Posovolone

{{Short description|Chemical compound}}

{{Infobox drug

| drug_name =

| image = Posovolone.svg

| width =

| caption =

| 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 =

| duration_of_action =

| excretion =

| CAS_number = 256955-84-7

| CAS_supplemental =

| PubChem = 9802683

| IUPHAR_ligand =

| DrugBank =

| ChemSpiderID = 7978445

| UNII = 1GA9JVO9ZA

| KEGG =

| ChEBI =

| ChEMBL =

| NIAID_ChemDB =

| PDB_ligand =

| synonyms = CO-134444; Co 134444; V-134444; 3β-Hydroxy-21-(1H-imidazol-1-yl)-3α-(methoxymethyl)-5α-pregnan-20-one

| IUPAC_name = 1-[(3R,5S,8R,9S,10S,13S,14S,17S)-3-hydroxy-3-(methoxymethyl)-10,13-dimethyl-1,2,4,5,6,7,8,9,11,12,14,15,16,17-tetradecahydrocyclopenta[a]phenanthren-17-yl]-2-imidazol-1-ylethanone

| C=26 | H=40 | N=2 | O=3

| SMILES = C[C@]12CC[C@@](C[C@@H]1CC[C@@H]3[C@@H]2CC[C@]4([C@H]3CC[C@@H]4C(=O)CN5C=CN=C5)C)(COC)O

| StdInChI = 1S/C26H40N2O3/c1-24-10-11-26(30,16-31-3)14-18(24)4-5-19-20-6-7-22(25(20,2)9-8-21(19)24)23(29)15-28-13-12-27-17-28/h12-13,17-22,30H,4-11,14-16H2,1-3H3/t18-,19-,20-,21-,22+,24-,25-,26+/m0/s1

| StdInChIKey = BRVGKZNQWCQKTC-MVCIVNJCSA-N

}}

Posovolone (developmental code name Co 134444) is a synthetic neurosteroid which was under development as a sedative/hypnotic medication for the treatment of insomnia.{{Cite web | url=https://adisinsight.springer.com/drugs/800013177 | title=CO 134444 - AdisInsight }}{{cite journal | vauthors = Vanover KE, Hogenkamp DJ, Lan NC, Gee KW, Carter RB | title = Behavioral characterization of Co 134444 (3alpha-hydroxy-21-(1'-imidazolyl)-3beta-methoxymethyl-5alpha- pregnan-20-one), a novel sedative-hypnotic neuroactive steroid | journal = Psychopharmacology (Berl) | volume = 155 | issue = 3 | pages = 285–91 | date = May 2001 | pmid = 11432691 | doi = 10.1007/s002130100695 | s2cid = 44353086 | url = }}{{cite journal | vauthors = Hamilton NM | title = Interaction of steroids with the GABA(A) receptor | journal = Curr Top Med Chem | volume = 2 | issue = 8 | pages = 887–902 | date = August 2002 | pmid = 12171578 | doi = 10.2174/1568026023393570 | url = }}{{cite journal | vauthors = Belelli D, Hogenkamp D, Gee KW, Lambert JJ | title = Realising the therapeutic potential of neuroactive steroid modulators of the GABAA receptor | journal = Neurobiol Stress | volume = 12 | issue = | pages = 100207 | date = May 2020 | pmid = 32435660 | pmc = 7231973 | doi = 10.1016/j.ynstr.2019.100207 | url = }} It is orally active and acts as a GABA_A receptor positive allosteric modulator. In animals, posovolone shows anticonvulsant, anxiolytic-like, ataxic, and sleep-promoting effects and appeared to produce effects similar to those of pregnanolone.{{cite journal | vauthors = Vanover KE, Edgar DM, Seidel WF, Hogenkamp DJ, Fick DB, Lan NC, Gee KW, Carter RB | title = Response-rate suppression in operant paradigm as predictor of soporific potency in rats and identification of three novel sedative-hypnotic neuroactive steroids | journal = J Pharmacol Exp Ther | volume = 291 | issue = 3 | pages = 1317–23 | date = December 1999 | pmid = 10565857 | doi = 10.1016/S0022-3565(24)35242-5| url = }} Development of the agent was started by 1999 and appears to have been discontinued by 2007. In 2021, an {{Abbrlink|INN|International Nonproprietary Name}} was registered for posovolone with the descriptor of "antidepressant".{{Cite web| title=International Nonproprietary Names for Pharmaceutical Substances (INN) | url=https://cdn.who.int/media/docs/default-source/international-nonproprietary-names-(inn)/pl126.pdf#page=137 | archive-url=https://web.archive.org/web/20220204014036/https://cdn.who.int/media/docs/default-source/international-nonproprietary-names-(inn)/pl126.pdf | archive-date=2022-02-04}} Posovolone was originally developed by Purdue Pharma.