Tamoxifen

Tamoxifen
Clinical data
Trade namesNolvadex, Genox, Tamifen, others[1]
Other namesTMX; ICI-46474
AHFS/Drugs.comMonograph
MedlinePlusa682414
License data
Pregnancy
category
Routes of
administration		By mouth
Drug classSelective estrogen receptor modulator
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability~100%[5][6]
Protein binding>99% (albumin)[5][7]
MetabolismLiver (CYP3A4, CYP2C9, CYP2D6)[5][12][8]
Metabolites• N-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
  • (Z)-2-[4-(1,2-Diphenylbut-1-enyl)phenoxy]-N,N-dimethylethanamine
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
PDB ligand
CompTox Dashboard (EPA)
ECHA InfoCard100.031.004 Edit this at Wikidata
Chemical and physical data
FormulaC26H29NO
Molar mass371.524 g·mol−1
3D model (JSmol)
  • CN(C)CCOc1ccc(cc1)/C(c2ccccc2)=C(/CC)c3ccccc3
  • 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.