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Oxaliplatin

CAT: 0804-HY-17371-02Size: 50 mgDry Ice: NoHazardous: No
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CAT#:0804-HY-17371-02Size:50 mg
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Description
Oxaliplatin is a DNA synthesis inhibitor. Oxaliplatin causes DNA crosslinking damage, prevents DNA replication and transcription and induces apoptosis. Oxaliplatin can be used for cancer research[1][2][3].
CAS Number
61825-94-3
UNSPSC
12352101
Hazard Statement
H315, H317, H319, H335, H351
Target
Apoptosis; DNA/RNA Synthesis
Type
Reference compound
Related Pathways
Apoptosis; Cell Cycle/DNA Damage
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/Oxaliplatin.html
Purity
99.86
Solubility
DMF : 1.67 mg/mL (ultrasonic) |DMSO : 20.83 mg/mL (ultrasonic; warming) |H2O : 2.17 mg/mL (ultrasonic; warming; heat to 60°C)
Smiles
O=C(O1)C(O[Pt]21[NH2][C@@H]3CCCC[C@H]3[NH2]2)=O
Molecular Formula
C8H14N2O4Pt
Molecular Weight
397.29
Precautions
H315, H317, H319, H335, H351
References & Citations
[1]Raymond E, et al. Oxaliplatin: a review of preclinical and clinical studies. Ann Oncol. 1998 Oct;9 (10) :1053-71.|[2]Mohammed MQ, et al. Oxaliplatin is active in vitro against human melanoma cell lines: comparison with NSC 119875 and NSC 241240. Anticancer Drugs. 2000 Nov;11 (10) :859-63.|[3]Pendyala L, et al. In vitro cytotoxicity, protein binding, red blood cell partitioning, and biotransformation of oxaliplatin. Cancer Res. 1993 Dec 15;53 (24) :5970-6.|[4]Wang Z, et al. Oxaliplatin induces apoptosis in hepatocellular carcinoma cells and inhibits tumor growth. Expert Opin Investig Drugs. 2009 Nov;18 (11) :1595-604|[5]Mathé G, et al. Oxalato-platinum or 1-OHP, a third-generation platinum complex: an experimental and clinical appraisal and preliminary comparison with cis-platinum. Biomed Pharmacother. 1989;43 (4) :237-50.|[6]Schellingerhout D, et al. Impairment of retrograde neuronal transport in oxaliplatin-induced neuropathy demonstrated by molecular imaging. PLoS One. 2012;7 (9) :e45776. doi: 10.1371/journal.pone.0045776. Epub 2012 Sep 20.|[7]Park GY, et al. Phenanthriplatin, a monofunctional DNA-binding platinum anticancer drug candidate with unusual potency and cellular activity profile. Proc Natl Acad Sci U S A. 2012 Jul 24;109 (30) :11987-92.|[8]Yi Yao, et al. Comparative proteomic analysis of colon cancer cells in response to oxaliplatin treatment. Biochim Biophys Acta. 2009 Oct;1794 (10) :1433-40.|[9]Garrett MJ, et, al. Capecitabine, Oxaliplatin, and Bevacizumab (BCapOx) Regimen for Metastatic Colorectal Cancer. Hosp Pharm. 2017 May;52 (5) :341-347.
Shipping Conditions
Room Temperature
Storage Conditions
4°C (Powder, protect from light)
Scientific Category
Reference compound1
Clinical Information
Launched

Chemical Information

Oxaliplatin

Oxaliplatin is a platinum-based chemotherapy drug in the same family as cisplatin and carboplatin. Compared to cisplatin the two amine groups are replaced by diamino cyclohexane (DACH) group to provide a greater antitumor effect. However, this leads to poorer water solubility, which was compensated by the addition of the chloride moieties. Due to this chemical moiety, oxaliplatin readily undergoes non-enzymatic biotransformation, thus complicating oxaliplatin's pharmacokinetics. Like most platinum-based compounds, oxaliplatin's mechanism of action is primarily through DNA damage through DNA crosslinking, particularly intrastrand and interstrand crosslinking. However, due to the structure of oxaliplatin, its adducts make the binding of mismatch repair protein to DNA harder compared to cisplatin or carboplatin's adducts, resulting in greater cytotoxic effects. The DACH moiety also prevents cross-resistance with cisplatin and carboplatin. Although oxaliplatin has been investigated as a monotherapy, it is typically administered in combination with fluorouracil and leucovorin, known as the FOLFOX regimen, for the treatment of colorectal cancer. This is an effective combination treatment both as a first-line treatment and in patients refractory to an initial fluorouracil and leucovorin combination. Ongoing trials have also shown promising results for oxaliplatin use in nonHodgkin’s lymphoma, breast cancer, mesothelioma, and non-small cell lung cancer. Oxaliplatin was approved by the FDA on January 9, 2004 and is currently marketed by Sanofi-Aventis under the trademark Eloxatin®.

CAS Number61825-94-3
PubChem CID9887054
IUPAC Nameoxalate;platinum(2+);trans-(1R,2R)-cyclohexane-1,2-diamine
Molecular FormulaC8H14N2O4Pt
Molecular Weight397.29
Topological Polar Surface Area132
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count0
Heavy Atom Count15
Formal Charge0
Complexity123
SMILES
C1CC[C@H]([C@@H](C1)N)N.C(=O)(C(=O)[O-])[O-].[Pt+2]
InChI
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
Chemical Structure
2D Structure
2D structure of Oxaliplatin
CAS: 61825-94-3
CID: 9887054
Formula: C8H14N2O4Pt
MW: 397.29
Interactive 3D Structure
Loading 3D structure...
Computed Properties
PropertyValue
Molecular Weight397.29
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count6
Rotatable Bond Count0
Exact Mass397.060151
Monoisotopic Mass397.060151
Topological Polar Surface Area132 Ų
Heavy Atom Count15
Formal Charge0
Complexity123
Isotope Atom Count0
Defined Atom Stereocenter Count2
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count3
Compound Is CanonicalizedYes

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