Acriflavinium chloride

Acriflavinium chloride
Names

Pure acriflavinium chloride
IUPAC name 3,6-Diamino-10-methylacridin-10-ium chloride
Identifiers
ATC code	R02AA13 QG01AC90
CAS Registry Number	65589-70-0^N 10597-46-3 (HCl)^Y
ChEBI	CHEBI:383703^N
ChEMBL	ChEMBL354349^N
ChemSpider	391386^Y 21018 (HCl)^N
EC number	201-668-8
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 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
Jmol-3D images	Image Image
PubChem	443101 15558347 (HCl)
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
Molecular formula	C₁₄H₁₄ClN₃
Molar mass	259.73 g·mol⁻¹
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
N verify (what is: Y/N?)
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]

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

↑ 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.

Encyclopædia Britannica (accessed 2005-08-16)
ChemExper Chemical Directory (accessed 2005-08-16)
Houghton Mifflin definition (accessed 2005-08-16)