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Oxaliplatin CAS 61825-94-3

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  • Appearance: White flaky solid crystal
  • Assay: 99. 0%min
  • Stock: In stock
  • Sample: Available
  • Zhishang Chemical: Oxaliplatin Supplement

Basic Info of Oxaliplatin

What is Oxaliplatin?

Oxaliplatin, additionally called oxadine and oxalate platinum, is a platinum derivative as well as is scientifically used to deal with people with intestines cancer metastasis after fluorouracil treatment failure. It can be made use of alone or in mix with fluorouracil. The third generation of brand-new platinum-based antitumor compounds after carboplatin is also the only platinum-based medicine with substantial activity on intestines cancer thus far. The principle of action is to hinder DNA synthesis as well as duplication by producing alkylated conjugates on DNA to develop intra- as well as inter-strand crosslinks. It also inhibits spreading of ovarian cancer cells and also melanoma cell lines.

Oxaliplatin (L-OHP) is a platinum-based anticancer medicine marketed after cisplatin and carboplatin. Oxaliplatin blocks its duplication and also transcription through the cross-linking of platinum atoms with DNA chains, consequently producing anticancer medications. energetic. Oxaliplatin has a substantial inhibitory result on various tumor cells such as colon cancer cells, non-small cell lung cancer cells, ovarian cancer and breast cancer cells, as well as has a good enhancement to numerous antitumor medicines such as 5-fluorouracil, paclitaxel, cyclophosphamide, etc or synergy. Compared with cisplatin as well as carboplatin, the poisoning of oxaliplatin to stomach tract, liver, kidney and also bone marrow was dramatically reduced, as well as it was well tolerated.

In August 2002, the U.S. Food and Drug Administration (FDA) accepted the anticancer drug oxaliplatin (Eloxatin) of Sanofi-Straburg for the second-line therapy of metastatic colon cancer. In January 2004, the US Fda (FDA) formally approved the mix of oxaliplatin (Loxadine) for shot with 5-fluorouracil (5FU) as well as leucovorin (LV) (FOLFOX routine) for sophisticated phase First-line therapy of colon cancer. The domestic market is generally monopolized by 3 makers, Sanofi-Aventis (Lexadine), Jiangsu Hengrui Drug Co., Ltd. (Aiheng), and Jiangsu Nanjing Drug Manufacturing Facility (Aobo), occupying more than 85% of the domestic market share.

Oxaliplatin Uses

  1. The third generation platinum complex. An anti-tumor representative with anti-colorectal cancer task. Cytotoxicity follows the formation of DNA adducts. Antitumor.
  2. Oxaliplatin is a platinum-based antineoplastic drug that works by specifically creating DNA adducts in cancer cells, protecting against DNA replication as well as transcription that lead to cell death.
  3. Oxaliplatin is cytotoxic in numerous cell lines consisting of colon, ovarian and also lung cancer cells with IC50 values of 0.5-240, 0.12-19.8 as well as 2.6-6.1 μM, respectively.
  4. Via its general cytotoxic results, oxaliplatin has antitumor task versus advanced intestines cancer cells, normally in combination with fluorouracil as well as leucovorin, referred to as FOLFOX.

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Oxaliplatin Mechanism of Action

Like other platinum drugs, oxaliplatin exerts its cytotoxicity almost by damaging DNA. Oxaliplatin cross-links with DNA through its metabolites in cells to form DNA complexes, thereby terminating the replication of tumor cells and leading to apoptosis. Oxaliplatin induces tumor cell apoptosis by damaging its DNA, inhibiting DNA and RNA synthesis, and triggering the body’s immune response.

On cancer cell chromosomal DNA, but its complexes can also be formed in nucleosomes. In cells, oxaliplatin induces three types of cross-linking.

  • Intra-strand cross-linking of DNA
    Intra-strand crosslinking of DNA means that in base pairing, two G bases form pairings, or less frequently form G-A base pairs instead of normal G-C pairings. Meanwhile, intra-strand cross-linking of DNA appears to be the main mechanism for inducing DNA damage.
  • Cross-linking of DNA strands
    DNA strand crosslinking is thought to be of great importance in the cytotoxicity of cisplatin. DNA cross-linking appears to be less important in the anticancer mechanism of oxaliplatin.
  • DNA-protein cross-linking
    As for DNA-protein cross-linking, although it can denature enzymes and other important proteins in cells, current research has not demonstrated that it can cause cell death.

Oxaliplatin can inhibit DNA synthesis because it is an inhibitor of thymidine synthase itself. Many studies have found that when oxaliplatin and fluorouracil are combined with fluorouracil, the intracellular thymidine synthase is lower than that of single drug. The specific mechanism Not yet known.

There are three mechanisms by which oxaliplatin inhibits RNA transcription:

  • Binding to transcription factors
    During the initiation stage of transcription, platinum-DNA complexes can act as binding sites for transcription factors, thereby preventing the normal binding of transcription factors to promoters.
  • Inhibit RNA polymerase
    Cisplatin can form a complex with some polymerases (such as polymerase II), so that the enzyme cannot enter its active site, thereby inhibiting its action. Oxaliplatin should also have this effect.
  • Involvement in the mechanism of nucleosome-histone-DNA complexes
    Nucleosomal histone-DNA complexes affect the binding of DNA strands to RNA polymerase to prevent its transcription, and oxaliplatin enhances this pathway.

Both animal tumor models and human experiments have found that oxaliplatin can lead to immune death of tumors. After induction of colon cancer in mice, oxaliplatin treatment showed that colon cancer cells send out several immunological signals on their surface before apoptosis. These signals are the product of interferon gamma in T cells and can interact with dendritic cells. Receptor 4 interaction.

The reason for this phenomenon is currently speculated to be that oxaliplatin causes the body’s immune system to respond, thereby secreting anti-tumor antibodies. This is because in animal models deficient in dendritic cell receptor 4 and colon cancer patients, despite oxaliplatin infusion, the immune signal described above was not observed, and these patients had shorter disease-free periods and better overall survival. low, the results were statistically significant.

Preparation of Oxaliplatin

  1. Cis-dichloro(trans-L-1,2-cyclohexanediamine)platinum (II) (3) Under the dark condition, potassium chloroplatinite (20.75g, 0.05mol), 2 (5.7g, 0.05mol) and water (150ml) were stirred at room temperature for 6h, suction filtered, and the filter cake was dried under reduced pressure to obtain yellow solid 3.奥沙利铂的合成路线
  2. Oxaliplatin (1) Potassium oxalate (18.4g, 0.1mol) was dissolved in water (100ml) under stirring, and a solution of silver nitrate (34.0g, 0.2mol) in water (100ml) was added dropwise at room temperature. Continue to stir for 0.5 h, filter with suction, and dry the filter cake under reduced pressure to obtain 5 (27.5 g, 90.5%) as a white solid. 3 (9.5g, 0.025mol), 5 (7.6g, 0.025mol) and water (800ml) were stirred at room temperature for 2h under the dark condition, filtered, the filtrate was concentrated under reduced pressure to 80ml, after cooling, suction filtration, and the filter cake was decompressed Dry to give 1 as a white solid.

Reference

  1. Oxaliplatin – PubChem
  2. Lin Wanlong, Chen Qiang. Pharmacological effects and clinical application of oxaliplatin[J]. Chinese Oncology Clinic, 2000(11):872-874. – ChemicalBook

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