Azidomorphine: Difference between revisions

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+{{Short description|Chemical compound}}
 {{Drugbox
+| Verifiedfields = changed
-| IUPAC_name = 6-β-azido- 4,5-α-epoxy- 17-methyl- morphinan- 3-ol
+| Watchedfields = changed
-| image = Azidomorphine.png
+| verifiedrevid = 458966745
-| width = 220
+| IUPAC_name = (6β)-Azido-4,5-α-epoxy-17-methyl morphinan-3-ol
+| image = Azidomorphine2DCSD2.svg
+| alt = Skeletal formula of azidomorphine
+| width = 200
+| image2 = Azidomorphine-3D-spacefill.png
+| alt2 = Space-filling model of the azidomorphine molecule
+| width2 = 180
 <!--Clinical data-->
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 | legal_UK = <!-- GSL         / P       / POM / CD / Class A, B, C -->
 | legal_US =
 | legal_status =
 | routes_of_administration =
 <!--Pharmacokinetic data-->
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 | metabolism =
 | elimination_half-life =
 | excretion =
 <!--Identifiers-->
+| CAS_number_Ref = {{cascite|changed|CAS}}
-| CAS_number = <!-- blanked - oldvalue: 22952-87-0 -->
+| CAS_number = 22952-87-0
+| UNII_Ref = {{fdacite|correct|FDA}}
+| UNII = U973VU74ER
 | ATC_prefix = none
 | ATC_suffix =
+| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChI = 1S/C17H20N4O2/c1-21-7-6-17-10-3-4-11(19-20-18)16(17)23-15-13(22)5-2-9(14(15)17)8-12(10)21/h2,5,10-12,16,22H,3-4,6-8H2,1H3/t10-,11+,12+,16-,17-/m0/s1
+| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
 | StdInChIKey = KZOKOEQTKWBKOK-XHQKLZHNSA-N
 | PubChem = 5488848
+| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
 | DrugBank =
+| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
 | ChemSpiderID = 4590009
 <!--Chemical data-->
 | C=17 | H=20 | N=4 | O=2
-| molecular_weight = 312.366 g/mol
 | smiles = [N-]=[N+]=N\[C@H]4[C@@H]5Oc1c2c(ccc1O)C[C@H]3N(CC[C@]25[C@H]3CC4)C
-| InChI = 1/C17H20N4O2/c1-21-7-6-17-10-3-4-11(19-20-18)16(17)23-15-13(22)5-2-9(14(15)17)8-12(10)21/h2,5,10-12,16,22H,3-4,6-8H2,1H3/t10-,11+,12+,16-,17-/m0/s1
-| InChIKey = KZOKOEQTKWBKOK-XHQKLZHNBX
 | synonyms = Azidomorphine
 }}
-'''Azidomorphine'''<ref>US Patent 3880862</ref> is an [[opiate]] analogue that is a derivative of [[morphine]], where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an [[azide]] group.<ref>Knoll J, Furst S, Kelemen K. The pharmacology of azidomorphine and azidocodeine. ''Journal of Pharmacy and Pharmacology''. 1973;25(12):929-939. PMID 4150295</ref>
+'''Azidomorphine'''<ref>{{cite patent | country = GB | number = 1396663 | title = Analgesic Compositions }}</ref> is an [[opiate]] analogue that is a derivative of [[morphine]], where the 7,8 double bond has been saturated and the 6-hydroxy group has been replaced by an [[azide]] group.<ref>{{cite journal | vauthors = Knoll J, Fürst S, Kelemen K | title = The pharmacology of azidomorphine and azidocodeine | journal = The Journal of Pharmacy and Pharmacology | volume = 25 | issue = 12 | pages = 929–39 | date = December 1973 | pmid = 4150295 | doi = 10.1111/j.2042-7158.1973.tb09982.x | s2cid = 41506653 }}</ref>
-Azidomorphine binds with high affinity to the [[mu opioid receptor]],<ref>Horváth K, Wollemann M. Azidomorphine is an agonist of high-affinity opioid receptor binding sites. ''Neurochemical Research''. 1986 Nov;11(11):1565-9. PMID 2825053</ref> and is around 40x more potent than morphine ''in vivo''. It has similar effects to morphine including [[analgesia]], [[sedation]] and [[respiratory depression]]. However its addiction liability has been found to be slightly lower than that of morphine in animal studies.<ref>Knoll J. Azidomorphines: a new family of potent analgesics with low dependence capacity. ''Progress in Neuropsychopharmacology''. 1979;3(1-3):95-108. PMID 45567</ref><ref>Hill RC, Roemer D, Buescher H. Investigations of the analgesic and morphine-like properties of azidomorphine. ''Journal of Pharmacology and Experimental Therapeutics''. 1977 Jun;201(3):580-6. PMID 405472</ref>
+Azidomorphine binds with high affinity to the [[mu opioid receptor]],<ref>{{cite journal | vauthors = Horváth K, Wollemann M | title = Azidomorphine is an agonist of high-affinity opioid receptor binding sites | journal = Neurochemical Research | volume = 11 | issue = 11 | pages = 1565–9 | date = November 1986 | pmid = 2825053 | doi = 10.1007/bf00965775 | s2cid = 29580383 }}</ref> and is around 40× more potent than morphine ''in vivo''.  It has similar effects to morphine, including [[analgesia]], [[sedation]], and [[respiratory depression]].  However, its addiction liability has been found to be slightly lower than that of morphine in animal studies.<ref>{{cite journal | vauthors = Knoll J | title = Azidomorphines: a new family of potent analgesics with low dependence capacity | journal = Progress in Neuro-Psychopharmacology | volume = 3 | issue = 1–3 | pages = 95–108 | year = 1979 | pmid = 45567 | doi = 10.1016/0364-7722(79)90074-2 }}</ref><ref>{{cite journal | vauthors = Hill RC, Roemer D, Buescher H | title = Investigations of the analgesic and morphine-like properties of azidomorphine | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 201 | issue = 3 | pages = 580–6 | date = June 1977 | pmid = 405472 }}</ref>
 == References ==
-{{reflist}}
+{{Reflist|2}}
+{{Opioidergics}}
-[[Category:Morphinans]]
+[[Category:4,5-Epoxymorphinans]]
 [[Category:Phenols]]
 [[Category:Ethers]]
-[[Category:Azides]]
+[[Category:Organoazides]]
-[[Category:Mu-opioid agonists]]
+[[Category:Mu-opioid receptor agonists]]
-[[Category:Semisynthetic_opioids]]
+[[Category:Semisynthetic opioids]]