Antrafenine

Antrafenine (Stakane) is a phenylpiperazine derivative drug invented in 1979.[1] It acts as an analgesic and anti-inflammatory drug with similar efficacy to naproxen,[2] but is not widely used as it has largely been replaced by newer drugs.

Antrafenine

Clinical data
Routes of administration	Oral
ATC code	none
Legal status
Legal status	In general: ℞ (Prescription only)
Pharmacokinetic data
Metabolism	Hepatic
Excretion	Renal
Identifiers
IUPAC name 2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl 2-{[7-(trifluoromethyl)quinolin-4-yl]amino}benzoate
CAS Number	55300-30-6^Y
PubChem CID	68723
DrugBank	DB01419^Y
ChemSpider	61973^Y
UNII	21FS93Y6OE
ChEMBL	ChEMBL345524^Y
CompTox Dashboard (EPA)	DTXSID60203833
Chemical and physical data
Formula	C30H26F6N4O2
Molar mass	588.554 g·mol^−1
3D model (JSmol)	Interactive image
SMILES FC(F)(F)c5ccc1c(nccc1Nc2ccccc2C(=O)OCCN4CCN(c3cc(ccc3)C(F)(F)F)CC4)c5
InChI InChI=1S/C30H26F6N4O2/c31-29(32,33)20-4-3-5-22(18-20)40-14-12-39(13-15-40)16-17-42-28(41)24-6-1-2-7-25(24)38-26-10-11-37-27-19-21(30(34,35)36)8-9-23(26)27/h1-11,18-19H,12-17H2,(H,37,38)^Y Key:NWGGKKGAFZIVBJ-UHFFFAOYSA-N^Y
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See also

• Phenylpiperazine
• Trifluoromethylphenylpiperazine

References

1. Manoury PM, Dumas AP, Najer H, Branceni D, Prouteau M, Lefevre-Borg FM. Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates. Journal of Medicinal Chemistry. 1979 May;22(5):554-9.
2. Leatham PA, Bird HA, Wright V, Seymour D, Gordon A. A double blind study of antrafenine, naproxen and placebo in osteoarthrosis. European Journal of Rheumatology and Inflammation. 1983;6(2):209-11.