Diethylstilbestrol
From Wikipedia, the free encyclopedia
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| Diethylstilbestrol
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| Systematic (IUPAC) name | |
| 4-[4-(4-hydroxyphenyl)hex-3-en-3-yl]phenol | |
| Identifiers | |
| CAS number | 56-53-1 |
| ATC code | G03CB02 G03CC05, L02AA01 |
| PubChem | 3054 |
| DrugBank | APRD00920 |
| Chemical data | |
| Formula | C18H20O2 |
| Mol. weight | 268.35 g/mol |
| Pharmacokinetic data | |
| Bioavailability | ? |
| Metabolism | Hepatic |
| Half life | ? |
| Excretion | ? |
| Therapeutic considerations | |
| Pregnancy cat. |
? |
| Legal status | |
| Routes | IV, oral |
Diethylstilbestrol (DES) is a drug, a synthetic estrogen that was developed to supplement a woman's natural estrogen production.
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[edit] Clinical use
First prescribed by physicians in 1938 for women who experienced miscarriages or premature deliveries, DES was originally considered effective and safe for both the pregnant woman and the developing baby. A double-blind study was not done until DES had been on the market for more than a decade (Dieckmann, 1953). Even though it found that pregnant women given DES had just as many miscarriages and premature deliveries as the control group, DES continued to be aggressively marketed and routinely prescribed.
In the United States, an estimated 5-10 million persons were exposed to DES during 1938-1971, including women who were prescribed DES while pregnant and the female and male children born of these pregnancies.
[edit] Associated health problems
In 1971, the Food and Drug Administration (FDA) issued a Drug Bulletin advising physicians to stop prescribing DES to pregnant women because it was linked to a rare vaginal cancer in female offspring. DES was, however, never banned and continued to be prescribed in the U.S. and other countries well beyond 1971 (until 1978 in most European countries and as late as 1994 in some third world countries).
More than 30 years of research have confirmed that DES is a teratogen, an agent that can cause malformations of an embryo or fetus. However, not all exposed persons will experience the following DES-related health problems.
[edit] First generation
- Women prescribed DES while pregnant are at a modestly increased risk for breast cancer.
[edit] Second generation
- A new study shows DES daughters as having a 2.5 fold increase in breast cancer after age 40.
- Women exposed to DES before birth (in the womb), known as DES Daughters, are at an increased risk for clear cell adenocarcinoma (CCA) of the vagina and cervix, reproductive tract structural differences, pregnancy complications, infertility, and auto-immune disorders. Although DES Daughters appear to be at highest risk for clear cell cancer in their teens and early 20s, cases have been reported in DES Daughters in their 30s and 40s (Hatch, 1998).
- Men exposed to DES before birth (in the womb), known as DES Sons, are at an increased risk for non-cancerous epididymal cysts and auto-immune disorders. Diethylstilbestrol can also cause feminisation of the male foetus, as DES undergoes metabolic epoxidation, and the epoxide product has affinity towards the estrogen receptors.
Researchers are still following the health of persons exposed to DES to determine whether other health problems occur as they grow older.
[edit] Third generation
Current research also looks at DES Third Generation. Third Generation refers to the offspring of DES Sons and Daughters. There is not yet much information available, because the Third Generation is not old enough to fully manifest possible physiological effects of inherited DES exposure.
Third generation injuries are associated with preterm labor or deliveries resulting in premature birth and cerebral palsy, blindess or other neurological deficits or death of a child. One DES Daughter had a child who, at the age of four years, had such a severe case of cerebral palsy that the child was unable to turn himself over; the cerebral palsy was linked to the DES exposure of the mother.
Another study (J Pediatr Hematol Oncol 2003; 25:635-636.) found DES to be transgenerational, meaning that the maternal grandmother had taken DES while pregnant but the mother did not experience any health associated with the DES exposure. This was realized when a rare tumor was discovered on a 15 year old girl.
[edit] DES for canines
DES has been very successful in treating female canine incontinence stemming from poor sphincter control. It is still available from compounding pharmacies, and at the low (1mg) dose, does not have the carcinogenic properties that were so problematic in humans. It is generally administered once a day for five days and then once every 4 to 7 days as needed.
[edit] External links
- DES Action USA offers information and resources for DES-exposed mothers, daughters, and sons who may need special health care.
- DES-AD Project longterm cohort study of DES-exposed persons
- DES Update from the U.S. Centers for Disease Control and Prevention
- DES Cancer Network
- National Cancer Institutes's Cancer Information Service
- University of Chicago DES Program is a registry of patients with CCA of the vagina and/or cervix.
[edit] Other Resources
