Acriflavine

Last updated
Acriflavine
Acriflavine.png
Acriflavinium chloride substance photo.jpg
Sample of pure acriflavine
Names
Preferred IUPAC name
3,6-Diamino-10-methylacridin-10-ium chloride
Other names
Acriflavinium chloride (INN)
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard 100.211.047 OOjs UI icon edit-ltr-progressive.svg
EC Number
  • 201-668-8
PubChem CID
UNII
  • InChI=1S/C14H13N3.ClH/c1-17-13-7-11(15)4-2-9(13)6-10-3-5-12(16)8-14(10)17;/h2-8H,1H3,(H3,15,16);1H X mark.svgN
    Key: KKAJSJJFBSOMGS-UHFFFAOYSA-N X mark.svgN
  • InChI=1S/C14H13N3.C13H11N3.ClH/c1-17-13-7-11(15)4-2-9(13)6-10-3-5-12(16)8-14(10)17;14-10-3-1-8-5-9-2-4-11(15)7-13(9)16-12(8)6-10;/h2-8H,1H3,(H3,15,16);1-7H,14-15H2;1H
    Key: PEJLNXHANOHNSU-UHFFFAOYSA-N
  • Key: PEJLNXHANOHNSU-UHFFFAOYSA-N
  • [Cl-].C[N+]1=C2C=C(N)C=CC2=CC2=C1C=C(N)C=C2
  • [Cl-].n1c3c(cc2c1cc(N)cc2)ccc(c3)N.Nc3cc2[n+](c1cc(N)ccc1cc2cc3)C
Properties
C14H14ClN3
Molar mass 259.74 g·mol−1
Pharmacology
R02AA13 ( WHO ) QG01AC90 ( 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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Acriflavine (INN: acriflavinium chloride) is a topical antiseptic. It has the form of an orange or brown powder. It may be harmful in the eyes or if inhaled. It is a dye and it stains the skin and may irritate. The hydrochloride form is more irritating than the neutral form. It is derived from acridine. Commercial preparations are often mixtures with proflavine. [1] It is known by a variety of commercial names.

Contents

Uses

Medical use

Acriflavine was developed in 1912 by Paul Ehrlich, a German medical researcher, and was used during the First World War against sleeping sickness and as a topical antiseptic. [2]

Other uses

Acriflavine is used in biochemistry for fluorescently labeling high molecular weight RNA. [1]

It is used as treatment for external fungal infections of aquarium fish. [3]

Research

In an animal model, acriflavine has been shown to inhibit HIF-1, which prevents blood vessels growing to supply tumors with blood and interferes with glucose uptake and use. [4]

Acriflavine might be effective in fighting common cold virus, and also aid the fight against increasingly antibiotic resistant bacteria [5] [6] [7] because it can cure (remove) plasmids containing antimicrobial resistance genes from Gram positive bacteria. [8]

Since 2014, acriflavine has been undergoing testing as an antimalarial drug to treat parasites with resistance to quinine and modern anti-parasitic medicines. [9]

Australia

Acriflavine is a controlled substance in Australia and dependent on situation,[ clarification needed ] is considered either a Schedule 5 (Caution) or Schedule 7 (Dangerous Poison) substance. The use, storage and preparation of the chemical is subject to strict state and territory laws.[ citation needed ]

Related Research Articles

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A bactericide or bacteriocide, sometimes abbreviated Bcidal, is a substance which kills bacteria. Bactericides are disinfectants, antiseptics, or antibiotics. However, material surfaces can also have bactericidal properties based solely on their physical surface structure, as for example biomaterials like insect wings.

<span class="mw-page-title-main">Beta-lactamase</span> Class of enzymes

Beta-lactamases (β-lactamases) are enzymes produced by bacteria that provide multi-resistance to beta-lactam antibiotics such as penicillins, cephalosporins, cephamycins, monobactams and carbapenems (ertapenem), although carbapenems are relatively resistant to beta-lactamase. Beta-lactamase provides antibiotic resistance by breaking the antibiotics' structure. These antibiotics all have a common element in their molecular structure: a four-atom ring known as a beta-lactam (β-lactam) ring. Through hydrolysis, the enzyme lactamase breaks the β-lactam ring open, deactivating the molecule's antibacterial properties.

<span class="mw-page-title-main">Macrolide</span> Class of natural products

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<span class="mw-page-title-main">Drug resistance</span> Pathogen resistance to medications

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<span class="mw-page-title-main">Polypeptide antibiotic</span> Class of antibiotics

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References

  1. 1 2 "Acriflavine". Sigma-Aldrich.
  2. acriflavine Encyclopædia Britannica
  3. "Acriflavine use in aquaria". Archived from the original on 2016-01-29. Retrieved 2016-01-24.
  4. Lee, K.; Zhang, H.; Qian, D. Z.; Rey, S.; Liu, J. O.; Semenza, G. L. (2009). "Acriflavine inhibits HIF-1 dimerization, tumor growth, and vascularization". Proceedings of the National Academy of Sciences. 106 (42): 17910–5. Bibcode:2009PNAS..10617910L. doi: 10.1073/pnas.0909353106 . PMC   2764905 . PMID   19805192.
  5. "Antiseptic used in WWI could hold key to treating superbugs, viral infections, Melbourne researchers say". ABC. November 28, 2016.
  6. "This forgotten WWI antiseptic could be the key to fighting antibiotic resistance". Science Alert. November 30, 2016.
  7. Pépin, Geneviève; Nejad, Charlotte; Thomas, Belinda J; Ferrand, Jonathan; McArthur, Kate; Bardin, Philip G; Williams, Bryan RG; Gantier, Michael P (2016). "Activation of cGAS-dependent antiviral responses by DNA intercalating agents". Nucleic Acids Research. 45 (1): 198–205. doi:10.1093/nar/gkw878. PMC   5224509 . PMID   27694309.
  8. Mesas, J.M.; Rodriguez, M.C.; Alegre, M.T. (2004). "Plasmid curing of Oenococcus oeni". Plasmid. 51 (1): 37–40. doi:10.1016/S0147-619X(03)00074-X. PMID   14711527.
  9. Dana, Srikanta; Prusty, Dhaneswar; Dhayal, Devender; Gupta, Mohit Kumar; Dar, Ashraf; Sen, Sobhan; Mukhopadhyay, Pritam; Adak, Tridibesh; Dhar, Suman Kumar (2014). "Potent Antimalarial Activity of Acriflavine In Vitroand In Vivo". ACS Chemical Biology. 9 (10): 2366–73. doi:10.1021/cb500476q. PMC   4201339 . PMID   25089658.