Hexamidine

{{chembox

| Verifiedfields = changed

| verifiedrevid = 443856387

| ImageFile = Hexamidine.png

| ImageSize = 250px

| ImageName = Skeletal formula of hexamidine

| ImageFile1 = Hexamidine-3D-balls.png

| ImageSize1 = 250px

| ImageName1 = Ball-and-stick model

| PIN = 4,4′-[Hexane-1,6-diylbis(oxy)]di(benzene-1-carboximidamide)

| OtherNames = 4-[6-(4-carbamimidoylphenoxy)hexoxy]benzamidine

|Section1={{Chembox Identifiers

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = 3483C2H13H

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 58639

| ChEBI_Ref = {{ebicite|changed|EBI}}

| ChEBI = 87184

| 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)

| InChIKey = OQLKNTOKMBVBKV-UHFFFAOYAW

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 25105

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 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)

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = OQLKNTOKMBVBKV-UHFFFAOYSA-N

| CASNo_Ref = {{cascite|correct|??}}

| CASNo=3811-75-4

| PubChem=65130

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank = DB03808

| SMILES = O(c1ccc(cc1)C(=[N@H])N)CCCCCCOc2ccc(C(=[N@H])N)cc2

}}

|Section2={{Chembox Properties

| Formula=C₂₀H₂₆N₄O₂

| MolarMass=354.446

| Appearance=

| Density=

| MeltingPt=

| BoilingPt=

| Solubility=

}}

|Section6={{Chembox Pharmacology

| ATCCode_prefix = D08

| ATCCode_suffix = AC04

| ATC_Supplemental = {{ATC|R01|AX07}} {{ATC|R02|AA18}} {{ATC|S01|AX08}} {{ATC|S03|AA05}}

}}

|Section7={{Chembox Hazards

| MainHazards=

| FlashPt=

| AutoignitionPt =

}}

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Hexamidine is an antiseptic and a disinfectant. Hexomedine is the trade name of a diisethionate solution (1/1.000) of hexamidine.{{Cite journal

| doi = 10.1080/10915810701663168

| title = Final Report on the Safety Assessment of Hexamidine and Hexamidine Diisethionate

| journal = International Journal of Toxicology

| volume = 26

| issue = 3_suppl

| pages = 79–88

| year = 2007

| pmid = 18273451

| pmc =

| s2cid = 2059780

}} 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).{{citation | author=Parisi, N.|display-authors=etal | title=Hexamidine salts - applications in skin health and personal care products | journal=International Journal of Cosmetic Science | volume=39 | issue=4 |pages=361–365 | year=2017 | pmid=28129440 | doi=10.1111/ics.12392|s2cid=3385063 |url=http://discovery.ucl.ac.uk/1540352/1/PDF.pdf | doi-access=free }}