Fipexide: Difference between revisions

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{{drugbox
{{Drugbox
| IUPAC_name       = 1-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-<br>2-(4-chlorophenoxy)ethanone
| verifiedrevid = 443216648
| image             = Fipexide.png
| IUPAC_name = 1-[4-(1,3-benzodioxol-5-ylmethyl)piperazin-1-yl]-<br>2-(4-chlorophenoxy)ethanone
| CAS_number        = 34161-24-5
| image = Fipexide.svg
| ATC_prefix        = N06
 
| ATC_suffix        = BX05
<!--Clinical data-->
| PubChem          = 3351
| tradename =   
| DrugBank          =
| pregnancy_AU = <!-- A / B1 / B2 / B3 / C / D / X -->
| C = 20 | H = 21 | Cl = 1 | N = 2 | O = 4
| pregnancy_US = <!-- A / B            / C / D / X -->
| molecular_weight = 388.845 g/mol
| legal_AU = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| bioavailability  =
| legal_CA = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| protein_bound    =
| legal_UK = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| metabolism        =
| legal_US = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| elimination_half-life =
 
| excretion        =
<!--Identifiers-->
| pregnancy_AU     = <!-- A / B1 / B2 / B3 / C / D / X -->
| CAS_number_Ref = {{cascite|correct|??}}
| pregnancy_US     = <!-- A / B            / C / D / X -->
| CAS_number = 34161-24-5
| pregnancy_category= 
| ATC_prefix = N06
| legal_AU         = <!-- Unscheduled / S2 / S3 / S4 / S5 / S6 / S7 / S8 / S9 -->
| ATC_suffix = BX05
| legal_CA         = <!--            / Schedule I, II, III, IV, V, VI, VII, VIII -->
| PubChem = 3351
| legal_UK         = <!-- GSL        / P      / POM / CD / Class A, B, C -->
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
| legal_US         = <!-- OTC                  / Rx-only  / Schedule I, II, III, IV, V -->
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| legal_status      =  
| ChemSpiderID = 3234
| routes_of_administration =  
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = TG44VME01D
| KEGG_Ref = {{keggcite|correct|kegg}}
| KEGG = D07345
| ChEMBL_Ref = {{ebicite|correct|EBI}}
| ChEMBL = 254857
 
<!--Chemical data-->
| C=20 | H=21 | Cl=1 | N=2 | O=4
| molecular_weight = 388.845 g/mol
| smiles = Clc4ccc(OCC(=O)N1CCN(CC1)Cc2ccc3OCOc3c2)cc4
| InChI = 1/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
| InChIKey = BFUJHVVEMMWLHC-UHFFFAOYAN
| 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''' is a [[piperazine]] derivative drug invented in Italy in 1983.<ref> Missale C, Pasinetti G, Govoni S, Spano PF, Trabucchi M. Fipexide: a new drug for the regulation of dopaminergic system at the macromolecular level. Bollettino Chimico Farmaceutico. 1983 Feb;122(2):79-85. </ref>


It was used as a [[nootropic]] drug in France and Italy, mainly for the treatment of senile dementia,<ref> Bompani R, Scali G. Fipexide, an effective cognition activator in the elderly: a placebo-controlled, double-blind clinical trial. Current Medical Research and Opinion. 1986;10(2):99-106. </ref> but is no longer in common use due to the occurrence of rare adverse drug reactions including [[fever]]<ref> Guy C, Blay N, Rousset H, Fardeau V, Ollagnier M. Fever caused by fipexide. Evaluation of the national pharmacovigilance survey. Therapie. 1990 Sep-Oct;45(5):429-31. </ref> and [[hepatitis]]. Fipexide is similar in action to other nootropic drugs such as [[piracetam]] and is structurally similar to another more well-known nootropic, [[centrophenoxine]].
'''Fipexide''' ('''Attentil''', '''Vigilor''') is a [[psychoactive drug]] of the [[piperazine]] [[chemical class]] which was developed in [[Italy]] in 1983.<ref>Missale C, Pasinetti G, Govoni S, Spano PF, Trabucchi M. Fipexide: a new drug for the regulation of dopaminergic system at the macromolecular level. Bollettino Chimico Farmaceutico. 1983 Feb;122(2):79-85.</ref> It was used as a [[nootropic]] drug in Italy and [[France]], mainly for the treatment of senile dementia,<ref>Bompani R, Scali G. Fipexide, an effective cognition activator in the elderly: a placebo-controlled, double-blind clinical trial. Current Medical Research and Opinion. 1986;10(2):99-106.</ref> but is no longer in common use due to the occurrence of rare adverse drug reactions including [[fever]]<ref>Guy C, Blay N, Rousset H, Fardeau V, Ollagnier M. Fever caused by fipexide. Evaluation of the national pharmacovigilance survey. Therapie. 1990 Sep-Oct;45(5):429-31.</ref> and [[hepatitis]]. Fipexide is similar in action to other nootropic drugs such as [[piracetam]] and is structurally similar to another more well-known nootropic, [[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.
 
==See also==
* [[Befuraline]]
* [[Piberaline]]
 
==References==
{{Reflist|2}}
 


== References ==
{{Nootropics}}
{{reflist|2}}
{{Monoaminergics}}
{{Piperazines}}


{{Psychostimulants, agents used for ADHD and nootropics}}
[[Category:Nootropics]]
[[Category:Nootropics]]
{{WikiDoc Sources}}
[[Category:Benzodioxoles]]
[[Category:Piperazines]]
[[Category:Amides]]
[[Category:Phenol ethers]]
[[Category:Organochlorides]]
[[Category:Serotonin-norepinephrine-dopamine releasing agents]]
 
 
{{nervous-system-drug-stub}}

Revision as of 15:22, 13 April 2015

Fipexide
File:Fipexide.svg
Clinical data
ATC code
Identifiers
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
E number{{#property:P628}}
ECHA InfoCard{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
FormulaC20H21ClN2O4
Molar mass388.845 g/mol
3D model (JSmol)
  (verify)

Fipexide (Attentil, Vigilor) is a psychoactive drug of the piperazine chemical class which was developed in Italy in 1983.[1] It was used as a nootropic drug in Italy and France, mainly for the treatment of senile dementia,[2] but is no longer in common use due to the occurrence of rare adverse drug reactions including fever[3] and hepatitis. Fipexide is similar in action to other nootropic drugs such as piracetam and is structurally similar to another more well-known nootropic, 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.

See also

References

  1. ↑ Missale C, Pasinetti G, Govoni S, Spano PF, Trabucchi M. Fipexide: a new drug for the regulation of dopaminergic system at the macromolecular level. Bollettino Chimico Farmaceutico. 1983 Feb;122(2):79-85.
  2. ↑ Bompani R, Scali G. Fipexide, an effective cognition activator in the elderly: a placebo-controlled, double-blind clinical trial. Current Medical Research and Opinion. 1986;10(2):99-106.
  3. ↑ Guy C, Blay N, Rousset H, Fardeau V, Ollagnier M. Fever caused by fipexide. Evaluation of the national pharmacovigilance survey. Therapie. 1990 Sep-Oct;45(5):429-31.


Template:Nootropics Template:Monoaminergics Template:Piperazines


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