8-Hydroxyamoxapine

{{Short description|Chemical compound}}

{{Infobox drug

| drug_name = 8-Hydroxyamoxapine

| image = 8-Hydroxyamoxapine.svg

| width =

| alt = Chemical structure of 8-Hydroxyamoxapine

| pronounce =

| tradename =

| Drugs.com =

| MedlinePlus =

| licence_CA =

| licence_EU =

| DailyMedID =

| licence_US =

| pregnancy_AU =

| pregnancy_category =

| dependency_liability =

| addiction_liability =

| routes_of_administration =

| class =

| ATC_prefix =

| ATC_suffix =

| legal_status =

| bioavailability =

| protein_bound =

| metabolism =

| metabolites =

| onset =

| elimination_half-life = 30 hours

| duration_of_action =

| excretion =

| CAS_number = 61443-78-5

| CAS_supplemental =

| PubChem = 43656

| IUPHAR_ligand =

| DrugBank =

| ChemSpiderID = 39784

| UNII = 0D4T741I48

| KEGG =

| ChEBI = 143289

| ChEMBL =

| NIAID_ChemDB =

| PDB_ligand =

| DTXSID = DTXSID40210388

| synonyms =

| IUPAC_name = 8-chloro-6-piperazin-1-ylbenzo[b][1,4]benzoxazepin-3-ol

| C=17 | H=16 | Cl=1 | N=3 | O=2

| SMILES = C1CN(CCN1)C2=NC3=C(C=CC(=C3)O)OC4=C2C=C(C=C4)Cl

| StdInChI = 1S/C17H16ClN3O2/c18-11-1-3-15-13(9-11)17(21-7-5-19-6-8-21)20-14-10-12(22)2-4-16(14)23-15/h1-4,9-10,19,22H,5-8H2

| StdInChIKey = QDWNOKXUZTYVGO-UHFFFAOYSA-N

}}

8-Hydroxyamoxapine is an active metabolite of the antidepressant drug amoxapine (Asendin). It contributes to amoxapine's pharmacology.{{cite journal | vauthors = Jue SG, Dawson GW, Brogden RN | title = Amoxapine: a review of its pharmacology and efficacy in depressed states | journal = Drugs | volume = 24 | issue = 1 | pages = 1–23 | date = July 1982 | pmid = 7049659 | doi = 10.2165/00003495-198224010-00001 | s2cid = 7279867 }}{{cite journal | vauthors = Calvo B, García MJ, Pedraz JL, Mariño EL, Domínguez-Gil A | title = Pharmacokinetics of amoxapine and its active metabolites | journal = International Journal of Clinical Pharmacology, Therapy, and Toxicology | volume = 23 | issue = 4 | pages = 180–185 | date = April 1985 | pmid = 3997304 }} It is a serotonin-norepinephrine reuptake inhibitor (SNRI) with similar norepinephrine, but more serotonin, reuptake inhibition as its parent compound. It plays a part in balancing amoxapine's ratio of serotonin to norepinephrine transporter blockage.{{cite journal | vauthors = Midha KK, Hubbard JW, McKay G, Rawson MJ, Hsia D | title = The role of metabolites in a bioequivalence study II: amoxapine, 7-hydroxyamoxapine, and 8-hydroxyamoxapine | journal = International Journal of Clinical Pharmacology and Therapeutics | volume = 37 | issue = 9 | pages = 428–38 |date=September 1999 | pmid = 10507241 }}