Levofenfluramine

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Levofenfluramine
Clinical data
ATC code
  • None
Identifiers
  • (2R)-N-ethyl-1-[3-(trifluoromethyl)phenyl]-2-propanamine
JSmol)
  • FC(F)(F)c1cccc(c1)C[C@H](NCC)C
  • InChI=1S/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3/t9-/m1/s1
  • Key:DBGIVFWFUFKIQN-SECBINFHSA-N

Levofenfluramine (

dextrorotatory enantiomer is dexfenfluramine.[2] Both fenfluramine and dexfenfluramine are anorectic agents that have been used clinically in the treatment of obesity (and hence, levofenfluramine has been as well since it is a component of fenfluramine).[2] However, they have since been discontinued due to reports of causing cardiovascular conditions such as valvular heart disease and pulmonary hypertension,[3] adverse effects that are likely to be caused by excessive stimulation of 5-HT2B receptors expressed on heart valves.[4][5]

Dexfenfluramine is believed to be solely responsible for the

increased appetite and weight gain—effects that their actions on dopamine receptors have been implicated in playing a role in the development of,[13]
is an action that could in theory cancel out the hypothetical serotonergically-mediated appetite suppressant effects of the compound. However, this is speculation and has not been proven.

Levonorfenfluramine, an active metabolite of levofenfluramine, is also a fairly potent serotonin releasing agent (with a potency of approximately 1/2 that of norfenfluramine and 1/6 that of dexfenfluramine) and, similarly to dexnorfenfluramine, is a 5-HT2B and 5-HT2C receptor agonist, as well as a somewhat less potent norepinephrine reuptake inhibitor (about 1/2 that of its efficacy as a serotonin releaser).[5][7][10] As such, it likely contributes significantly to the biological activity—though not necessarily appetite suppressant effects—of not only levofenfluramine but of racemic fenfluramine as well. In contrast to levonorfenfluramine, levofenfluramine is virtually inactive as a reuptake inhibitor or releaser of norepinephrine,[10] and neither compound has any effect on dopamine reuptake or release.[10]

See also

References

  1. ISBN 978-0-412-54090-5
    . Retrieved 12 May 2012.
  2. ^
    ISBN 978-0-19-511853-7
    . Retrieved 12 May 2012.
  3. PMID 12357124
    .
  4. S2CID 20796556
    .
  5. ^
    PMID 11104741
    .
  6. PMID 20647205
    .
  7. ^
    S2CID 24296122
    .
  8. PMID 16249524
    .
  9. S2CID 8056638
    .
  10. ^
    PMID 17017961
    .
  11. ISBN 978-0-913875-27-8
    . Retrieved 12 May 2012.
  12. S2CID 34370594
    .
  13. PMID 19931306
    .
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