emapunil

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 444150720

| IUPAC_name = N-benzyl-N-ethyl-2-(7-methyl-8-oxo-2-phenylpurin-9-yl)acetamide

| image = Emapunil.png

| width = 200

| tradename =

| pregnancy_category =

| routes_of_administration =

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 226954-04-7

| ATC_prefix = none

| PubChem = 6433109

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

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

| UNII = OG837L732J

| ChEMBL = 513922

| ChemSpiderID = 4938297

| C=23 | H=23 | N=5 | O=2

| smiles = CCN(Cc1ccccc1)C(=O)Cn2c3c(cnc(n3)c4ccccc4)n(c2=O)C

| StdInChI = 1S/C23H23N5O2/c1-3-27(15-17-10-6-4-7-11-17)20(29)16-28-22-19(26(2)23(28)30)14-24-21(25-22)18-12-8-5-9-13-18/h4-14H,3,15-16H2,1-2H3

| StdInChIKey = NBMBIEOUVBHEBM-UHFFFAOYSA-N

}}

Emapunil (AC-5216, XBD-173) is an anxiolytic drug which acts as a selective agonist at the peripheral benzodiazepine receptor, also known as the mitochondrial 18 kDa translocator protein or TSPO.{{cite journal |vauthors=Kita A, Kohayakawa H, Kinoshita T, Ochi Y, Nakamichi K, Kurumiya S, Furukawa K, Oka M |title=Antianxiety and antidepressant-like effects of AC-5216, a novel mitochondrial benzodiazepine receptor ligand |journal=British Journal of Pharmacology |volume=142 |issue=7 |pages=1059–72 |date=August 2004 |pmid=15249420 |pmc=1575165 |doi=10.1038/sj.bjp.0705681 }}{{cite journal |vauthors=Mealy NE, Bayés M, Lupone B, Balcells M | year = 2006 | title = Psychiatric Disorders | journal = Drugs of the Future | volume = 31 | issue = 3| page = 259 }} This protein has multiple functions, among which is regulation of steroidogenesis,{{cite journal |vauthors=Veenman L, Papadopoulos V, Gavish M |title=Channel-like functions of the 18-kDa translocator protein (TSPO): regulation of apoptosis and steroidogenesis as part of the host-defense response |journal=Current Pharmaceutical Design |volume=13 |issue=23 |pages=2385–405 |year=2007 |pmid=17692008 |doi= 10.2174/138161207781368710}}{{cite journal |vauthors=Falchi AM, Battetta B, Sanna F, Piludu M, Sogos V, Serra M, Melis M, Putzolu M, Diaz G |title=Intracellular cholesterol changes induced by translocator protein (18 kDa) TSPO/PBR ligands |journal=Neuropharmacology |volume=53 |issue=2 |pages=318–29 |date=August 2007 |pmid=17631921 |doi=10.1016/j.neuropharm.2007.05.016 |s2cid=39793765 }} particularly the production of neuroactive steroids such as allopregnanolone in the brain.{{cite journal |vauthors=Kita A, Furukawa K |title=Involvement of neurosteroids in the anxiolytic-like effects of AC-5216 in mice |journal=Pharmacology Biochemistry and Behavior |volume=89 |issue=2 |pages=171–8 |date=April 2008 |pmid=18201755 |doi=10.1016/j.pbb.2007.12.006 |s2cid=24094283 }}{{cite journal |vauthors=Da Settimo F, Simorini F, Taliani S, La Motta C, Marini AM, Salerno S, Bellandi M, Novellino E, Greco G, Cosimelli B, Da Pozzo E, Costa B, Simola N, Morelli M, Martini C |title=Anxiolytic-like effects of N,N-dialkyl-2-phenylindol-3-ylglyoxylamides by modulation of translocator protein promoting neurosteroid biosynthesis |journal=Journal of Medicinal Chemistry |volume=51 |issue=18 |pages=5798–806 |date=September 2008 |pmid=18729350 |doi=10.1021/jm8003224 }}{{cite journal |vauthors=Taliani S, Da Settimo F, Da Pozzo E, Chelli B, Martini C |title=Translocator Protein Ligands as Promising Therapeutic Tools for Anxiety Disorders |journal=Current Medicinal Chemistry |volume= 16|issue= 26|pages= 3359–80|date=September 2009 |pmid=19548867 |doi= 10.2174/092986709789057653}} In both animal and human trials, emapunil produced fast acting anxiolytic and anti-panic effects, without producing sedation or withdrawal symptoms following cessation of use.{{cite journal |vauthors=Rupprecht R, Rammes G, Eser D, Baghai TC, Schüle C, Nothdurfter C, Troxler T, Gentsch C, Kalkman HO, Chaperon F, Uzunov V, McAllister KH, Bertaina-Anglade V, La Rochelle CD, Tuerck D, Floesser A, Kiese B, Schumacher M, Landgraf R, Holsboer F, Kucher K |s2cid=26125316 |title=Translocator Protein (18 kD) as Target for Anxiolytics Without Benzodiazepine-Like Side Effects |journal=Science |volume= 325|issue= 5939|pages= 490–3|date=June 2009 |pmid=19541954 |doi=10.1126/science.1175055 |bibcode=2009Sci...325..490R }}{{cite journal |vauthors=Kita A, Kinoshita T, Kohayakawa H, Furukawa K |title=Lack of tolerance to anxiolysis and withdrawal symptoms in mice repeatedly treated with AC-5216, a selective TSPO ligand |journal=Progress in Neuro-psychopharmacology & Biological Psychiatry |volume= 33|issue= 6|pages= 1040–5|date=June 2009 |pmid=19497344 |doi=10.1016/j.pnpbp.2009.05.018 |s2cid=8195889 }} Emapunil is also used in its ¹¹C radiolabelled form to map the distribution of TSPO receptors in the brain.{{cite journal |vauthors=Zhang MR, Kumata K, Maeda J, Yanamoto K, Hatori A, Okada M, Higuchi M, Obayashi S, Suhara T, Suzuki K |title=11C-AC-5216: a novel PET ligand for peripheral benzodiazepine receptors in the primate brain |journal=Journal of Nuclear Medicine |volume=48 |issue=11 |pages=1853–61 |date=November 2007 |pmid=17978354 |doi=10.2967/jnumed.107.043505 |doi-access=free }}{{cite journal |vauthors=Miyoshi M, Ito H, Arakawa R, Takahashi H, Takano H, Higuchi M, Okumura M, Otsuka T, Kodaka F, Sekine M, Sasaki T, Fujie S, Seki C, Maeda J, Nakao R, Zhang MR, Fukumura T, Matsumoto M, Suhara T |title=Quantitative Analysis of Peripheral Benzodiazepine Receptor in the Human Brain Using PET with 11C-AC-5216 |journal=Journal of Nuclear Medicine |volume= 50|issue= 7|pages= 1095–101|date=June 2009 |pmid=19525461 |doi=10.2967/jnumed.109.062554 |doi-access=free }}