Antrafenine
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Antrafenine
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Clinical data |
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Routes of administration |
Oral |
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ATC code |
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Legal status |
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Legal status |
- In general: ℞ (Prescription only)
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Pharmacokinetic data |
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Metabolism |
Hepatic |
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Excretion |
Renal |
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Identifiers |
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IUPAC name - 2-4-[3-(trifluoromethyl)phenyl]piperazin-1-ylethyl 2-[7-(trifluoromethyl)quinolin-4-yl]aminobenzoate
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CAS Number |
55300-30-6 Y
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PubChem CID
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DrugBank |
DB01419 Y
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ChemSpider |
61973 Y
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UNII |
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ChEMBL |
ChEMBL345524 Y
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Chemical and physical data |
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Formula |
C30H26F6N4O2 |
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Molar mass |
588.543 g/mol |
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3D model (JSmol) |
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SMILES FC(F)(F)c5ccc1c(nccc1Nc2ccccc2C(=O)OCCN4CCN(c3cc(ccc3)C(F)(F)F)CC4)c5
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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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.mw-parser-output .noboldfont-weight:normal (verify)
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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an analgesic and anti-inflammatory drug with similar efficacy to naproxen,[2] but is not widely used as it has largely been replaced by newer drugs.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[edit]
- Phenylpiperazine
- Trifluoromethylphenylpiperazine
References[edit]
^ 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.
^ 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.
Analgesics (N02A, N02B)
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Opioids |
Opiates/opium
|
Codeine# (+paracetamol, +aspirin)
Morphine# (+naltrexone)
- Opium
- Laudanum
- Paregoric
|
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Semisynthetic |
- Acetyldihydrocodeine
- Benzylmorphine
Buprenorphine (+naloxone)
- Desomorphine
- Diamorphine (heroin)
Dihydrocodeine (+paracetamol)
- Dihydromorphine
- Ethylmorphine
Hydrocodone (+paracetamol, +ibuprofen, +aspirin)
- Hydromorphinol
- Hydromorphone
- Nicocodeine
- Nicodicodeine
- Nicomorphine
Oxycodone (+paracetamol, +aspirin, +ibuprofen, +naloxone, +naltrexone)
- Oxymorphone
- Thebacon
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Synthetic |
- Alfentanil
- Alphaprodine
- Anileridine
- Butorphanol
- Carfentanil
- Dextromoramide
- Dextropropoxyphene
- Dezocine
Fentanyl# (+fluanisone)
- Ketobemidone
- Levorphanol
- Lofentanil
- Meptazinol
Methadone#
- Nalbuphine
- NFEPP
- Pentazocine
- Pethidine (meperidine)
- Phenadoxone
- Phenazocine
- Piminodine
- Piritramide
- Propiram
- Remifentanil
- Sufentanil
- Tapentadol
- Tilidine
- Tramadol
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Paracetamol-type |
Acetanilide‡
Bucetin‡
Butacetin‡
Paracetamol (acetaminophen)#
Parapropamol‡
Phenacetin‡
Propacetamol‡
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NSAIDs |
Propionates |
- Fenoprofen
- Flurbiprofen
Ibuprofen#
- Ketoprofen
- Naproxen
- Oxaprozin
|
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Oxicams |
|
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Acetates |
- Diclofenac
- Indometacin
- Ketorolac
- Nabumetone
- Sulindac
- Tolmetin
|
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COX-2 inhibitors |
- Celecoxib
- Etoricoxib
- Lumiracoxib
- Parecoxib
Rofecoxib ‡
Valdecoxib ‡
|
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Fenamates |
- Meclofenamic acid
- Mefenamic acid
|
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Salicylates |
Aspirin (acetylsalicylic acid)# (+paracetamol/caffeine)
- Benorylate
- Diflunisal
- Ethenzamide
- Magnesium salicylate
- Salicin
- Salicylamide
- Salsalate
Wintergreen (methyl salicylate)
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Pyrazolones |
Aminophenazone‡
- Ampyrone
- Metamizole (dipyrone)
- Nifenazone
- Phenazone
Propyphenazone (+paracetamol/caffeine)
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Others |
|
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Cannabinoids |
- Cannabidiol
- Cannabis
- Nabilone
- Nabiximols
- Tetrahydrocannabinol (dronabinol)
|
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Ion channel modulators |
Calcium blockers |
- Gabapentin
- Gabapentin enacarbil
- Pregabalin
- Ziconotide
|
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Sodium blockers |
- Carbamazepine
- Lacosamide
Local anesthetics (e.g., cocaine, lidocaine)
- Mexiletine
- Nefopam
Tricyclic antidepressants (e.g., amitriptyline#)
Nav1.7/1.8-selective: DSP-2230§
Funapide§
PF-05089771§
|
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Potassium openers |
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Myorelaxants |
- Carisoprodol
- Chlorzoxazone
- Cyclobenzaprine
- Mephenoxalone
- Methocarbamol
- Orphenadrine
|
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Others |
- Analgesic adjuvant
- Analgecine
- Camphor
- Capsaicin
- Clonidine
- Ketamine
- Menthol
- Methoxyflurane
- Nefopam
- Proglumide
Tricyclic antidepressants (e.g., amitriptyline#)
|
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#WHO-EM
‡Withdrawn from market
Clinical trials:
†Phase III
§Never to phase III
|
Prostanoid signaling modulators
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Receptor (ligands)
|
|
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Enzyme (inhibitors)
|
COX (PTGS) |
|
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PGD2S |
- Retinoids
Selenium (selenium tetrachloride, sodium selenite, selenium disulfide)
|
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PGES |
HQL-79 |
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PGFS |
Bimatoprost |
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PGI2S |
Tranylcypromine |
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TXAS |
- Camonagrel
- Dazmegrel
- Dazoxiben
- Furegrelate
- Isbogrel
- Midazogrel
- Nafagrel
- Nicogrelate
- Ozagrel
- Picotamide
- Pirmagrel
- Ridogrel
- Rolafagrel
- Samixogrel
- Terbogrel
- U63557A
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Others |
Precursors: Linoleic acid
- γ-Linolenic acid (gamolenic acid)
- Dihomo-γ-linolenic acid
- Diacylglycerol
- Arachidonic acid
- Prostaglandin G2
- Prostaglandin H2
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- See also
- Receptor/signaling modulators
- Leukotriene signaling modulators
- Nuclear receptor modulators
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Piperazines
|
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Simple piperazines (no additional rings)
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- 1-Cyclohexylpiperazine
- Aminoethylpiperazine
- Diethylcarbamazine
- HEPPS
- Midafotel
- Piperazine
- PIPES
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Phenylpiperazines |
- 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
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Benzylpiperazines |
- 2C-B-BZP
- Befuraline
- Bifeprunox
- Buclizine
- BZP
- Chlorbenzoxamine
- DBZP
- Fipexide
- Imatinib
- MBZP
- MDBZP
- Meclozine
- Methoxypiperamide
- Piberaline
- Piribedil
- Sunifiram
- Trimetazidine
- Vesnarinone
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Diphenylalkylpiperazines (benzhydrylalkylpiperazines)
|
- AD-1211
- Almitrine
- Amperozide
- BRL-15,572
- Buclizine
- BW373U86
- Cetirizine
- Chlorbenzoxamine
- Chlorcyclizine
- Cinnarizine
- Clocinizine
- Cyclizine
- DBL-583
- Diphenylmethylpiperazine
- Dotarizine
- DPI-221
- DPI-287
- DPI-3290
- GBR-12,783
- GBR-12,935
- GBR-13,069
- GBR-13,098
- GBR-13,119
- Hydroxyzine
- Lidoflazine
- Manidipine
- Meclozine
- MT-45
- Oxatomide
- SNC-80
- Vanoxerine
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Pyrimidinylpiperazines |
- Buspirone
- Dasatinib
- Eptapirone
- Gepirone
- Ipsapirone
- Piribedil
- Prazitone
- Pyrimidinylpiperazine
- Revospirone
- Tandospirone
- Tirilazad
- Trimazosin
- Umespirone
- Zalospirone
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Pyridinylpiperazines |
- Atevirdine
- Azaperone
- Delavirdine
- Mirtazapine
- Pyridinylpiperazine
|
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Benzo(iso)thiazolylpiperazines
|
- Lurasidone
- Perospirone
- Revospirone
- Tiospirone
- Ziprasidone
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Tricyclics (piperazine attached via side chain)
|
- Amoxapine
- Clopenthixol
- Clorotepine
- Clozapine
- Cyanothepin
- Doclothepin
- Docloxythepin
- Flupentixol
- Fluphenazine
- Isofloxythepin
- Loxapine
- Meperathiepin
- Metitepine
- Octomethothepin
- Olanzapine
- Opipramol
- Oxyclothepin
- Oxyprothepin
- Peradithiepin
- Perathiepin
- Perazine
- Perphenazine
- Pirenzepine
- Prochlorperazine
- Thiethylperazine
- Thiothixene
- Trifluoperazine
- Trifluthepin
- Zuclopenthixol
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Others/Uncategorized |
- 6-Nitroquipazine
- Azimilide
- Cinepazet
- Cinepazic acid
- Cinepazide
- Cyclohexylpiperazine
- EGIS-7625
- Hexocyclium
- Indinavir
- JNJ-7777120
- Lodenafil
- Mirodenafil
- PB-28
- Quipazine
- Ranolazine
- SA-4503
- Sildenafil
- Tadalafil
- Vardenafil
- VUF-6002
- Zipeprol
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Categories:
- Drugs not assigned an ATC code
- Piperazines
- Trifluoromethyl compounds
- Anthranilates
- Quinolines
- Pharmacology stubs
Hidden categories:
- Drugs with non-standard legal status
- Articles without KEGG source
- Drugboxes which contain changes to watched fields
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