HPTP

{{Short description|Monoaminergic neurotoxin}} {{Infobox drug | drug_name = | image = HPTP.svg | image_class = skin-invert-image | width = 250px | caption =

<!-- Clinical data --> | pronounce = | tradename = | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = | class = [[Serotonergic neurotoxin|Serotonergic]] and [[dopaminergic neurotoxin]] | ATC_prefix = | ATC_suffix =

<!-- Legal status --> | legal_status =

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

<!-- Identifiers --> | CAS_number = 52669-92-8 | CAS_supplemental = | PubChem = 171187 | IUPHAR_ligand = | DrugBank = | ChemSpiderID = 149659 | UNII = | KEGG = | ChEBI = 177523 | ChEMBL = 3544895 | NIAID_ChemDB = | PDB_ligand = | synonyms =

<!-- Chemical data --> | IUPAC_name = 4-[4-(4-chlorophenyl)-3,6-dihydro-2''H''-pyridin-1-yl]-1-(4-fluorophenyl)butan-1-one | C=21 | H=21 | Cl=1 | F=1 | N=1 | O=1 | SMILES = C1CN(CC=C1C2=CC=C(C=C2)Cl)CCCC(=O)C3=CC=C(C=C3)F | StdInChI = 1S/C21H21ClFNO/c22-19-7-3-16(4-8-19)17-11-14-24(15-12-17)13-1-2-21(25)18-5-9-20(23)10-6-18/h3-11H,1-2,12-15H2 | StdInChIKey = ZNOLNAPJKOYTHY-UHFFFAOYSA-N }}

'''HPTP''' is a [[monoaminergic neurotoxin]] related to [[MPTP]].<ref name="Kostrzewa2022">{{cite book | vauthors = Kostrzewa RM | title=Handbook of Neurotoxicity | chapter=Survey of Selective Monoaminergic Neurotoxins Targeting Dopaminergic, Noradrenergic, and Serotoninergic Neurons | publisher=Springer International Publishing | publication-place=Cham | date=2022 | isbn=978-3-031-15079-1 | doi=10.1007/978-3-031-15080-7_53 | pages=159–198}}</ref><ref name="Igarashi1998">{{cite journal | last=Igarashi | first=Kazuo | title=The Possible Role of an Active Metabolite Derived from the Neuroleptic Agent Haloperidol in Drug-Induced Parkinsonism | journal=Journal of Toxicology: Toxin Reviews | volume=17 | issue=1 | date=1998 | issn=0731-3837 | doi=10.3109/15569549809006488 | pages=27–38}}</ref><ref name="GórskaMarszałłSloderbach2015">{{cite journal | vauthors = Górska A, Marszałł M, Sloderbach A | title = [The neurotoxicity of pyridinium metabolites of haloperidol] | language = Polish | journal = Postepy Higieny I Medycyny Doswiadczalnej | volume = 69 | issue = | pages = 1169–1175 | date = October 2015 | pmid = 26561842 | doi = 10.5604/17322693.1175009 | doi-broken-date = 12 July 2025 | trans-title = The neurotoxicity of pyridinium metabolites of haloperidol | doi-access = free }}</ref><ref name="CastagnoliCastagnoliVanderSchyf1999">{{cite journal | vauthors = Castagnoli N, Castagnoli KP, Van der Schyf CJ, Usuki E, Igarashi K, Steyn SJ, Riker RR | title = Enzyme-catalyzed bioactivation of cyclic tertiary amines to form potential neurotoxins | journal = Pol J Pharmacol | volume = 51 | issue = 1 | pages = 31–38 | date = 1999 | pmid = 10389142 | doi = | url = }}</ref> It is the [[dehydration reaction|dehydration]] [[product (chemistry)|product]] of [[haloperidol]].<ref name="Kostrzewa2022" /><ref name="Igarashi1998" /><ref name="CastagnoliCastagnoliVanderSchyf1999" /> The agent is specifically a [[dopaminergic neurotoxin|dopaminergic]] and [[serotonergic neurotoxin]].<ref name="Kostrzewa2022" /> HPTP is a [[prodrug]] of [[HPP+|HPP⁺]], which mediates its monoaminergic neurotoxicity.<ref name="Kostrzewa2022" /><ref name="Igarashi1998" /><ref name="CastagnoliCastagnoliVanderSchyf1999" /> This is analogous to how [[MPP+|MPP⁺]] mediates the neurotoxicity of MPTP.<ref name="Kostrzewa2022" /><ref name="Igarashi1998" /><ref name="CastagnoliCastagnoliVanderSchyf1999" /> Other related compounds include [[RHPTP]] and [[RHPP+|RHPP⁺]].<ref name="AventDeVossGillam2006">{{cite journal | vauthors = Avent KM, DeVoss JJ, Gillam EM | title = Cytochrome P450-mediated metabolism of haloperidol and reduced haloperidol to pyridinium metabolites | journal = Chem Res Toxicol | volume = 19 | issue = 7 | pages = 914–920 | date = July 2006 | pmid = 16841959 | doi = 10.1021/tx0600090 | url = }}</ref>

==References== {{Reflist}}

{{Monoamine neurotoxins}}

[[Category:4-Chlorophenyl compounds]] [[Category:4-Fluorophenyl compounds]] [[Category:Monoaminergic neurotoxins]] [[Category:Prodrugs]] [[Category:Tetrahydropyridines]]

{{Nervous-system-drug-stub}}