Oxaliplatin

Source: Wikipedia, the free encyclopedia.

Oxaliplatin
Clinical data
Trade namesEloxatin
AHFS/Drugs.comMonograph
MedlinePlusa607035
License data
Intravenous
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityComplete
Elimination half-life~10 – 25 minutes[4]
ExcretionKidney
Identifiers
  • [(1R,2R)-cyclohexane-1,2-diamine](ethanedioato-O,O')platinum(II)
JSmol)
  • O1C(=O)C(=O)O[Pt-2]12[NH2+]C0CCCCC0[NH2+]2
 ☒NcheckY (what is this?)  (verify)

Oxaliplatin, sold under the brand name Eloxatin among others, is a

injection into a vein.[5]

Common side effects include

allergic reactions.[6][5] Use in pregnancy is known to harm the baby.[5] Oxaliplatin is in the platinum-based antineoplastic family of medications.[7] It is believed to work by blocking the duplication of DNA.[5]

Oxaliplatin was patented in 1976 in Japan and approved for medical use in 1996 in Europe.[8] It is on the 2023 World Health Organization's List of Essential Medicines.[9]

Medical uses

Oxaliplatin is used for treatment of

XELOX.[12] It may also be effective against breast cancer, germ cell tumor, ovarian cancer, non-small-cell lung cancer, and pancreatic cancer.[13]

Advanced colorectal cancer

Oxaliplatin by itself has modest activity against advanced colorectal cancer.

5-fluorouracil and folinic acid administered according to the de Gramont regimen, a FOLFOX4 regime produced no significant increase in overall survival, but did produce an improvement in progression-free survival, the primary end-point of the phase III randomized trial.[15]

Adverse effects

Side-effects of oxaliplatin treatment can potentially include:

In addition, some patients may experience an allergic reaction to platinum-containing drugs. This is more common in women.[19]

Oxaliplatin has less ototoxicity and nephrotoxicity than cisplatin and carboplatin.[16]

Structure and mechanism

The compound features a

trans-1,2-diaminocyclohexane in place of the two monodentate ammine ligands. It also features a bidentate oxalate group.[7] The three-dimensional structure of the molecule has been elucidated by X-ray crystallography, although the presence of pseudosymmetry in the crystal structure has caused confusion in its interpretation.[22]

According to

cytotoxic effects. Like other platinum compounds, its cytotoxicity is thought to result from inhibition of DNA synthesis in cells. In particular, oxaliplatin forms both inter- and intra-strand cross links in DNA,[23]
which prevent DNA replication and transcription, causing cell death.

History

Oxaliplatin was first synthesized in 1978 at

U.S. Food and Drug Administration in 2002.[26] Generic oxaliplatin was first approved in the United States in August 2009.[27] Patent disputes caused generic production to stop in 2010, but it restarted in 2012.[28][29]

Patent information

Eloxatin was covered by patent numbers 5338874 (expired 7 April 2013), 5420319 (expired 8 August 2016), 5716988 (expired 7 August 2015) and 5290961 (expired 12 January 2013) (see Electronic Orange Book patent info for Eloxatin).[30] Exclusivity code I-441, which expired on 4 November 2007, is for use combination with infusional 5-FU/LV for adjuvant treatment stage III colon cancer patients who have undergone complete resection primary tumor-based on improvement in disease free survival with no demonstrated benefit overall survival after 4 years. Exclusivity code NCE, New Chemical Entity, expired on 9 August 2007.[30]

References

  1. FDA
    . Retrieved 22 October 2023.
  2. ^ "Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  3. ^ "Eloxatin- oxaliplatin injection, solution, concentrate". DailyMed. 22 October 2019. Retrieved 26 May 2022.
  4. S2CID 1068099
    .
  5. ^ a b c d e f "Oxaliplatin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  6. ^
    PMID 29632935
    .
  7. ^
    PMID 26113607
    .
  8. ISBN 9783527607495. Archived
    from the original on 20 December 2016.
  9. hdl:10665/371090
    . WHO/MHP/HPS/EML/2023.02.
  10. ^ "FOLFOX". National Cancer Institute. 18 September 2009. Retrieved 26 May 2022.
  11. ^ "CAPOX". National Cancer Institute. 4 April 2012. Retrieved 26 May 2022.
  12. ^ "XELOX". National Cancer Institute. 6 January 2012. Retrieved 26 May 2022.
  13. ISBN 9780080552323
    .
  14. PMID 9704726
    .
  15. PMID 10944126
    .
  16. ^
    PMID 16806962
    .
  17. PMID 16231011
    .
  18. PMID 29649985
    .
  19. ^
    S2CID 33026126
    .
  20. ^ "Oxaliplatin Side Effects". Drugs.com. Archived from the original on 5 September 2014. Retrieved 5 September 2014.
  21. ^ "Eloxatin information". mein.sanofi.de (in German). Archived from the original on 27 August 2016. Retrieved 15 June 2016.
  22. PMID 24415827
    .
  23. PMID 14756144
    .
  24. ISBN 9780080965291
    .
  25. ISBN 978-0-323-04971-9
    .
  26. ^ "Eloxatin FDA Approval History". Drugs.com.
  27. ^ "Generic Eloxatin availability". Drugs.com. Archived from the original on 7 June 2013. Retrieved 19 April 2014.
  28. ^ "Hospira Announces U.S. Re-Launch Of Generic Oxaliplatin Injection" (Press release). Archived from the original on 24 September 2015. Retrieved 25 August 2015.
  29. ^ "Top 10 best-selling cancer drugs: Eloxatin–$1.2 billion". FiercePharma. 15 May 2012. Archived from the original on 21 April 2014. Retrieved 20 April 2014.
  30. ^ a b "Patent and Exclusivity Search Results from query on Appl No 021759 Product 001 in the OB_Rx list". Orange Book. U.S. Food and Drug Administrartion. Archived from the original on 26 September 2007.. Accessed on: 22 July 2007.

Further reading

External links
Retrieved from "https://en.wikipedia.org/w/index.php?title=Oxaliplatin&oldid=1216587740"