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Pharmaceutical drug From Wikipedia, the free encyclopedia
Oxaliplatin, sold under the brand name Eloxatin among others, is a cancer medication (platinum-based antineoplastic class) used to treat colorectal cancer.[5] It is given by infusion into a vein.[5]
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| Clinical data | |
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| Trade names | Eloxatin |
| AHFS/Drugs.com | Monograph |
| MedlinePlus | a607035 |
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| Routes of administration | Intravenous |
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| Pharmacokinetic data | |
| Bioavailability | Complete |
| Elimination half-life | ~10 – 25 minutes[4] |
| Excretion | Kidney |
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| DrugBank | |
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| PDB ligand | |
| CompTox Dashboard (EPA) | |
| ECHA InfoCard | 100.150.118 |
| Chemical and physical data | |
| Formula | C8H14N2O4Pt |
| Molar mass | 397.294 g·mol−1 |
| 3D model (JSmol) | |
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Common side effects include numbness, feeling tired, nausea, diarrhea, and low blood cell counts.[5][6] Other serious 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]
Oxaliplatin is used for treatment of colorectal cancer, typically along with folinic acid (leucovorin) and fluorouracil in a combination known as FOLFOX[10] or along with capecitabine in a combination known as CAPOX[11] or XELOX.[12] It also has uses in pancreatic cancer[13] and stomach cancer or esophageal cancer.[14] It may also be effective against breast cancer, germ cell tumor, ovarian cancer and non-small-cell lung cancer.[15]
Oxaliplatin by itself has modest activity against advanced colorectal cancer.[16] 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.[17]
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.[21]
Oxaliplatin has less ototoxicity and nephrotoxicity than cisplatin and carboplatin.[18]
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.[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.[24]
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,[25] which prevent DNA replication and transcription, causing cell death.
Oxaliplatin was first synthesized in 1978 at Nagoya City University by Yoshinori Kidani.[26] It was later developed in Europe as a less toxic and more effective alternative to cisplatin. It gained European approval in 1996,[27] and approval by the U.S. Food and Drug Administration in 2002.[28] Generic oxaliplatin was first approved in the United States in August 2009.[29] Patent disputes caused generic production to stop in 2010, but it restarted in 2012.[30][31]
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).[32] 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.[32]
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