Chemistry:Fenproporex

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Short description: Stimulant drug used to treat obesity
Fenproporex
Fenproporex.svg
Clinical data
AHFS/Drugs.comInternational Drug Names
Routes of
administration
By mouth[1]
ATC code
  • none
Legal status
Legal status
Pharmacokinetic data
Metabolismpartly converted to amphetamine (30 to 60%)[1]
Excretionurine, mainly as amphetamine, about 5 to 9% unchanged[1]
Identifiers
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
Chemical and physical data
FormulaC12H16N2
Molar mass188.274 g·mol−1
3D model (JSmol)
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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.[2]

Fenproporex produces amphetamine as a metabolite[3][4] and was withdrawn in many countries following problems with abuse,[5] but it is still prescribed in some countries.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".[6][7][8]

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.[9] Fenproporex is designated a Schedule IV controlled substance in the US pursuant to the Controlled Substances Act.[10]

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.[11]

References

  1. 1.0 1.1 1.2 Drug dosage in renal insufficiency. Springer. 1991. pp. 245–246. ISBN 978-0-7923-0964-2. https://books.google.com/books?id=FubgMz6aOWAC. 
  2. 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.
  3. "Amphetamine concentrations in rat brain and human urine after fenproporex administration". European Journal of Pharmacology 20 (1): 125–6. October 1972. doi:10.1016/0014-2999(72)90227-0. PMID 4637940. 
  4. "Metabolic Precursors to Amphetamine and Methamphetamine". Forensic Science Review 5 (2): 109–27. December 1993. PMID 26270078. 
  5. "Abusive prescription of psychostimulants: a study of two cases". Journal of Forensic Sciences 51 (2): 407–10. March 2006. doi:10.1111/j.1556-4029.2006.00078.x. PMID 16566781. 
  6. "Imported fenproporex-based diet pills from Brazil: a report of two cases". Journal of General Internal Medicine 24 (3): 430–3. March 2009. doi:10.1007/s11606-008-0878-4. PMID 19096898. 
  7. "Imported compounded diet pill use among Brazilian women immigrants in the United States". Journal of Immigrant and Minority Health 11 (3): 229–36. June 2009. doi:10.1007/s10903-007-9099-x. PMID 18066718. 
  8. "The return of rainbow diet pills". American Journal of Public Health 102 (9): 1676–86. September 2012. doi:10.2105/AJPH.2012.300655. PMID 22813089. 
  9. "Consumer Directed Questions and Answers about FDA's Initiative Against Contaminated Weight Loss Products". FDA/Center for Drug Evaluation and Research. https://www.fda.gov/cder/consumerinfo/weight_loss_products.htm. 
  10. "21 CFR 1308.14(e)(4)". U.S. Government Printing Office. 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. 
  11. The 2009 Prohibited List International Standard . World Anti-Doping Agency (2009). Retrieved on 2009-08-18.