Hexamidine

Hexamidine is an antiseptic and 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]

Hexamidine

Names
IUPAC name 4,4'-[hexane-1,6-diylbis(oxy)]dibenzenecarboximidamide
Other names 4-[6-(4-carbamimidoylphenoxy)hexoxy]benzamidine
Identifiers
CAS Number	3811-75-4^Y
3D model (JSmol)	Interactive image
ChEBI	CHEBI:87184^N
ChEMBL	ChEMBL25105^Y
ChemSpider	58639^Y
DrugBank	DB03808^Y
PubChem CID	65130
UNII	3483C2H13H^Y
CompTox Dashboard (EPA)	DTXSID60191524
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)^Y Key: OQLKNTOKMBVBKV-UHFFFAOYSA-N^Y 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 ^YN ?)
Infobox references

References

1. "Final Report on the Safety Assessment of Hexamidine and Hexamidine Diisethionate". International Journal of Toxicology. 26 (3_suppl): 79–88. 2007. doi:10.1080/10915810701663168. PMID 18273451.
2. Parisi, N.; et al. (2017), "Hexamidine salts - applications in skin health and personal care products" (PDF), International Journal of Cosmetic Science, 39 (4): 361–365, doi:10.1111/ics.12392, PMID 28129440