Antrafenine: Difference between revisions
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{{Short description|Chemical compound}} |
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| width = 175px |
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<!--Clinical data--> |
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| tradename = |
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<!--Pharmacokinetic data--> |
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<!--Identifiers--> |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| UNII_Ref = {{fdacite|correct|FDA}} |
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| UNII = 21FS93Y6OE |
| UNII = 21FS93Y6OE |
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| 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) |
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| InChIKey = NWGGKKGAFZIVBJ-UHFFFAOYAT |
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| ChEMBL_Ref = {{ebicite|correct|EBI}} |
| ChEMBL_Ref = {{ebicite|correct|EBI}} |
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| ChEMBL = 345524 |
| ChEMBL = 345524 |
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<!--Chemical data--> |
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| C=30 | H=26 |
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| F=6 | N=4 |
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| O=2 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| 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) |
| 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) |
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| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChIKey = NWGGKKGAFZIVBJ-UHFFFAOYSA-N |
| StdInChIKey = NWGGKKGAFZIVBJ-UHFFFAOYSA-N |
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| C = 30 | H = 26 | F = 6 | N = 4 | O = 2 |
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| molecular_weight = 588.543 g/mol |
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'''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 |
'''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. |
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==Synthesis== |
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[[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>]] |
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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'''). |
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Method G: Alkylation with 4-chloro-7-(trifluoromethyl)quinoline [346-55-4] ('''4''') completed the synthesis of antrafenine ('''5'''). |
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== See also == |
== See also == |
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* [[Phenylpiperazine]] |
* [[Phenylpiperazine]] |
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*[[Trifluoromethylphenylpiperazine]] |
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== References == |
== References == |
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{{Reflist}} |
{{Reflist}} |
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{{Anti-inflammatory}} |
{{Anti-inflammatory}} |
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{{Analgesics}} |
{{Analgesics}} |
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{{Prostanoidergics}} |
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{{Piperazines}} |
{{Piperazines}} |
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[[Category: |
[[Category:meta-Trifluoromethylphenylpiperazines]] |
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[[Category:Organofluorides]] |
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[[Category:Anthranilates]] |
[[Category:Anthranilates]] |
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[[Category:Quinolines]] |
[[Category:Quinolines]] |
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{{musculoskeletal-drug-stub}} |