Diethylstilbestrol dipropionate

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;
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;

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 (BANM), 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]

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

Oral potencies of estrogens
Estrogen	Type	Class	ETD (mg/14 days)	EPD (mg/14 days)	EPD (mg/day)	MSD (mg/14 days)	MSD (mg/day)	TSD (mg/day)
Estradiol (non-micronized)	Bioidentical	Steroidal	?	≥120–300	?	?	?	?
Estradiol (micronized)	Bioidentical	Steroidal	?	60–80	4.3	14–28	1.0–2.0	>8
Estradiol valerate	Bioidentical	Steroidal	6–10	60–80	4.3	14–28	1.0–2.0	>8
Estradiol benzoate	Bioidentical	Steroidal	?	60–140	4.5	?	?	?
Estriol	Bioidentical	Steroidal	20^a	120–150^b	10.0–10.7^b	28–84	1.0–6.0	?
Estriol succinate	Bioidentical	Steroidal	?	140–150^b	10.0–10.7^b	28–84	2.0–6.0	?
Conjugated estrogens	Natural	Steroidal	5–12	60–80	4.3	8.4–17.5	0.625–1.25	7.5
Ethinylestradiol	Synthetic	Steroidal	0.2	1.0–2.0	0.071–0.11	0.28	0.02–0.04	0.1
Mestranol	Synthetic	Steroidal	0.3	1.5–3.0	0.11–0.13	0.3–0.5	0.025	?
Quinestrol	Synthetic	Steroidal	0.3	2.0–4.0	0.14–0.29	?	0.025–0.05	?
Methylestradiol	Synthetic	Steroidal	?	2.0	?	?	?	?
Diethylstilbestrol	Synthetic	Nonsteroidal	2.5	20–30	1.4–2.1	?	0.5–2.0	3
Diethylstilbestrol dipropionate	Synthetic	Nonsteroidal	?	15–30	1.1–1.4	?	?	?
Dienestrol	Synthetic	Nonsteroidal	?	30	?	?	0.5–4.0	?
Dienestrol diacetate	Synthetic	Nonsteroidal	3–5	30–60	2.9–4.3	?	?	?
Hexestrol	Synthetic	Nonsteroidal	?	70–110	?	?	?	?
Hexestrol diacetate	Synthetic	Nonsteroidal	?	45	?	?	?	?
Chlorotrianisene	Synthetic	Nonsteroidal	?	>100	?	?	?	?
Methallenestril	Synthetic	Nonsteroidal	?	400	?	?	?	?
Note: The OID of EE is 0.1 mg/day. Footnotes: ^a = Very variable, often higher. ^b = In divided doses, 3x/day; irregular and atypical proliferation. Sources: See template.

Parenteral potencies and durations of nonsteroidal estrogens
Estrogen	Form	Major brand name(s)	EPD (14 days)	Duration
Diethylstilbestrol (DES)	Oil solution	?	20 mg	3 mg ≈ 3 days
Diethylstilbestrol dipropionate	Oil solution	Cyren B	12.5–15 mg	2.5 mg ≈ 5 days
Diethylstilbestrol dipropionate	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 diphosphate^a	Aqueous solution	Cytostesin, Pharmestrin, Retalon Aquosum	?	Very short
Note: All by intramuscular injection unless otherwise noted. Footnotes: ^a = By intravenous injection. Sources: See template.

References

J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 397. ISBN 978-1-4757-2085-3.
Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 332–. ISBN 978-3-88763-075-1.
Charles Owens Wilson; Ole Gisvold (1949). Organic Chemistry in Pharmacy. J. B. Lippincott. p. 168.
G. Dallenbach-Hellweg (6 December 2012). Histopathology of the Endometrium. Springer Science & Business Media. pp. 200–. ISBN 978-3-642-96249-3.
Heinrich Kahr (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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[Elks2014-1] J. Elks (14 November 2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer. p. 397. ISBN 978-1-4757-2085-3.

[IndexNominum2000-2] Index Nominum 2000: International Drug Directory. Taylor & Francis. January 2000. pp. 332–. ISBN 978-3-88763-075-1.

[WilsonGisvold1949-3] Charles Owens Wilson; Ole Gisvold (1949). Organic Chemistry in Pharmacy. J. B. Lippincott. p. 168.

[Dallenbach-Hellweg2012-4] G. Dallenbach-Hellweg (6 December 2012). Histopathology of the Endometrium. Springer Science & Business Media. pp. 200–. ISBN 978-3-642-96249-3.

[Kahr2013-5] Heinrich Kahr (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.

Diethylstilbestrol dipropionate

See also

References