Oxaliplatin

• CAT Number: A001065
• CAS Number: 61825-94-3
• Molecular Formula: C8H14N2O4Pt
• Molecular Weight: 397.3
• Purity: ≥95%
• Target: DNA Synthesis
• Solubility: Limited solubility
• Storage: -20°C
• InChI: 1S/C6H14N2.C2H2O4.Pt/c7-5-3-1-2-4-6(5)8;3-1(4)2(5)6;/h5-6H,1-4,7-8H2;(H,3,4)(H,5,6);/q;;+2/p-2/t5-,6-;;/m1../s1
• InChIKey: ZROHGHOFXNOHSO-BNTLRKBRSA-L
• SMILES: C1CCC(C(C1)N)N.C(=O)(C(=O)[O-])[O-].[Pt+2]

Oxaliplatin is an organoplatinum complex in which the platinum atom is complexed with 1,2-diaminocyclohexane (DACH) and with an oxalate ligand as a /’leaving group./’ A /’leaving group/’ is an atom or a group of atoms that is displaced as a stable species taking with it the bonding electrons. After displacement of the labile oxalate ligand leaving group, active oxaliplatin derivatives, such as monoaquo and diaquo DACH platinum, alkylate macromolecules, forming both inter- and intra-strand platinum-DNA crosslinks, which result in inhibition of DNA replication and transcription and cell-cycle nonspecific cytotoxicity. The DACH side chain appears to inhibit alkylating-agent resistance. Check for active clinical trials or closed clinical trials using this agent. (NCI Thesaurus)

Reference

1: van Berlo-van de Laar IRF, Brummelhuis WJ, Imholz ALT, Schellens JH, Huitema
ADR, Jansman FGA. Dosing oxaliplatin in a haemodialysis patient with metastatic
rectum cancer monitored by free platinum concentrations. J Clin Pharm Ther. 2018
Jan 5. doi: 10.1111/jcpt.12661. [Epub ahead of print] PubMed PMID: 29315736.

2: Viatchenko-Karpinski V, Ling J, Gu JG. Down-regulation of Kv4.3 channels and
a-type K(+) currents in V2 trigeminal ganglion neurons of rats following
oxaliplatin treatment. Mol Pain. 2018 Jan-Dec;14:1744806917750995. doi:
10.1177/1744806917750995. PubMed PMID: 29313436.

3: Saeki H, Emi Y, Oki E, Tokunaga S, Kakeji Y, Akagi Y, Baba H, Baba E, Maehara
Y; Kyushu Study group of Clinical Cancer (KSCC). Study protocol of a phase II
clinical trial (KSCC1501A) examining oxaliplatin + S-1 for treatment of
HER2-negative advanced/recurrent gastric cancer previously untreated with
chemotherapy. BMC Cancer. 2018 Jan 8;18(1):57. doi: 10.1186/s12885-017-3937-6.
PubMed PMID: 29310611.

4: Pereira AF, de Oliveira FFB, de Freitas Alves BW, de Menezes KLS, de Mesquita
AKV, Lisboa MRP, de Sousa KKO, Vale ML. Neurotoxic effect of oxaliplatin:
Comparison with its oxalate-free analogue
cis-[PtII(1R,2R-DACH)(3-acetoxy-1,1-cyclobutanedicarboxylato)] (LLC-1402) in
mice. Toxicol Appl Pharmacol. 2018 Jan 4. pii: S0041-008X(18)30001-2. doi:
10.1016/j.taap.2018.01.001. [Epub ahead of print] PubMed PMID: 29307816.

5: Bullock A, Stuart K, Jacobus S, Abrams T, Wadlow R, Goldstein M, Miksad R.
Capecitabine and oxaliplatin as first and second line treatment for locally
advanced and metastatic pancreatic ductal adenocarcinoma. J Gastrointest Oncol.
2017 Dec;8(6):945-952. doi: 10.21037/jgo.2017.06.06. PubMed PMID: 29299353;
PubMed Central PMCID: PMC5750180.

6: Shen Y, Li C, Liu W, Mao W, Qian H, Wang H, Xu Q. Clinical Analysis of
Hypersensitivity Reactions to Oxaliplatin among Colorectal Cancer Patients. Oncol
Res. 2018 Jan 2. doi: 10.3727/096504017X15139039328978. [Epub ahead of print]
PubMed PMID: 29295722.

7: Ando H, Abu Lila AS, Tanaka M, Doi Y, Terada Y, Yagi N, Shimizu T, Okuhira K,
Ishima Y, Ishida T. Intratumoral visualization of oxaliplatin within a liposomal
formulation using X-ray fluorescence spectrometry. Mol Pharm. 2017 Dec 29. doi:
10.1021/acs.molpharmaceut.7b00762. [Epub ahead of print] PubMed PMID: 29287147.

8: Curtis SA, Curtis BR, Lee AI, Hendrickson JE, Lacy J, Podoltsev NA. A patient
with oxaliplatin immune-induced syndrome (OIIS) who also developed leucovorin and
palonosetron-associated thrombocytopenia. Hematology. 2017 Dec 28:1-4. doi:
10.1080/10245332.2017.1419600. [Epub ahead of print] PubMed PMID: 29281948.

9: Chukyo A, Chiba T, Kambe T, Yamamoto K, Kawakami K, Taguchi K, Abe K.
Oxaliplatin-induced changes in expression of transient receptor potential
channels in the dorsal root ganglion as a neuropathic mechanism for cold
hypersensitivity. Neuropeptides. 2017 Dec 15. pii: S0143-4179(17)30226-3. doi:
10.1016/j.npep.2017.12.002. [Epub ahead of print] PubMed PMID: 29274843.

10: Chocry M, Leloup L, Kovacic H. Reversion of resistance to oxaliplatin by
inhibition of p38 MAPK in colorectal cancer cell lines: involvement of the
calpain / Nox1 pathway. Oncotarget. 2017 Oct 10;8(61):103710-103730. doi:
10.18632/oncotarget.21780. eCollection 2017 Nov 28. PubMed PMID: 29262595; PubMed
Central PMCID: PMC5732761.