Oxaliplatin

Specifications / Handling

More Information
Product Details
Synonyms	1-OHP; ACT 078; RP 54780; NSC 266046; Diaminocyclohexane oxalatoplatinum
Product Type	Chemical
Properties
Formula	C₈H₁₄N₂O₄Pt
MW	397.3
Merck Index	14: 6912
CAS	61825-94-3
RTECS	TP2275850
Purity Chemicals	≥98% (¹H-NMR)
Appearance	White to off-white powder.
Solubility	Soluble in DMSO (20mg/ml)* or water (2mg/ml). Slightly soluble in methanol. Insoluble in ethanol.
Identity	Determined by ¹H-NMR.
Other Product Data	*Solvent Note: Even though Oxaliplatin is soluble in DMSO, the use of DMSO to dissolve Oxaliplatin in biological studies is not recommended. The DMSO was found to insert itself into the ligand, resulting in loss of activity (see M.D. Hall, et al.; 2014).
InChi Key	ZROHGHOFXNOHSO-USPAICOZSA-L
Smiles	O=C1O[Pt]2(N[C@H]3CCCC[C@@H]3N2)OC1=O
Shipping and Handling
Shipping	AMBIENT
Short Term Storage	+4°C
Long Term Storage	-20°C
Handling Advice	Keep cool and dry. Protect from light and moisture.
Use/Stability	Stable for at least 2 years after receipt when stored at -20°C.
Documents
MSDS	Download PDF
Product Specification Sheet
Datasheet	Download PDF

Product-specific References

Description

Potent platinum-based antineoplastic agent with wide spectrum anticancer activity [2, 7-9].
Anticancer compound. Forms inter- and intrastrand DNA adducts/crosslinks, consequently blocking DNA replication and transcription and inducing cell death [1, 4, 7, 10, 13].
Shows antitumor activity in cisplatin resistant cell lines [3, 8].
Shows better biochemical, pharmacological and cytotoxic properties than cisplatin (Prod. No. AG-CR1-3590) and carboplatin (Prod. No. AG-CR1-3591) [5, 7, 8].
Apoptosis inducer [10, 11].
Targets other proteins and enzymes [6].
Anticancer activity and antitumor specificity depends on selective uptake through human organic cation transporters 1 (OCT1) and OCT2 [12].
Neurotoxic profile depends on organic cation transporter 2 (OCT2) uptake [14].

Product References

Cytotoxicity, cellular accumulation and DNA binding of oxaliplatin isomers: L. Pendyala, et al.; Cancer Lett. 97, 177 (1995)
Oxaliplatin: mechanism of action and antineoplastic activity: E. Raymond, et al.; Semin. Oncol. 25, 4 (1998) (Review)
Induction of JNK and c-Abl signalling by cisplatin and oxaliplatin in mismatch repair-proficient and -deficient cells: A Nehme, et al.; Br. J. Cancer 79, 1104 (1999)
Oxaliplatin-induced damage of cellular DNA: J.M. Woynarowski, et al.; Mol. Pharmacol. 58, 920 (2000)
What is the "best" platinum: cisplatin, carboplatin, or oxaliplatin? J. Lokich; Cancer Invest. 19, 756 (2001)
Biomolecular targets for platinum antitumor drugs: R.N. Bose; Mini Rev. Med. Chem. 2, 103 (2002)
Cellular and molecular aspects of drugs of the future: oxaliplatin: A.M. Di Francesco, et al.; Cell. Mol. Life Sci. 59, 1914 (2002) (Review)
Cellular and molecular pharmacology of oxaliplatin: E. Raymond, et al.; Mol. Cancer Ther. 1, 227 (2002)
New clues for platinum antitumor chemistry: Kinetically controlled metal binding to DNA: J. Reedijk; PNAS 100, 3611 (2003)
DNA strand breaks and apoptosis induced by oxaliplatin in cancer cells: S. Faivre, et al.; Biochem. Pharmacol. 66, 225 (2003)
Apoptosis induced by oxaliplatin in human colon cancer HCT15 cell line: P. Marchetti, et al.; Anticancer Res. 24, 219 (2004)
Organic cation transporters are determinants of oxaliplatin cytotoxicity: S. Zhang, ;et al.; Cancer Res. 66, 8847 (2006)
Inhibition of transcription by platinum antitumor compounds: R.C. Todd & S.J. Lippard; Metallomics 1, 280 (2009) (Review)
Oxaliplatin-induced neurotoxicity is dependent on the organic cation transporter OCT2: J.A. Sprowl, et al.; PNAS 110, 11199 (2013)
Say No to DMSO: Dimethylsulfoxide Inactivates Cisplatin, Carboplatin and Other Platinum Complexes: M.D. Hall, et al.; Cancer Res. 74, 3913 (2014)

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