Doxanthrine: Difference between revisions

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+{{short description|Chemical compound}}
 {{Drugbox
-| verifiedrevid = 414757440
+| verifiedrevid = 449581815
-| IUPAC_name               = (6aS,12bR)-6a,7,8,12b-tetrahydro-6''H''-chromeno[3,4-c]isoquinoline-2,3-diol
+| IUPAC_name = (6aS,12bR)-6a,7,8,12b-tetrahydro-6''H''-chromeno[3,4-c]isoquinoline-2,3-diol
+| image = Doxanthrine Structure.svg
-| image                    = Doxanthrine_structure.png
-| CAS_number               =
+<!--Clinical data-->
-| ATC_prefix               = none
+| tradename =
-| ATC_suffix               =
+| pregnancy_category =
-| PubChem                  = 15981509
+| legal_status =
-| C = 16 | H = 15 | N = 1 | O = 3
+| routes_of_administration =
-| molecular_weight         = 269.295 g/mol
-| smiles                   = Oc4cc2C3c1ccccc1CNC3COc2cc4O
+<!--Pharmacokinetic data-->
-| bioavailability          =
+| bioavailability =
-| metabolism               =
+| metabolism =
-| elimination_half-life    =
+| elimination_half-life =
-| excretion                =
+| excretion =
-| pregnancy_category       =
-| legal_status             =
+<!--Identifiers-->
-| routes_of_administration =
+| CAS_number =
+| ATC_prefix = none
+| ATC_suffix =
+| PubChem = 15981509
+| ChemSpiderID      = 13112900
+<!--Chemical data-->
+| C=16 | H=15 | N=1 | O=3
+| smiles            = c1ccc2c(c1)CN[C@H]3[C@H]2c4cc(c(cc4OC3)O)O
+| StdInChI          = 1S/C16H15NO3/c18-13-5-11-15(6-14(13)19)20-8-12-16(11)10-4-2-1-3-9(10)7-17-12/h1-6,12,16-19H,7-8H2/t12-,16-/m1/s1
+| StdInChIKey       = QDUNOUQOKOYLCH-MLGOLLRUSA-N
 }}
-'''Doxanthrine''' is a [[synthetic compound]] which is a [[potency (pharmacology)|potent]] and [[binding selectivity|selective]] [[full agonist]] for the [[dopamine]] [[D1 receptor|D<sub>1</sub> receptor]].<ref name="pmid17154515">{{cite journal |author=Cueva JP, Giorgioni G, Grubbs RA, Chemel BR, Watts VJ, Nichols DE |title=trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline: synthesis, resolution, and preliminary pharmacological characterization of a new dopamine D1 receptor full agonist |journal=Journal of Medicinal Chemistry |volume=49 |issue=23 |pages=6848–57 |year=2006 |month=November |pmid=17154515 |doi=10.1021/jm0604979 |url=}}</ref><ref name="pmid19028082">{{cite journal |author=Przybyla JA, Cueva JP, Chemel BR, Hsu KJ, Riese DJ, McCorvy JD, Chester JA, Nichols DE, Watts VJ |title=Comparison of the enantiomers of (+/-)-doxanthrine, a high efficacy full dopamine D(1) receptor agonist, and a reversal of enantioselectivity at D(1) versus alpha(2C) adrenergic receptors |journal=European Neuropsychopharmacology : the Journal of the European College of Neuropsychopharmacology |volume=19 |issue=2 |pages=138–46 |year=2009 |month=February |pmid=19028082 |doi=10.1016/j.euroneuro.2008.10.002 |url= |pmc=2636714}}</ref>
+'''Doxanthrine''' is a [[synthetic compound]] which is a [[potency (pharmacology)|potent]] and [[binding selectivity|selective]] [[full agonist]] for the [[dopamine]] [[D1 receptor|D<sub>1</sub> receptor]].<ref name="pmid17154515">{{cite journal |vauthors=Cueva JP, Giorgioni G, Grubbs RA, Chemel BR, Watts VJ, Nichols DE |title=trans-2,3-dihydroxy-6a,7,8,12b-tetrahydro-6H-chromeno[3,4-c]isoquinoline: synthesis, resolution, and preliminary pharmacological characterization of a new dopamine D1 receptor full agonist |journal=Journal of Medicinal Chemistry |volume=49 |issue=23 |pages=6848–57 |date=November 2006 |pmid=17154515 |doi=10.1021/jm0604979 }}</ref><ref name="pmid19028082">{{cite journal |vauthors=Przybyla JA, Cueva JP, Chemel BR, Hsu KJ, Riese DJ, McCorvy JD, Chester JA, Nichols DE, Watts VJ |title=Comparison of the enantiomers of (±)-doxanthrine, a high efficacy full dopamine D1 receptor agonist, and a reversal of enantioselectivity at D1 versus alpha2C adrenergic receptors |journal=European Neuropsychopharmacology |volume=19 |issue=2 |pages=138–46 |date=February 2009 |pmid=19028082 |doi=10.1016/j.euroneuro.2008.10.002 |pmc=2636714}}</ref> Doxanthrine has been shown to be [[oral administration|orally active]] in producing contralateral rotation in the [[6-hydroxydopamine]] [[animal model|rat model]] of [[Parkinson's disease]].<ref>{{cite journal |vauthors=McCorvey JD, Watts VJ, Nichols DE |date=July 2012 |title= Comparison of the D1 dopamine full agonists, dihydrexidine and doxanthrine, in the 6-OHDA rat model of Parkinson's disease |journal=Psychopharmacology |volume=222 |pages=81–87 |doi=10.1007/s00213-011-2625-5 |pmid=22222862 |issue=1|s2cid=7641172 }}</ref>
 == References ==
-{{Reflist|2}}
+{{Reflist}}
+{{Dopamine receptor modulators}}
-{{Dopaminergics}}
-[[Category:Dopamine agonists]]
+[[Category:Catechols]]
-[[Category:Synthetic phenolic drugs]]
+[[Category:D1-receptor agonists]]