View source for Chemistry:Indantadol

{{short description|Chemical compound}}
{{Drugbox
| IUPAC_name = ''N''-(2,3-dihydro-1''H''-inden-2-yl)glycinamide
| image = Indantadol.svg

<!--Clinical data-->
| tradename =  
| pregnancy_category =  
| legal_status = Uncontrolled
| routes_of_administration = Oral

<!--Pharmacokinetic data-->
| bioavailability =  
| metabolism =  
| elimination_half-life =  
| excretion =

<!--Identifiers-->
| CAS_number = 202844-10-8
| ATC_prefix = none
| ATC_suffix =  
| PubChem =  
| ChemSpiderID = 16017060
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = Z3867B9SQP

<!--Chemical data-->
| C=11 | H=14 | N=2 | O=1 
| smiles = NCC(=O)NC1Cc2ccccc2C1
}}

'''Indantadol''' ('''CHF-3381''', '''V-3381''') is a drug which was formerly being investigated as an [[Chemistry:Anticonvulsant|anticonvulsant]] and neuroprotective and is now under development for the treatment of neuropathic pain and chronic cough in [[Earth:Europe|Europe]] by Vernalis and Chiesi.<ref name="pmid11378157">{{cite journal  |vauthors=Villetti G, Bregola G, Bassani F, etal | title = Preclinical evaluation of CHF3381 as a novel antiepileptic agent | journal = Neuropharmacology | volume = 40 | issue = 7 | pages = 866–78 |date=June 2001 | pmid = 11378157 | doi = 10.1016/S0028-3908(01)00026-0| s2cid = 23709155 }}</ref><ref name="pmid11566153">{{cite journal  |vauthors=Gandolfi O, Bonfante V, Voltattorni M, etal | title = Anticonvulsant preclinical profile of CHF 3381: dopaminergic and glutamatergic mechanisms | journal = Pharmacology Biochemistry and Behavior | volume = 70 | issue = 1 | pages = 157–66 |date=September 2001 | pmid = 11566153 | doi = 10.1016/S0091-3057(01)00591-3| s2cid = 24029988 }}</ref><ref name="pmid12438928">{{cite journal |vauthors=Zucchini S, Buzzi A, Bergamaschi M, Pietra C, Villetti G, Simonato M | title = Neuroprotective activity of CHF3381, a putative N-methyl-D-aspartate receptor antagonist | journal = NeuroReport | volume = 13 | issue = 16 | pages = 2071–4 |date=November 2002 | pmid = 12438928 | doi = 10.1097/00001756-200211150-00016| s2cid = 32235961 }}</ref><ref name="pmid12750440">{{cite journal  |vauthors=Villetti G, Bergamaschi M, Bassani F, etal | title = Antinociceptive activity of the N-methyl-D-aspartate receptor antagonist N-(2-Indanyl)-glycinamide hydrochloride (CHF3381) in experimental models of inflammatory and neuropathic pain | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 306 | issue = 2 | pages = 804–14 |date=August 2003 | pmid = 12750440 | doi = 10.1124/jpet.103.050039 | s2cid = 12703264 }}</ref><ref name="pmid14725488">{{cite journal | title = CHF 3381 | journal = Drugs in R&D | volume = 5 | issue = 1 | pages = 28–30 | year = 2004 | pmid = 14725488 | doi = 10.2165/00126839-200405010-00005| s2cid = 29253197 }}</ref><ref name="pmid17786847">{{cite journal |vauthors=Mattia C, Coluzzi F | title = Indantadol, a novel NMDA antagonist and nonselective MAO inhibitor for the potential treatment of neuropathic pain | journal = IDrugs: The Investigational Drugs Journal | volume = 10 | issue = 9 | pages = 636–44 |date=September 2007 | pmid = 17786847 }}</ref><ref name="urlIN-STEP Phase IIb study results">{{cite web | url = http://www.vernalis.com/media-centre/latest-releases/567-in-step-phase-iib-study-results- | title = IN-STEP Phase IIb study results | archive-url = https://web.archive.org/web/20140813231215/http://www.vernalis.com/media-centre/latest-releases/567-in-step-phase-iib-study-results- | archive-date = 2014-08-13 | url-status = dead }}</ref><ref name="urlVernalis initiates Pilot Study of V3381 in patients with chronic cough">{{cite web | url = http://www.vernalis.com/media-centre/latest-releases/2009-releases/389 | title = Vernalis initiates Pilot Study of V3381 in patients with chronic cough | archive-url = https://web.archive.org/web/20140813231218/http://www.vernalis.com/media-centre/latest-releases/2009-releases/389 | archive-date = 2014-08-13 | url-status = dead }}</ref> It acts as a [[Chemistry:Competitive inhibition|competitive]], [[Biology:Enzyme inhibitor#Reversible inhibitors|reversible]], and non-[[Chemistry:Binding selectivity|selective]] [[Biology:Monoamine oxidase inhibitor|monoamine oxidase inhibitor]],<ref name="pmid14725488"/><ref name="pmid17786847"/><ref name="pmid16885013">{{cite journal |vauthors=Mathiesen O, Imbimbo BP, Hilsted KL, Fabbri L, Dahl JB | title = CHF3381, a N-methyl-D-aspartate receptor antagonist and monoamine oxidase-A inhibitor, attenuates secondary hyperalgesia in a human pain model | journal = The Journal of Pain | volume = 7 | issue = 8 | pages = 565–74 |date=August 2006 | pmid = 16885013 | doi = 10.1016/j.jpain.2006.02.004 | doi-access = free }}</ref> and as a low affinity, non-competitive [[Chemistry:NMDA receptor antagonist|NMDA receptor antagonist]].<ref name="pmid11378157"/><ref name="pmid11566153"/><ref name="pmid12890713">{{cite journal  |vauthors=Barbieri M, Bregola G, Buzzi A, etal | title = Mechanisms of action of CHF3381 in the forebrain | journal = British Journal of Pharmacology | volume = 139 | issue = 7 | pages = 1333–41 |date=August 2003 | pmid = 12890713 | pmc = 1573965 | doi = 10.1038/sj.bjp.0705381 }}</ref> A [[Pilot experiment|pilot study]] of indantadol for chronic cough was initiated in October 2009 and in April 2010 it failed to achieve significant efficacy in neuropathic pain in [[Engineering:Clinical trial#Phase II|phase IIb]] [[Engineering:Clinical trial|clinical trial]]s.<ref name="urlIN-STEP Phase IIb study results"/><ref name="urlVernalis initiates Pilot Study of V3381 in patients with chronic cough"/><ref name="urlV3381CC">{{cite web | url = http://www.vernalis.com/component/content/article/387 | title = V3381CC | archive-url = https://web.archive.org/web/20140813230051/http://www.vernalis.com/component/content/article/387 | archive-date = 2014-08-13 | url-status = dead }}</ref><ref name="urlVernalis completes recruitment in V3381 Phase II IN-STEP study for neuropathic pain">{{cite web | url = http://www.vernalis.com/media-centre/latest-releases/2009-releases/391 | title = Vernalis completes recruitment in V3381 Phase II IN-STEP study for neuropathic pain | archive-url = https://web.archive.org/web/20140813231805/http://www.vernalis.com/media-centre/latest-releases/2009-releases/391 | archive-date = 2014-08-13 | url-status = dead }}</ref>
== See also ==
* [[Chemistry:2-Aminoindane|2-Aminoindane]]
* [[Chemistry:Glycine|Glycine]]

== References ==
{{Reflist}}

{{Analgesics}}
{{Anticonvulsants}}
{{Ionotropic glutamate receptor modulators}}
{{Monoamine metabolism modulators}}

[[Category:Analgesics]]
[[Category:Anticonvulsants]]
[[Category:Antitussives]]
[[Category:Monoamine oxidase inhibitors]]
[[Category:NMDA receptor antagonists]]
[[Category:2-Aminoindanes]]
[[Category:Acetamides]]

{{Sourceattribution|Indantadol}}