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an analgesic and anti-inflammatory drug with similar efficacy to naproxen,^[2] but is not widely used as it has largely been replaced by newer drugs.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	55300-29-3 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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Synthesis

Thieme Synthesis:^[1] Patents:^[3][4][5]

Method E: The reaction between 2-[4-[3-(trifluoromethyl)phenyl]-1-piperazinyl]ethanol [40004-29-3] (1) and Isatoic anhydride [118-48-9] (2) goes on to give 4-(3-(Trifluoromethyl)phenyl)piperazine-1-ethyl 2-aminobenzoate [51941-08-3] (3).

Method G: Alkylation with 4-chloro-7-(trifluoromethyl)quinoline [346-55-4] (4) completed the synthesis of antrafenine (5).

See also

• Phenylpiperazine
• Trifluoromethylphenylpiperazine

References

1. Manoury PM, Dumas AP, Najer H, Branceni D, Prouteau M, Lefevre-Borg FM (May 1979). "Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates". Journal of Medicinal Chemistry. 22 (5): 554–9. doi:10.1021/jm00191a017. PMID 458805.
2. Leatham PA, Bird HA, Wright V, Seymour D, Gordon A (1983). "A double blind study of antrafenine, naproxen and placebo in osteoarthrosis". European Journal of Rheumatology and Inflammation. 6 (2): 209–11. PMID 6673985.
3. Don Pierre Rene Lucien Giudicelli, et al. U.S. patent 4,017,623 (1977 to Synthelabo SA).
4. Don Pierre Rene Lucien Giudicelli, et al. U.S. patent 3,935,229 (1976 to Synthelabo SA).
5. Don Pierre Rene Lucien Giudicelli, et al. U.S. patent 3,953,449 (1976 to Synthelabo SA).