Fenproporex

DB01550

small molecule experimental illicit withdrawn

Deskripsi

Fenproporex is an orally active stimulant drug, which was developed in the 1960s. It is used as an appetite suppressant and a treatment for obesity. It is listed as an illicit substance in many countries due to addiction issues and listed as a prohibited substance by the World Anti-Doping Agency. Structurally, fenproporex (N-2-cyanoethylamphetamine) falls within the phenylethamine and amphetamine chemical class of drugs. The N-2-cyanoethyl substituent was once believed to be resistant to cleavage, because fenproporex -- once recommended as an obesity treatment for patients with cardiovascular disease -- was originally claimed to lack stimulant properties. Contrary to the claim, research has demonstrated easy in vivo cleavage of the N-2-cyanothyl substituent to yield amphetamine as a metabolite. 5 However, in clinical practice, central nervous system stimulative effects are less notorious than with some other agents such as diethylpropion and mazindol. 7

In the United States fenproporex was never approved by the FDA for clinical use due to a lack of efficacy and safety data, and is listed as a drug in Schedule IV of the Controlled Substances Act. In 2006 and 2009, the FDA issued warnings that it had been detected in diet pills sold online, and imported from foreign manufacturers.

Despite being banned in the United States, fenproporex has been described as the second most commonly consumed appetite suppressant worldwide, 6 with fenproporex containing anorectics still being commonly prescribed in South America. Little is known about the specific hazards of amphetamine based diet pills, however case reports have noted side effects such as chest pain, palpitations, headaches, and insomnia. In addition, placebo controlled studies have shown that participants using fenproporex experience more joint pain, sweating, blurred vision and tremor. 2

Struktur Molekul 2D

Berat 188.2688
Wujud solid

Peta Jejaring Molekuler
Legenda: ObatTargetGenEnzim(Panah → menunjukkan arah efek / relasi)TransporterCarrier

Profil Farmakokinetik

Waktu Paruh (Half-Life) -
Volume Distribusi -
Klirens (Clearance) The amphetamine metabolite can be detected for several days after the administration of forproporex (up to 119h, in one study). [2]

Absorpsi

Data absorpsi tidak tersedia.

Metabolisme

A large portion, 60-80%, of fenproporex is rapidly converted into amphetamine. Besides amphetamine, and unchanged fenproporex, 14 other metabolites were identified from urine samples. Two interacting metabolic pathways are believed to exist. The major pathway is believed to involve ring-degradation by aromatic hydroxylation, methylation, and side chain degradation by N-dealkyation to form amphetamine. The minor pathway involves the beta-hydroxylation of amphetamine to form norephedrine. 6

Rute Eliminasi

Renally eliminated in the urine, mainly as amphetamine, but 5-9% as unchanged drug.

Interaksi Obat

727 Data
Cyclosporine Cyclosporine may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Icosapent Icosapent may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefotiam Cefotiam may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Mesalazine Mesalazine may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefmenoxime Cefmenoxime may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefmetazole Cefmetazole may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Pamidronic acid Pamidronic acid may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Tenofovir disoproxil Tenofovir disoproxil may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Indomethacin Indomethacin may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cidofovir Cidofovir may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefpiramide Cefpiramide may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Ceftazidime Ceftazidime may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Loracarbef Loracarbef may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefalotin Cefalotin may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Nabumetone Nabumetone may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Ketorolac Ketorolac may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Tenoxicam Tenoxicam may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Celecoxib Celecoxib may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefotaxime Cefotaxime may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Tolmetin Tolmetin may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Foscarnet Foscarnet may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Rofecoxib Rofecoxib may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Piroxicam Piroxicam may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Methotrexate Methotrexate may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cephalexin Cephalexin may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Fenoprofen Fenoprofen may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Valaciclovir Valaciclovir may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Valdecoxib Valdecoxib may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Diclofenac Diclofenac may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Sulindac Sulindac may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Bacitracin Bacitracin may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Amphotericin B Amphotericin B may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cephaloglycin Cephaloglycin may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Flurbiprofen Flurbiprofen may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Adefovir dipivoxil Adefovir dipivoxil may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Pentamidine Pentamidine may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Etodolac Etodolac may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Mefenamic acid Mefenamic acid may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Acyclovir Acyclovir may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Naproxen Naproxen may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Sulfasalazine Sulfasalazine may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Phenylbutazone Phenylbutazone may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Meloxicam Meloxicam may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Carprofen Carprofen may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefaclor Cefaclor may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Diflunisal Diflunisal may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Tacrolimus Tacrolimus may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Ceforanide Ceforanide may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Salicylic acid Salicylic acid may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Meclofenamic acid Meclofenamic acid may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Acetylsalicylic acid Acetylsalicylic acid may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Carboplatin Carboplatin may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Oxaprozin Oxaprozin may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Ketoprofen Ketoprofen may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Balsalazide Balsalazide may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Ibuprofen Ibuprofen may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefditoren Cefditoren may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Atazanavir Atazanavir may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Colistimethate Colistimethate may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefuroxime Cefuroxime may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefapirin Cefapirin may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefadroxil Cefadroxil may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefprozil Cefprozil may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Ceftriaxone Ceftriaxone may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Olsalazine Olsalazine may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Lumiracoxib Lumiracoxib may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefamandole Cefamandole may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefazolin Cefazolin may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefonicid Cefonicid may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefoperazone Cefoperazone may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefotetan Cefotetan may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefoxitin Cefoxitin may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Ceftizoxime Ceftizoxime may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefradine Cefradine may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Magnesium salicylate Magnesium salicylate may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Salsalate Salsalate may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Choline magnesium trisalicylate Choline magnesium trisalicylate may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefepime Cefepime may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefacetrile Cefacetrile may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Ceftibuten Ceftibuten may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cefpodoxime Cefpodoxime may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Antrafenine Antrafenine may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Aminophenazone Aminophenazone may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Antipyrine Antipyrine may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Tiaprofenic acid Tiaprofenic acid may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Lopinavir Lopinavir may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Etoricoxib Etoricoxib may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Hydrolyzed Cephalothin Hydrolyzed Cephalothin may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cephalothin Group Cephalothin Group may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Oxyphenbutazone Oxyphenbutazone may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Latamoxef Latamoxef may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Nimesulide Nimesulide may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Benoxaprofen Benoxaprofen may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Metamizole Metamizole may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Zomepirac Zomepirac may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Ceftobiprole Ceftobiprole may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Cimicoxib Cimicoxib may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Ceftaroline fosamil Ceftaroline fosamil may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Lornoxicam Lornoxicam may decrease the excretion rate of Fenproporex which could result in a higher serum level.
Aceclofenac Aceclofenac may decrease the excretion rate of Fenproporex which could result in a higher serum level.

Referensi & Sumber

Synthesis reference: Rohrbach, P. and Blum, J.; U.S. Patent 3,485,924; December 23, 1969; assigned to Manufactures J.R. Bottu (France).
Artikel (PubMed)
  • PMID: 11054601
    Bray GA: A concise review on the therapeutics of obesity. Nutrition. 2000 Oct;16(10):953-60.
  • PMID: 8889679
    Cody JT, Valtier S: Detection of amphetamine following administration of fenproporex. J Anal Toxicol. 1996 Oct;20(6):425-31.
  • PMID: 18066718
    Cohen PA, McCormick D, Casey C, Dawson GF, Hacker KA: Imported compounded diet pill use among Brazilian women immigrants in the United States. J Immigr Minor Health. 2009 Jun;11(3):229-36. Epub 2007 Dec 9.
  • PMID: 19096898
    Cohen PA: Imported fenproporex-based diet pills from Brazil: a report of two cases. J Gen Intern Med. 2009 Mar;24(3):430-3. doi: 10.1007/s11606-008-0878-4.
  • PMID: 3756624
    Coutts RT, Nazarali AJ, Baker GB, Pasutto FM: Metabolism and disposition of N-(2-cyanoethyl)amphetamine (fenproporex) and amphetamine: study in the rat brain. Can J Physiol Pharmacol. 1986 Jun;64(6):724-8.
  • PMID: 10778932
    Kraemer T, Theis GA, Weber AA, Maurer HH: Studies on the metabolism and toxicological detection of the amphetamine-like anorectic fenproporex in human urine by gas chromatography-mass spectrometry and fluorescence polarization immunoassay. J Chromatogr B Biomed Sci Appl. 2000 Jan 28;738(1):107-18.
  • PMID: 21723935
    Rezin GT, Jeremias IC, Ferreira GK, Cardoso MR, Morais MO, Gomes LM, Martinello OB, Valvassori SS, Quevedo J, Streck EL: Brain energy metabolism is activated after acute and chronic administration of fenproporex in young rats. Int J Dev Neurosci. 2011 Dec;29(8):937-42. doi: 10.1016/j.ijdevneu.2011.06.007. Epub 2011 Jun 23.
  • PMID: 4637940
    Tognoni G, Morselli PL, Garattini S: Amphetamine concentrations in rat brain and human urine after fenproporex administration. Eur J Pharmacol. 1972 Oct;20(1):125-6.
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Contoh Produk & Brand

Produk: 0 • International brands: 4
International Brands
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  • Lipenan — Sanofi-Aventis
  • Salcal — Saval

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