Eloxatin (TN)

Base Information

• Chemical Name: Eloxatin (TN)
• CAS No.: 61825-94-3
• Molecular Formula: C8H14N2O4Pt
• Molecular Weight: 397.29
• Hs Code.: 28439000
• UNII: 04ZR38536J
• Wikidata: Q422327
• Metabolomics Workbench ID: 145264
• Mol file: 61825-94-3.mol

Synonyms:Eloxatin (TN);(1R,2R)-cyclohexane-1,2-diamine;oxalate;platinum(2+);Xaliplatin;JM-83;Oxaliplatin (TN);Medac (TN);Oxaliplatin (Eloxatin);OXALIPLATIN [MI];OXALIPLATIN [INN];OXALIPLATIN [JAN];OXALIPLATIN [USAN];Xelox component oxaliplatin;D0Y3ME;Folfox component oxaliplatin;OXALIPLATIN [VANDF];SCHEMBL4859;OXALIPLATIN [MART.];OXALIPLATIN [USP-RS];OXALIPLATIN [WHO-DD];Oxaliplatin (JAN/USP/INN);Oxaliplatin (JAN/USAN/INN);OXALIPLATIN [EP IMPURITY];OXALIPLATIN [ORANGE BOOK];OXALIPLATIN [EP MONOGRAPH];OXALIPLATIN [USP MONOGRAPH];s1224;AKOS015920125;CCG-264868;MBP-426 (LIPOSOMAL OXALIPLATIN);O0372;SW219151-1;D01790;AB01568250_01;(trans-1,2-Cyclohexanediamine)oxalatoplatinum(II);A833434;Q422327;METHYL-2-N-(ACETYLAMINO)-DIMETHYLPHOSPHONOACETATE;OXALATO[(1R-TRANS)-1,2-CYCLOHEXANEDIAMINE]PLATINUM(II);PLATINUM, ((1R,2R)-1,2-CYCLOHEXANEDIAMINE-.KAPPA.N,.KAPPA.N')(ETHANEDIOATO(2-)-.KAPPA.O1,.KAPPA.O2)-, (SP-4-2)-

Chemical Property of Eloxatin (TN)

Chemical Property:

• Appearance/Colour: White crystalline solid
• Boiling Point: 193.6oC at 760 mmHg
• Flash Point: 75oC
• PSA: 104.64000
• LogP: 0.61450
• Storage Temp.: Store at +4°C
• Solubility.: Slightly soluble in water, very slightly soluble in methanol, practically insoluble in anhydrous ethanol.
• Water Solubility.: Soluble in water with heating and/or sonication
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 397.060151
• Heavy Atom Count: 15
• Complexity: 124

Purity/Quality:

99.0%, ^*data from raw suppliers

trans-L-Diaminocyclohexane oxalatoplatinum ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn, Xi
• Hazard Codes: Xn,Xi
• Statements: 36/37/38-40-42/43
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CCC(C(C1)N)N.C(=O)(C(=O)[O-])[O-].[Pt+2]
• Isomeric SMILES: C1CC[C@H]([C@@H](C1)N)N.C(=O)(C(=O)[O-])[O-].[Pt+2]
• Recent ClinicalTrials: XELOX III. Xeloda in Combination With Eloxatin for Patients With Advanced or Metastatic Colorectal Cancer
• Description: 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.
• Uses: 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

Technology Process of Eloxatin (TN)

There total 41 articles about Eloxatin (TN) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 67.0%

cis-diacetato-trans-l-diaminocyclohexane platinum(II) + potassium oxalate (583-52-8) → oxaliplatin (61825-94-3)

Guidance literature:

In water; at 60 - 70 ℃; for 5 - 6h; Product distribution / selectivity; Heating / reflux;

Reference yield: 67.0%

cis-diacetato-trans-l-1,2-diaminocyclohexane platinum(II) + potassium oxalate (583-52-8) → oxaliplatin (61825-94-3)

Guidance literature:

In water; for 5 - 6h; Product distribution / selectivity; Heating / reflux;

Reference yield: 62.9%

oxalic acid (144-62-7,97993-78-7) → oxaliplatin (61825-94-3)

Guidance literature:

(1R,2R)-1,2-diaminocyclohexanedichloroplatinum(II); With water; silver nitrate; at 20 - 45 ℃; for 2.08333h;

oxalic acid; With potassium hydroxide; In water; at 20 ℃; for 4h; pH=2.9; Product distribution / selectivity;

upstream raw materials:

(1R,2R)-1,2-diaminocyclohexanedichloroplatinum(II)

bis(tetrabutylammonium)oxalate

oxalic acid

potassium oxalate

Downstream raw materials:

cis-oxalic acid (trans-1,2-cyclohexanediamine)dihydroxyplatinum(II)

5'-AGU-3'

Refernces

• 1、 Williams, Kevin M.,Poynter, Amy D.,Hendrie, Jonathan D.,Jackson, Daniel C.,Martin, Virginia K.. "Comparison of N-acetylmethionine reactivity between oxaliplatin and an oxaliplatin derivative with chiral (S,S) amine nitrogen atoms". . p. 64 - 69. Retrieved 2013.
• 2、 Tolan, Dina,Almotairy, Awatif Rashed Z.,Howe, Orla,Devereux, Michael,Montagner, Diego,Erxleben, Andrea. "Cytotoxicity and ROS production of novel Pt(IV)oxaliplatin derivatives with indole propionic acid". . p. 262 - 267. Retrieved 2019.
• 3、 Chen, Shu,Deng, Zhiqin,Hirao, Hajime,Li, Cai,Wang, Zhigang,Xu, Zoufeng,Yao, Houzong,Zhou, Qiyuan,Zhu, Guangyu. "An intramolecular photoswitch can significantly promote photoactivation of Pt(iv) prodrugs". . p. 6536 - 6542. Retrieved 2021/05/31.
• 4、 Tolan, Dina A.,Abdel-Monem, Yasser K.,El-Nagar, Mohamed A.. "Anti-tumor platinum (IV) complexes bearing the anti-inflammatory drug naproxen in the axial position". . . Retrieved 2019/01/16.