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Tamoxifen information


Tamoxifen
Clinical data
Trade namesNolvadex, Genox, Tamifen, others[1]
Other namesTMX; ICI-46474
AHFS/Drugs.comMonograph
MedlinePlusa682414
License data
  • US DailyMed: Tamoxifen
Pregnancy
category
  • AU: B3[2]
Routes of
administration
By mouth
Drug classSelective estrogen receptor modulator
ATC code
  • L02BA01 (WHO)
Legal status
Legal status
  • AU: S4 (Prescription only)
  • CA: ℞-only
  • UK: POM (Prescription only)
  • US: ℞-only[3][4]
Pharmacokinetic data
Bioavailability~100%[5][6]
Protein binding>99% (albumin)[5][7]
MetabolismLiver (CYP3A4, CYP2C9, CYP2D6)[5][12][8]
MetabolitesN-Desmethyltamoxifen[8][9]
• Endoxifen (4-hydroxy-N-desmethyltamoxifen)[8][9]
• Afimoxifene (4-hydroxytamoxifen)[8][9]
N,N-Didesmethyltamoxifen[8]
• Norendoxifen (4-hydroxy-N,N-didesmethyltamoxifen)[8]
• Others, conjugates[8][10][11]
Elimination half-life5–7 days[5][8]
ExcretionFeces: 65%
Urine: 9%
Identifiers
IUPAC name
  • (Z)-2-[4-(1,2-Diphenylbut-1-enyl)phenoxy]-N,N-dimethylethanamine
CAS Number
  • 10540-29-1 checkY
  • citrate: 54965-24-1
PubChem CID
  • 2733526
  • citrate: 2733525
IUPHAR/BPS
  • 1016
DrugBank
  • DB00675 checkY
  • citrate: DBSALT000168
ChemSpider
  • 2015313 checkY
  • citrate: 2015312
UNII
  • 094ZI81Y45
  • citrate: 7FRV7310N6
KEGG
  • D08559 checkY
  • citrate: D00966
ChEBI
  • CHEBI:41774 checkY
  • citrate: CHEBI:9397
ChEMBL
  • ChEMBL83 checkY
  • citrate: ChEMBL786
PDB ligand
  • CTX (PDBe, RCSB PDB)
CompTox Dashboard (EPA)
  • DTXSID1034187 Edit this at Wikidata
ECHA InfoCard100.031.004 Edit this at Wikidata
Chemical and physical data
FormulaC26H29NO
Molar mass371.524 g·mol−1
3D model (JSmol)
  • Interactive image
SMILES
  • CN(C)CCOc1ccc(cc1)/C(c2ccccc2)=C(/CC)c3ccccc3
InChI
  • InChI=1S/C26H29NO/c1-4-25(21-11-7-5-8-12-21)26(22-13-9-6-10-14-22)23-15-17-24(18-16-23)28-20-19-27(2)3/h5-18H,4,19-20H2,1-3H3/b26-25- checkY
  • Key:NKANXQFJJICGDU-QPLCGJKRSA-N checkY
  (verify)

Tamoxifen, sold under the brand name Nolvadex among others, is a selective estrogen receptor modulator used to prevent breast cancer in women and men.[13] It is also being studied for other types of cancer.[13] It has been used for Albright syndrome.[14] Tamoxifen is typically taken daily by mouth for five years for breast cancer.[14]

Serious side effects include a small increased risk of uterine cancer, stroke, vision problems, and pulmonary embolism.[14] Common side effects include irregular periods, weight loss, and hot flashes.[14] It may cause harm to the baby if taken during pregnancy or breastfeeding.[14] It is a selective estrogen-receptor modulator (SERM) and works by decreasing the growth of breast cancer cells.[14][15] It is a member of the triphenylethylene group of compounds.[16]

Tamoxifen was initially made in 1962, by chemist Dora Richardson.[17][18] It is on the World Health Organization's List of Essential Medicines.[19] Tamoxifen is available as a generic medication.[14] In 2020, it was the 317th most commonly prescribed medication in the United States, with more than 900 thousand prescriptions.[20][21]

  1. ^ "NCI Drug Dictionary". 2 February 2011. Archived from the original on 8 December 2015. Retrieved 12 September 2021.
  2. ^ "Tamoxifen Use During Pregnancy". Drugs.com. 25 July 2019. Retrieved 27 January 2020.
  3. ^ "Tamoxifen citrate tablet, film coated". DailyMed. Retrieved 12 September 2021.
  4. ^ "Soltamox- tamoxifen citrate liquid". DailyMed. Retrieved 12 September 2021.
  5. ^ a b c d Cite error: The named reference MorelloWurz2003 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference BrennerStevens2017 was invoked but never defined (see the help page).
  7. ^ Cite error: The named reference ChabnerLongo2011 was invoked but never defined (see the help page).
  8. ^ a b c d e f g h Cite error: The named reference Sanchez-SpitmanSwen2019 was invoked but never defined (see the help page).
  9. ^ a b c Cite error: The named reference pmid23962908 was invoked but never defined (see the help page).
  10. ^ Cite error: The named reference pmid21451508 was invoked but never defined (see the help page).
  11. ^ Cite error: The named reference Nagar2010 was invoked but never defined (see the help page).
  12. ^ "Nolvadex (Tamoxifen Citrate) tablets". DailyMed. 3 November 2016. Retrieved 12 September 2021.
  13. ^ a b "Tamoxifen Citrate". NCI. 26 August 2015. Archived from the original on 4 January 2016. Retrieved 28 November 2015.
  14. ^ a b c d e f g "Tamoxifen Citrate". The American Society of Health-System Pharmacists. Archived from the original on 4 January 2014. Retrieved 27 November 2015.
  15. ^ "Selective estrogen receptor modulators". Archived from the original on 9 December 2013. Retrieved 28 November 2015.
  16. ^ Cano A, Calaf i Alsina J, Duenas-Diez JL, eds. (2006). Selective Estrogen Receptor Modulators a New Brand of Multitarget Drugs. Berlin, Heidelberg: Springer-Verlag Berlin Heidelberg. p. 52. ISBN 9783540347422.
  17. ^ Cite error: The named reference Viviane M 2017 was invoked but never defined (see the help page).
  18. ^ Jordan VC (January 2006). "Tamoxifen (ICI46,474) as a targeted therapy to treat and prevent breast cancer". British Journal of Pharmacology. 147 (Suppl 1): S269–S276. doi:10.1038/sj.bjp.0706399. PMC 1760730. PMID 16402113.
  19. ^ World Health Organization (2019). World Health Organization model list of essential medicines: 21st list 2019. Geneva: World Health Organization. hdl:10665/325771. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
  20. ^ "The Top 300 of 2020". ClinCalc. Retrieved 7 October 2022.
  21. ^ "Tamoxifen Citrate - Drug Usage Statistics". ClinCalc. Archived from the original on 22 September 2020. Retrieved 7 October 2022.

and 27 Related for: Tamoxifen information

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Tamoxifen

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Tamoxifen, sold under the brand name Nolvadex among others, is a selective estrogen receptor modulator used to prevent breast cancer in women and men...

Word Count : 8561

Selective estrogen receptor modulator

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SERMs are used dependent on their pattern of action in various tissues: Tamoxifen is a first-line hormonal treatment of ER-positive metastatic breast cancer...

Word Count : 6397

Clomifene

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treatment of some cases of gynecomastia but it is not as effective as tamoxifen or raloxifene for this indication. It has shown variable results for gynecomastia...

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Anastrozole

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the treatment and prevention of breast cancer in women. The Arimidex, Tamoxifen, Alone or in Combination (ATAC) trial was of localized breast cancer and...

Word Count : 2332

Aromatase inhibitor

Last Update:

women with breast cancer. Tamoxifen (a SERM) traditionally was the drug treatment of choice, but the ATAC trial (Arimidex, Tamoxifen, Alone or in Combination)...

Word Count : 2051

Gynecomastia

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effective than tamoxifen or raloxifene. Tamoxifen may be used to treat gynecomastia in adults and of the medical treatments used, tamoxifen is the most effective...

Word Count : 6473

Study of Tamoxifen and Raloxifene

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Tamoxifen and Raloxifene (STAR) is a clinical trial from the early 2000s designed determine how the drug raloxifene compares with the drug tamoxifen in...

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Letrozole

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receptor positive or has an unknown receptor status in postmenopausal women. Tamoxifen is also used to treat hormonally-responsive breast cancer, but it does...

Word Count : 1843

Endoxifen

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active metabolite of tamoxifen and has been found to be effective in patients that have failed previous hormonal therapies (tamoxifen, aromatase inhibitors...

Word Count : 1428

Exemestane

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positive early breast cancer who have received two to three years of tamoxifen and are switched to it for completion of a total of five consecutive years...

Word Count : 1764

Cre recombinase

Last Update:

recombinase, resulting in Cre becoming specifically activated by tamoxifen. In the absence of tamoxifen, CreER will result in the shuttling of the mutated recombinase...

Word Count : 1745

Floxing

Last Update:

Further, these knockouts can be inducible. In several mouse studies, tamoxifen is used to induce the Cre recombinase. In this case, Cre recombinase is...

Word Count : 1436

Antihormone therapy

Last Update:

Metastatic breast cancer, tamoxifen can be prescribed to selectively block estrogen's effect on certain cells. SERMs like tamoxifen attach to receptors on...

Word Count : 1108

AFPep

Last Update:

toxicities of tamoxifen. Tamoxifen has been a very effective drug for the treatment of estrogen receptor-positive breast cancer. But tamoxifen has certain...

Word Count : 1078

Antiestrogen withdrawal response

Last Update:

documented rarely with the selective estrogen receptor modulators (SERMs) tamoxifen and raloxifene. The phenomenon indicates that these agents can somehow...

Word Count : 293

Toremifene

Last Update:

closely related to tamoxifen. Toremifene was introduced for medical use in 1997. It was the first antiestrogen to be introduced since tamoxifen in 1978. It is...

Word Count : 3523

Antiestrogen

Last Update:

Antiestrogens include selective estrogen receptor modulators (SERMs) like tamoxifen, clomifene, and raloxifene, the ER silent antagonist and selective estrogen...

Word Count : 803

Timeline of cancer treatment development

Last Update:

Introduction of laser therapy in treatment of cancer 1960  – Invention of tamoxifen breast cancer anti-estrogen (SERM) hormonal therapy drug 1961  – Vincristine...

Word Count : 2580

Etacstil

Last Update:

receptor-positive breast cancer. It was shown to overcome antiestrogen (tamoxifen, aromatase inhibitor, fulvestrant) resistance in breast cancer by altering...

Word Count : 694

Estrogen receptor

Last Update:

genistein, miroestrol) Selective estrogen receptor modulators (e.g., tamoxifen, clomifene, raloxifene) Antiestrogens (e.g., fulvestrant, ICI-164384,...

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Autocrine signaling

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gefitinib-resistant NSCLC cell lines. In breast cancer, the acquisition of tamoxifen resistance is another major therapeutic problem. It has been shown that...

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Grignard reagent

Last Update:

reaction is a key step in the (non-stereoselective) industrial production of Tamoxifen (currently used for the treatment of estrogen receptor positive breast...

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Raloxifene

Last Update:

120 mg/m2/day. In the Study of Tamoxifen and Raloxifene (STAR) trial, 60 mg/day raloxifene was 78% as effective as 20 mg/day tamoxifen in preventing non-invasive...

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Droloxifene

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effective than tamoxifen in the treatment of breast cancer in two phase III clinical trials. Droloxifene is an analogue of tamoxifen, specifically 3-hydroxytamoxifen...

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Ovulation induction

Last Update:

Medications in use for this effect are mainly clomifene citrate and tamoxifen (both being selective estrogen-receptor modulators), as well as letrozole...

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Endometrial polyp

Last Update:

obesity, high blood pressure and a history of cervical polyps. Taking tamoxifen or hormone replacement therapy can also increase the risk of uterine polyps...

Word Count : 938

Progonadotropin

Last Update:

a pulsatile (as opposed to continuous) manner, antiestrogens such as tamoxifen, clomifene, fulvestrant, and aromatase inhibitors like anastrozole, and...

Word Count : 279

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