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Antrafenine Routes of administration Oral ATC code Legal status
In general: ℞ (Prescription only)
Metabolism Hepatic Excretion Renal
2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl 2-{[7-(trifluoromethyl)quinolin-4-yl]amino}benzoate
CAS Number PubChem CID DrugBank ChemSpider UNII ChEMBL CompTox Dashboard (EPA ) Formula C 30 H 26 F 6 N 4 O 2 Molar mass 588.554 g·mol−1 3D model (JSmol )
FC(F)(F)c5ccc1c(nccc1Nc2ccccc2C(=O)OCCN4CCN(c3cc(ccc3)C(F)(F)F)CC4)c5
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
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an analgesic and anti-inflammatory drug with similar efficacy to naproxen ,[2] but is not widely used as it has largely been replaced by newer drugs.
See also [ ]
Phenylpiperazine
Trifluoromethylphenylpiperazine
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 .
Non-steroidal anti-inflammatory drugs (NSAIDs) (primarily M01A and M02A , also N02BA )
pyrazolones /pyrazolidines salicylates acetic acid derivatives and related substancesoxicams propionic acid derivatives (profens)n -arylanthranilic acids (fenamates )COX-2 inhibitors (coxibs)other
Aminopropionitrile
Benzydamine
Chondroitin sulfate
Diacerein
Fluproquazone
Glucosamine
Glycosaminoglycan
Hyperforin
Nabumetone
Nimesulide
Oxaceprol
Proquazone
Superoxide dismutase / orgotein
Tenidap
NSAID combinations Key: underline indicates initially developed first-in-class compound of specific group; # WHO-Essential Medicines ; † withdrawn drugs ; ‡ veterinary use .
Analgesics (N02A , N02B )
Opioids
Opiates /opium
Codeine #
Morphine # (+naltrexone )
Opium
Laudanum
Paregoric
Semisynthetic Synthetic
Paracetamol -typeNSAIDs
Propionates Oxicams
Isoxicam
Lornoxicam
Meloxicam
Piroxicam
Tenoxicam
Acetates COX-2 inhibitors Fenamates Salicylates Pyrazolones
Aminophenazone ‡
Ampyrone
Metamizole (dipyrone)
Nifenazone
Phenazone
Propyphenazone (+paracetamol/caffeine )
Others
Cannabinoids
Cannabidiol
Cannabis
Nabilone
Nabiximols
Tetrahydrocannabinol (dronabinol)
Ion channel modulators
Calcium blockers
Alcohol (ethanol)
Gabapentin
Gabapentin enacarbil
Leconotide
Mirogabalin
Pregabalin
Ziconotide
Sodium blockers
Carbamazepine
Lacosamide
Local anesthetics (e.g., cocaine , lidocaine )
Mexiletine
Nefopam
Tricyclic antidepressants (e.g., amitriptyline # )
Nav 1.7/1.8-selective: DSP-2230 §
Funapide §
PF-05089771 §
Potassium openers
Myorelaxants
Carisoprodol
Chlorzoxazone
Cyclobenzaprine
Mephenoxalone
Methocarbamol
Orphenadrine
Others
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
Receptor (ligands )
DP (D2 )
DP1
Agonists: Prostaglandin D2
Treprostinil
DP2
EP (E2 )
EP1
Agonists: Beraprost
Enprostil
Iloprost (ciloprost)
Latanoprost
Lubiprostone
Misoprostol
Prostaglandin E1 (alprostadil)
Prostaglandin E2 (dinoprostone)
Sulprostone
EP2
Agonists:
Misoprostol
Prostaglandin E1 (alprostadil)
Prostaglandin E2 (dinoprostone)
Treprostinil
EP3
Agonists: Beraprost
Enprostil
Iloprost (ciloprost)
Latanoprost
Misoprostol
Prostaglandin D2
Prostaglandin E1 (alprostadil)
Prostaglandin E2 (dinoprostone)
Ricinoleic acid
Sulprostone
EP4
Agonists: Lubiprostone
Misoprostol
Prostaglandin E1 (alprostadil)
Prostaglandin E2 (dinoprostone)
Unsorted
FP (F2α ) IP (I2 )
Agonists:
Beraprost
Iloprost (ciloprost)
Prostacyclin (prostaglandin I2 , epoprostenol)
Prostaglandin E1 (alprostadil)
Selexipag
Treprostinil
TP (TXA2 )
Agonists:
Thromboxane A2
U-46619
Unsorted
Enzyme (inhibitors )
COX (PTGS )PGD2 S
Retinoids
Selenium (selenium tetrachloride , sodium selenite , selenium disulfide )
PGES
PGFS Bimatoprost
PGI2 S TXAS
Others
Precursors: Linoleic acid
γ-Linolenic acid (gamolenic acid)
Dihomo-γ-linolenic acid
Diacylglycerol
Arachidonic acid
Prostaglandin G2
Prostaglandin H2
See also
Receptor/signaling modulators
Leukotriene signaling modulators
Piperazines
Simple piperazines(no additional rings)
Aminoethylpiperazine
Diethylcarbamazine
HEPPS
Midafotel
Piperazine
PIPES
Phenylpiperazines
2C-B-PP
3,4-CFP
Acaprazine
Antrafenine
Aripiprazole
Batoprazine
Bifeprunox
BRL-15,572
Ciprofloxacin
CSP-2503
Dapiprazole
DCPP
DMPP
Diphenylpiperazine
Dropropizine
EGIS-12,233
Elopiprazole
Eltoprazine
Enpiprazole
Ensaculin
Etoperidone
Flesinoxan
Fluanisone
Flibanserin
Fluprazine
Itraconazole
Ketoconazole
Levodropropizine
Lorpiprazole
mCPP
Mefway
MeOPP
Mepiprazole
Naftopidil
Naluzotan
Naphthylpiperazine
Nefazodone
Niaprazine
Oxypertine
Pardoprunox
pCPP
pFPP
Posaconazole
S-14,506
S-14,671
S-15,535
SB-258,585
SB-271,046
SB-357,134
SB-399,885
Sonepiprazole
TFMPP
Tolpiprazole
Trazodone
Urapidil
Vesnarinone
Vilazodone
Vortioxetine
WAY-100,135
WAY-100,635
Benzylpiperazines Diphenylalkylpiperazines (benzhydrylalkylpiperazines) Pyrimidinylpiperazines Pyridinylpiperazines Benzo(iso)thiazolyl piperazines Tricyclics (piperazine attached via side chain) Others/Uncategorized
Categories :
Drugs not assigned an ATC code Meta-Trifluoromethylphenylpiperazines Anthranilates Quinolines Musculoskeletal system drug stubs Hidden categories:
Drugs with non-standard legal status Articles without KEGG source Drugboxes which contain changes to watched fields All stub articles