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Tamoxifen, sold under the brand name Nolvadex among others, is a medication that is used to prevent breast cancer in women and treat breast cancer in women and men.
Serious side effects include a small increased risk of uterine cancer, stroke, vision problems, and pulmonary embolism.
Tamoxifen was initially made in 1962 by chemist Dora Richardson.
Contents
1 Medical uses
1.1 Breast cancer
1.2 Infertility
1.3 Gynecomastia
1.4 Others
2 Side effects
2.1 Bone
2.2 Endometrial cancer
2.3 Cardiovascular and metabolic
2.4 Central nervous system
2.5 Premature growth plate fusion
3 Interactions
4 Pharmacology
5 History
6 Society and culture
6.1 Economics
7 Research
7.1 Riedel’s thyroiditis
7.2 Bipolar disorder
7.3 McCune-Albright syndrome
8 References
9 External links
Medical uses
Breast cancer
Tamoxifen is currently used for the treatment of both early and advanced estrogen receptor -positive (ER-positive or ER+) breast cancer in pre- and post- menopausal women.
In 2006, the large STAR clinical study concluded that raloxifene is equally effective in reducing the incidence of breast cancer, but after an average 4-year follow-up, although the difference was not statistically significant, there were 36% fewer uterine cancers and 29% fewer blood clots in women taking raloxifene than in women taking tamoxifen.
Infertility
Tamoxifen is used to treat infertility in women with anovulatory disorders. It is given at days 3 to 7 of a woman’s cycle.
Tamoxifen improves fertility in males with infertility by disinhibiting the hypothalamic–pituitary–gonadal axis (HPG axis) via ER antagonism and thereby increasing the secretion of luteinizing hormone (LH) and follicle-stimulating hormone (FSH) and increasing testicular testosterone production.
Gynecomastia
Tamoxifen is used to prevent or treat gynecomastia. It is taken as a preventative measure in small doses, or used at the onset of any symptoms such as nipple soreness or sensitivity. Other drugs are taken for similar purposes such as clomifene and the anti-aromatase drugs which are used in order to try to avoid the hormone-related adverse effects.
Others
Occasionally tamoxifen is used in treatment of the rare conditions of retroperitoneal fibrosis
Side effects
A report in September 2009 from Health and Human Services’ Agency for Healthcare Research and Quality suggests that tamoxifen, raloxifene, and tibolone used to treat breast cancer significantly reduce invasive breast cancer in midlife and older women, but also increase the risk of adverse side effects.
Some cases of lower-limb lymphedema have been associated with the use of tamoxifen, due to the blood clots and deep vein thrombosis (DVT) that can be caused by this medication. Resolution of the blood clots or DVT is needed before lymphedema treatment can be initiated.
Bone
A beneficial side effect of tamoxifen is that it prevents bone loss by acting as an ER agonist (i.e., mimicking the effects of estrogen) in this cell type. Therefore, by inhibiting osteoclasts, it prevents osteoporosis.
Endometrial cancer
Tamoxifen is a SERM.
The American Cancer Society lists tamoxifen as a known carcinogen, stating that it increases the risk of some types of uterine cancer while lowering the risk of breast cancer recurrence. The ACS states that its use should not be avoided in cases where the risk of breast cancer recurrence without the drug is higher than the risk of developing uterine cancer with the drug.
Cardiovascular and metabolic
Tamoxifen treatment of postmenopausal women is associated with beneficial effects on serum lipid profiles. However, long-term data from clinical trials have failed to demonstrate a cardioprotective effect.
Central nervous system
Tamoxifen-treated breast cancer patients show evidence of reduced cognition,
A significant number of tamoxifen-treated breast cancer patients experience a reduction of libido.
Premature growth plate fusion
While tamoxifen has been shown to antagonize the actions of estrogen in tissues such as the breast, its effects in other tissues such as bones has not been documented fully. There have been studies done in mice showing tamoxifen mimic the effects of estrogen on bone metabolism and skeletal growth, thus increasing the possibility of premature bone fusion. This effect would be less of a concern in adults who have stopped growing.
Interactions
Nolvadex (tamoxifen) 20 mg tablets
Patients with variant forms of the gene CYP2D6 (also called simply 2D6) may not receive full benefit from tamoxifen because of too slow metabolism of the tamoxifen prodrug into its active metabolites.
Certain CYP2D6 variations in breast cancer patients lead to a worse clinical outcome for tamoxifen treatment. Genotyping therefore has the potential for identification of women who have these CYP2D6 phenotypes and for whom the use of tamoxifen is associated with poor outcomes.
Recent studies suggest that taking the selective serotonin reuptake inhibitors (SSRIs) antidepressants paroxetine (Paxil), fluoxetine (Prozac), and sertraline (Zoloft) can decrease the effectiveness of tamoxifen, as these drugs compete for the CYP2D6 enzyme which is needed to metabolize tamoxifen into its active forms.
Recent research has shown that 7–10% of women with breast cancer may not receive the full medical benefit from taking tamoxifen due to their genetic make-up. DNA Drug Safety Testing can examine DNA variations in the CYP2D6 and other important drug processing pathways. More than 20% of all clinically used medications are metabolized by CYP2D6 and knowing the CYP2D6 status of a person can help the doctor with the future selection of medications.
Pharmacology
Crystallographic structure of 4-hydroxy-tamoxifen ( carbon = white, oxygen = red, nitrogen = blue) complexed with ligand binding domain of estrogen receptor alpha (ERα) (cyan ribbon).
Tamoxifen itself is a prodrug, having relatively little affinity for its target protein, the estrogen receptor (ER). It is metabolized in the liver by the cytochrome P450 isoform CYP2D6 and CYP3A4 into active metabolites such as afimoxifene (4-hydroxytamoxifen; 4-OHT) and endoxifen ( N -desmethyl-4-hydroxytamoxifen)
4-OHT binds to ER, the ER/tamoxifen complex recruits other proteins known as co-repressors and then binds to DNA to modulate gene expression. Some of these proteins include NCoR and SMRT.
4-OHT binds to ER competitively (with respect to the endogenous agonist estrogen) in tumor cells and other tissue targets, producing a nuclear complex that decreases DNA synthesis and inhibits estrogen effects. It is a nonsteroidal agent with potent antiestrogenic properties which compete with estrogen for binding sites in breast and other tissues. Tamoxifen causes cells to remain in the G 0 and G 1 phases of the cell cycle. Because it prevents (pre)cancerous cells from dividing but does not cause cell death, tamoxifen is cytostatic rather than cytocidal.
The scientific literature is complex with respect to the activity of tamoxifen, and care should be taken to establish whether tamoxifen, or the 4-hydroxy metabolite was used, especially in in vitro assays.
Norendoxifen ( N, N -didesmethyl-4-hydroxytamoxifen), another active metabolite of tamoxifen, has been found to act as a potent competitive aromatase inhibitor ( IC 50 = 90 nM), and may also be involved in its antiestrogenic activity.
Tamoxifen has been found to decrease insulin-like growth factor 1 levels by 17 to 38% in women and men.
History
In the late 1950s, pharmaceutical companies were actively researching a newly discovered class of anti-estrogen compounds in the hope of developing a morning-after contraceptive pill. Arthur L Walpole was a reproductive endocrinologist who led such a team at the Alderley Park research laboratories of ICI Pharmaceuticals.
This compound was originally created to work as an estrogen inhibitor, but instead was found to stimulate ovulation in participants of the drug testing trial.
Tamoxifen is one of three drugs in an anti-angiogenetic protocol developed by Dr. Judah Folkman, a researcher at Children’s Hospital at Harvard Medical School in Boston. Folkman discovered in the 1970s that angiogenesis – the growth of new blood vessels – plays a significant role in the development of cancer. Since his discovery, an entirely new field of cancer research has developed. Clinical trials on angiogenesis inhibitors have been underway since 1992 using many different drugs. The Harvard researchers developed a specific protocol for a golden retriever named Navy who was cancer-free after receiving the prescribed cocktail of celecoxib, doxycycline, and tamoxifen – the treatment subsequently became known as the Navy Protocol.
The first clinical study took place at the Christie Hospital in 1971, and showed a convincing effect in advanced breast cancer, but nevertheless ICI’s development programme came close to termination when it was reviewed in 1972. Two books, Estrogen Action, Selective Estrogen Receptor Modulators and Women’s Health (Imperial College Press 2013) and Tamoxifen Pioneering Medicine in Breast Cancer (Springer 2013) tell this story.
1980 saw the publication of the first trial to show that tamoxifen given in addition to chemotherapy improved survival for patients with early breast cancer. Nevertheless, tamoxifen had a relatively mild side-effect profile, and a number of large trials continued.
The pharmacology of SERMs was discovered, defined, and deciphered during the 1980s that led to the creation of SERMs as a group of multifunctional medicines aimed at the treatment or prevention of many conditions in postmenopausal women, e.g. osteoporosis and breast cancer. This story is told in: V. Craig Jordan, ed. 2013. “Estrogen Action, Selective Estrogen Receptor Modulators and Women’s Health” Imperial College Press, Singapore.
The early sales of tamoxifen in both the UK and in the U.S. far exceeded ICI’s original estimate, but despite this, at the annual portfolio review ICI’s board members still asserted that “there was no market for cancer”, leaving the drug’s marketing success to rely on its clinical results and clinicians and scientists interests in it. Shortly after, Dora Richardson published a history of Tamoxifen that, unusually for that type of paper, included personal accounts and letters from patients who attributed their healing to the drug. It is by giving voice to cancer patients using Tamoxifen, and so helping to push it forward, by justifying it both morally and scientifically to corporations.
It was not until 1998 that the meta-analysis of the Oxford-based Early Breast Cancer Trialists’ Collaborative Group showed definitively that tamoxifen saved lives in early breast cancer.
Society and culture
Tamoxifen is available as a tablet or oral solution.
Economics
Global sales of tamoxifen in 2001 were $1,024 million.
Since the expiration of the patent in 2002, it is now widely available as a generic drug around the world.
As of 2004, tamoxifen was the world’s largest selling hormonal drug for the treatment of breast cancer.
Research
Tamoxifen is used as a research tool to trigger tissue-specific gene expression in many conditional expression constructs in genetically modified animals including a version of the Cre-Lox recombination technique.
The drug has also been studied in several additional indications.
Riedel’s thyroiditis
Tamoxifen has been proposed as part of a treatment plan for Riedel’s thyroiditis.
Bipolar disorder
Tamoxifen has been shown to be effective in the treatment of mania in patients with bipolar disorder by blocking protein kinase C (PKC), an enzyme that regulates neuron activity in the brain. Researchers believe PKC is over-active during the mania in bipolar patients.
McCune-Albright syndrome
In McCune-Albright syndrome (MAS) tamoxifen has been used to treat premature puberty and the consequences of premature puberty. Tamoxifen has been seen to decrease rapid bone maturation which is the result of excessive estrogen and alter predicted adult height (PAH).
However, one in vitro study in 2007 and later an in vivo study in 2008 have shown that tamoxifen induces apoptosis in growth plate chondrocytes, reduces serum insulin-like growth factor 1 (IGF-1) levels and causes persistent retardation of longitudinal and cortical radial bone growth in young male rats, leading the researchers to express concern giving tamoxifen to growing individuals.

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