Propamidine

Last updated
Propamidine
Propamidine.png
Propamidine-3D-balls.png
Names
Preferred IUPAC name
4,4′-[Propane-1,3-diylbis(oxy)]di(benzene-1-carboximidamide)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.002.905 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
UNII
  • InChI=1S/C17H20N4O2/c18-16(19)12-2-6-14(7-3-12)22-10-1-11-23-15-8-4-13(5-9-15)17(20)21/h2-9H,1,10-11H2,(H3,18,19)(H3,20,21) Yes check.svgY
    Key: WTFXJFJYEJZMFO-UHFFFAOYSA-N Yes check.svgY
  • InChI=1/C17H20N4O2/c18-16(19)12-2-6-14(7-3-12)22-10-1-11-23-15-8-4-13(5-9-15)17(20)21/h2-9H,1,10-11H2,(H3,18,19)(H3,20,21)
    Key: WTFXJFJYEJZMFO-UHFFFAOYAO
  • O(c1ccc(cc1)C(=[N@H])N)CCCOc2ccc(C(=[N@H])N)cc2
Properties
C17H20N4O2
Molar mass 312.373 g·mol−1
Pharmacology
D08AC03 ( WHO ) S01AX15 ( WHO )
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Propamidine is an antiseptic and disinfectant.

Propamidine isethionate, the salt of propamidine with isethionic acid, is used in the treatment of Acanthamoeba infection. [1]

Propamidine is a member of the aromatic diamidine group of compounds which possess bacteriostatic properties against a wide range of organisms. These diamidines exert antibacterial action against pyrogenic cocci, antibiotic resistant staphylococci and some Gram-negative bacilli, the activity of the diamidines being retained in the presence of organic matter such as tissue fluids, pus and serum. [2]

Related Research Articles

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Keratitis is a condition in which the eye's cornea, the clear dome on the front surface of the eye, becomes inflamed. The condition is often marked by moderate to intense pain and usually involves any of the following symptoms: pain, impaired eyesight, photophobia, red eye and a 'gritty' sensation.

<span class="mw-page-title-main">Amoebozoa</span> Phylum of protozoans

Amoebozoa is a major taxonomic group containing about 2,400 described species of amoeboid protists, often possessing blunt, fingerlike, lobose pseudopods and tubular mitochondrial cristae. In traditional and currently no longer supported classification schemes, Amoebozoa is ranked as a phylum within either the kingdom Protista or the kingdom Protozoa. In the classification favored by the International Society of Protistologists, it is retained as an unranked "supergroup" within Eukaryota. Molecular genetic analysis supports Amoebozoa as a monophyletic clade. Modern studies of eukaryotic phylogenetic trees identify it as the sister group to Opisthokonta, another major clade which contains both fungi and animals as well as several other clades comprising some 300 species of unicellular eukaryotes. Amoebozoa and Opisthokonta are sometimes grouped together in a high-level taxon, variously named Unikonta, Amorphea or Opimoda.

<i>Acanthamoeba</i> keratitis Eye infection caused by a protist

Acanthamoeba keratitis (AK) is a rare disease in which amoebae of the genus Acanthamoeba invade the clear portion of the front (cornea) of the eye. It affects roughly 100 people in the United States each year. Acanthamoeba are protozoa found nearly ubiquitously in soil and water and can cause infections of the skin, eyes, and central nervous system.

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<span class="mw-page-title-main">Hexamidine</span> Chemical compound

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

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<span class="mw-page-title-main">Acanthamoebidae</span>

Acanthamoebidae is a family of single-celled eukaryotes within the group Amoebozoa.

<i>Acanthamoeba</i> infection Medical condition

Acanthamoeba infection is a cutaneous condition resulting from Acanthamoeba that may result in various skin lesions. Acanthamoeba strains can also infect human eyes causing Acanthamoeba keratitis.

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Amoebozoa of the free living genus Acanthamoeba and the social amoeba genus Dictyostelium are single celled eukaryotic organisms that feed on bacteria, fungi, and algae through phagocytosis, with digestion occurring in phagolysosomes. Amoebozoa are present in most terrestrial ecosystems including soil and freshwater. Amoebozoa contain a vast array of symbionts that range from transient to permanent infections, confer a range of effects from mutualistic to pathogenic, and can act as environmental reservoirs for animal pathogenic bacteria. As single celled phagocytic organisms, amoebas simulate the function and environment of immune cells like macrophages, and as such their interactions with bacteria and other microbes are of great importance in understanding functions of the human immune system, as well as understanding how microbiomes can originate in eukaryotic organisms.

References

  1. Perrine D, Chenu JP, Georges P, Lancelot JC, Saturnino C, Robba M (February 1995). "Amoebicidal efficiencies of various diamidines against two strains of Acanthamoeba polyphaga". Antimicrob. Agents Chemother. 39 (2): 339–42. doi:10.1128/aac.39.2.339. PMC   162538 . PMID   7726493.
  2. "Brolene Eye Drops - Summary of Product Characteristics (SmPC) - (eMC)". www.medicines.org.uk. Retrieved 2018-11-23.