fipexide

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 443216648

| IUPAC_name = 1-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-
2-(4-chlorophenoxy)ethanone

| image = Fipexide.svg

| tradename =

| pregnancy_AU =

| pregnancy_US =

| legal_AU =

| legal_CA =

| legal_UK =

| legal_US =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 34161-24-5

| ATC_prefix = N06

| ATC_suffix = BX05

| PubChem = 3351

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

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 3234

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

| UNII = TG44VME01D

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D07345

| ChEMBL_Ref = {{ebicite|correct|EBI}}

| ChEMBL = 254857

| C=20 | H=21 | Cl=1 | N=2 | O=4

| smiles = Clc4ccc(OCC(=O)N1CCN(CC1)Cc2ccc3OCOc3c2)cc4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C20H21ClN2O4/c21-16-2-4-17(5-3-16)25-13-20(24)23-9-7-22(8-10-23)12-15-1-6-18-19(11-15)27-14-26-18/h1-6,11H,7-10,12-14H2

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = BFUJHVVEMMWLHC-UHFFFAOYSA-N

}}

Fipexide (Attentil, Vigilor) is a psychoactive drug of the piperazine chemical class which was developed in Italy in 1983.{{cite journal | vauthors = Missale C, Pasinetti G, Govoni S, Spano PF, Trabucchi M | title = [Fipexide: a new drug for the regulation of dopaminergic system at the macromolecular level] | language = it | journal = Bollettino Chimico Farmaceutico | volume = 122 | issue = 2 | pages = 79–85 | date = February 1983 | pmid = 6871040 }} It was used as a nootropic drug in Italy and France, mainly for the treatment of senile dementia,{{cite journal | vauthors = Bompani R, Scali G | title = Fipexide, an effective cognition activator in the elderly: a placebo-controlled, double-blind clinical trial | journal = Current Medical Research and Opinion | volume = 10 | issue = 2 | pages = 99–106 | date = 1986 | pmid = 3519097 | doi = 10.1185/03007998609110426 }} but is no longer in common use due to the occurrence of rare adverse drug reactions including fever{{cite journal | vauthors = Guy C, Blay N, Rousset H, Fardeau V, Ollagnier M | title = [Fever caused by fipexide. Evaluation of the national pharmacovigilance survey] | language = fr | journal = Therapie | volume = 45 | issue = 5 | pages = 429–31 | date = 1990 | pmid = 2260037 }} and hepatitis. Fipexide is similar in action to other nootropic drugs such as piracetam{{Citation needed|date=February 2017}} and has a few similarities in chemical structure to centrophenoxine. Chemically, it is an amide union of parachlorophenoxyacetate and methylenedioxybenzylpiperazine (MDBZP), and has been shown to metabolize to the latter, which plays a significant role in its effects{{Citation needed|date=February 2017}}.