Diethylstilbestrol dipropionate

Diethylstilbestrol dipropionate (DESDP) (brand names Agostilben, Biokeral, Clinestrol, Cyclen, Estilbin, Estril, Neobenzoestrol, Orestol, Oroestrol, Ostregenin, Prostilbene, Stilbestriol DP, Stilboestrolum Dipropionicum, Stilboestrol, Synestrin, Willestrol, others), or diethylstilbestrol dipropanoate, also known as stilboestrol dipropionate (BANMTooltip British Approved Name), is a synthetic nonsteroidal estrogen of the stilbestrol group that was formerly marketed widely throughout Europe.^[1][2] It is an ester of diethylstilbestrol with propionic acid,^[1] and is more slowly absorbed in the body than diethylstilbestrol.^[3] The medication has been said to be one of the most potent estrogens known.^[4]

Diethylstilbestrol dipropionate

Clinical data
Other names	DESDP; Diethylstilbestrol dipropanoate; Stilboestrol dipropionate; Stilbestrol dipropionate
Routes of administration	Intramuscular injection
Drug class	Nonsteroidal estrogen; Estrogen ester
Identifiers
IUPAC name [4-[(E)-4-(4-propanoyloxyphenyl)hex-3-en-3-yl]phenyl] propanoate
CAS Number	130-80-3
PubChem CID	657220
ChemSpider	571380
UNII	Y98CK3J0OL
CompTox Dashboard (EPA)	DTXSID7047146
ECHA InfoCard	100.004.543
Chemical and physical data
Formula	C24H28O4
Molar mass	380.484 g·mol−1
3D model (JSmol)	Interactive image
SMILES CCC(=O)Oc1ccc(cc1)\C(CC)=C(/CC)c2ccc(OC(=O)CC)cc2
InChI InChI=1S/C24H28O4/c1-5-21(17-9-13-19(14-10-17)27-23(25)7-3)22(6-2)18-11-15-20(16-12-18)28-24(26)8-4/h9-16H,5-8H2,1-4H3/b22-21+ Key:VZMLEMYJUIIHNF-QURGRASLSA-N

The medication has been available in both oral and intramuscular formulations.^[5]

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Potencies of oral estrogens^{[data sources 1]}

Compound	Dosage for specific uses (mg usually)[a]
	ETD[b]	EPD[b]	MSD[b]	MSD[c]	OID[c]	TSD[c]
Estradiol (non-micronized)	30	≥120–300	120	6	-	-
Estradiol (micronized)	6–12	60–80	14–42	1–2	>5	>8
Estradiol valerate	6–12	60–80	14–42	1–2	-	>8
Estradiol benzoate	-	60–140	-	-	-	-
Estriol	≥20	120–150[d]	28–126	1–6	>5	-
Estriol succinate	-	140–150[d]	28–126	2–6	-	-
Estrone sulfate	12	60	42	2	-	-
Conjugated estrogens	5–12	60–80	8.4–25	0.625–1.25	>3.75	7.5
Ethinylestradiol	200 μg	1–2	280 μg	20–40 μg	100 μg	100 μg
Mestranol	300 μg	1.5–3.0	300–600 μg	25–30 μg	>80 μg	-
Quinestrol	300 μg	2–4	500 μg	25–50 μg	-	-
Methylestradiol	-	2	-	-	-	-
Diethylstilbestrol	2.5	20–30	11	0.5–2.0	>5	3
DES dipropionate	-	15–30	-	-	-	-
Dienestrol	5	30–40	42	0.5–4.0	-	-
Dienestrol diacetate	3–5	30–60	-	-	-	-
Hexestrol	-	70–110	-	-	-	-
Chlorotrianisene	-	>100	-	-	>48	-
Methallenestril	-	400	-	-	-	-
Sources and footnotes: [6][7][8][9][10][11] [12][13][14][15] [16][17][18][19][20][21][22][23][24] Dosages are given in milligrams unless otherwise noted. Dosed every 2 to 3 weeks Dosed daily In divided doses, 3x/day; irregular and atypical proliferation.

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Parenteral potencies and durations of nonsteroidal estrogens

Estrogen	Form	Major brand name(s)	EPD (14 days)	Duration
Diethylstilbestrol (DES)	Oil solution	Metestrol	20 mg	1 mg ≈ 2–3 days; 3 mg ≈ 3 days
Diethylstilbestrol dipropionate	Oil solution	Cyren B	12.5–15 mg	2.5 mg ≈ 5 days
	Aqueous suspension	?	5 mg	? mg = 21–28 days
Dimestrol (DES dimethyl ether)	Oil solution	Depot-Cyren, Depot-Oestromon, Retalon Retard	20–40 mg	?
Fosfestrol (DES diphosphate)a	Aqueous solution	Honvan	?	<1 day
Dienestrol diacetate	Aqueous suspension	Farmacyrol-Kristallsuspension	50 mg	?
Hexestrol dipropionate	Oil solution	Hormoestrol, Retalon Oleosum	25 mg	?
Hexestrol diphosphatea	Aqueous solution	Cytostesin, Pharmestrin, Retalon Aquosum	?	Very short
Note: All by intramuscular injection unless otherwise noted. Footnotes: a = By intravenous injection. Sources: See template.

See also

• List of estrogen esters § Diethylstilbestrol esters
• List of sex-hormonal aqueous suspensions

References

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2. Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 332–. ISBN 978-3-88763-075-1.
3. Wilson CO, Gisvold O (1949). Organic Chemistry in Pharmacy. J. B. Lippincott. p. 168.
4. Dallenbach-Hellweg G (6 December 2012). "Iatrogenic Changes of the Endometrium". Histopathology of the Endometrium. Springer Science & Business Media. pp. 200–. ISBN 978-3-642-96249-3.
5. Kahr H (8 March 2013). Konservative Therapie der Frauenkrankheiten: Anzeigen, Grenzen und Methoden Einschliesslich der Rezeptur. Springer-Verlag. pp. 19–20. ISBN 978-3-7091-5694-0.
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11. Horský J, Presl J (1981). "Hormonal Treatment of Disorders of the Menstrual Cycle". In Horsky J, Presl J (eds.). Ovarian Function and its Disorders: Diagnosis and Therapy. Springer Science & Business Media. pp. 309–332. doi:10.1007/978-94-009-8195-9_11. ISBN 978-94-009-8195-9.
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15. Kopera H (1991). "Hormone der Gonaden". Hormonelle Therapie für die Frau. Kliniktaschenbücher. pp. 59–124. doi:10.1007/978-3-642-95670-6_6. ISBN 978-3-540-54554-5. ISSN 0172-777X.
16. Scott WW, Menon M, Walsh PC (April 1980). "Hormonal Therapy of Prostatic Cancer". Cancer. 45 (Suppl 7): 1929–1936. doi:10.1002/cncr.1980.45.s7.1929. PMID 29603164.
17. Leinung MC, Feustel PJ, Joseph J (2018). "Hormonal Treatment of Transgender Women with Oral Estradiol". Transgender Health. 3 (1): 74–81. doi:10.1089/trgh.2017.0035. PMC 5944393. PMID 29756046.
18. Ryden AB (1950). "Natural and synthetic oestrogenic substances; their relative effectiveness when administered orally". Acta Endocrinologica. 4 (2): 121–39. doi:10.1530/acta.0.0040121. PMID 15432047.
19. Ryden AB (1951). "The effectiveness of natural and synthetic oestrogenic substances in women". Acta Endocrinologica. 8 (2): 175–91. doi:10.1530/acta.0.0080175. PMID 14902290.
20. Kottmeier HL (1947). "Ueber blutungen in der menopause: Speziell der klinischen bedeutung eines endometriums mit zeichen hormonaler beeinflussung: Part I". Acta Obstetricia et Gynecologica Scandinavica. 27 (s6): 1–121. doi:10.3109/00016344709154486. ISSN 0001-6349. There is no doubt that the conversion of the endometrium with injections of both synthetic and native estrogenic hormone preparations succeeds, but the opinion whether native, orally administered preparations can produce a proliferation mucosa changes with different authors. PEDERSEN-BJERGAARD (1939) was able to show that 90% of the folliculin taken up in the blood of the vena portae is inactivated in the liver. Neither KAUFMANN (1933, 1935), RAUSCHER (1939, 1942) nor HERRNBERGER (1941) succeeded in bringing a castration endometrium into proliferation using large doses of orally administered preparations of estrone or estradiol. Other results are reported by NEUSTAEDTER (1939), LAUTERWEIN (1940) and FERIN (1941); they succeeded in converting an atrophic castration endometrium into an unambiguous proliferation mucosa with 120–300 oestradiol or with 380 oestrone.
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24. Duncan CJ, Kistner RW, Mansell H (October 1956). "Suppression of ovulation by trip-anisyl chloroethylene (TACE)". Obstetrics and Gynecology. 8 (4): 399–407. PMID 13370006.