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Estradiol monopropionate

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Estradiol monopropionate
Clinical data

Trade names	Acrofollin, Akrofollin, Follhormon
Other names	EP; Estradiol monopropionate; Estradiol propanoate; Estradiol 17β-propionate; Estradiol 17β-propanoate; Estra-1,3,5(10)-trien-3,17β-diol 17β-propionate
Routes of administration	Intramuscular injection
Drug class	Estrogen; Estrogen ester
Identifiers
IUPAC name [(8R,9S,13S,14S,17S)-3-Hydroxy-13-methyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-17-yl] propanoate
CAS Number	3758-34-7
PubChem CID	19571
ChemSpider	18438
UNII	K31PC34297
CompTox Dashboard (EPA)	DTXSID4048985
ECHA InfoCard	100.021.059
Chemical and physical data
Formula	C₂₁H₂₈O₃
Molar mass	328.452 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CCC(=O)OC1CCC2C1(CCC3C2CCC4=C3C=CC(=C4)O)C
InChI InChI=1S/C21H28O3/c1-3-20(23)24-19-9-8-18-17-6-4-13-12-14(22)5-7-15(13)16(17)10-11-21(18,19)2/h5,7,12,16-19,22H,3-4,6,8-11H2,1-2H3/t16-,17-,18+,19+,21+/m1/s1 Key:PQCRZWCSVWBYSC-AGRFSFNASA-N

Estradiol propionate (EP), also known as estradiol monopropionateorestradiol 17β-propionate and sold under the brand names Acrofollin, Akrofollin, and Follhormon, is an estrogen medication and estrogen ester which is no longer marketed.^[1]^[2] It is the C17β propionate esterofestradiol.^[1]^[2] EP was provided in an oil solution and was administered by intramuscular injection.^[3]^[4]^[5]^[6] The medication was first marketed by 1938 or 1939.^[7]^[8]

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Affinities and estrogenic potencies of estrogen esters and ethers at the estrogen receptors
Estrogen	Other names	RBATooltip Relative binding affinity (%)^a	REP (%)^b
Estrogen	Other names	ER	ERα	ERβ
Estradiol	E2	100	100	100
Estradiol 3-sulfate	E2S; E2-3S	?	0.02	0.04
Estradiol 3-glucuronide	E2-3G	?	0.02	0.09
Estradiol 17β-glucuronide	E2-17G	?	0.002	0.0002
Estradiol benzoate	EB; Estradiol 3-benzoate	10	1.1	0.52
Estradiol 17β-acetate	E2-17A	31–45	24	?
Estradiol diacetate	EDA; Estradiol 3,17β-diacetate	?	0.79	?
Estradiol propionate	EP; Estradiol 17β-propionate	19–26	2.6	?
Estradiol valerate	EV; Estradiol 17β-valerate	2–11	0.04–21	?
Estradiol cypionate	EC; Estradiol 17β-cypionate	?^c	4.0	?
Estradiol palmitate	Estradiol 17β-palmitate	0	?	?
Estradiol stearate	Estradiol 17β-stearate	0	?	?
Estrone	E1; 17-Ketoestradiol	11	5.3–38	14
Estrone sulfate	E1S; Estrone 3-sulfate	2	0.004	0.002
Estrone glucuronide	E1G; Estrone 3-glucuronide	?	<0.001	0.0006
Ethinylestradiol	EE; 17α-Ethynylestradiol	100	17–150	129
Mestranol	EE 3-methyl ether	1	1.3–8.2	0.16
Quinestrol	EE 3-cyclopentyl ether	?	0.37	?
Footnotes: ^a = Relative binding affinities (RBAs) were determined via in-vitro displacement of labeled estradiol from estrogen receptors (ERs) generally of rodent uterine cytosol. Estrogen esters are variably hydrolyzed into estrogens in these systems (shorter ester chain length -> greater rate of hydrolysis) and the ER RBAs of the esters decrease strongly when hydrolysis is prevented. ^b = Relative estrogenic potencies (REPs) were calculated from half-maximal effective concentrations (EC₅₀) that were determined via in-vitro β‐galactosidase (β-gal) and green fluorescent protein (GFP) production assaysinyeast expressing human ERα and human ERβ. Both mammalian cells and yeast have the capacity to hydrolyze estrogen esters. ^c = The affinities of estradiol cypionate for the ERs are similar to those of estradiol valerate and estradiol benzoate (figure). Sources: See template page.

References[edit]

^ ^a ^b Elks J (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 898. ISBN 978-1-4757-2085-3.

^ ^a ^b Negwer M (1994). Organic-chemical Drugs and Their Synonyms: (an International Survey). Akademie Verlag. p. 1967. ISBN 978-3-05-500156-7. Estra-1,3,5(10)-triene-3,17β-diol 17-propionate = 3,17β-Estradiol 17-monopropionate = (17β)-Estra-1,3,5(10)-triene-3,17-diol 17-propanoate (e) S Acrofollin, Akrofollin, Estradiol monopropionate, Follhormon "Saper", Ostradiolmonopropionat, Oestrolum propionicum U Estrogen

^ United States. Department of the Treasury (1942). Treasury Decisions Under the Customs, Internal Revenue, and Other Laws: Including the Decisions of the Board of General Appraisers and the Court of Customs Appeals. U.S. Government Printing Office. p. 135. [...] T. D. 50714-C, covering akrofollin intramuscular oily solution of estrogenic hormone manufactured by Specific Pharmaceuticals, Inc., New York, N. Y., with the use of imported oestradiol-17-propionate crystals, [...]

^ Csillag M, Vaczy L, Turr E (January 1951). "Apparent differences between the parenteral and intrauterine administration of estrogen substances". Gynaecologia. 131 (1): 9–18. doi:10.1159/000311707. PMID 14813560. For the following two groups we have chosen estradiol propionate (Akrofollin) in a dose of 3 X 5 mg. In each instance we performed biopsic strip-abrasion on the third day after the termination of intrauterine, resp. intramuscular hormone administration.

^ Orosz M, Csapó I, Varga B (August 1983). "Alteration in the reactivity of hamster cheek pouch arterioles to prostaglandin E2 and noradrenaline during pregnancy or sex steroid treatment". Prostaglandins. 26 (2): 165–73. doi:10.1016/0090-6980(83)90085-0. PMID 6580678. [...] they were treated each second day with 0.2 ml sunflower oil, 0.2 mg/lOO g bw of oestradiol propionate (Akrofollin, Richter), [...]

^ Wachnik A, Biró G, Biró L, Korom M, Gergely A, Antal M (1993). "Effect of sex hormones on copper, zinc, iron nutritional status and hepatic lipid peroxidation in rats". Die Nahrung. 37 (1): 28–34. doi:10.1002/food.19930370106. PMID 8464456. injected subcutaneously with oily solution of estradiol propionate (Acrofollin, Richter Gedeon)

^ Boletín oficial de la propiedad industrial. Carasa y Cía. 1938. Fecha del Fecha de la solicitud de la marca: Abril 13, 1938. Certificado de propiedad: Octubre 23, 1939. Nombre y domicilio del concesionario: Chinoin Fábrica de Productos Farmacéuticos y Química S. A., Ujpest, Hungría. AKROFOLLIN.

^ Dubrauszky V, St. Martzy (1941).『Die Wirkung natürlicher und künstlicher Brunststoffe im Tierversuch』[The effect of natural and artificial compounds in animal experiments]. Archiv für Gynäkologie. 171 (2): 242–253. doi:10.1007/BF01714680. ISSN 0003-9128. S2CID 9251783.

Estradiol

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ERTooltip Estrogen receptor antagonists (incl. SERMsTooltip selective estrogen receptor modulators/SERDsTooltip selective estrogen receptor downregulators)	Acolbifene^† Anordrin Bazedoxifene Broparestrol Clomifene^# Cyclofenil Enclomifene^† Epitiostanol Lasofoxifene Mepitiostane Ormeloxifene Ospemifene Raloxifene Tamoxifen^# Toremifene Exclusively antagonistic: Elacestrant Fulvestrant Noncompetitive inhibitors: Trilostane
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