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    Fenproporex

    ACTIVE PHARMA INGREDIENTS

    MARKET PLACE

    PharmaCompass
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    2D Structure
    Also known as: Desobesi, 16397-28-7, Femproporex, Fenorex, 3-(1-phenylpropan-2-ylamino)propanenitrile, 3-[(1-methyl-2-phenylethyl)amino]propiononitrile
    Molecular Formula
    C12H16N2
    Molecular Weight
    188.27  g/mol
    InChI Key
    IQUFSXIQAFPIMR-UHFFFAOYSA-N
    FDA UNII
    W0194S5FOA
    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]
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    3-(1-phenylpropan-2-ylamino)propanenitrile
    2.1.2 InChI
    InChI=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
    2.1.3 InChI Key
    IQUFSXIQAFPIMR-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CC(CC1=CC=CC=C1)NCCC#N
    2.2 Other Identifiers
    2.2.1 UNII
    W0194S5FOA
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. Fenproporex Monohydrochloride

    2. Fenproporex Monohydrochloride, (+-)-isomer

    3. Fenproporex, (+-)-isomer

    4. Ifa Diety

    2.3.2 Depositor-Supplied Synonyms

    1. Desobesi

    2. 16397-28-7

    3. Femproporex

    4. Fenorex

    5. 3-(1-phenylpropan-2-ylamino)propanenitrile

    6. 3-[(1-methyl-2-phenylethyl)amino]propiononitrile

    7. W0194s5foa

    8. Fenproporex (inn)

    9. J268.797f

    10. Fenproporex [inn]

    11. Fenproporex [inn:dcf]

    12. Femproporex [inn-spanish]

    13. Fenproporexum [inn-latin]

    14. 3-((1-methyl-2-phenylethyl)amino)propiononitrile

    15. Einecs 239-772-0

    16. Unii-w0194s5foa

    17. Dea No. 1575

    18. Einecs 240-444-4

    19. Fenorex (tn)

    20. Fenproporex [mi]

    21. N-2-cyanoethylamphetamine

    22. N-(2-cyanoethyl)amphetamine

    23. Fenproporex [who-dd]

    24. 15686-61-0

    25. Schembl157687

    26. Chembl2105566

    27. Dtxsid0043921

    28. Chebi:134837

    29. (.+/-.)-n-2-cyanoethylamphetamine

    30. Db01550

    31. D07947

    32. 3-[(1-methyl-2-phenylethyl)amino]propanenitrile #

    33. Q5443577

    34. (.+/-.)-3-[(.alpha.-methylphenethyl)amino]propionitrile

    35. (+/-)-3-((.alpha.-methylphenethyl)amino)propionitrile

    36. Propanenitrile, 3-[(1-methyl-2-phenylethyl)amino]-, (.+/-.)-

    37. Propionitrile, 3-((.alpha.-methylphenethyl)amino)-, (.+/-.)-

    2.4 Create Date
    2005-03-27
    3 Chemical and Physical Properties
    Molecular Weight 188.27 g/mol
    Molecular Formula C12H16N2
    XLogP31.9
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count2
    Rotatable Bond Count5
    Exact Mass188.131348519 g/mol
    Monoisotopic Mass188.131348519 g/mol
    Topological Polar Surface Area35.8 Ų
    Heavy Atom Count14
    Formal Charge0
    Complexity186
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count1
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug 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]

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Fenproporex was first claimed to not exert a stimulant effect on the body, however research into its metabolism has shown that it is converted into a considerable amount of amphetamine in the body, which leads to stimulant effects. [9]

    5.2 Absorption, Distribution and Excretion

    Route of Elimination

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

    Clearance

    The amphetamine metabolite can be detected for several days after the administration of forproporex (up to 119h, in one study). [2]

    5.3 Metabolism/Metabolites

    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]

    5.4 Mechanism of Action

    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]