Acriflavine

Acriflavine
Names

Sample of pure acriflavine
IUPAC name 3,6-Diamino-10-methylacridin-10-ium chloride
Other names Acriflavinium chloride (INN)
Identifiers
CAS Number	65589-70-0^N 10597-46-3 (HCl)^Y
3D model (Jmol)	Interactive image Interactive image
ChEBI	CHEBI:383703^N
ChEMBL	ChEMBL354349^N
ChemSpider	391386^Y 21018 (HCl)^Y
EC Number	201-668-8
PubChem	443101 15558347 (HCl)
UNII	1S73VW819C^N
InChI 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^N Key: KKAJSJJFBSOMGS-UHFFFAOYSA-N^N 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
SMILES [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
Chemical formula	C₁₄H₁₄ClN₃
Molar mass	259.74 g·mol⁻¹
Pharmacology
ATC code	R02AA13 (WHO) QG01AC90 (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

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.

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

Acriflanvine 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].

Legal status

Australia

Acriflavine is a controlled substance in Australia and dependent on situation, 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.

References

1 2 "Acriflavine". Sigma-Aldrich.
↑ acriflavine Encyclopedia Britannica
↑ Acriflavine use in aquaria
↑ 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. doi:10.1073/pnas.0909353106.
↑ "Antiseptic used in WWI could hold key to treating superbugs, viral infections, Melbourne researchers say". ABC. November 28, 2016.
↑ "This forgotten WWI antiseptic could be the key to fighting antibiotic resistance". Science Alert. November 30, 2016.
↑ "Activation of cGAS-dependent antiviral responses by DNA intercalating agents". Nucleic Acids Research. 2016. doi:10.1093/nar/gkw878.

External links

ChemExper Chemical Directory

This article is issued from Wikipedia - version of the 12/4/2016. The text is available under the Creative Commons Attribution/Share Alike but additional terms may apply for the media files.