diethylstilbestrol
Trade name: Fosfestrol
Approved
Jun 1, 1941
Diethylstilbestrol (DES), also known as stilbestrol or stilboestrol, is a nonsteroidal estrogen medication, which is presently rarely used. In the past, it was widely used for a variety of indications, including pregnancy support for those with a history of recurrent miscarriage, hormone therapy for menopausal symptoms and estrogen deficiency, treatment of prostate cancer and breast cancer, and other uses. By 2007, it was only used in the treatment of prostate cancer and breast cancer. In 2011, Hoover and colleagues reported adverse reproductive health outcomes linked to DES including infertility, miscarriage, ectopic pregnancy, preeclampsia, preterm birth, stillbirth, infant death, menopause prior to age 45, breast cancer, cervical cancer, and vaginal cancer. While most commonly taken by mouth, DES was available for use by other routes as well, for instance, vaginal, topical, and by injection. — Wikipedia
Clinical trial activity
2 trials · 3 clinical orgs · 3 marketing orgs
Earliest trial started Dec 1, 2002 (NCT00136526)
Timeline
Indications
Approved for
Studied for
Mechanism of action
- Estrogen receptor alphaAGONIST
ESR1 agonist
Approval history
- approvedJun 1, 1941
Chemistry & pharmacology
SMILES
CC/C(=C(/CC)c1ccc(O)cc1)c1ccc(O)cc1- Mol. weight
- 268.36 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Achiral Molecule
- Inorganic
- No
- Polymer
- No
- Delivery
- Oral, Parenteral, Topical
- Availability
- Discontinued
Oral
Yes
Parenteral
Yes
Topical
Yes
Sources
- WikipediaDiethylstilbestrol ↗
- ChEMBLCHEMBL411 ↗
Also known as
- 4,4'-dihydroxy-alpha,beta-diethylstilbene
- 4,4'-dihydroxy-alpha,beta-diethylstilbene
- 4,4'-dihydroxy-α,β-diethylstilbene
- 4,4'-dihydroxy-α,β-diethylstilbene
- agostilben
- alpha,alpha'-diethyl-(e)-4,4'-stilbenediol
- alpha,alpha'-diethyl-(e)-4,4'-stilbenediol
- antigestil
- apstil
- apstil
- cyren a
- cyren a
- des
- des
- diethylstilbestrol
- diethylstilbestrol
- diethylstilbestrol
- diethylstilbestrol
- diethylstilbestrol
- diethylstilbestrol
- diethylstilbestrol
- diethylstilbestrol
- diethylstilbestrol
- diethylstilbestrol
- diethylstilbestrol
- diethylstilbestrolum
- diethylstilbestrolum
- dietilestilbestrol
- dietilestilbestrol
- distilbene
- distilbene
- distilbene
- distilbene
- (e)-3,4-bis(4-hydroxyphenyl)-3-hexene
- (e)-3,4-bis(4-hydroxyphenyl)-3-hexene
- (e)-4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenol
- (e)-4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenol
- estrobene
- estrobene
- estrobene
- estrogenine
- estrogenine
- estromenin
- estromenin
- estromenin
- fonatol
- fonatol
- new-estranol 1
- new-estranol 1
- palestrol
- palestrol
- stilbestroform
- stilbestroform
- stilbestrol
- stilbestrol
- stilbestrol
- stilbetin
- stilbetin
- stilboesterol
- stilboestrol
- stilboestrol
- stilboestrol
- synestrin
- synestrin
- synthestrin
- synthestrin
- tampovagan
- tampovagan
- trans-4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenol
- trans-4,4'-(1,2-diethyl-1,2-ethenediyl)bisphenol
- trans-diethylstilbesterol
- trans-diethylstilbesterol
- trans-diethylstilbestrol
- trans-diethylstilbestrol
- trans-diethylstilboesterol
- trans-diethylstilboesterol
- α,α'-diethyl-(e)-4,4'-stilbenediol
- α,α'-diethyl-(e)-4,4'-stilbenediol
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT00136526 | Phase 2 | Dec 1, 2002 | Sanofi, University of Washington |
| NCT00316927 | Phase 3 | Dec 1, 2002 | Barts & The London NHS Trust |
Organizations
Research & Development (3)
| Organization | Org type | Trials | As lead sponsor | Phases | Earliest year |
|---|---|---|---|---|---|
| Barts & The London NHS Trust | Academic/Hospital | 1 | 1 | 1 | 2002 |
| Sanofi | For profit | 1 | 0 | 1 | 2002 |
| University of Washington | Academic/Hospital | 1 | 1 | 1 | 2002 |
Marketing (3)
| Organization | Org type | Relationship | Date |
|---|---|---|---|
| Bristol-Myers Squibb | For profit | NDA2 | — |
| Eli Lilly | For profit | NDA | — |
| Tablicaps | For profit | MKTG | May 30, 1973 |