Antrafenine

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 ;
PubChem CID	68723;
DrugBank	DB01419 ;
ChemSpider	61973 ;
UNII	21FS93Y6OE;
ChEMBL	ChEMBL345524 ;
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) ; Key:NWGGKKGAFZIVBJ-UHFFFAOYSA-N ;
	(verify)

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analgesic and anti-inflammatory drug with similar efficacy to naproxen,^[2] but is not widely used as it has largely been replaced by newer drugs.

References

^ 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.
^ 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.

[pmid458805-1] 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.

[pmid6673985-2] 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.

[1]

[2]

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
PubChem CID	68723
DrugBank	DB01419
ChemSpider	61973
UNII	21FS93Y6OE
ChEMBL	ChEMBL345524
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) Key:NWGGKKGAFZIVBJ-UHFFFAOYSA-N
(verify)

Antrafenine

See also

References