- Product Name:
- trans-l-diaminocyclohexane oxalatoplatinum
- Product Categories:
- Intermediates & Fine Chemicals
- Pharmaceutical material and intermeidates
- Active Pharmaceutical Ingredients
- chemical reaction,pharm,electronic,materials
- Mol File:
Oxaliplatin Chemical Properties
- +74.5-78.0 (D/20)(c=0.5,H2O)
- storage temp.
- Slightly soluble in water, very slightly soluble in methanol, practically insoluble in anhydrous ethanol.
- Water Solubility
- Soluble in water with heating and/or sonication
- Stable. Store cool. Incompatible with oxidizing agents.
- CAS DataBase Reference
- Language:English Provider:SigmaAldrich
Oxaliplatin Usage And Synthesis
Indications and Usage
Oxaliplatin, also called Eloxatin or Eloxatine, is a platinum derivative.
Used clinically to treat patients with metastatic colorectal cancer after failure of fluorouracil treatment, can be used alone or in combination with 5-fluorouracil. It is the third-generation platinum antitumor compound after cisplatin and carboplatin, and so far the only platinum-based drug with significant effectiveness against colorectal cancer. It also inhibits proliferation of ovarian cancer and melanoma cell lines.
Mechanisms of Action
Acts on DNA through production of alkylating conjugates, inhibiting its synthesis and reproduction by forming interchain and intrachain cross-links.
- Hematopoietec system: Oxaliplatin has a certain blood toxicity. When used alone, it can cause the following adverse effects: anemia, leukopenia, neutropenia, thrombocytopenia, sometimes reaching grade 3 or 4. Increases hematologic toxicities such as neutropenia and thrombocytopenia when combined with 5-fluorouracil.
- Digestive system: can cause nausea, vomiting, and diarrhea when used alone. These symptoms can sometimes be very serious. These side effects are significantly exacerbated when used in combination with 5-fluorouacil. Use of prophylactic and/or therapeutic antiemetic drugs is recommended.
- Nervous system: Peripheral sensory neuropathy characterized by peripheral neuritis. Sometimes associated with convulsions and sensory disturbances in the mouth, upper respiratory tract, and upper GI tract.
Oxaliplatin is a platinum-containing DNA-crosslinking agent. It induces the formation of DNA inter- and intrastrand crosslinks and DNA-protein crosslinks, inhibits DNA and RNA synthesis, and induces apoptosis in cancer cells. Oxaliplatin is cytotoxic to cisplatin-sensitive A2780(1A9) and KB-3-1 cells and cisplatin-resistant A2780-E(80) and KB-CP20 cells (IC50s = 0.12, 0.39, 4.7, and 2.7 μM, respectively). It reduces tumor growth in an HCCLM3 mouse xenograft model when administered at doses of 5 or 10 mg/kg once per week. Formulations containing oxaliplatin have been used in the treatment of advanced colorectal cancer and as an adjuvant in stage III colon cancer.
Eloxatin was launched in France for second-line treatment of metastatic colorectal cancer. Oxaliplatin is a second generation platinum drug prepared in three steps from either k2tCl4 or K2Ptl4. It has an antitumor spectrum similar to cisplatin, however, it is more effective against L1210 leukemia and cisplatin resistant L1210. It is also effective against B16 melanoma but has a dose limiting toxicity of peripheral sensory neuropathy that is reversible upon cessation of the drug. The (R,R)- enantiomer has greater activity than the (S,S)-isomer but this is tumor line dependent, e.g., there was no difference found for P-388 or Sarcoma 180. Clinical drug administration based on circadium timing showed it was better tolerated when given 16 h after the onset of light. Oxaliplatin binds to guanineN7 and can lead to bidentate chelation that results in the bending of DNA. This feature is recognized by high mobility group proteins (HMG) which impedes repair reactions and stops replication and transcription.
White Crystalline Solid
Third generation platinum complex. An antitumor agent with activity against colorectal cancer. Cytotoxicity follows the formation of adducts with DNA. Antineoplastic.
A potent anti-neoplastic agent that binds to DNA and shows efficacy in Cisplatin resistant cell lines
Oxaliplatin is a platinum-based antineoplastic agent that functions by forming DNA adducts specifically in cancer cells, preventing DNA replication and transcription which leads to cell death. Oxaliplatin has cytotoxic effects in a broad range of cell lines, including colon, ovarian, and lung cancer, with IC50 values ranging from 0.5-240, 0.12-19.8, and 2.6-6.1 μM, respectively. Through its general cytotoxic effects, oxaliplatin has anti-tumor activity against advanced colorectal cancer and is typically administered with fluorouracil and leucovorin in a combination known as FOLFOX.
A antitumor agent with activity against colorectal cancer. Cytotoxicity follows the formation of adducts with DNA
Eloxatin (Sanofi Aventis).
Oxaliplatin is available in 50- and 100-mg vials for IV administrationin the treatment of ovarian cancer, metastaticcolorectal cancer, and early stage colon cancer in combinationwith 5-fluorouracil/leucovorin. The activation of theagent occurs in low-chloride environments to give theaquated species, which subsequently reacts with DNA in amanner similar to cisplatin. The mechanisms of resistance aresimilar for the two agents; however, oxaliplatin is not recognizedby MMR enzymes and does not show cross-resistancewith cisplatin. The agent is widely distributed, highly proteinbound (85%–88%), and irreversibly binds to erythrocytes.Numerous metabolites have been identified many of whichare produced as a result of nonenzymatic processes and includechloro-, dichloro-, monoaquo-, and diaquo-species.The parent and metabolites are eliminated primarily in theurine with a long terminal elimination half-life of 240 hours.Neurotoxicity is dose limiting and normally presents as peripheralneuropathy, which may be exacerbated by exposureto low temperatures. The neurotoxicity is normally reversiblein contrast to that seen with cisplatin, which may be irreversible.Other adverse effects include nausea, vomiting, diarrhea,myelosuppression, and hypersensitivity reactions.Ototoxicity and renal toxicity occur only rarely in contrast tocisplatin.
Antitumor agent that forms platinum-DNA adducts. Causes intra- and interstrand DNA crosslinks blocking DNA replication and transcription. Displays higher cytotoxicity and lower nephrotoxicity than analog cisplatin (cis-Diaminodichloroplatinum ) and shows antitumor activity in cell lines with acquired cisplatin resistance.
Oxaliplatin a platinum analogue, causes DNA damage and cell death by binding to DNA and forming inter and intrastrand crosslinks preventing replication and transcription. Oxaliplatin is an anti-tumor agent with activity against colorectal cancer; cytotoxicity follows the formation of adducts with DNA. Oxaliplatin is an approved drug for treating colorectal cancer. It is an active ingredient in FOLFOX (Folinic acid:5-FU:oxaliplatin in the ratio 1:10:1 of micromolar concentrations respectively). Oxaliplatin causes both acute and chronic neurotoxicity in patients in a dose dependent manner and is reversible either by reducing or stopping the drug.
A poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx and Pt.
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- Oxaliplatin impurity D
- Methyl D-(-)-4-hydroxy-phenylglycinate
- Oxalic acid dihydrate
- OXALIPLATIN IMPURITY D
- Oxaliplatin for Injection
- OXALIPLATIN IMPURITY C
- OXALIPLATIN IMPURITY B
- (1,2-Cyclohexanediamine)hydroxy platinum