(1R,2R)-cyclohexane-1,2-diamine; 1,3-dioxa-2-platinacyclopentane-4,5-dione

• ChemBase ID: 72580
• Molecular Formular: C8H14N2O4Pt
• Molecular Mass: 397.28576
• Monoisotopic Mass: 397.06014794
• SMILES: [Pt]1OC(=O)C(=O)O1.C1CC[C@H]([C@@H](C1)N)N
• Canonical SMILES: O=C1O[Pt]OC1=O.N[C@@H]1CCCC[C@H]1N
• 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

NAMES AND DATABASE IDS

Names

• IUPAC name: (1R,2R)-cyclohexane-1,2-diamine; 1,3-dioxa-2-platinacyclopentane-4,5-dione
• IUPAC Traditional name: (1R,2R)-cyclohexane-1,2-diamine; 1,3-dioxa-2-platinacyclopentane-4,5-dione
• Synonyms: Oxaliplatin; Eloxatin; [SP-4-2-(1R-trans)]-(1,2-Cyclohexanediamine-N,N′)[ethanedioata(2--)-O,O’]platinum; Oxaliplatin; Oxaliplatin

Database IDs

• CAS Number: 61825-94-3
• MDL Number: MFCD00866327
• PubChem SID: 162037505
• PubChem CID: 5310940

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -4.8559394
• LogD (pH = 7.4): -2.7383268
• Log P: -0.007973737
• Molar Refractivity: 33.952 cm^3
• Polarizability: 14.118806 Å^3
• Polar Surface Area: 52.04 Å^2
• Rotatable Bonds: 0
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Apperance: solid

Safety Information

• Storage Condition: -20°C
• RTECS: TP2275850
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 36/37/38-40-42/43
• Safety Statements: 26-36
• GHS Pictograms: GHS07; GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H317-H319-H335-H351
• GHS Precautionary statements: P261-P280-P305 + P351 + P338
• Personal Protective Equipment: Eyeshields, Faceshields, full-face particle respirator type N100 (US), Gloves, respirator cartridge type N100 (US), type P1 (EN143) respirator filter, type P3 (EN 143) respirator cartridges
• Storage Temperature: 2-8°C

Pharmacology Properties

• Target: DNA/RNA synthesis

Product Information

• Purity: 95+%
• Salt Data: Free Base
• Empirical Formula (Hill Notation): C8H14N2O4Pt

DETAILS

Selleck Chemicals - S1224

Research Area: Cancer
Biological Activity:
Oxaliplatin (Eloxatin) is a 1,2-diaminocyclohexane (DACH) carrier ligand-based groups of platinum antitumor agent with IC50 of median 1.3, 6.2 and 1.5 mM for SW480 DLD1, HT29, respectively. Cytotoxicity of platinum agents is believed to result from the formation of platinum-DNA adducts. Eukaryotic cells respond to the presence of oxaliplatin adducts in DNA by activating signal transduction pathways that result in cell cycle arrest, an increase in DNA repair activity and apoptosis. Oxaliplatin was found to be active against C32 and G361 cell lines with IC50 values of 49.48 and 9.07 μM (1 h exposure), 9.47 and 1.30 μM (4 h exposure), and 0.98 and 0.14 μM (24 h exposure), respectively. [1][2][3]

Sigma Aldrich - O9512

Frequently Asked Questions
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Biochem/physiol Actions
Oxaliplatin is an anti-tumor agent with activity against colorectal cancer; cytotoxicity follows the formation of adducts with DNA.

REFERENCES

• Nehmé A et al. Br J Cancer. 1999 Mar;79