pipofezine

{{Short description|Chemical compound}}

{{Drugbox

| IUPAC_name = 5-methyl-3-(4-methylpiperazin-1-yl)pyridazino[3,4-b][1,4]benzoxazine

| image = Pipofezine.png

| tradename = Azafen, Azaphen

| pregnancy_category =

| legal_status = Rx-only

| routes_of_administration = Oral

| bioavailability =

| metabolism =

| elimination_half-life =

| excretion =

| CAS_number = 24886-52-0

| ATC_prefix = none

| ATC_suffix =

| PubChem = 159977

| ChemSpiderID = 140640

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

| UNII = P8T739L1FA

| C=16 | H=19 | N=5 | O=1

}}

Pipofezine, sold under the brand name Azafen or Azaphen, is a tricyclic antidepressant approved in Russia for the treatment of depression.{{cite journal | vauthors = Aleeva GN, Molodavkin GM, Voronina TA | title = Comparison of antidepressant effects of azafan, tianeptine, and paroxetine | journal = Bulletin of Experimental Biology and Medicine | volume = 148 | issue = 1 | pages = 54–56 | date = July 2009 | pmid = 19902096 | doi = 10.1007/s10517-009-0638-4 | s2cid = 23923093 }}{{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 | page = 843 | isbn = 3-88763-075-0 | url = https://google.co.in/books/edition/_/5GpcTQD_L2oC?hl=en&gbpv=1&dq=pipofezine&pg=PA843}}{{cite book | vauthors = Muller NF, Dessing RP | title = European Drug Index, 4th Edition | publisher = CRC Press | location = Boca Raton | year = 1998 | page = 126| isbn = 3-7692-2114-1 | url = https://books.google.com/books?id=GCBiEAAAQBAJ&dq=Pipofezine&pg=PA126}}{{cite book | vauthors = Macor JE | title = Annual Reports in Medicinal Chemistry, Volume V44 | publisher = Academic Press | page = 16 | location = Boston | year = 2009 | isbn = 978-0-12-374766-2 | url = https://books.google.com/books?id=dBGM4WSV_YEC&dq=azaphen&pg=PA16}} It was introduced in the late 1960s and is still used today.{{cite journal | vauthors = Mashkovskii MD, Polezhaeva AI, Avrutskii GI, Vertozgadova OP, Smulevich AB | title = [The pharmacologic properties and therapeutic effectiveness of the new antidepressant preparation Azaphen] | language = ru | journal = Zhurnal Nevropatologii I Psikhiatrii imeni S.S. Korsakova | volume = 69 | issue = 8 | pages = 1234–1238 | year = 1969 | pmid = 5392529 }}{{cite journal | vauthors = Shinaev NN, Akzhigitov RG | title = [Azaphen: a return to clinical practice] | language = ru | journal = Zhurnal Nevrologii I Psikhiatrii imeni S.S. Korsakova | volume = 105 | issue = 10 | pages = 55–56 | year = 2005 | pmid = 16281382 }}

Pipofezine has been shown to act as a potent inhibitor of the reuptake of serotonin.{{cite journal | vauthors = Avdulov NA, Maĭsov NI | title = [Atypical antidepressants: effect on synaptosomal uptake of serotonin and GABA] | language = ru | journal = Biulleten' Eksperimental'noi Biologii I Meditsiny | volume = 92 | issue = 11 | pages = 564–566 | date = November 1981 | pmid = 7198493 }}{{cite journal | vauthors = Valdman AV, Avdulov NA, Rozganets VV, Rusacov DY | title = Behavioural and neurochemical studies of the action of atypical antidepressants | journal = Acta Physiologica et Pharmacologica Bulgarica | volume = 9 | issue = 3 | pages = 3–10 | year = 1983 | pmid = 6142583 }} In addition to its antidepressant action, pipofezine has sedative effects as well, suggesting antihistamine activity.{{cite book | vauthors = Macor JE | title = Annual Reports in Medicinal Chemistry, Volume V44 | publisher = Academic Press | location = Boston | year = 2009 | isbn = 978-0-12-374766-2 | url = https://books.google.com/books?id=dBGM4WSV_YEC&q=azaphen&pg=PA16}} Other properties such as anticholinergic or antiadrenergic actions are less clear but are likely.{{Citation needed|date=October 2014}}