Diethylstilbestrol dipropionate

Diethylstilbestrol dipropionate
Clinical data
Other namesDESDP; Diethylstilbestrol dipropanoate; Stilboestrol dipropionate; Stilbestrol dipropionate
Routes of
administration
Intramuscular injection
Drug classNonsteroidal estrogen; Estrogen ester
Identifiers
IUPAC name
  • [4-[(E)-4-(4-propanoyloxyphenyl)hex-3-en-3-yl]phenyl] propanoate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.004.543
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Chemical and physical data
FormulaC24H28O4
Molar mass380.484 g·mol−1
3D model (JSmol)
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]

Potencies of oral estrogens[data sources 1]
Compound Dosage for specific uses (mg usually)[lower-alpha 1]
ETD[lower-alpha 2] EPD[lower-alpha 2] MSD[lower-alpha 2] MSD[lower-alpha 3] OID[lower-alpha 3] TSD[lower-alpha 3]
Estradiol (non-micron.) 30≥120–3001206--
Estradiol (micronized) 6–1260–8014–421–2>5>8
Estradiol valerate 6–1260–8014–421–2->8
Estradiol benzoate -60–140----
Estriol ≥20120–150[lower-alpha 4]28–1261–6>5-
Estriol succinate -140–150[lower-alpha 4]28–1262–6--
Estrone sulfate 1260422--
Conjugated estrogens 5–1260–808.4–250.625–1.25>3.757.5
Ethinylestradiol 200 μg1–2280 μg20–40 μg100 μg100 μg
Mestranol 300 μg1.5–3.0300–600 μg25–30 μg>80 μg-
Quinestrol 300 μg2–4500 μg25–50 μg--
Methylestradiol -2----
Diethylstilbestrol 2.520–30110.5–2.0>53
DES dipropionate -15–30----
Dienestrol 530–40420.5–4.0--
Dienestrol diacetate 3–530–60----
Hexestrol -70–110----
Chlorotrianisene ->100-->48-
Methallenestril -400----
Sources and footnotes:
  1. Dosages are given in milligrams unless otherwise noted.
  2. 1 2 3 Dosed every 2 to 3 weeks
  3. 1 2 3 Dosed daily
  4. 1 2 In divided doses, 3x/day; irregular and atypical proliferation.
Parenteral potencies and durations of nonsteroidal estrogens
EstrogenFormMajor brand name(s)EPD (14 days)Duration
Diethylstilbestrol (DES)Oil solutionMetestrol20 mg1 mg ≈ 2–3 days; 3 mg ≈ 3 days
Diethylstilbestrol dipropionateOil solutionCyren B12.5–15 mg2.5 mg ≈ 5 days
Aqueous suspension ?5 mg ? mg = 21–28 days
Dimestrol (DES dimethyl ether)Oil solutionDepot-Cyren, Depot-Oestromon, Retalon Retard20–40 mg ?
Fosfestrol (DES diphosphate)aAqueous solutionHonvan ?<1 day
Dienestrol diacetateAqueous suspensionFarmacyrol-Kristallsuspension50 mg ?
Hexestrol dipropionateOil solutionHormoestrol, Retalon Oleosum25 mg ?
Hexestrol diphosphateaAqueous solutionCytostesin, Pharmestrin, Retalon Aquosum ?Very short
Note: All by intramuscular injection unless otherwise noted. Footnotes: a = By intravenous injection. Sources: See template.

See also

References

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