ipsapirone

{{Short description|Antidepressant and anxiolytic drug}}

{{Drugbox

| verifiedrevid = 437153617

| IUPAC_name = 9,9-dioxo-8-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-
9λ⁶-thia-8-azabicyclo[4.3.0]nona-1,3,5-trien-7-one

| image = Ipsapirone.svg

| tradename =

| pregnancy_category =

| legal_status = Uncontrolled

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life = 1.3–2.7 hours{{medcn|date=November 2023}}

| excretion =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 95847-70-4

| ATC_prefix = none

| ATC_suffix =

| PubChem = 56971

| IUPHAR_ligand = 42

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 51365

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

| UNII = 6J9B11MN0K

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 8412

| C=19 | H=23 | N=5 | O=3 | S=1

| smiles = O=C2c1ccccc1S(=O)(=O)N2CCCCN4CCN(c3ncccn3)CC4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C19H23N5O3S/c25-18-16-6-1-2-7-17(16)28(26,27)24(18)11-4-3-10-22-12-14-23(15-13-22)19-20-8-5-9-21-19/h1-2,5-9H,3-4,10-15H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = TZJUVVIWVWFLCD-UHFFFAOYSA-N

}}

Ipsapirone is a selective 5-HT_1A receptor partial agonist of the piperazine and azapirone chemical classes.{{cite journal | vauthors = Fanelli RJ, Schuurman T, Glaser T, Traber J | title = Ipsapirone: a novel anxiolytic and selective 5-HT1A receptor ligand | journal = Progress in Clinical and Biological Research | volume = 361 | pages = 461–467 | year = 1990 | pmid = 1981264 }} It has antidepressant and anxiolytic effects. Ipsapirone was studied in several placebo-controlled trials for depression and continues to be used in research.{{cite journal | vauthors = Chessick CA, Allen MH, Thase M, Batista Miralha da Cunha AB, Kapczinski FF, de Lima MS, dos Santos Souza JJ | title = Azapirones for generalized anxiety disorder | journal = The Cochrane Database of Systematic Reviews | volume = 2006 | issue = 3 | pages = CD006115 | date = July 2006 | pmid = 16856115 | pmc = 8915394 | doi = 10.1002/14651858.CD006115 }}