DPI-3290: Difference between revisions

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+{{Short description|Chemical compound}}
-{{drugbox
+{{Drugbox
-| verifiedrevid = 410886293
+| Verifiedfields = changed
+| Watchedfields = changed
+| verifiedrevid = 430788679
+| IUPAC_name = 3-[(R)-[(2S,5R)-2,5-dimethyl-4-prop-2-enylpiperazin-1-yl]-(3-hydroxyphenyl)methyl]-N-(3-fluorophenyl)-N-methylbenzamide
 | image = DPI-3290.svg
-| width = 240
+<!--Clinical data-->
-| IUPAC_name = (+)-3-((αR)-α-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-(3-fluorophenyl)-N-methylbenzamide
-| PubChem = 5242141
+| tradename =
+| legal_status =
-| C = 30 | H = 34 | F = 1 | N = 3 | O = 2
-| molecular_weight  = 487.607 g/mol
+<!--Identifiers-->
-| smiles = c2c(O)cccc2C(N(CC1C)C(C)CN1CC=C)c(ccc3)cc3C(=O)N(C)c4cc(F)ccc4
+| CAS_number_Ref = {{cascite|changed|??}}
-| CAS_number =
+| CAS_number = 182417-73-8
-| legal_status =
+| PubChem = 9826770
+| UNII_Ref = {{fdacite|changed|FDA}}
+| UNII = R3UO4Y068S
+| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
+| ChemSpiderID = 8002513
+| ChEMBL_Ref = {{ebicite|changed|EBI}}
+| ChEMBL = 155892
+<!--Chemical data-->
+| C=30 | H=34 | F=1 | N=3 | O=2
+| smiles = C[C@H]1CN([C@@H](CN1[C@@H](C2=CC(=CC=C2)O)C3=CC=CC(=C3)C(=O)N(C)C4=CC(=CC=C4)F)C)CC=C
+| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChI = 1S/C30H34FN3O2/c1-5-15-33-19-22(3)34(20-21(33)2)29(24-10-7-14-28(35)17-24)23-9-6-11-25(16-23)30(36)32(4)27-13-8-12-26(31)18-27/h5-14,16-18,21-22,29,35H,1,15,19-20H2,2-4H3/t21-,22+,29-/m1/s1
+| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChIKey = LZXRQLIIMYJZDA-UETOGOEVSA-N
 }}
-'''DPI-3290''' is a drug that is used in scientific research. It is a potent [[analgesic]] drug,<ref>{{cite journal | last1 = Gengo | first1 = PJ | last2 = Pettit | first2 = HO | last3 = O'Neill | first3 = SJ | last4 = Wei | first4 = K | last5 = McNutt | first5 = R | last6 = Bishop | first6 = MJ | last7 = Chang | first7 = KJ | title = DPI-3290 (+)-3-((alpha-R)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-(3-fluorophenyl)-N-methylbenzamide. I. A mixed opioid agonist with potent antinociceptive activity | journal = The Journal of pharmacology and experimental therapeutics | volume = 307 | issue = 3 | pages = 1221–6 | year = 2003 | pmid = 14534368 | doi = 10.1124/jpet.103.054361 }}</ref> which produces little [[respiratory depression]].<ref>{{cite journal | last1 = Gengo | first1 = PJ | last2 = Pettit | first2 = HO | last3 = O'Neill | first3 = SJ | last4 = Su | first4 = YF | last5 = McNutt | first5 = R | last6 = Chang | first6 = KJ | title = DPI-3290 (+)-3-((alpha-R)-alpha-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-(3-fluorophenyl)-N-methylbenzamide. II. A mixed opioid agonist with potent antinociceptive activity and limited effects on respiratory function | journal = The Journal of pharmacology and experimental therapeutics | volume = 307 | issue = 3 | pages = 1227–33 | year = 2003 | pmid = 14534367 | doi = 10.1124/jpet.103.054429 }}</ref>
+'''DPI-3290''' was discovered by scientists at Burroughs Wellcome and licensed to Delta Pharmaceutical <ref>US Patent 5552404 - Opioid compounds and methods for using same</ref> and is a drug that is used in scientific research. It is a potent [[analgesic]] drug,<ref>{{cite journal | vauthors = Gengo PJ, Pettit HO, O'Neill SJ, Wei K, McNutt R, Bishop MJ, Chang KJ | title = DPI-3290 [(+)-3-((alpha-R)-alpha-((2S,5R)-4-allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-(3-fluorophenyl)-N-methylbenzamide]. I. A mixed opioid agonist with potent antinociceptive activity | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 307 | issue = 3 | pages = 1221–6 | date = December 2003 | pmid = 14534368 | doi = 10.1124/jpet.103.054361 | s2cid = 93569860 }}</ref> which produces little [[respiratory depression]].<ref>{{cite journal | vauthors = Gengo PJ, Pettit HO, O'Neill SJ, Su YF, McNutt R, Chang KJ | title = DPI-3290 [(+)-3-((alpha-R)-alpha-((2S,5R)-4-Allyl-2,5-dimethyl-1-piperazinyl)-3-hydroxybenzyl)-N-(3-fluorophenyl)-N-methylbenzamide]. II. A mixed opioid agonist with potent antinociceptive activity and limited effects on respiratory function | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 307 | issue = 3 | pages = 1227–33 | date = December 2003 | pmid = 14534367 | doi = 10.1124/jpet.103.054429 | s2cid = 45159720 }}</ref>
-DPI-3290 acts as an [[agonist]] at both [[mu opioid receptor|μ-]] and [[delta opioid receptor|δ-opioid]] [[Receptor (biochemistry)|receptors]], with an IC50 of 6.2nM at μ and 1.0nM at δ.<ref>Ananthan S. Opioid ligands with mixed mu/delta opioid receptor interactions: an emerging approach to novel analgesics. ''AAPS Journal''. 2006 Mar 10;8(1):E118-25. {{DOI|10.1208/aapsj080114}} PMID 16584118</ref>
+DPI-3290 acts as an [[agonist]] at both [[mu opioid receptor|μ-]] and [[delta opioid receptor|δ-opioid receptor]], with an IC50 of 6.2nM at μ and 1.0nM at δ.<ref>{{cite journal | vauthors = Ananthan S | title = Opioid ligands with mixed mu/delta opioid receptor interactions: an emerging approach to novel analgesics | journal = The AAPS Journal | volume = 8 | issue = 1 | pages = E118-25 | date = March 2006 | pmid = 16584118 | pmc = 2751430 | doi = 10.1208/aapsj080114 }}</ref>
-==References==
+==See also==
+* [[BW373U86]]
-{{reflist}}
+* [[DPI-221]]
+* [[DPI-287]]
+== References ==
+{{Reflist|2}}
+{{Opioidergics}}
 {{Piperazines}}
 [[Category:Synthetic opioids]]
-[[Category:Delta-opioid agonists]]
+[[Category:Delta-opioid receptor agonists]]
 [[Category:Piperazines]]
 [[Category:Benzanilides]]
 [[Category:Phenols]]
-[[Category:Organofluorides]]
+[[Category:Fluoroarenes]]
-[[Category:Alkenes]]
+[[Category:Allyl compounds]]
-[[Category:Mu-opioid agonists]]
+[[Category:Mu-opioid receptor agonists]]
-[[sr:DPI-3290]]