Umespirone

{{Short description|Anxiolytic and antipsychotic drug}}

{{cs1 config|name-list-style=vanc}}

{{Drugbox

| IUPAC_name = 3-butyl-7-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetrone

| image = Umespirone skeletal.svg

| tradename =

| legal_status = uncontrolled

| routes_of_administration = By mouth

| elimination_half-life = Unknown but effects last much longer than other azapirones, up to 23 hours after a single dose in human clinical studies.{{cite journal | vauthors = Holland RL, Wesnes K, Dietrich B | title = Single dose human pharmacology of umespirone | journal = European Journal of Clinical Pharmacology | volume = 46 | issue = 5 | pages = 461–8 | year = 1994 | pmid = 7957544 | doi = 10.1007/bf00191912| s2cid = 12117650 }}

| CAS_number = 107736-98-1

| ATC_prefix = none

| PubChem = 65902

| ChemSpiderID = 59311

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

| UNII = FG0A3VRL5K

| C=28 | H=40 | N=4 | O=5

| smiles = O=C1N(C(=O)C2C(=O)N(C(=O)C1C2(C)C)CCCCN4CCN(c3ccccc3OC)CC4)CCCC

}}

Umespirone (KC-9172) is a drug of the azapirone class which possesses anxiolytic and antipsychotic properties.{{cite journal |vauthors=Barnes NM, Costall B, Domeney AM, etal | title = The effects of umespirone as a potential anxiolytic and antipsychotic agent | journal = Pharmacology Biochemistry and Behavior | volume = 40 | issue = 1 | pages = 89–96 |date=September 1991 | pmid = 1685786 | doi = 10.1016/0091-3057(91)90326-W| s2cid = 9762359 }}{{cite journal | vauthors = Ruhland M, Krähling H, Fuchs A, Schön U | title = KC 9172 (free base of KC 7218)--an antipsychotic/anxiolytic compound. I. Antipsychotic and anxiolytic activity in comparison with chlorpromazine, clozapine, diazepam and buspirone | journal = Pharmacopsychiatry | volume = 21 | issue = 6 | pages = 396–8 |date=November 1988 | pmid = 2907649 | doi = 10.1055/s-2007-1017024| s2cid = 260241523 }}{{cite journal | vauthors = Krähling H, Fuchs A, Ruhland M, Schön U, Mol F, Tulp M | title = KC 9172 (free base of KC 7218)--an antipsychotic/anxiolytic compound. II. Discrimination from typical neuroleptics and benzodiazepine-like minor tranquilizers | journal = Pharmacopsychiatry | volume = 21 | issue = 6 | pages = 399–401 |date=November 1988 | pmid = 2907650 | doi = 10.1055/s-2007-1017025| s2cid = 260241655 }}{{cite journal | vauthors = Schmidt WJ, Krähling H, Ruhland M | title = Antagonism of AP-5-induced sniffing stereotypy links umespirone to atypical antipsychotics | journal = Life Sciences | volume = 48 | issue = 6 | pages = 499–505 | year = 1991 | pmid = 1671523 | doi = 10.1016/0024-3205(91)90464-M}} It behaves as a 5-HT_1A receptor partial agonist (K_i = 15 nM), D₂ receptor partial agonist (K_i = 23 nM), and α₁-adrenoceptor receptor antagonist (K_i = 14 nM), and also has weak affinity for the sigma receptor (K_i = 558 nM).{{cite journal | vauthors = Ahlenius S, Wijkström A | title = Mixed agonist-antagonist properties of umespirone at neostriatal dopamine receptors in relation to its behavioral effects in the rat | journal = European Journal of Pharmacology | volume = 222 | issue = 1 | pages = 69–74 |date=November 1992 | pmid = 1361441 | doi = 10.1016/0014-2999(92)90464-F}}{{cite journal | vauthors = Itzhak Y, Ruhland M, Krähling H | title = Binding of umespirone to the sigma receptor: evidence for multiple affinity states | journal = Neuropharmacology | volume = 29 | issue = 2 | pages = 181–4 |date=February 1990 | pmid = 1970425 | doi = 10.1016/0028-3908(90)90058-Y| s2cid = 54326248 | doi-access = free }} Unlike many other anxiolytics and antipsychotics, umespirone produces minimal sedation, cognitive/memory impairment, catalepsy, and extrapyramidal symptoms.