Repositioning Candidate Details
| Candidate ID: | R0527 |
| Source ID: | DB01550 |
| Source Type: | experimental; illicit; withdrawn |
| Compound Type: | small molecule |
| Compound Name: | Fenproporex |
| Synonyms: | Fenproporex |
| Molecular Formula: | C12H16N2 |
| SMILES: | CC(CC1=CC=CC=C1)NCCC#N |
| Structure: |
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| DrugBank 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. 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. However, in clinical practice, central nervous system stimulative effects are less notorious than with some other agents such as diethylpropion and mazindol. 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, 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. |
| CAS Number: | 16397-28-7 |
| Molecular Weight: | 188.2688 |
| DrugBank Indication: | Fenproporex is used as an appetite suppressant, and anti-obesity agent ; 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. |
| DrugBank 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. |
| DrugBank MoA: | 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. 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. The alpha 1 and beta 2 adrenoceptors are noted to be clinically important receptors in weight regulation. |
| Targets: | -- |
| Inclusion Criteria: | Indication associated |
| Strategy ID | Strategy | Synonyms | Related Targets | Related Drugs | |
|---|---|---|---|---|---|
| S07 | Anti-lipogenesis | de novo lipogenesis; de novo lipogenesis; DNL; anti-lipogenic mechanisms; adipogenesis; anti-obesity | stearoyl-CoA desaturase 1 (SCD-1); Acetyl-coenzyme carboxylase; acyl-CoA carboxylase inhibitor (ACC inhibitor); stearoyl Coenzyme A desaturase inhibitor (SCD inhibitor); THR-beta selective agonist; DGAT2 inhibitor; FASN inhibitor | Aramchol; Firsocostat (GS-0976); VK-2809; ION 224 | Details |
| Diseases ID | DO ID | Disease Name | Definition | Class | |
|---|---|---|---|---|---|
| I14 | 9970 | Obesity | An overnutrition that is characterized by excess body fat, traditionally defined as an elevated ratio of weight to height (specifically 30 kilograms per meter squared), has_material_basis_in a multifactorial etiology related to excess nutrition intake, decreased caloric utilization, and genetic susceptibility, and possibly medications and certain disorders of metabolism, endocrine function, and mental illness. https://en.wikipedia.org/wiki/Obesity | disease of metabolism/acquired metabolic disease/ nutrition disease/overnutrition | Details |