Paroxypropione

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Paroxypropione
Clinical data
Trade namesFrenantol, Frenormon, Hypophenon, Paroxon, Possipione, Profenone, others
Other namesParaoxypropiophenone; H-365; NSC-2834; 4'-Hydroxypropiophenone; Ethyl p-hydroxyphenyl ketone; p-Propionylphenol; Paroxypropiophenone; Parahydroxypropiophenone; PHP
Drug classNonsteroidal estrogen; Antigonadotropin
ATC code
  • None
Legal status
Legal status
  • In general: ℞ (Prescription only)
Identifiers
  • 1-(4-hydroxyphenyl)-1-propanone
JSmol)
  • CCC(=O)c1ccc(cc1)O
  • InChI=1S/C9H10O2/c1-2-9(11)7-3-5-8(10)6-4-7/h3-6,10H,2H2,1H3
  • Key:RARSHUDCJQSEFJ-UHFFFAOYSA-N

Paroxypropione, also known as paraoxypropiophenone, is a

synthetic nonsteroidal estrogen which has been used medically as an antigonadotropin in Spain and Italy but appears to no longer be marketed.[1][2][3][4] It was first synthesized in 1902.[1] The antigonadotropic properties of the drug were discovered in 1951[3] and it entered clinical use shortly thereafter.[5]

Pharmacology

Pharmacodynamics

Paroxypropione is closely related structurally to

affinity for the estrogen receptor[4] and must be given at high dosages to achieve significant estrogenic and antigonadotropic effects, for instance, 0.8 to 1.6 g/day.[10][11] It possesses 0.1% of the estrogenic activity and less than 0.5% of the antigonadotropic potency of estrone.[12]

Chemistry

Synthesis

The highest reported yield, approximately 96%, is from the between

esterification to give phenyl propionate, which then undergoes a Fries rearrangement
.

Derivatives

Paroxypropione is a precursor in the chemical synthesis of diethylstilbestrol and dienestrol.[14][15]

Society and culture

Names

Brand names Frenantol, Frenormon, Hypophenon, Paroxon, Possipione, Profenone, numerous others; former developmental code name NSC-2834), also known as paroxypropiophenone (P.O.P.) or 4'-hydroxypropiophenone.

Research

Paroxypropione was studied and used in the treatment of breast cancer.[16][17][18]

References

  1. ^
    ISBN 978-1-4757-2085-3
    .
  2. ISBN 978-3-88763-075-1
    .
  3. ^
    PMID 14861299
    .
  4. ^
    S2CID 19751228
    .
  5. ISSN 0022-3263
    .
  6. ISBN 978-3-642-67265-1
    .
  7. PMID 426279
    .
  8. ISBN 978-0-12-382185-0
    .
  9. S2CID 12342018
    .
  10. ^ De Vega R (1955). "Protein breakdown before and after operations. Influence of growth hormone and of inhibitors of the pituitary adrenal system". Cirug., Ginecol. Urol. 9: 289–326.
  11. PMID 5006470.[permanent dead link
    ]
  12. PMID 12980070
    .
  13. hdl:2115/44794
    .
  14. ISBN 978-0-8155-1856-3
    .
  15. ISBN 978-0-471-85545-3
    .
  16. PMID 13241536
    .
  17. S2CID 22364847
    .
  18. PMID 5188348
    .

Further reading
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