indantadol

{{short description|Chemical compound}}

{{Drugbox

| IUPAC_name = N-(2,3-dihydro-1H-inden-2-yl)glycinamide

| image = Indantadol.svg

| image_class = skin-invert-image

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 202844-10-8

| ATC_prefix = none

| ATC_suffix =

| PubChem =

| ChemSpiderID = 16017060

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = Z3867B9SQP

| 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 anticonvulsant and neuroprotective and is now under development for the treatment of neuropathic pain and chronic cough in Europe by Vernalis and Chiesi.{{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 }}{{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 }}{{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 }}{{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 }}{{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 }}{{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 }}{{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 }}{{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 }} It acts as a competitive, reversible, and non-selective monoamine oxidase inhibitor,{{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 }} and as a low affinity, non-competitive NMDA receptor antagonist.{{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 }} A 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 phase IIb clinical trials.{{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 }}{{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 }}