-invert-image
- Drug.alt
- Skeletal formula of hexachlorophene
- Drug.image2
- Hexachlorophene-3D-balls.png
- Drug.image_class2
- bg-transparent
- Drug.alt2
- Ball-and-stick model of the hexachlorophene molecule
- Drug.width2
- 200
- Drug.tradename
- pHisoHex, Gamophen, Septisol, Turgex, Germa-Medica, Hexachlorophane, Almederm
- Drug.legal_US
- Rx-only
- Drug.legal_US_comment
- for human use
- Drug.legal_status
- Rx-only for human use
- Drug.CAS_number
- 70-30-4
- Drug.ATC_prefix
- D08
- Drug.ATC_suffix
- AE01
- Drug.PubChem
- 3598
- Drug.DrugBank
- DB00756
- Drug.ChemSpiderID
- 3472
via Wikipedia infobox
Chemical data
- Formula
- C13H6Cl6O2
- Molecular weight
- 406.9 g/mol
- IUPAC name
- 3,4,6-trichloro-2-[(2,3,5-trichloro-6-hydroxyphenyl)methyl]phenol
- SMILES
- C1=C(C(=C(C(=C1Cl)Cl)CC2=C(C(=CC(=C2Cl)Cl)Cl)O)O)Cl
- InChIKey
- ACGUYXCXAPNIKK-UHFFFAOYSA-N
- XLogP
- 7.5
- Polar surface area
- 40.5 Ų
- H-bond donors
- 2
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Research
1,330 papers- Hexachlorophene.IARC monographs on the evaluation of the carcinogenic risk of chemicals to humans · 1979
- Hexachlorophene in perspective.Journal of clinical pharmacology · 1973
- Hexachlorophene today.Lancet (London, England) · 1982
- Hexachlorophene in the nursery.The Medical letter on drugs and therapeutics · 1973
- Hexachlorophene in the nursery.Canadian Medical Association journal · 1977
via PubMed
Wikidata facts
- Mass
- 403.84989551199993
Show 4 more facts
- chemical formula
- C₁₃H₆Cl₆O₂
- Commons category
- Hexachlorophene
- canonical SMILES
- C1=C(C(=C(C(=C1Cl)Cl)CC2=C(C(=CC(=C2Cl)Cl)Cl)O)O)Cl
- World Health Organisation international non-proprietary name
- hexachlorophene
via Wikidata · CC0
~5 min read
Article
9 sectionsContents
- Production
- Safety
- Selective removal from market
- France
- United States
- Germany
- Austria
- Trade names
- References
Hexachlorophene, also known as Nabac, is an organochlorine compound that was once widely used as a disinfectant. The compound occurs as a white odorless solid, although commercial samples can be off-white and possess a slightly phenolic odor. It is insoluble in water but dissolves in acetone, ethanol, diethyl ether, and chloroform. In medicine, hexachlorophene is useful as a topical anti-infective and anti-bacterial agent. It is also used in agriculture as a soil fungicide, plant bactericide, and acaricide. It has also been reported to bind tubulin, blocking its polymerization.
==Production== Hexachlorophene is produced by alkylation of 2,4,5-trichlorophenol with formaldehyde. Related antiseptics are prepared similarly, e.g., bromochlorophene and dichlorophene.