Antrafenine: Difference between revisions

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+{{Short description|Chemical compound}}
-{{drugbox
+{{Drugbox
-| Verifiedfields = changed
-| UNII_Ref = {{fdacite|changed|FDA}}
+| Watchedfields = changed
+| verifiedrevid = 437136259
+| IUPAC_name = 2-<nowiki/>{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl 2-<nowiki/>{[7-(trifluoromethyl)quinolin-4-yl]amino}benzoate
+| image = Antrafenine.svg
+| width = 175px
+<!--Clinical data-->
+| tradename =
+| pregnancy_category =
+| legal_status = Rx-only
+| routes_of_administration = [[Mouth|Oral]]
+<!--Pharmacokinetic data-->
+| bioavailability =
+| metabolism = [[Hepatic]]
+| elimination_half-life =
+| excretion = [[Renal]]
+<!--Identifiers-->
+| CAS_number_Ref = {{cascite|correct|??}}
+| CAS_number = 55300-29-3
+| ATC_prefix = none
+| ATC_suffix =
+| PubChem = 68723
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
+| DrugBank = DB01419
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
+| ChemSpiderID = 61973
+| UNII_Ref = {{fdacite|correct|FDA}}
 | UNII = 21FS93Y6OE
-| verifiedrevid = 413867963
-| IUPAC_name               = 2-{4-[3-(trifluoromethyl)phenyl]piperazin-1-yl}ethyl 2-{[7-(trifluoromethyl)quinolin-4-yl]amino}benzoate
-| image                    = Antrafenine.svg
-| CASNo_Ref = {{cascite|correct|CAS}}
-| InChI = 1/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)
-| InChIKey = NWGGKKGAFZIVBJ-UHFFFAOYAT
 | ChEMBL_Ref = {{ebicite|correct|EBI}}
 | ChEMBL = 345524
+<!--Chemical data-->
+| C=30 | H=26
+| F=6 | N=4
+| O=2
+| smiles = FC(F)(F)c5ccc1c(nccc1Nc2ccccc2C(=O)OCCN4CCN(c3cc(ccc3)C(F)(F)F)CC4)c5
 | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChI = 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)
 | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = NWGGKKGAFZIVBJ-UHFFFAOYSA-N
-| CAS_number               = 55300-30-6
-| ATC_prefix               = none
-| ATC_suffix               =
-| PubChem                  = 68723
-| DrugBank                 = DB01419
-| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
-| ChemSpiderID             = 61973
-| C = 30 | H = 26 | F = 6 | N = 4 | O = 2
-| molecular_weight         = 588.543 g/mol
-| smiles                   = FC(F)(F)c5ccc1c(nccc1Nc2ccccc2C(=O)OCCN4CCN(c3cc(ccc3)C(F)(F)F)CC4)c5
-| bioavailability          =
-| metabolism               = [[Hepatic]]
-| elimination_half-life    =
-| excretion                = [[Renal]]
-| pregnancy_category       =
-| legal_status             = Rx-only
-| routes_of_administration = [[Mouth|Oral]]
 }}
-'''Antrafenine''' ('''Stakane''') is a [[phenylpiperazine]] [[chemical derivative|derivative]] [[drug]] invented in 1979.<ref> 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. </ref> It acts as an [[analgesic]] and [[anti-inflammatory]] drug with similar efficacy to [[naproxen]],<ref> 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. </ref> but is not widely used as it has largely been replaced by newer drugs.
+'''Antrafenine''' ('''Stakane''') is a [[phenylpiperazine]] [[chemical derivative|derivative]] [[pharmaceutical drug|drug]] invented in 1979.<ref name="pmid458805">{{cite journal | vauthors = Manoury PM, Dumas AP, Najer H, Branceni D, Prouteau M, Lefevre-Borg FM | title = Synthesis and analgesic activities of some (4-substituted phenyl-1-piperazinyl)alkyl 2-aminobenzoates and 2-aminonicotinates | journal = Journal of Medicinal Chemistry | volume = 22 | issue = 5 | pages = 554–9 | date = May 1979 | pmid = 458805 | doi = 10.1021/jm00191a017 }}</ref> It acts as an [[analgesic]] and [[anti-inflammatory]] drug with similar efficacy to [[naproxen]],<ref name="pmid6673985">{{cite journal | vauthors = Leatham PA, Bird HA, Wright V, Seymour D, Gordon A | title = A double blind study of antrafenine, naproxen and placebo in osteoarthrosis | journal = European Journal of Rheumatology and Inflammation | volume = 6 | issue = 2 | pages = 209–11 | date = 1983 | pmid = 6673985 }}</ref> but is not widely used as it has largely been replaced by newer drugs.
+==Synthesis==
+[[File:Antrafenine synthesis.svg|thumb|500px|center|[https://pharmaceutical-substances.thieme.com/ps/search-results?docUri=KD-01-0141 Thieme] Synthesis:<ref name="pmid458805"/> Patents:<ref>Don Pierre Rene Lucien Giudicelli, et al. {{US patent|4017623}} (1977 to Synthelabo SA).</ref><ref>Don Pierre Rene Lucien Giudicelli, et al. {{US patent|3935229}} (1976 to Synthelabo SA).</ref><ref>Don Pierre Rene Lucien Giudicelli, et al. {{US patent|3953449}} (1976 to Synthelabo SA).</ref>]]
+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 ==
 {{Reflist}}
 {{Anti-inflammatory}}
 {{Analgesics}}
+{{Prostanoidergics}}
 {{Piperazines}}
-[[Category:Piperazines]]
+[[Category:meta-Trifluoromethylphenylpiperazines]]
-[[Category:Organofluorides]]
 [[Category:Anthranilates]]
 [[Category:Quinolines]]
+{{musculoskeletal-drug-stub}}