Fenproporex

Các tên gọi khác (2) :

Fenorex
Perphoxene

appetite depressants, stimulants

Thuốc Gốc

Small Molecule

CAS: 16397-28-7

CTHH: C₁₂H₁₆N₂

PTK: 188.2688

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]

Nhận Dạng Quốc Tế & Đặc Tính Hóa Học

Công thức hóa học

C₁₂H₁₆N₂

Phân tử khối

188.2688

Monoisotopic mass

188.131348522

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

InChI Key

InChIKey=IQUFSXIQAFPIMR-UHFFFAOYSA-N

IUPAC Name

3-[(1-phenylpropan-2-yl)amino]propanenitrile

Traditional IUPAC Name

fenproporex

SMILES

CC(CC1=CC=CC=C1)NCCC#N

Độ tan chảy

146

Độ hòa tan

1.84e-01 g/l

logP

2.01

logS

-3

pKa (Strongest Basic)

7.88

PSA

35.82 Å²

Refractivity

58.24 m³·mol^-1

Polarizability

22.04 Å³

Rotatable Bond Count

H Bond Acceptor Count

H Bond Donor Count

Physiological Charge

Number of Rings

Bioavailability

Rule of Five

true

Ghose Filter

true

Dược Lực Học : 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]

Cơ Chế Tác Dụng : 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] 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]

Dược Động Học :

▧ Metabolism :
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]
▧ 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]

Chỉ Định : 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]

Dữ Kiện Thương Mại

Nhà Sản Xuất

Công ty : Aché

Sản phẩm biệt dược : Desobesi-M
Công ty : Medix

Sản phẩm biệt dược : Feprorex
Công ty : Sanofi-Aventis

Sản phẩm biệt dược : Lipenan
Công ty : Saval

Sản phẩm biệt dược : Salcal

Tài Liệu Tham Khảo Thêm

drugbank

http://www.drugbank.ca/drugs/DB01550

PubChem Compound

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=61810

PubChem Substance

http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46508336

KEGG Drug

http://www.genome.jp/dbget-bin/www_bget?drug:D07947

ChemSpider

http://www.chemspider.com/Chemical-Structure.55690.html

Wikipedia

http://en.wikipedia.org/wiki/Fenproporex

Drugs.com

http://www.drugs.com/international/fenproporex.html

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