Hexamidine

Hexamidine
	Skeletal formula of hexamidineSkeletal formula of hexamidine
	Ball-and-stick modelBall-and-stick model
Names
	Preferred IUPAC name 4,4′-[Hexane-1,6-diylbis(oxy)]di(benzene-1-carboximidamide)
	Other names 4-[6-(4-carbamimidoylphenoxy)hexoxy]benzamidine
Identifiers
CAS Number	3811-75-4 check;
3D model (JSmol)	Interactive image;
ChEBI	CHEBI:87184 ☒;
ChEMBL	ChEMBL25105 check;
ChemSpider	58639 check;
DrugBank	DB03808 check;
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E number	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
PubChem CID	65130;
UNII	3483C2H13H check;
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	InChI InChI=1S/C20H26N4O2/c21-19(22)15-5-9-17(10-6-15)25-13-3-1-2-4-14-26-18-11-7-16(8-12-18)20(23)24/h5-12H,1-4,13-14H2,(H3,21,22)(H3,23,24) check Key: OQLKNTOKMBVBKV-UHFFFAOYSA-N check; InChI=1/C20H26N4O2/c21-19(22)15-5-9-17(10-6-15)25-13-3-1-2-4-14-26-18-11-7-16(8-12-18)20(23)24/h5-12H,1-4,13-14H2,(H3,21,22)(H3,23,24) Key: OQLKNTOKMBVBKV-UHFFFAOYAW;
	SMILES O(c1ccc(cc1)C(=[N@H])N)CCCCCCOc2ccc(C(=[N@H])N)cc2;
Properties
Chemical formula	C20H26N4O2
Molar mass	354.446
Pharmacology
ATC code	D08AC04 (WHO) R01AX07 (WHO) R02AA18 (WHO) S01AX08 (WHO) S03AA05 (WHO)
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒ verify (what is check☒ ?) Infobox references

Hexamidine is an antiseptic and a disinfectant. Hexomedine is the trade name of a diisethionate solution (1/1.000) of hexamidine.^[1] Hexamidine is used primarily as its diisethionate salt, which is more water-soluble than the dihydrochloride. The dihydrochloride was first synthesized and patented as a trypanocide for May & Baker in 1939. Its amoebicidal properties emerged in the 1990s. The exact mechanism of its biocidal action is unknown, but presumed similar to quaternary ammonium compounds, involving binding to the negatively charged lipid membranes of pathogens. Hexamidine and its shorter congener, propamidine, are used as antiseptics and preservatives in pharmaceuticals and cosmetics. They are particularly used for the topical treatment of acanthamoebiasis (Acanthamoeba keratitis).^[2]

References

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v t e Antiseptics and disinfectants (D08)
Acridine derivatives	Ethacridine lactate 9-Aminoacridine Euflavine
Biguanides and amidines	Dibrompropamidine Chlorhexidine^# Propamidine Hexamidine Polihexanide
Phenol and derivatives	Hexachlorophene Policresulen Phenol Triclosan Triclocarban Chloroxylenol^# Biphenylol Fenticlor
Nitrofuran derivatives	Nitrofurazone
Iodine products	Iodine/octylphenoxypolyglycolether Povidone-iodine^# Diiodohydroxypropane
Quinoline derivatives	Dequalinium Chlorquinaldol Oxyquinoline Clioquinol
Quaternary ammonium compounds	Benzalkonium Benzethonium chloride Cetrimonium (bromide/chloride) Cetylpyridinium Cetrimide Benzoxonium chloride Didecyldimethylammonium chloride
Mercurial products	Mercuric amidochloride Phenylmercuric borate Mercuric chloride Merbromin Nitromersol Thiomersal Mercuric iodide
Silver compounds	Silver nitrate
Alcohols	Propanol (propyl alcohol) Isopropanol (isopropyl alcohol) Ethanol (ethyl alcohol)^#
Other	Potassium permanganate Sodium hypochlorite Halazone Monalazone Hydrogen peroxide Eosin Chloramine-T (tosylchloramide) Octenidine dihydrochloride
^#WHO-EM ^‡Withdrawn from market Clinical trials: ^†Phase III ^§Never to phase III

Names
Skeletal formula of hexamidine Skeletal formula of hexamidine
Ball-and-stick model Ball-and-stick model
Preferred IUPAC name 4,4′-[Hexane-1,6-diylbis(oxy)]di(benzene-1-carboximidamide)
Other names 4-[6-(4-carbamimidoylphenoxy)hexoxy]benzamidine
Identifiers
CAS Number	3811-75-4^checkY
3D model (JSmol)	Interactive image
ChEBI	CHEBI:87184^☒N
ChEMBL	ChEMBL25105^checkY
ChemSpider	58639^checkY
DrugBank	DB03808^checkY
ECHA InfoCard	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value). Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
E number	Lua error in Module:Wikidata at line 880: attempt to index field 'wikibase' (a nil value).
PubChem CID	65130
UNII	3483C2H13H^checkY
CompTox Dashboard (EPA)	{{#property:P3117}}Lua error in Module:EditAtWikidata at line 29: attempt to index field 'wikibase' (a nil value).
InChI InChI=1S/C20H26N4O2/c21-19(22)15-5-9-17(10-6-15)25-13-3-1-2-4-14-26-18-11-7-16(8-12-18)20(23)24/h5-12H,1-4,13-14H2,(H3,21,22)(H3,23,24)^checkY Key: OQLKNTOKMBVBKV-UHFFFAOYSA-N^checkY InChI=1/C20H26N4O2/c21-19(22)15-5-9-17(10-6-15)25-13-3-1-2-4-14-26-18-11-7-16(8-12-18)20(23)24/h5-12H,1-4,13-14H2,(H3,21,22)(H3,23,24) Key: OQLKNTOKMBVBKV-UHFFFAOYAW
SMILES O(c1ccc(cc1)C(=[N@H])N)CCCCCCOc2ccc(C(=[N@H])N)cc2
Properties
Chemical formula	C₂₀H₂₆N₄O₂
Molar mass	354.446
Pharmacology
ATC code	D08AC04 (WHO) R01AX07 (WHO) R02AA18 (WHO) S01AX08 (WHO) S03AA05 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). ☒N verify (what is ^checkY☒N ?) Infobox references

Hexamidine

References

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