Acriflavine

Title: Acriflavine
CAS Registry Number: 8048-52-0
CAS Name: 3,6-Diamino-10-methylacridinium chloride mixt with 3,6-acridinediamine
Additional Names: neutral acriflavine; euflavine; trypaflavine; neutroflavine; gonacrine
Literature References: Contains 30-40% unmethylated compd. Prepn: L. Benda, Ber. 45, 1787 (1912); M. Gaillot, Q. J. Pharm. Pharmacol. 7, 63 (1934); J. Marshall, ibid. 514. Activity studies: C. H. Browning, W. Gilmour, J. Pathol. Bact. 18, 144 (1913); C. H. Browning et al., Br. Med. J. 1, 73 (1917); H. Berry, Q. J. Pharm. Pharmacol. 14, 149 (1941); H. McIlwain, Biochem. J. 35, 1311 (1941). Toxicology: J. Ungar et al., J. Pharmacol. Exp. Ther. 80, 217 (1944). Reviews: A. Adrien, The Acridines (St. Martin's Press, New York, 2nd ed., 1966); R. M. Acheson, Acridines (Interscience, New York, 2nd ed., 1973).
Properties: Deep orange, granular powder. One gram dissolves in about 3 ml water. Incompletely sol in alcohol; nearly insol in ether, chloroform, fixed oils. Aqueous solns are reddish orange and fluoresce on dilution. pH (1% soln) ~3.5.
Derivative Type: Dihydrochloride
CAS Registry Number: 8063-24-9
Additional Names: Acid acriflavine; acid trypaflavine; acriflavine hydrochloride
Trademarks: Panflavin (Chinosolfabrik)
Properties: Deep reddish-brown, crystalline powder. pH (1% soln) ~1.5.
Therap-Cat: Anti-infective.
Therap-Cat-Vet: Antiseptic; locally in wounds in trichomoniasis of bulls.
Keywords: Antiseptic/Disinfectant; Dyes.
Acrilan? Acrinathrin Acrisorcin Acrivastine Acrolein

Acriflavinium chloride
Wireframe of acriflavine
Pure Acriflavinium chloride: A brown powder
Pure Acriflavinium chloride
Identifiers
CAS number 65589-70-0 N, 10597-46-3 (hydrochloride)
PubChem 443101 YesY, 15558347 (hydrochloride) YesY
ChemSpider 391386 YesY, 21018 (hydrochloride) YesY
EC number 201-668-8
ChEBI CHEBI:383703 N
ChEMBL CHEMBL354349 N
ATC code R02AA13,QG01AC90
Jmol-3D images Image 1
Image 2
Properties
Molecular formula C14H14ClN3
Molar mass 259.73 g mol−1
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Acriflavine 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. Commercial preparations are often mixtures with proflavine. It is known by a variety of commercial names.

Acriflavine was developed in 1912 by Paul Ehrlich, a German medical researcher and was used during the First World War against sleeping sickness. It is derived from acridine. The hydrochloride form is more irritating than the neutral form.

Acriflavine is also used as treatment for external fungal infections of aquarium fish.

Acriflavine has been shown to have anti-cancer activity by inhibition of HIF-1 which prevents blood vessels growing to supply tumors with blood and interferes with glucose uptake and use.[1]