fenproporex

{{Short description|Stimulant drug used to treat obesity}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 449559848

| IUPAC_name = 3-(1-phenylpropan-2-ylamino)propanenitrile

| image = Fenproporex.svg

| image_class = skin-invert-image

| width = 200

| tradename =

| Drugs.com = {{drugs.com|international|fenproporex}}

| legal_BR = B2

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA = Schedule IV

| legal_US = Schedule IV

| legal_DE = Rx-only/Anlage III

| routes_of_administration = By mouth

| metabolism = partly converted to amphetamine (30 to 60%){{cite book | vauthors = Seyffart G | title = Drug dosage in renal insufficiency | year = 1991 | publisher = Springer | isbn = 978-0-7923-0964-2 | pages = 245–246 | url = https://books.google.com/books?id=FubgMz6aOWAC}}

| excretion = urine, mainly as amphetamine, about 5 to 9% unchanged

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

| CAS_number = 16397-28-7

| ATC_prefix = none

| PubChem = 61810

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 2105566

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

| DrugBank = DB01550

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

| ChemSpiderID = 55690

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

| UNII = W0194S5FOA

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

| KEGG = D07947

| C=12 | H=16 | N=2

| smiles = N#CCCNC(Cc1ccccc1)C

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

| StdInChI = 1S/C12H16N2/c1-11(14-9-5-8-13)10-12-6-3-2-4-7-12/h2-4,6-7,11,14H,5,9-10H2,1H3

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

| StdInChIKey = IQUFSXIQAFPIMR-UHFFFAOYSA-N

}}

Fenproporex (Perphoxene) (N-2-Cyanoethylamphetamine) (3-(1-phenylpropan-2-ylamino)propanenitrile) (3-[(1-Methyl-2-Phenylethyl)amino]propiononitrile) is a stimulant drug of the phenethylamine and amphetamine chemical classes that was developed in the 1960s. It is used as an appetite suppressant for the treatment of obesity.Warembourg H, Jaillard J. Clinical experimentation with fenproporex in the treatment of obesity. Apropos of 40 cases. (French). Journal de la Faculte de médecine et de pharmacie de l'Universite de Lille. 1968 Mar;13(3):Suppl:273-6.

Fenproporex produces amphetamine as a metabolite{{cite journal | vauthors = Tognoni G, Morselli PL, Garattini S | title = Amphetamine concentrations in rat brain and human urine after fenproporex administration | journal = European Journal of Pharmacology | volume = 20 | issue = 1 | pages = 125–6 | date = October 1972 | pmid = 4637940 | doi = 10.1016/0014-2999(72)90227-0 }}{{cite journal | vauthors = Cody JD | title = Metabolic Precursors to Amphetamine and Methamphetamine | journal = Forensic Science Review | volume = 5 | issue = 2 | pages = 109–27 | date = December 1993 | pmid = 26270078 }} and was withdrawn in many countries following problems with abuse,{{cite journal | vauthors = Pélissier-Alicot AL, Piercecchi-Marti MD, Bartoli C, Kuhlmann E, Coiffait PE, Sanvoisin A, Giocanti D, Léonetti G | display-authors = 6 | title = Abusive prescription of psychostimulants: a study of two cases | journal = Journal of Forensic Sciences | volume = 51 | issue = 2 | pages = 407–10 | date = March 2006 | pmid = 16566781 | doi = 10.1111/j.1556-4029.2006.00078.x | s2cid = 39460850 }} but it is still prescribed in some countries. It is sometimes combined with benzodiazepines, antidepressants, and other compounds to create a version of the "rainbow diet pill".{{cite journal | vauthors = Cohen PA | title = Imported fenproporex-based diet pills from Brazil: a report of two cases | journal = Journal of General Internal Medicine | volume = 24 | issue = 3 | pages = 430–3 | date = March 2009 | pmid = 19096898 | pmc = 2642570 | doi = 10.1007/s11606-008-0878-4 }}{{cite journal | vauthors = Cohen PA, McCormick D, Casey C, Dawson GF, Hacker KA | title = Imported compounded diet pill use among Brazilian women immigrants in the United States | journal = Journal of Immigrant and Minority Health | volume = 11 | issue = 3 | pages = 229–36 | date = June 2009 | pmid = 18066718 | doi = 10.1007/s10903-007-9099-x | s2cid = 8730835 }}{{cite journal | vauthors = Cohen PA, Goday A, Swann JP | title = The return of rainbow diet pills | journal = American Journal of Public Health | volume = 102 | issue = 9 | pages = 1676–86 | date = September 2012 | pmid = 22813089 | pmc = 3482033 | doi = 10.2105/AJPH.2012.300655 }}

Fenproporex has never been approved by the US Food and Drug Administration (FDA) for sale in the US due to lack of efficacy and safety data. However, in March 2009, the FDA warned consumers that it has been detected as an unlabeled component of diet pills available over the Internet.{{cite web | title = Consumer Directed Questions and Answers about FDA's Initiative Against Contaminated Weight Loss Products | work = FDA/Center for Drug Evaluation and Research | url = https://www.fda.gov/cder/consumerinfo/weight_loss_products.htm | archive-url = https://web.archive.org/web/20090317054247/https://www.fda.gov/cder/consumerinfo/weight_loss_products.htm | archive-date = 17 March 2009 }} Fenproporex is designated a Schedule IV controlled substance in the US pursuant to the Controlled Substances Act.{{cite web

|url = http://ecfr.gpoaccess.gov/cgi/t/text/text-idx?c=ecfr&rgn=div8&view=text&node=21:9.0.1.1.9.0.26.7&idno=21

|title = 21 CFR 1308.14(e)(4)

|access-date = 2011-04-20

|publisher = U.S. Government Printing Office

|url-status = dead

|archive-url = https://web.archive.org/web/20111016184126/http://ecfr.gpoaccess.gov/cgi/t/text/text-idx?c=ecfr&sid=49034c378cc5617a1af5088a76f6df73&rgn=div8&view=text&node=21%3A9.0.1.1.9.0.26.7&idno=21

|archive-date = 2011-10-16

}}

Fenproporex is on the list of substances banned by the World Anti-Doping Agency, and any sportsperson testing positive for the substance faces a ban from competition.[http://www.wada-ama.org/rtecontent/document/2009_Prohibited_List_ENG_Final_20_Sept_08.pdf The 2009 Prohibited List International Standard] {{webarchive |url=https://web.archive.org/web/20090203030039/http://www.wada-ama.org/rtecontent/document/2009_Prohibited_List_ENG_Final_20_Sept_08.pdf |date=February 3, 2009 }}. World Anti-Doping Agency (2009). Retrieved on 2009-08-18.