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Namespace Prefixes

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Statements

Subject Item
n2:DB01550
rdf:type
n3:Drug
n3:description
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. However, due to an addictive potential, it is listed as an illicit substance in many countries. 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. It is also listed as a prohibited substance by the World Anti-Doping Agency. [Wikipedia] 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]
n3:generalReferences
1. Bray, George A. "A concise review on the therapeutics of obesity." Nutrition 16.10 (2000): 953-960.9 2. Cody, John T., and Sandra Valtier. "Detection of amphetamine following administration of fenproporex." Journal of analytical toxicology 20.6 (1996): 425-431. 3. Cohen, Pieter A., et al. "Imported compounded diet pill use among Brazilian women immigrants in the United States." Journal of Immigrant and Minority Health 11.3 (2009): 229-236. 4. Cohen, Pieter A. "Imported fenproporex-based diet pills from Brazil: a report of two cases." Journal of general internal medicine 24.3 (2009): 430-433. 5. Coutts, R. T., et al. "Metabolism and disposition of N-(2-cyanoethyl) amphetamine (fenproporex) and amphetamine: study in the rat brain." Canadian Journal of Physiology and Pharmacology 64.6 (1986): 724-728. 6. Kraemer, Thomas, et al. "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." Journal of Chromatography B: Biomedical Sciences and Applications 738.1 (2000): 107-118. 7. Mancini, Marcio C., and Alfredo Halpern. "Pharmacological treatment of obesity." Arquivos Brasileiros de Endocrinologia & Metabologia 50.2 (2006): 377-389. 8. Rezin, Gislaine T., et al. "Brain energy metabolism is activated after acute and chronic administration of fenproporex in young rats." International Journal of Developmental Neuroscience 29.8 (2011): 937-942. 9. Tognoni, G., P. L. Morselli, and S. Garattini. "Amphetamine concentrations in rat brain and human urine after fenproporex administration." European Journal of Pharmacology 20.1 (1972): 125-126.
n3:group
illicit withdrawn approved
n3:indication
Fenproporex is used as an appetite suppressant, and anti-obesity agent [2]; however, due to substance abuse potential, it is an illicit substance in many countries. In some countries, such as Brazil, it is still prescribed -- often in the form of diet pills (ie. Brazilian Diet Pills) which combine amphetamines, benzodiazepines, antidepressants, diuretics and laxatives. In the United States the sale of such diet pills has been banned due to concerns over side effects, and the risk of potentially fatal overdose. However, internet sales and illicit markets has lead to international availability. It has been found by primary care physicians that Brazilian immigrant women utilized imported diet pills at particularly high rates, and sometimes suffered from side effects requiring hospitalization or experienced a loss of employment. [3]
owl:sameAs
n12:DB01550 n13:DB01550
dcterms:title
Fenproporex
adms:identifier
n7:D07947 n8:Fenproporex n15:DB01550 n16:61810 n17:55690 n18:46508336
n3:mechanismOfAction
Fenproporex is an amphetamine based anorectic which is rapidly metabolized into amphetamine in the body. Both acute and chronic fenproporex administration has been shown to increase brain energy metabolism in young rats, by increasing the activity of citrate synthase, malate dehydrogenase, succinate dehydrogenase, creatine kinase and complexes I,II, III, and IV. [8] Amphetamine based drugs are also known to reduce food intake. They are addictive substances due to their ability to increase dopamine release, however their anorectic effects are believed to be a result of noradrenergic neurotransmission. Activation of the alpha 1 and beta 2 adrenoceptors has been shown to decrease food intake, and drugs which release norepinephrine or block norepinephrine reuptake can activate these receptors. [3] The alpha 1 and beta 2 adrenoceptors are noted to be clinically important receptors in weight regulation. [3]
n3:routeOfElimination
Renally eliminated in the urine, mainly as amphetamine, but 5-9% as unchanged drug.
n3:synonym
Perphoxene Fenorex
n3:mixture
n5:271B547B-363D-11E5-9242-09173F13E4C5
n3:synthesisReference
Rohrbach, P. and Blum, J.; U.S. Patent 3,485,924; December 23, 1969; assigned to Manufactures J.R. Bottu (France).
foaf:page
n10:fenproporex.html
n3:IUPAC-Name
n4:271B5480-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5486-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5485-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B5482-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B5483-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5484-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B547E-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B547F-363D-11E5-9242-09173F13E4C5 n4:271B547C-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B547D-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Acceptor-Count
n4:271B548C-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B548D-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5487-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5488-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B548A-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5489-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B548B-363D-11E5-9242-09173F13E4C5
n3:casRegistryNumber
16397-28-7
n3:category
n3:clearance
The amphetamine metabolite can be detected for several days after the administration of forproporex (up to 119h, in one study). [2]
n3:Bioavailability
n4:271B5491-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5493-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5494-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B5495-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5490-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B548F-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5492-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B5481-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B548E-363D-11E5-9242-09173F13E4C5