Paroxypropione

Paroxypropione
Clinical data
Trade names	Frenantol, Frenormon, Hypophenon, Paroxon, Possipione, Profenone, others
Other names	Paraoxypropiophenone; H-365; NSC-2834; 4'-Hydroxypropiophenone; Ethyl p-hydroxyphenyl ketone; p-Propionylphenol; Paroxypropiophenone; Parahydroxypropiophenone; PHP
Drug class	Nonsteroidal estrogen; Antigonadotropin
ATC code	None;
Legal status
Legal status	In general: ℞ (Prescription only);
Identifiers
	IUPAC name 1-(4-hydroxyphenyl)-1-propanone;
CAS Number	70-70-2;
PubChem CID	6271;
ChemSpider	6035;
UNII	X9952001TG;
CompTox Dashboard (EPA)	DTXSID8023426 ;
ECHA InfoCard	100.000.676
Chemical and physical data
Formula	C9H10O2
Molar mass	150.177 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCC(=O)c1ccc(cc1)O;
	InChI 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]

^ ^a ^b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 662–. ISBN 978-1-4757-2085-3.
^ Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 796–. ISBN 978-3-88763-075-1.
^ ^a ^b Paulsen CA, Mortimore GE, Heller CG (August 1951). "The pituitary action and estrogenic effect of parahydroxy-propiophenone". The Journal of Clinical Endocrinology and Metabolism. 11 (8): 892–4. doi:10.1210/jcem-11-8-892. PMID 14861299.
^ Mombelli E (January 2012). "Evaluation of the OECD (Q)SAR Application Toolbox for the profiling of estrogen receptor binding affinities". SAR and QSAR in Environmental Research. 23 (1–2): 37–57. Bibcode:2012SQER...23...37M. doi:10.1080/1062936X.2011.623325. PMID 22014213. S2CID 19751228.
^ Buu-Hoi NP, Xuong ND, Lavit D (1953). "Fluorine-containing analogs of 4-hydroxypropiophenone". The Journal of Organic Chemistry. 18 (8): 910–915. doi:10.1021/jo50014a002. ISSN 0022-3263.

[Elks2014-1] Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. pp. 662–. ISBN 978-1-4757-2085-3.

[2] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 796–. ISBN 978-3-88763-075-1.

[PaulsenMortimore1951-3] Paulsen CA, Mortimore GE, Heller CG (August 1951). "The pituitary action and estrogenic effect of parahydroxy-propiophenone". The Journal of Clinical Endocrinology and Metabolism. 11 (8): 892–4. doi:10.1210/jcem-11-8-892. PMID 14861299.

[Mombelli2012-4] Mombelli E (January 2012). "Evaluation of the OECD (Q)SAR Application Toolbox for the profiling of estrogen receptor binding affinities". SAR and QSAR in Environmental Research. 23 (1–2): 37–57. Bibcode:2012SQER...23...37M. doi:10.1080/1062936X.2011.623325. PMID 22014213. S2CID 19751228.

[Buu-HoiXuong1953-5] Buu-Hoi NP, Xuong ND, Lavit D (1953). "Fluorine-containing analogs of 4-hydroxypropiophenone". The Journal of Organic Chemistry. 18 (8): 910–915. doi:10.1021/jo50014a002. ISSN 0022-3263.

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