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Revision as of 11:01, 20 February 2012 editBeetstra (talk | contribs)Edit filter managers, Administrators172,031 edits Saving copy of the {{drugbox}} taken from revid 456641132 of page Traxoprodil for the Chem/Drugbox validation project (updated: 'CAS_number').  Latest revision as of 10:12, 21 October 2024 edit JWBE (talk | contribs)Extended confirmed users10,126 edits added Category:4-Hydroxyphenyl compounds using HotCat 
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{{Short description|Chemical compound}}
{{ambox | text = This page contains a copy of the infobox ({{tl|drugbox}}) taken from revid of page ] with values updated to verified values.}}
{{Drugbox {{Drugbox
| Verifiedfields = changed | Verifiedfields = verified
| Watchedfields = verified
| verifiedrevid = 426610639 | verifiedrevid = 477864780
⚫ | IUPAC_name = (1S,2S)-1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanol
| image = Traxoprodil_structure.png | image = Traxoprodil.svg
| width = 260 | width = 250px


<!--Clinical data--> <!-- Clinical data -->
| tradename = | tradename =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X --> | pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| pregnancy_US = <!-- A / B / C / D / X --> | pregnancy_US = <!-- A / B / C / D / X -->
| pregnancy_category = | pregnancy_category =
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 --> | legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| legal_CA = <!-- Schedule I --> | legal_CA = <!-- Schedule I -->
| legal_UK = <!-- Class A --> | legal_UK = <!-- Class A -->
| legal_US = | legal_US =
| legal_status = | legal_status =


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


<!--Identifiers--> <!-- Identifiers -->
| CAS_number_Ref = {{cascite|correct|??}} | IUPHAR_ligand = 4163
| CAS_number_Ref = {{cascite|correct|CAS}}
| CAS_number = <!-- blanked - oldvalue: 134234-12-1 --> | CAS_number = 134234-12-1
| CAS_supplemental = <BR/>189894-57-3 (methanesulphonate) | CAS_supplemental = <br />189894-57-3 (methanesulphonate)
| ATC_prefix = none | ATC_prefix = None
| ATC_suffix = | ATC_suffix =
| PubChem = 219101 | PubChem = 219101
| DrugBank_Ref = {{drugbankcite|correct|drugbank}} | DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| DrugBank = | DrugBank =
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 189919 | ChemSpiderID = 189919
| UNII_Ref = {{fdacite|changed|FDA}} | UNII_Ref = {{fdacite|correct|FDA}}
| UNII = UTC046R5HM | UNII = UTC046R5HM
| ChEMBL_Ref = {{ebicite|changed|EBI}} | ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 17350 | ChEMBL = 17350
| KEGG_Ref = {{keggcite|correct|kegg}}
⚫ | synonyms = Traxoprodil, CP-101,606
| KEGG = D06204
⚫ | synonyms = CP-101606; CP-98113


<!--Chemical data--> <!-- Chemical data -->
⚫ | IUPAC_name = (1''S'',2''S'')-1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanol
| C=20 | H=25 | N=1 | O=3 | C=20 | H=25 | N=1 | O=3
| SMILES = C((C1=CC=C(C=C1)O)O)N2CCC(CC2)(C3=CC=CC=C3)O
| molecular_weight = 327.416 g/mol
| smiles = c2cc(O)ccc2C(O)C(C)N3CCC(O)(CC3)c1ccccc1
| StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI = 1S/C20H25NO3/c1-15(19(23)16-7-9-18(22)10-8-16)21-13-11-20(24,12-14-21)17-5-3-2-4-6-17/h2-10,15,19,22-24H,11-14H2,1H3/t15-,19+/m0/s1 | StdInChI = 1S/C20H25NO3/c1-15(19(23)16-7-9-18(22)10-8-16)21-13-11-20(24,12-14-21)17-5-3-2-4-6-17/h2-10,15,19,22-24H,11-14H2,1H3/t15-,19+/m0/s1
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| StdInChIKey = QEMSVZNTSXPFJA-HNAYVOBHSA-N | StdInChIKey = QEMSVZNTSXPFJA-HNAYVOBHSA-N
}} }}

'''Traxoprodil''' (developmental code name '''CP-101606''') is a drug developed by ] which acts as an ], selective for the ] subunit.<ref name="pmid7636876">{{cite journal |vauthors=Chenard BL, Bordner J, Butler TW, Chambers LK, Collins MA, De Costa DL, Ducat MF, Dumont ML, Fox CB, Mena EE |title=(1S,2S)-1-(4-hydroxyphenyl)-2-(4-hydroxy-4-phenylpiperidino)-1-propanol: a potent new neuroprotectant which blocks N-methyl-D-aspartate responses |journal=Journal of Medicinal Chemistry |volume=38 |issue=16 |pages=3138–45 |date=August 1995 |pmid=7636876 |doi= 10.1021/jm00016a017}}</ref><ref name="pmid9380752">{{cite journal |vauthors=Brimecombe JC, Boeckman FA, Aizenman E |title=Functional consequences of NR2 subunit composition in single recombinant N-methyl-D-aspartate receptors |journal=Proceedings of the National Academy of Sciences of the United States of America |volume=94 |issue=20 |pages=11019–24 |date=September 1997 |pmid=9380752 |pmc=23569 |doi= 10.1073/pnas.94.20.11019|bibcode=1997PNAS...9411019B |doi-access=free }}</ref> It has ],<ref name="pmid9368572">{{cite journal |vauthors=Di X, Bullock R, Watson J, Fatouros P, Chenard B, White F, Corwin F |title=Effect of CP101,606, a novel NR2B subunit antagonist of the N-methyl-D-aspartate receptor, on the volume of ischemic brain damage off cytotoxic brain edema after middle cerebral artery occlusion in the feline brain |journal=Stroke: A Journal of Cerebral Circulation |volume=28 |issue=11 |pages=2244–51 |date=November 1997 |pmid=9368572 |doi= 10.1161/01.str.28.11.2244}}</ref> ],<ref name="pmid9384494">{{cite journal |vauthors=Taniguchi K, Shinjo K, Mizutani M, Shimada K, Ishikawa T, Menniti FS, Nagahisa A |title=Antinociceptive activity of CP-101,606, an NMDA receptor NR2B subunit antagonist |journal=] |volume=122 |issue=5 |pages=809–12 |date=November 1997 |pmid=9384494 |pmc=1565002 |doi=10.1038/sj.bjp.0701445 }}</ref> and ] effects in animal studies.<ref name="pmid10785463">{{cite journal |vauthors=Steece-Collier K, Chambers LK, Jaw-Tsai SS, Menniti FS, Greenamyre JT |title=Antiparkinsonian actions of CP-101,606, an antagonist of NR2B subunit-containing N-methyl-d-aspartate receptors |journal=Experimental Neurology |volume=163 |issue=1 |pages=239–43 |date=May 2000 |pmid=10785463 |doi=10.1006/exnr.2000.7374 |s2cid=23889057 }}</ref><ref name="pmid15246846">{{cite journal |vauthors=Nash JE, Ravenscroft P, McGuire S, Crossman AR, Menniti FS, Brotchie JM |title=The NR2B-selective NMDA receptor antagonist CP-101,606 exacerbates L-DOPA-induced dyskinesia and provides mild potentiation of anti-parkinsonian effects of L-DOPA in the MPTP-lesioned marmoset model of Parkinson's disease |journal=Experimental Neurology |volume=188 |issue=2 |pages=471–9 |date=August 2004 |pmid=15246846 |doi=10.1016/j.expneurol.2004.05.004 |s2cid=41219412 }}</ref> Traxoprodil has been researched in humans as a potential treatment to lessen the damage to the brain after ],<ref name="pmid10668412">{{cite journal |vauthors=Merchant RE, Bullock MR, Carmack CA, Shah AK, Wilner KD, Ko G, Williams SA |title=A double-blind, placebo-controlled study of the safety, tolerability and pharmacokinetics of CP-101,606 in patients with a mild or moderate traumatic brain injury |journal=Annals of the New York Academy of Sciences |volume=890 |pages=42–50 |year=1999 |issue=1 |pmid=10668412 |doi= 10.1111/j.1749-6632.1999.tb07979.x|bibcode=1999NYASA.890...42M |s2cid=25863512 }}</ref><ref name="pmid11249721">{{cite journal |author=Chazot PL |title=CP-101606 Pfizer Inc |journal=Current Opinion in Investigational Drugs |volume=1 |issue=3 |pages=370–4 |date=November 2000 |pmid=11249721 }}</ref><ref name="pmid14987468">{{cite journal |vauthors=Kundrotiene J, Cebers G, Wägner A, Liljequist S |title=The NMDA NR2B subunit-selective receptor antagonist, CP-101,606, enhances the functional recovery the NMDA NR2B subunit-selective receptor and reduces brain damage after cortical compression-induced brain ischemia |journal=Journal of Neurotrauma |volume=21 |issue=1 |pages=83–93 |date=January 2004 |pmid=14987468 |doi=10.1089/089771504772695977 }}</ref><ref name="pmid15857299">{{cite journal |vauthors=Wang CX, Shuaib A |title=NMDA/NR2B selective antagonists in the treatment of ischemic brain injury |journal=Current Drug Targets. CNS and Neurological Disorders |volume=4 |issue=2 |pages=143–51 |date=April 2005 |pmid=15857299 |doi= 10.2174/1568007053544183}}</ref> but results from ]s showed only modest benefit.<ref name="pmid16379581">{{cite journal |vauthors=Yurkewicz L, Weaver J, Bullock MR, Marshall LF |title=The effect of the selective NMDA receptor antagonist traxoprodil in the treatment of traumatic brain injury |journal=Journal of Neurotrauma |volume=22 |issue=12 |pages=1428–43 |date=December 2005 |pmid=16379581 |doi=10.1089/neu.2005.22.1428 }}</ref> The drug was found to cause EKG abnormalities (QT prolongation) and its clinical development was stopped.<ref name="Löscher">{{cite book |vauthors=Löscher W, Rogawski MA |veditors=Lodge D, Danysz W, Parsons CG |title=Ionotropic Glutamate Receptors as Therapeutic Targets |publisher=FP Graham Publishing Co., Johnson City, TN |date=2002 |pages=91–132 |chapter=Chapter 3: Epilepsy|url=http://works.bepress.com/michael_rogawski/25/}}</ref> More recent animal studies have suggested traxoprodil may exhibit rapid-acting ] effects similar to those of ],<ref name="pmid19011431">{{cite journal |vauthors=Preskorn SH, Baker B, Kolluri S, Menniti FS, Krams M, Landen JW |title=An innovative design to establish proof of concept of the antidepressant effects of the NR2B subunit selective N-methyl-D-aspartate antagonist, CP-101,606, in patients with treatment-refractory major depressive disorder |journal=Journal of Clinical Psychopharmacology |volume=28 |issue=6 |pages=631–7 |date=December 2008 |pmid=19011431 |doi=10.1097/JCP.0b013e31818a6cea |s2cid=29461252 }}</ref> although there is some evidence for similar psychoactive side effects and abuse potential at higher doses,<ref name="pmid17989511">{{cite journal |vauthors=Nicholson KL, Mansbach RS, Menniti FS, Balster RL |title=The phencyclidine-like discriminative stimulus effects and reinforcing properties of the NR2B-selective N-methyl-D-aspartate antagonist CP-101 606 in rats and rhesus monkeys |journal=Behavioural Pharmacology |volume=18 |issue=8 |pages=731–43 |date=December 2007 |pmid=17989511 |doi=10.1097/FBP.0b013e3282f14ed6 |s2cid=32577038 }}</ref> which might limit clinical acceptance of traxoprodil for this application.

Traxoprodil showed ]-like rapidly-acting ] effects in a small clinical trial of 30&nbsp;patients with depression who were non-responders to 6&nbsp;weeks of ] treatment.<ref name="pmid26724279">{{cite journal | vauthors = Machado-Vieira R, Henter ID, Zarate CA | title = New targets for rapid antidepressant action | journal = Prog. Neurobiol. | volume = 152 | pages = 21–37 | year = 2017 | pmid = 26724279 | doi = 10.1016/j.pneurobio.2015.12.001 | pmc=4919246}}</ref> The response rate was 60%, relative to 20% for ], and 33% of the participants met remission criteria by day five following a single administration.<ref name="pmid26724279" /> After one week, 78% of responders still showed an antidepressant response, and after 15 days, 42% did so.<ref name="pmid26724279" /> In the study, half of the participants had to have their dose lowered due to a high incidence of dissociative side effects at the higher doses.<ref name="pmid26724279" /> Development was stopped due to incidence of ].<ref name="pmid26724279" /> Other NR2B subunit-selective antagonists of the NMDA receptor are still under development for depression, such as ] (CERC-301, MK-0657).<ref name="pmid26724279" />

Chemically, traxoprodil is a ] and ] ].<ref name="PubChem">{{cite web | title=Traxoprodil | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/219101 | access-date=2 September 2024}}</ref>

==See also==
* ]
* ] (another β-hydroxyamphetamine NMDA receptor antagonist)

==References==
{{Reflist}}

{{Ionotropic glutamate receptor modulators}}
{{Phenethylamines}}

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