ICI-199,441: Difference between revisions

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+{{short description|Chemical compound}}
 {{Drugbox
+| Verifiedfields     = changed
-| IUPAC_name        = 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1-phenyl-2-pyrrolidin-1-ylethyl]acetamide
-| image             = ICI-199441_structure.png
+| Watchedfields      = changed
-| width             = 200
+| verifiedrevid      = 411032066
+| IUPAC_name         = 2-(3,4-dichlorophenyl)-N-methyl-N-[(1S)-1-phenyl-2-pyrrolidin-1-ylethyl]acetamide
-| CAS_number        = 115199-84-3
-| smiles            = Clc1ccc(cc1Cl)CC(=O)N(C)C(c3ccccc3)CN2CCCC2
+| image              = ICI-199,441 Structure.svg
-| ATC_prefix        =
-| ATC_suffix        =
+<!--Clinical data-->| tradename          =
-| PubChem           = 3082718
+| pregnancy_AU       = <!-- A / B1 / B2 / B3 / C / D / X -->
+| pregnancy_US       = <!-- A / B            / C / D / X -->
-| IUPHAR_ligand =
-| DrugBank          =
+| pregnancy_category =
+| legal_AU           = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
-| C=21|H=24|Cl=2|N=2|O=1
+| legal_CA           = <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
-| molecular_weight  = 391.333 g/mol
+| legal_UK           = <!-- GSL         / P       / POM / CD / Class A, B, C -->
-| bioavailability   =
+| legal_US           = <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
-| protein_bound     =
-| metabolism        =
+| legal_status       =
+| routes_of_administration = <!--Pharmacokinetic data-->
+| bioavailability    =
+| protein_bound      =
+| metabolism         =
 | elimination_half-life =
-| excretion         =
+| excretion          = <!--Identifiers-->
+| CAS_number_Ref     = {{cascite|correct|CAS}}
-| pregnancy_AU      =  <!-- A / B1 / B2 / B3 / C / D / X -->
-| pregnancy_US      =  <!-- A / B            / C / D / X -->
+| CAS_number         = 116508-24-8
+| UNII_Ref           = {{fdacite|correct|FDA}}
-| pregnancy_category=
+| UNII               = Q5R50X7L6M
-| legal_AU          =  <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
+| ATC_prefix         =
-| legal_CA          =  <!--             / Schedule I, II, III, IV, V, VI, VII, VIII -->
+| ATC_suffix         =
-| legal_UK          =  <!-- GSL         / P       / POM / CD / Class A, B, C -->
+| PubChem            = 3082718
-| legal_US          =  <!-- OTC                   / Rx-only  / Schedule I, II, III, IV, V -->
-| legal_status      =
+| IUPHAR_ligand      = 11691
+| DrugBank_Ref       = {{drugbankcite|correct|drugbank}}
-| routes_of_administration =
+| DrugBank           =
+| ChEMBL_Ref         = {{ebicite|changed|EBI}}
+| ChEMBL             = 38576
+| ChemSpiderID_Ref   = {{chemspidercite|changed|chemspider}}
+| ChemSpiderID       = 2340095
+<!--Chemical data-->| C                  = 21
+| H                  = 24
+| Cl                 = 2
+| N                  = 2
+| O                  = 1
+| smiles             = CN([C@H](CN1CCCC1)c2ccccc2)C(=O)Cc3ccc(c(c3)Cl)Cl
+| StdInChI_Ref       = {{stdinchicite|changed|chemspider}}
+| StdInChI           = 1S/C21H24Cl2N2O/c1-24(21(26)14-16-9-10-18(22)19(23)13-16)20(15-25-11-5-6-12-25)17-7-3-2-4-8-17/h2-4,7-10,13,20H,5-6,11-12,14-15H2,1H3/t20-/m1/s1
+| StdInChIKey_Ref    = {{stdinchicite|changed|chemspider}}
+| StdInChIKey        = AEJOEPSMZCEYJN-HXUWFJFHSA-N
 }}
-'''ICI-199,441''' is a drug which acts as a potent and selective [[kappa opioid receptor|κ-opioid]] [[agonist]], and has [[analgesic]] effects.<ref name="pmid2850924">{{cite journal |author=Costello GF, Main BG, Barlow JJ, Carroll JA, Shaw JS |title=A novel series of potent and selective agonists at the opioid kappa-receptor |journal=European Journal of Pharmacology |volume=151 |issue=3 |pages=475–8 |year=1988 |month=July |pmid=2850924 |doi= |url=}}</ref><ref name="pmid16123756">{{cite journal |author=Narita M, Kaneko C, Miyoshi K, Nagumo Y, Kuzumaki N, Nakajima M, Nanjo K, Matsuzawa K, Yamazaki M, Suzuki T |title=Chronic pain induces anxiety with concomitant changes in opioidergic function in the amygdala |journal=Neuropsychopharmacology : Official Publication of the American College of Neuropsychopharmacology |volume=31 |issue=4 |pages=739–50 |year=2006 |month=April |pmid=16123756 |doi=10.1038/sj.npp.1300858 |url=}}</ref>
+'''ICI-199,441''' is a drug which acts as a potent and selective [[kappa opioid receptor|κ-opioid]] [[agonist]], and has [[analgesic]] effects.<ref name="pmid2850924">{{cite journal | vauthors = Costello GF, Main BG, Barlow JJ, Carroll JA, Shaw JS | title = A novel series of potent and selective agonists at the opioid kappa-receptor | journal = European Journal of Pharmacology | volume = 151 | issue = 3 | pages = 475–478 | date = July 1988 | pmid = 2850924 | doi = 10.1016/0014-2999(88)90546-8 }}</ref><ref name="pmid16123756">{{cite journal | vauthors = Narita M, Kaneko C, Miyoshi K, Nagumo Y, Kuzumaki N, Nakajima M, Nanjo K, Matsuzawa K, Yamazaki M, Suzuki T | display-authors = 6 | title = Chronic pain induces anxiety with concomitant changes in opioidergic function in the amygdala | journal = Neuropsychopharmacology | volume = 31 | issue = 4 | pages = 739–750 | date = April 2006 | pmid = 16123756 | doi = 10.1038/sj.npp.1300858 | doi-access = free }}</ref> It is a [[biased agonist]] of the KOR, and is one of relatively few KOR ligands that is [[G protein]]-biased rather than [[β-arrestin]]-biased.<ref>{{cite journal | vauthors = DiMattio KM, Ehlert FJ, Liu-Chen LY | title = Intrinsic relative activities of κ opioid agonists in activating Gα proteins and internalizing receptor: Differences between human and mouse receptors | journal = European Journal of Pharmacology | volume = 761 | pages = 235–244 | date = August 2015 | pmid = 26057692 | pmc = 4532598 | doi = 10.1016/j.ejphar.2015.05.054 }}</ref>
+== See also ==
+*[[U-47700]]
+*[[U-50488]]
+*[[U-69,593]]
+== References ==
+{{Reflist|2}}
+{{Opioidergics}}
-==References==
-<references/>
-[[Category:Synthetic opioids]]
-[[Category:Organochlorides]]
 [[Category:Acetamides]]
-[[Category:Pyrrolidines]]
+[[Category:Biased ligands]]
-[[Category:Kappa agonists]]
+[[Category:Chloroarenes]]
+[[Category:Kappa-opioid receptor agonists]]
+[[Category:1-Pyrrolidinyl compounds]]
+[[Category:Synthetic opioids]]