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