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Oxaliplatin
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<h2 id="medical-uses">Medical uses</h2> <p>Oxaliplatin is used for treatment of <a href="/facts/Colorectal_cancer/nV592sW7">colorectal cancer</a>, typically along with <a href="/facts/Folinic_acid/SPubEUDE">folinic acid</a> (leucovorin) and <a href="/facts/Fluorouracil/6xH4uUaf">fluorouracil</a> in a combination known as <a href="/facts/FOLFOX/dKVtRr3C">FOLFOX</a><a class="footnote-ref" id="fnref:12" href="#fn:12"><sup>12</sup></a> or along with <a href="/facts/Capecitabine/EF5GmqBc">capecitabine</a> in a combination known as <a href="/facts/CAPOX/2PbElkWH">CAPOX</a><a class="footnote-ref" id="fnref:13" href="#fn:13"><sup>13</sup></a> or <a href="/facts/XELOX/2PbElkWH">XELOX</a>.<a class="footnote-ref" id="fnref:14" href="#fn:14"><sup>14</sup></a> It also has uses in <a href="/facts/Pancreatic_cancer/6h9GIInW">pancreatic cancer</a><a class="footnote-ref" id="fnref:15" href="#fn:15"><sup>15</sup></a> and <a href="/facts/Stomach_cancer/HJjYtkqS">stomach cancer</a> or <a href="/facts/Esophageal_cancer/vN32X3uc">esophageal cancer</a>.<a class="footnote-ref" id="fnref:16" href="#fn:16"><sup>16</sup></a> It may also be effective against <a href="/facts/Breast_cancer/6hME580v">breast cancer</a>, <a href="/facts/Germ_cell_tumor/GUT0PtFk">germ cell tumor</a>, <a href="/facts/Ovarian_cancer/fsWbh3Tn">ovarian cancer</a> and <a href="/facts/Non-small-cell_lung_cancer/9T47knRp">non-small-cell lung cancer</a>.<a class="footnote-ref" id="fnref:17" href="#fn:17"><sup>17</sup></a> </p> <h3>Advanced colorectal cancer</h3> <p>Oxaliplatin by itself has modest activity against advanced colorectal cancer.<a class="footnote-ref" id="fnref:18" href="#fn:18"><sup>18</sup></a> When compared with just <a href="/facts/5-fluorouracil/6xH4uUaf">5-fluorouracil</a> and <a href="/facts/Folinic_acid/SPubEUDE">folinic acid</a> administered according to the de Gramont regimen, a FOLFOX4 regime produced no significant increase in overall survival, but did produce an improvement in <a href="/facts/Progression-free_survival/6SIDoGTV">progression-free survival</a>, the primary end-point of the phase III randomized trial.<a class="footnote-ref" id="fnref:19" href="#fn:19"><sup>19</sup></a> </p> <h2 id="adverse-effects">Adverse effects</h2> <p>Side-effects of oxaliplatin treatment can potentially include: </p> <ul><li><a href="/facts/Neurotoxicity/FrgTICfX">Neurotoxicity</a> leading to <a href="/facts/Chemotherapy-induced_peripheral_neuropathy/xyAXlJNX">chemotherapy-induced peripheral neuropathy</a>, a progressive, enduring and often irreversible tingling numbness, intense pain and hypersensitivity to cold, beginning in the hands and feet and sometimes involving the arms and legs, often with deficits in <a href="/facts/Proprioception/Ik79bA2x">proprioception</a>.<a class="footnote-ref" id="fnref:20" href="#fn:20"><sup>20</sup></a> This chronic neuropathy may also be preceded by a transient acute neuropathy occurring at the time of infusion and associated with excitation of <a href="/facts/Sodium_channel/pXb4n2Vz">voltage-gated Na+ channels</a>.<a class="footnote-ref" id="fnref:21" href="#fn:21"><sup>21</sup></a><a class="footnote-ref" id="fnref:22" href="#fn:22"><sup>22</sup></a></li> <li><a href="/facts/Fatigue_(physical)/C2oo4Hvg">Fatigue</a></li> <li><a href="/facts/Nausea/dyhkcbeD">Nausea</a>, <a href="/facts/Vomiting/R2vQkHqV">vomiting</a>, or <a href="/facts/Diarrhea/6TBHaRdA">diarrhea</a></li> <li><a href="/facts/Neutropenia/qasEurVu">Neutropenia</a> (low number of a type of <a href="/facts/White_blood_cell/vsDunUK0">white blood cells</a>)</li> <li><a href="/facts/Ototoxicity/yXsCQ00n">Ototoxicity</a> (hearing loss)</li> <li><a href="/facts/Extravasation/ht89d2LM">Extravasation</a> if oxaliplatin leaks from the infusion vein it may cause severe damage to the connective tissues.</li> <li><a href="/facts/Hypokalemia/XvS1S7s6">Hypokalemia</a> (low blood potassium), which is more common in women than men<a class="footnote-ref" id="fnref:23" href="#fn:23"><sup>23</sup></a></li> <li>Persistent <a href="/facts/Hiccups/dTyQsvSn">hiccups</a><a class="footnote-ref" id="fnref:24" href="#fn:24"><sup>24</sup></a></li> <li><a href="/facts/Rhabdomyolysis/Cs08YHfR">Rhabdomyolysis</a><a class="footnote-ref" id="fnref:25" href="#fn:25"><sup>25</sup></a></li></ul> <p>In addition, some patients may experience an <a href="/facts/Allergy/dYAVosh8">allergic reaction</a> to platinum-containing drugs. This is more common in women.<a class="footnote-ref" id="fnref:26" href="#fn:26"><sup>26</sup></a> </p><p>Oxaliplatin has less ototoxicity and <a href="/facts/Nephrotoxicity/QaWn5pwB">nephrotoxicity</a> than cisplatin and carboplatin.<a class="footnote-ref" id="fnref:27" href="#fn:27"><sup>27</sup></a> </p> <h2 id="structure-and-mechanism">Structure and mechanism</h2> <p>The compound features a <a href="/facts/Square_planar/2mLqCvd0">square planar</a> platinum(II) center. In contrast to other drugs of the <a href="/facts/Platinum-based_antineoplastic/eg5qQtd7">platinum-based antineoplastic</a> class of drugs <a href="/facts/Cisplatin/eXLc7Fzw">cisplatin</a> and <a href="/facts/Carboplatin/7o4Blex0">carboplatin</a>, oxaliplatin features the <a href="/facts/Bidentate/hJF1lAJz">bidentate</a> ligand <a href="/facts/Trans-1%2c2-diaminocyclohexane/4RdP3xSm"><i>trans</i>-1,2-diaminocyclohexane</a> in place of the two <a href="/facts/Denticity/hJF1lAJz">monodentate</a> ammine <a href="/facts/Ligand/6etB3qeW">ligands</a>. It also features a bidentate <a href="/facts/Oxalate/u0Gdem0A">oxalate</a> group.<a class="footnote-ref" id="fnref:28" href="#fn:28"><sup>28</sup></a> The three-dimensional structure of the molecule has been elucidated by <a href="/facts/X-ray_crystallography/WtI0F5DN">X-ray crystallography</a>, although the presence of pseudosymmetry in the crystal structure has caused confusion in its interpretation.<a class="footnote-ref" id="fnref:29" href="#fn:29"><sup>29</sup></a> </p><p>According to <i><a href="/facts/In_vivo/kWcWyl6f">in vivo</a></i> studies, oxaliplatin fights <a href="/facts/Carcinoma/NE9UY4VB">carcinoma</a> of the <a href="/facts/Colon_(anatomy)/vQtlNBv9">colon</a> through non-targeted <a href="/facts/Cytotoxic/SQuTTLoL">cytotoxic</a> effects. Like other platinum compounds, its cytotoxicity is thought to result from inhibition of <a href="/facts/DNA_synthesis/ywV1plto">DNA synthesis</a> in cells. In particular, oxaliplatin forms both inter- and intra-strand cross links in DNA,<a class="footnote-ref" id="fnref:30" href="#fn:30"><sup>30</sup></a> which prevent DNA replication and transcription, causing cell death. </p> <h2 id="history">History</h2> <p>Oxaliplatin was first synthesized in 1978 at <a href="/facts/Nagoya_City_University/TzofWVbg">Nagoya City University</a> by Yoshinori Kidani.<a class="footnote-ref" id="fnref:31" href="#fn:31"><sup>31</sup></a> It was later developed in Europe as a less toxic and more effective alternative to cisplatin. It gained European approval in 1996,<a class="footnote-ref" id="fnref:32" href="#fn:32"><sup>32</sup></a> and approval by the <a href="/facts/Food_and_Drug_Administration_(United_States)/rCEnh9WB">U.S. Food and Drug Administration</a> in 2002.<a class="footnote-ref" id="fnref:33" href="#fn:33"><sup>33</sup></a> <a href="/facts/Generic_drug/IF6AXDVX">Generic</a> oxaliplatin was first approved in the United States in August 2009.<a class="footnote-ref" id="fnref:34" href="#fn:34"><sup>34</sup></a> Patent disputes caused generic production to stop in 2010, but it restarted in 2012.<a class="footnote-ref" id="fnref:35" href="#fn:35"><sup>35</sup></a><a class="footnote-ref" id="fnref:36" href="#fn:36"><sup>36</sup></a> </p> <h2 id="patent-information">Patent information</h2> <p>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).<a class="footnote-ref" id="fnref:37" href="#fn:37"><sup>37</sup></a> 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.<a class="footnote-ref" id="fnref:38" href="#fn:38"><sup>38</sup></a> </p> <h2 id="further-reading">Further reading</h2> <ul><li>Graham J, Mushin M, Kirkpatrick P (January 2004). <a href="https://web.archive.org/web/20041108160042/http://www.dresources.com/nature/ntr_0104.pdf">"Oxaliplatin"</a> (PDF). <i>Nature Reviews. Drug Discovery</i>. 3 (1): 11–12. <a href="/facts/Doi_(identifier)/muM9Etpq">doi</a>:<a href="https://doi.org/10.1038%2Fnrd1287">10.1038/nrd1287</a>. <a href="/facts/PMID_(identifier)/JlHAvMHt">PMID</a> <a href="https://pubmed.ncbi.nlm.nih.gov/14756144">14756144</a>. Archived from <a href="http://www.dresources.com/nature/ntr_0104.pdf">the original</a> (PDF) on 8 November 2004. Retrieved 19 July 2005.</li></ul> <h2 id="external-links">External links</h2> <ul><li><a href="https://www.cancer.gov/about-cancer/treatment/drugs/oxaliplatin">"Oxaliplatin"</a>. <i>National Cancer Institute</i>. 5 October 2006.</li></ul> <h2 id="references">References</h2> <ol> <li id="fn:1"><p>"Oxaliplatin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016. <a href="https://www.drugs.com/monograph/oxaliplatin.html" target="_blank">https://www.drugs.com/monograph/oxaliplatin.html</a> <a href="#fnref:1" class="footnote-back-ref">↩</a></p></li> <li id="fn:2"><p>"Oxaliplatin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016. <a href="https://www.drugs.com/monograph/oxaliplatin.html" target="_blank">https://www.drugs.com/monograph/oxaliplatin.html</a> <a href="#fnref:2" class="footnote-back-ref">↩</a></p></li> <li id="fn:3"><p>"Oxaliplatin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016. <a href="https://www.drugs.com/monograph/oxaliplatin.html" target="_blank">https://www.drugs.com/monograph/oxaliplatin.html</a> <a href="#fnref:3" class="footnote-back-ref">↩</a></p></li> <li id="fn:4"><p>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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:4" class="footnote-back-ref">↩</a></p></li> <li id="fn:5"><p>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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:5" class="footnote-back-ref">↩</a></p></li> <li id="fn:6"><p>"Oxaliplatin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016. <a href="https://www.drugs.com/monograph/oxaliplatin.html" target="_blank">https://www.drugs.com/monograph/oxaliplatin.html</a> <a href="#fnref:6" class="footnote-back-ref">↩</a></p></li> <li id="fn:7"><p>"Oxaliplatin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016. <a href="https://www.drugs.com/monograph/oxaliplatin.html" target="_blank">https://www.drugs.com/monograph/oxaliplatin.html</a> <a href="#fnref:7" class="footnote-back-ref">↩</a></p></li> <li id="fn:8"><p>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. <a href="https://doi.org/10.1530%2FERC-15-0237" target="_blank">https://doi.org/10.1530%2FERC-15-0237</a> <a href="#fnref:8" class="footnote-back-ref">↩</a></p></li> <li id="fn:9"><p>"Oxaliplatin". The American Society of Health-System Pharmacists. Archived from the original on 21 December 2016. Retrieved 8 December 2016. <a href="https://www.drugs.com/monograph/oxaliplatin.html" target="_blank">https://www.drugs.com/monograph/oxaliplatin.html</a> <a href="#fnref:9" class="footnote-back-ref">↩</a></p></li> <li id="fn:10"><p>Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 513. ISBN 9783527607495. Archived from the original on 20 December 2016. <a href="9783527607495" target="_blank">9783527607495</a> <a href="#fnref:10" class="footnote-back-ref">↩</a></p></li> <li id="fn:11"><p>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. <a href="/wiki/World_Health_Organization" target="_blank">/wiki/World_Health_Organization</a> <a href="#fnref:11" class="footnote-back-ref">↩</a></p></li> <li id="fn:12"><p>"FOLFOX". National Cancer Institute. 18 September 2009. Retrieved 26 May 2022. <a href="https://www.cancer.gov/about-cancer/treatment/drugs/folfox" target="_blank">https://www.cancer.gov/about-cancer/treatment/drugs/folfox</a> <a href="#fnref:12" class="footnote-back-ref">↩</a></p></li> <li id="fn:13"><p>"CAPOX". National Cancer Institute. 4 April 2012. Retrieved 26 May 2022. <a href="https://www.cancer.gov/about-cancer/treatment/drugs/capox" target="_blank">https://www.cancer.gov/about-cancer/treatment/drugs/capox</a> <a href="#fnref:13" class="footnote-back-ref">↩</a></p></li> <li id="fn:14"><p>"XELOX". National Cancer Institute. 6 January 2012. Retrieved 26 May 2022. <a href="https://www.cancer.gov/about-cancer/treatment/drugs/xelox" target="_blank">https://www.cancer.gov/about-cancer/treatment/drugs/xelox</a> <a href="#fnref:14" class="footnote-back-ref">↩</a></p></li> <li id="fn:15"><p>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. <a href="https://doi.org/10.1056%2FNEJMoa1011923" target="_blank">https://doi.org/10.1056%2FNEJMoa1011923</a> <a href="#fnref:15" class="footnote-back-ref">↩</a></p></li> <li id="fn:16"><p>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. <a href="https://doi.org/10.1056%2FNEJMoa073149" target="_blank">https://doi.org/10.1056%2FNEJMoa073149</a> <a href="#fnref:16" class="footnote-back-ref">↩</a></p></li> <li id="fn:17"><p>Townsend D (2007). "Oxaliplatin". xPharm: The Comprehensive Pharmacology Reference. Elsevier. pp. 1–4. doi:10.1016/B978-008055232-3.62973-3. ISBN 9780080552323. <a href="9780080552323" target="_blank">9780080552323</a> <a href="#fnref:17" class="footnote-back-ref">↩</a></p></li> <li id="fn:18"><p>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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:18" class="footnote-back-ref">↩</a></p></li> <li id="fn:19"><p>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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:19" class="footnote-back-ref">↩</a></p></li> <li id="fn:20"><p>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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:20" class="footnote-back-ref">↩</a></p></li> <li id="fn:21"><p>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. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1751225" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1751225</a> <a href="#fnref:21" class="footnote-back-ref">↩</a></p></li> <li id="fn:22"><p>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. <a href="https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5897924" target="_blank">https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5897924</a> <a href="#fnref:22" class="footnote-back-ref">↩</a></p></li> <li id="fn:23"><p>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. <a href="https://doi.org/10.3109%2F02841860903464015" target="_blank">https://doi.org/10.3109%2F02841860903464015</a> <a href="#fnref:23" class="footnote-back-ref">↩</a></p></li> <li id="fn:24"><p>"Oxaliplatin Side Effects". Drugs.com. Archived from the original on 5 September 2014. Retrieved 5 September 2014. <a href="https://www.drugs.com/sfx/oxaliplatin-side-effects.html" target="_blank">https://www.drugs.com/sfx/oxaliplatin-side-effects.html</a> <a href="#fnref:24" class="footnote-back-ref">↩</a></p></li> <li id="fn:25"><p>"Eloxatin information". mein.sanofi.de (in German). Archived from the original on 27 August 2016. Retrieved 15 June 2016. <a href="https://mein.sanofi.de/produkte/Eloxatin/Downloads?id=dafcc9b3-4397-4205-aeb3-581a3fa90edd" target="_blank">https://mein.sanofi.de/produkte/Eloxatin/Downloads?id=dafcc9b3-4397-4205-aeb3-581a3fa90edd</a> <a href="#fnref:25" class="footnote-back-ref">↩</a></p></li> <li id="fn:26"><p>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. <a href="https://doi.org/10.3109%2F02841860903464015" target="_blank">https://doi.org/10.3109%2F02841860903464015</a> <a href="#fnref:26" class="footnote-back-ref">↩</a></p></li> <li id="fn:27"><p>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. <a href="/wiki/Doi_(identifier)" target="_blank">/wiki/Doi_(identifier)</a> <a href="#fnref:27" class="footnote-back-ref">↩</a></p></li> <li id="fn:28"><p>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. <a href="https://doi.org/10.1530%2FERC-15-0237" target="_blank">https://doi.org/10.1530%2FERC-15-0237</a> <a href="#fnref:28" class="footnote-back-ref">↩</a></p></li> <li id="fn:29"><p>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. 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