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20-September-2008 09:55:56 - Fenfluramine Fenfluramine Systematic IUPAC name N-ethyl-1-3-trifluoromethyl- phenylpropan-2-amine Identifiers CAS number 458-24-2 ATC code A08AA02 PubChem 3337 DrugBank APRD00319 Chemical data Formula C12H16F3N Mol. mass 231.257 Pharmacokinetic data Bioavailability ? Metabolism Hepatic Half life 20 hours Excretion Renal Therapeutic considerations Pregnancy cat. ? Legal status Schedule IVUS Withdrawn from market Routes Oral Fenfluramine is a drug that was part of the Fen/Phen anti-obesity medication the other drug being phentermine. Also known as Pondimin, fenfluramine was introduced on the U.S. market in 1973. It is the racemic mixture of two enantiomers, dextrofenfluramine and levofenfluramine. It increases the level of the neurotransmitter serotonin, a chemical that regulates mood, appetite and other functions. Fenfluramine causes the release of serotonin by disrupting vesicular storage of the neurotransmitter, and reversing serotonin transporter function.1 The end result is a feeling of fullness and loss of appetite. Contents 1 Withdrawal due to heart disease 2 References 3 Further reading 4 External links Withdrawal due to heart disease The drug was withdrawn from the U.S. market in 1997 after reports of heart valve disease,23 and pulmonary hypertension, including a condition known as cardiac fibrosis. After the US withdrawal of fenfluramine, it was also withdrawn from other markets around the world. The distinctive valvular abnormality seen with fenfluramine is a thickening of the leaflet and chordae tendineae. Roth suggested a mechanism by which fenfluramine damaged the valves.4 Heart valves also have serotonin receptors, which regulate their growth. He reported that fenfluramine and its active metabolite norfenfluramine stimulated the serotonin receptors 5-hydroxytryptamine 5-HT. In particular norfenfluramine is a potent agonist of 5-HT2B receptors. These receptors are plentiful in human cardiac valves and appear to be essential for normal cardiac development. Roth suggested that the mechanism by which fenfluramine causes damage is through inappropriately stimulating the valve cells to divide. This valve damage is found in other drugs that act on 5-HT2B receptors. References ^ Nestler, Eric J. Molecular Neuropharmacology: A Foundation for Clinical Neuroscience McGraw-Hill, 2001. ^ Connolly HM, Crary JL, McGoon MD, et al 1997. Valvular heart disease associated with fenfluramine-phentermine. N. Engl. J. Med. 337 9: 581-8. doi:10.1056/NEJM199708283370901. PMID 9271479. ^ Weissman NJ 2001. Appetite suppressants and valvular heart disease. Am. J. Med. Sci. 321 4: 285-91. doi:10.1097/00000441-200104000-00008. PMID 11307869. ^ Roth BL 2007. Drugs and valvular heart disease. N. Engl. J. Med. 356 1: 6-9. doi:10.1056/NEJMp068265. PMID 17202450. Further reading Welch JT, Lim DS. 2007: The synthesis and biological activity of pentafluorosulfanyl analogs of fluoxetine, fenfluramine, and norfenfluramine. Bioorg Med Chem. 1521:6659. PMID 17765553. External links RxList.com - Fenfluramine Inchem.org - Fenfluramine v d e Phenethylamines 2C-B 2C-C 2C-D 2C-E 2C-I 2C-N 2C-T-2 2C-T-21 2C-T-4 2C-T-7 2C-T-8 3C-E 4-FMP Bupropion Cathine Cathinone Clenbuterol DESOXY Dextroamphetamine Methamphetamine Diethylcathinone Dimethylcathinone DOC DOB DOI DOM bk-MBDB Dopamine Br-DFLY Ephedrine Epinephrine Escaline Etafedrine Fenfluramine Levosalbutamol Levmetamfetamine MBDB MDA MDMA MDMC MDEA MDPV Mescaline Methcathinone Norepinephrine Phentermine Salbutamol Tyramine Venlafaxine v d e Antiobesity preparations A08 -- see also anorectic Centrally acting Phentermine - Fenfluramine - Amfepramone - Dexfenfluramine - Mazindol - Cathine - Clobenzorex - Sibutramine - cannabinoids Rimonabant, Taranabant Peripherally acting Orlistat Tablets This pharmacology-related article is a stub. Retrieved from http://en..org/wiki/Fenfluramine Categories: Anorectics | Obesity | Amphetamines | Withdrawn drugs | Organofluorides | Serotonin receptor agonists | Pharmacology stubs Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Français Polski 中文 This page was last modified on 15 August 2008, at 17:03
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