Afloqualone

Afloqualone
Clinical data
AHFS/Drugs.com	International Drug Names
ATC code	none;
Legal status
Legal status	US: Unscheduled;
Identifiers
	IUPAC name 6-Amino-2-(fluoromethyl)-3-(2-methylphenyl)quinazolin-4-one;
CAS Number	56287-74-2 ;
PubChem CID	2040;
ChemSpider	1960 ;
UNII	CO4U2C8ORZ;
KEGG	D01638 ;
ChEMBL	ChEMBL2105918 ;
CompTox Dashboard (EPA)	DTXSID5022562 ;
Chemical and physical data
Formula	C16H14FN3O
Molar mass	283.306 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C1C2=CC(N)=CC=C2N=C(CF)N1C3=CC=CC=C3C;
	InChI InChI=1S/C16H14FN3O/c1-10-4-2-3-5-14(10)20-15(9-17)19-13-7-6-11(18)8-12(13)16(20)21/h2-8H,9,18H2,1H3 ; Key:VDOSWXIDETXFET-UHFFFAOYSA-N ;
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Afloqualone (Arofuto) is a quinazolinone family GABAergic drug and is an analogue of methaqualone developed in the 1970s by a team at Tanabe Seiyaku.^[1] It has sedative and muscle-relaxant effects resulting from its agonist activity at the β subtype of the GABA_a receptor^[2] and has had some clinical use, although it causes photosensitization as a side-effect that can cause skin problems such as dermatitis.^[3]

^ US 3966731, Inoue I, Oine T, Yamada Y, Tani J, Ishida R, Ochiai T, "2-Fluoromethyl-3-o-tolyl-6-amino-4(3H)-quinazolinone", issued 29 June 1976, assigned to Tanabe Seiyaku Co Ltd
^ Ochiai T, Ishida R (June 1982). "Pharmacological studies on 6-amino-2-fluoromethyl-3-(O-tolyl)-4(3H)-quinazolinone (afloqualone), a new centrally acting muscle relaxant. (II) Effects on the spinal reflex potential and the rigidity". Japanese Journal of Pharmacology. 32 (3): 427–38. doi:10.1254/jjp.32.427. PMID 7109348.
^ Ishikawa T, Kamide R, Niimura M (June 1994). "Photoleukomelanodermatitis (Kobori) induced by afloqualone". The Journal of Dermatology. 21 (6): 430–3. doi:10.1111/j.1346-8138.1994.tb01768.x. PMID 8064007. S2CID 7486566.