Mepiprazole

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 1-(3-Chlorophenyl)-4-[2-(5-methyl-1H-pyrazol-3-yl)ethyl]piperazine

| image = Mepiprazole structure.svg

| width =

| tradename = Psigodal

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 20326-12-9

| CAS_supplemental =
20344-15-4 (hydrochloride)

| ATC_prefix = none

| ATC_suffix =

| PubChem = 71897

| ChemSpiderID = 64909

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

| UNII = 977BAL0NR7

| synonyms = PAP; EMD-16923; H-4007

| C=16 | H=21 | Cl=1 | N=4

| SMILES = Cc3cc(CCN2CCN(c1cccc(Cl)c1)CC2)n[nH]3

}}

Mepiprazole (INN, BAN) (brand name Psigodal) is an anxiolytic drug of the phenylpiperazine group with additional antidepressant properties that is marketed in Spain.{{cite book|author=J. Elks|title=The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies|url=https://books.google.com/books?id=0vXTBwAAQBAJ&pg=PA768|date=14 November 2014|publisher=Springer|isbn=978-1-4757-2085-3|pages=768–}}{{cite book | author = Swiss Pharmaceutical Society | title = Index Nominum 2000: International Drug Directory (Book with CD-ROM) | publisher = Medpharm Scientific Publishers | location = Boca Raton | year = 2000 | isbn = 3-88763-075-0 | url = https://books.google.com/books?id=5GpcTQD_L2oC&q=mepiprazole&pg=PA648}}{{cite journal | author = Pöldinger W | title = Clinical trial of 3-methyl-5-(beta-N'-(N-m-chlorophenylpiperazino)ethyl)-pyrazole dihydrochloride (Mepiprazol) in the therapy of psychovegetative disorders | journal = International Pharmacopsychiatry | volume = 10 | issue = 1 | pages = 1–8 | year = 1975 | pmid = 1095510 | doi = 10.1159/000468162}}{{cite journal |vauthors=De Buck R, Van Durme R, Pelc I | title = [A controlled double-blind crossover study of the efficacy of mepiprazol (EMD 16.923) and of diazepam in the treatment of neurotic disorders] | language = fr | journal = Acta Psychiatrica Belgica | volume = 75 | issue = 3 | pages = 320–33 |date=May 1975 | pmid = 769484 }}{{cite journal |vauthors=Saldaña Hernández OH, Hernández González J | title = [Psychopharmological research with EMD 16-923 in patients with different degrees of anxiety] | language = es| journal = Neurología, Neurocirugía, Psiquiatría | volume = 17 | issue = 1 | pages = 29–33 | year = 1976 | pmid = 1052713 }} It acts as a 5-HT_2A and α₁-adrenergic receptor antagonist{{cite journal | vauthors = Cohen ML, Fuller RW, Kurz KD | title = Evidence that blood pressure reduction by serotonin antagonists is related to alpha receptor blockade in spontaneously hypertensive rats | journal = Hypertension | volume = 5 | issue = 5 | pages = 676–81 | year = 1983 | pmid = 6311738 | doi = 10.1161/01.hyp.5.5.676 | doi-access = free }}{{cite journal |vauthors=Maj J, Sypniewska M | title = Central action of mepiprazole | journal = Polish Journal of Pharmacology and Pharmacy | volume = 32 | issue = 4 | pages = 475–84 | year = 1980 | pmid = 7255266 }}{{cite journal |vauthors=Fuxe K, Agnati LF, Ungerstedt U | title = The effect of mepiprazole on central monoamine neurons. Evidence for increased 5-hydroxytryptamine and dopamine receptor activity | journal = European Journal of Pharmacology | volume = 35 | issue = 1 | pages = 93–108 |date=January 1976 | pmid = 943291 | doi = 10.1016/0014-2999(76)90304-6}} and inhibits the reuptake and induces the release of serotonin, dopamine, and norepinephrine to varying extents,{{cite journal |vauthors=Placheta P, Singer E, Kriwanek W, Hertting G | title = Mepiprazole, a new psychotropic drug: effects on uptake and retention of monoamines in rat brain synaptosomes | journal = Psychopharmacology | volume = 48 | issue = 3 | pages = 295–301 |date=August 1976 | pmid = 9660 | doi = 10.1007/BF00496865| s2cid = 9194743 }} and has been described as a serotonin antagonist and reuptake inhibitor (SARI).{{cite journal | vauthors = Fagiolini A, Comandini A, Catena Dell'Osso M, Kasper S | title = Rediscovering trazodone for the treatment of major depressive disorder | journal = CNS Drugs | volume = 26 | issue = 12 | pages = 1033–1049 | date = December 2012 | pmid = 23192413 | pmc = 3693429 | doi = 10.1007/s40263-012-0010-5 }} Controlled clinical trials of mepiprazole in patients with irritable bowel syndrome (IBS) were also carried out and suggested some benefits of the drug in relieving symptoms of IBS in some patients.{{cite journal |vauthors=Dotevall G, Groll E | title = Controlled clinical trial of mepiprazole in irritable bowel syndrome | journal = The British Medical Journal | volume = 4 | issue = 5935 | pages = 16–8 |date=October 1974 | pmid = 4609545 | doi = 10.1136/bmj.4.5935.16| pmc=1612118}} Similarly to other phenylpiperazines like trazodone, nefazodone, and etoperidone, mepiprazole produces mCPP as an active metabolite.{{cite journal |vauthors=Fong MH, Garattini S, Caccia S | title = 1-m-Chlorophenylpiperazine is an active metabolite common to the psychotropic drugs trazodone, etoperidone and mepiprazole | journal = The Journal of Pharmacy and Pharmacology | volume = 34 | issue = 10 | pages = 674–5 |date=October 1982 | pmid = 6128394 | doi = 10.1111/j.2042-7158.1982.tb04701.x| s2cid = 44968564 }}