Oxaliplatin

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Oxaliplatin
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Clinical data
Trade namesEloxatin
AHFS/Drugs.comMonograph
MedlinePlusa607035
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Routes of
administration		Intravenous
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Legal status
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Pharmacokinetic data
BioavailabilityComplete
Elimination half-life~10 – 25 minutes[3]
ExcretionKidney
Identifiers
  • [(1R,2R)-cyclohexane-1,2-diamine](ethanedioato-O,O')platinum(II)
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Chemical and physical data
FormulaC8H14N2O4Pt
Molar mass397.294 g·mol−1
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  • O1C(=O)C(=O)O[Pt-2]12[NH2+]C0CCCCC0[NH2+]2
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Oxaliplatin, sold under the brand name Eloxatin among others, is a cancer medication (platinum-based antineoplastic class) used to treat colorectal cancer.[4] It is given by infusion into a vein.[4]

Common side effects include numbness, feeling tired, nausea, diarrhea, and low blood cell counts.[4][5] Other serious side effects include allergic reactions.[5][4] Use in pregnancy is known to harm the baby.[4] Oxaliplatin is in the platinum-based antineoplastic family of medications.[6] It is believed to work by blocking the duplication of DNA.[4]

Oxaliplatin was patented in 1976 in Japan and approved for medical use in 1996 in Europe.[7] It is on the 2023 World Health Organization's List of Essential Medicines.[8]

Medical uses

Oxaliplatin is used for treatment of colorectal cancer, typically along with folinic acid (leucovorin) and fluorouracil in a combination known as FOLFOX[9] or along with capecitabine in a combination known as CAPOX[10] or XELOX.[11] It also has uses in pancreatic cancer[12] and stomach cancer or esophageal cancer.[13] It may also be effective against breast cancer, germ cell tumor, ovarian cancer and non-small-cell lung cancer.[14]

Advanced colorectal cancer

Oxaliplatin by itself has modest activity against advanced colorectal cancer.[15] When compared with just 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.[16]

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.[20]

Oxaliplatin has less ototoxicity and nephrotoxicity than cisplatin and carboplatin.[17]

Structure and mechanism

The compound features a square planar platinum(II) center. In contrast to other drugs of the platinum-based antineoplastic class of drugs cisplatin and carboplatin, oxaliplatin features the bidentate ligand trans-1,2-diaminocyclohexane in place of the two monodentate ammine ligands. It also features a bidentate oxalate group.[6] 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.[23]

According to in vivo studies, oxaliplatin fights carcinoma of the colon through non-targeted 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,[24] which prevent DNA replication and transcription, causing cell death.

History

Oxaliplatin was first synthesized in 1978 at Nagoya City University by Yoshinori Kidani.[25] It was later developed in Europe as a less toxic and more effective alternative to cisplatin. It gained European approval in 1996,[26] and approval by the U.S. Food and Drug Administration in 2002.[27] Generic oxaliplatin was first approved in the United States in August 2009.[28] Patent disputes caused generic production to stop in 2010, but it restarted in 2012.[29][30]

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).[31] 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.[31]

References

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  1. ^ Page Module:Citation/CS1/styles.css has no content."Prescription medicines: registration of new generic medicines and biosimilar medicines, 2017". Therapeutic Goods Administration (TGA). 21 June 2022. Retrieved 30 March 2024.
  2. ^ Page Module:Citation/CS1/styles.css has no content."Eloxatin- oxaliplatin injection, solution, concentrate". DailyMed. 22 October 2019. Retrieved 26 May 2022.
  3. ^ Page Module:Citation/CS1/styles.css has no content.Ehrsson H, Wallin I, Yachnin J (2002). "Pharmacokinetics of oxaliplatin in humans". Medical Oncology. 19 (4): 261–265. doi:10.1385/MO:19:4:261. PMID 12512920. S2CID 1068099.
  4. ^ a b c d e f Page Module:Citation/CS1/styles.css has no content."Oxaliplatin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016.
  5. ^ a b Page Module:Citation/CS1/styles.css has no content.Oun R, Moussa YE, Wheate NJ (May 2018). "The side effects of platinum-based chemotherapy drugs: a review for chemists". Dalton Transactions. 47 (19): 6645–6653. doi:10.1039/c8dt00838h. PMID 29632935.
  6. ^ a b Page Module:Citation/CS1/styles.css has no content.Apps MG, Choi EH, Wheate NJ (August 2015). "The state-of-play and future of platinum drugs". Endocrine-Related Cancer. 22 (4): R219–R233. doi:10.1530/ERC-15-0237. hdl:2123/24426. PMID 26113607.
  7. ^ Page Module:Citation/CS1/styles.css has no content.Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 513. ISBN 9783527607495. Archived from the original on 20 December 2016.
  8. ^ Page Module:Citation/CS1/styles.css has no content.World Health Organization (2023). The selection and use of essential medicines 2023: web annex A: World Health Organization model list of essential medicines: 23rd list (2023). Geneva: World Health Organization. hdl:10665/371090. WHO/MHP/HPS/EML/2023.02.
  9. ^ Page Module:Citation/CS1/styles.css has no content."FOLFOX". National Cancer Institute. 18 September 2009. Retrieved 26 May 2022.
  10. ^ Page Module:Citation/CS1/styles.css has no content."CAPOX". National Cancer Institute. 4 April 2012. Retrieved 26 May 2022.
  11. ^ Page Module:Citation/CS1/styles.css has no content."XELOX". National Cancer Institute. 6 January 2012. Retrieved 26 May 2022.
  12. ^ Page Module:Citation/CS1/styles.css has no content.Conroy T, Desseigne F, Ychou M, Bouché O, Guimbaud R, Bécouarn Y, et al. (May 2011). "FOLFIRINOX versus gemcitabine for metastatic pancreatic cancer". The New England Journal of Medicine. 364 (19): 1817–1825. doi:10.1056/NEJMoa1011923. PMID 21561347.
  13. ^ Page Module:Citation/CS1/styles.css has no content.Cunningham D, Starling N, Rao S, Iveson T, Nicolson M, Coxon F, et al. (January 2008). "Capecitabine and oxaliplatin for advanced esophagogastric cancer". The New England Journal of Medicine. 358 (1): 36–46. doi:10.1056/NEJMoa073149. PMID 18172173.
  14. ^ Page Module:Citation/CS1/styles.css has no content.Townsend D (2007). "Oxaliplatin". xPharm: The Comprehensive Pharmacology Reference. Elsevier. pp. 1–4. doi:10.1016/B978-008055232-3.62973-3. ISBN 9780080552323.
  15. ^ Page Module:Citation/CS1/styles.css has no content.Bécouarn Y, Ychou M, Ducreux M, Borel C, Bertheault-Cvitkovic F, Seitz JF, et al. (August 1998). "Phase II trial of oxaliplatin as first-line chemotherapy in metastatic colorectal cancer patients. Digestive Group of French Federation of Cancer Centers". Journal of Clinical Oncology. 16 (8): 2739–2744. doi:10.1200/JCO.1998.16.8.2739. PMID 9704726.
  16. ^ Page Module:Citation/CS1/styles.css has no content.de Gramont A, Figer A, Seymour M, Homerin M, Hmissi A, Cassidy J, et al. (August 2000). "Leucovorin and fluorouracil with or without oxaliplatin as first-line treatment in advanced colorectal cancer". Journal of Clinical Oncology. 18 (16): 2938–2947. doi:10.1200/JCO.2000.18.16.2938. PMID 10944126.
  17. ^ a b Page Module:Citation/CS1/styles.css has no content.Pasetto LM, D'Andrea MR, Rossi E, Monfardini S (August 2006). "Oxaliplatin-related neurotoxicity: how and why?". Critical Reviews in Oncology/Hematology. 59 (2): 159–168. doi:10.1016/j.critrevonc.2006.01.001. PMID 16806962.
  18. ^ Page Module:Citation/CS1/styles.css has no content.Webster RG, Brain KL, Wilson RH, Grem JL, Vincent A (December 2005). "Oxaliplatin induces hyperexcitability at motor and autonomic neuromuscular junctions through effects on voltage-gated sodium channels". British Journal of Pharmacology. 146 (7): 1027–1039. doi:10.1038/sj.bjp.0706407. PMC 1751225. PMID 16231011.
  19. ^ Page Module:Citation/CS1/styles.css has no content.Gebremedhn EG, Shortland PJ, Mahns DA (April 2018). "The incidence of acute oxaliplatin-induced neuropathy and its impact on treatment in the first cycle: a systematic review". BMC Cancer. 18 (1) 410. doi:10.1186/s12885-018-4185-0. PMC 5897924. PMID 29649985.
  20. ^ a b Page Module:Citation/CS1/styles.css has no content.Chay WY, Chew L, Yeoh TT, Tan MH (May 2010). "An association between transient hypokalemia and severe acute oxaliplatin-related toxicity predominantly in women". Acta Oncologica. 49 (4): 515–517. doi:10.3109/02841860903464015. PMID 20092386. S2CID 33026126.
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  23. ^ Page Module:Citation/CS1/styles.css has no content.Johnstone TC (January 2014). "The Crystal Structure of Oxaliplatin: A Case of Overlooked Pseudo Symmetry". Polyhedron. 67: 429–435. doi:10.1016/j.poly.2013.10.003. PMC 3885251. PMID 24415827.
  24. ^ Page Module:Citation/CS1/styles.css has no content.Graham J, Mushin M, Kirkpatrick P (January 2004). "Oxaliplatin". Nature Reviews. Drug Discovery. 3 (1): 11–12. doi:10.1038/nrd1287. PMID 14756144.
  25. ^ Page Module:Citation/CS1/styles.css has no content.Pizarro AM, Barry NP, Sadler PJ (2013). "3.25 - Metal–DNA Coordination Complexes". Comprehensive Inorganic Chemistry II (2nd ed.). Elsevier. pp. 751–784. doi:10.1016/B978-0-08-097774-4.00330-2. ISBN 9780080965291.
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  29. ^ Page Module:Citation/CS1/styles.css has no content."Hospira Announces U.S. Re-Launch Of Generic Oxaliplatin Injection" (Press release). Archived from the original on 24 September 2015. Retrieved 25 August 2015.
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Further reading

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