Oxaliplatin (Eloxatin; L-OHP; JM-83; RP-54780; SR-96669)

Alias: L-OHP; diaminocyclohexane oxalatoplatinum; oxalatoplatin; oxalatoplatinum; US brand name: Eloxatin Foreign brand names: Dacotin; Dacplat; Eloxatine; Abbreviations: 1OHP; LOHP; Code names: JM83; RP54780; SR96669.
Cat No.:V0057 Purity: ≥98%
Oxaliplatin (Eloxatin; L-OHP; JM83; RP54780; SR96669),an anticancer drug used for treating colorectal cancer,is an organoplatinum complex (1,2-diaminocyclohexane (DACH) and with an oxalate ligand), acnting by inhibiting DNA synthesis by forming DNA adducts in RT4, TCCSUP, A2780, HT-29, U-373MG, U-87MG, SK-MEL-2, and HT-144 cells.
Oxaliplatin (Eloxatin; L-OHP; JM-83; RP-54780; SR-96669) Chemical Structure CAS No.: 61825-94-3
Product category: DNA(RNA) Synthesis
This product is for research use only, not for human use. We do not sell to patients.
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Purity & Quality Control Documentation

Purity: ≥98%

Product Description

Oxaliplatin (Eloxatin; L-OHP; JM83; RP54780; SR96669), an anticancer drug used for treating colorectal cancer, is an organoplatinum complex (1,2-diaminocyclohexane (DACH) and with an oxalate ligand), acnting by inhibiting DNA synthesis by forming DNA adducts in RT4, TCCSUP, A2780, HT-29, U-373MG, U-87MG, SK-MEL-2, and HT-144 cells. As a leaving group, an oxalate ligand and DACH form a complex with the platinum atom of oxaliplatin. Once the labile oxalate ligand has left the group, active oxaliplatin derivatives, like monoaquo and diaquo DACH platinum, alkylate macromolecules to form inter- and intra-strand platinum-DNA crosslinks. These crosslinks inhibit DNA replication and transcription and cause non-specific cytotoxicity that is specific to the cell cycle.

Biological Activity I Assay Protocols (From Reference)
Targets
DNA synthesis
ln Vitro

Oxaliplatin's primary mode of action is mediated by the creation of DNA adducts. Cell death is caused by primary and secondary DNA lesions induced by oxaliplatin. Oxaliplatin has an IC50 of 0.98 mM and 0.14 mM, respectively, against the human melanoma cell lines C32 and G361. With IC50 values of 11 μM, 15 μM, 0.17 μM, 0.97 μM, 2.95 μM, 17.6 μM, 30.9 μM, and 7.85 μM, respectively, Oxaliplatin effectively inhibits the bladder carcinoma cell lines RT4 and TCCSUP, ovarian carcinoma cell line A2780, colon carcinoma cell line HT-29, glioblastoma cell lines U-373MG and U-87MG, and melanoma cell lines SK-MEL-2 and HT-144.

ln Vivo
Oxaliplatin, administered intraperitoneally (i.p.) once a week at a dose of 10 mg/kg, dramatically lowers the tumor volume and apoptotic index in nude mice with hepatocellular HCCLM3 tumors. T-leukemia-lymphoma L40 AKR response to Oxaliplatin (5 mg/kg, i.v. on days 1, 5, and 9) is 1.77 T/C. Additionally, Oxaliplatin works well on xenografts of B16 melanoma, MA 16-C melanoma, Lewis lung xenografts, C26 colon carcinoma, and intracerebrally grafted L1210 leukemia. n mice, Oxaliplatin causes impairment of retrograde neuronal transport.
Cell Assay
The sulforhodamine-B microculture colorimetrie assay is used to conduct the cytotoxicity investigations. The sulforhodamine-B test is typically conducted 48 hours after the cells (RT4, TCCSUP, A2780, HT-29, U-373MG, U-87MG, SK-MEL-2, and HT-144 cell lines) are plated into 96-well plates on day 0 and exposed to oxaliplatin on day 1. Except for when adding oxaliplatin and during the final assay period, the plates are always incubated at 37 °C in 5% CO2 and 100% relative humidity. The assay started with 2–20 × 103 cells/50 nL/well plated on a slide. On the day of the assay, the cells in control wells must still be in the log phase of growth; the maximum absorbance for the untreated controls must fall between 1.0 and 1.5; and the cells must undergo more than two doublings during the drug exposure. These criteria are based on pilot studies. A concentration is made up of eight wells. Using an IBM PC-compatible computer as the interface, a Biotek Instruments model EL309 microplate reader is used to read the plates at 570–540 nm. The computer program DATALOG transfers the data and converts it into a LOTUS 1-2-3 format. The drug treated and control are compared to determine the survival fractions.
Animal Protocol
Dissolved in water; 10 mg/kg; i.p. injection.
Human hepatocellular carcinoma xenografts HCCLM3
References

[1]. Oxaliplatin: a review of preclinical and clinical studies. Ann Oncol. 1998 Oct;9(10):1053-71.

[2]. 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]. In vitro cytotoxicity, protein binding, red blood cell partitioning, and biotransformation of oxaliplatin. Cancer Res. 1993 Dec 15;53(24):5970-6.

[4]. Oxaliplatin induces apoptosis in hepatocellular carcinoma cells and inhibits tumor growth. Expert Opin Investig Drugs. 2009 Nov;18(11):1595-604.

[5]. 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]. 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]. 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]. Comparative proteomic analysis of colon cancer cells in response to oxaliplatin treatment. Biochim Biophys Acta. 2009 Oct;1794(10):1433-40.

[9]. Capecitabine, Oxaliplatin, and Bevacizumab (BCapOx) Regimen for Metastatic Colorectal Cancer. Hosp Pharm. 2017 May;52(5):341-347.

These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Molecular Formula
C8H14N2O4PT
Molecular Weight
397.29
Exact Mass
397.06
Elemental Analysis
C, 24.19; H, 3.55; N, 7.05; O, 16.11; Pt, 49.10
CAS #
61825-94-3
Appearance
White solid powder
SMILES
C1CC[C@H]([C@@H](C1)[NH-])[NH-].C(=O)(C(=O)O)O.[Pt+2]
InChi Key
DRMCATBEKSVAPL-BNTLRKBRSA-N
InChi Code
InChI=1S/C6H12N2.C2H2O4.Pt/c7-5-3-1-2-4-6(5)8;3-1(4)2(5)6;/h5-8H,1-4H2;(H,3,4)(H,5,6);/q-2;;+2/t5-,6-;;/m1../s1
Chemical Name
[(1R,2R)-2-azanidylcyclohexyl]azanide;oxalic acid;platinum(2+)
Synonyms
L-OHP; diaminocyclohexane oxalatoplatinum; oxalatoplatin; oxalatoplatinum; US brand name: Eloxatin Foreign brand names: Dacotin; Dacplat; Eloxatine; Abbreviations: 1OHP; LOHP; Code names: JM83; RP54780; SR96669.
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
DMSO: <1 mg/mL
Water: <1 mg/mL
Ethanol: <1 mg/mL
Preparing Stock Solutions 1 mg 5 mg 10 mg
1 mM 2.5171 mL 12.5853 mL 25.1705 mL
5 mM 0.5034 mL 2.5171 mL 5.0341 mL
10 mM 0.2517 mL 1.2585 mL 2.5171 mL

*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.

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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT01061515 Active
Recruiting
Drug: Bevacizumab
Drug: Capecitabine
Carcinoma Washington University School
of Medicine
May 10, 2011 Phase 1
NCT03451331 Active
Recruiting
Drug: Oxaliplatin
Drug: Carboplatin
Metastatic Urothelial Cancer Matthew Galsky May 10, 2018 Phase 2
NCT03153280 Active
Recruiting
Drug: Lithium
Drug: Oxaliplatin
Colorectal Neoplasms
Stomach Neoplasm
Cancer Trials Ireland January 13, 2022 Phase 1
NCT03255434 Active
Recruiting
Drug: Oxaliplatin
Drug: Oxaliplatin LBM
Stage III Colon Cancer Institut du Cancer de Montpellier
- Val d'Aurelle
November 1, 2017 Phase 2
NCT03567629 Active
Recruiting
Drug: Irinotecan
Drug: Oxaliplatin
mCRC Peking University May 29, 2018 Phase 2
Biological Data
  • 6-Mercaptopurine (6-MP) Monohydrate(1)

    Oxaliplatin: Western blot analysis of survivin expression in untreated (A) and Oxaliplatin treated (B) HCT 116 whole cell lysates. Note down regulation of survivin expression in lane B. Antibody tested: survivin (D-8).
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