Oxaliplatin
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MedKoo CAT#: 100680

CAS#: 61825-94-3

Description: 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.


Chemical Structure

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Oxaliplatin
CAS# 61825-94-3

Theoretical Analysis

MedKoo Cat#: 100680
Name: Oxaliplatin
CAS#: 61825-94-3
Chemical Formula: C8H14N2O4Pt
Exact Mass:
Molecular Weight: 397.29
Elemental Analysis: C, 24.19; H, 3.55; N, 7.05; O, 16.11; Pt, 49.10

Price and Availability

Size Price Availability Quantity
100.0mg USD 110.0 Same day
200.0mg USD 140.0 Same day
500.0mg USD 160.0 Same day
1.0g USD 210.0 Same day
2.0g USD 390.0 Same day
5.0g USD 680.0 Same day
10.0g USD 1250.0 Same day
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Synonym: diaminocyclohexane oxalatoplatinum; oxalatoplatin; oxalatoplatinum; US brand name: Eloxatin Foreign brand names: Dacotin; Dacplat; Eloxatine; Abbreviations: 1OHP; LOHP; Code names: JM83; RP54780; SR96669.

IUPAC/Chemical Name: [(1R,2R)-cyclohexane-1,2-diamine](ethanedioato-O,O')platinum(II)

InChi Key: ZROHGHOFXNOHSO-UHFFFAOYSA-L

InChi Code: 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

SMILES Code: O=C1[O-][Pt+2]2([O-]C1=O)[NH2]C3CCCCC3[NH2]2

Appearance: white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in water at 4 mg/mL and DMSO at 20 mg/mL; slightly soluble in methanol; insoluble in ethanol.

Shelf Life: >10 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 397.29 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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1: Ye F, Liu Z, Tan A, Liao M, Mo Z, Yang X. XRCC1 and GSTP1 polymorphisms and prognosis of oxaliplatin-based chemotherapy in colorectal cancer: a meta-analysis. Cancer Chemother Pharmacol. 2013 Mar;71(3):733-40. doi: 10.1007/s00280-012-2067-8. Epub 2013 Jan 9. Review. PubMed PMID: 23299794.

2: Leon-Ferre RA, Abu Hejleh TB, Halfdanarson TR. Extravasation of oxaliplatin into the mediastinum: a case report and review of the literature. Clin Adv Hematol Oncol. 2012 Aug;10(8):546-8. Review. PubMed PMID: 23073056.

3: Di Francia R, Siesto RS, Valente D, Spart D, Berretta M. Pharmacogenomics panel test for prevention toxicity in patient who receive Fluoropirimidine/Oxaliplatin-based therapy. Eur Rev Med Pharmacol Sci. 2012 Sep;16(9):1211-7. Review. PubMed PMID: 23047504.

4: Niu J, Mims MP. Oxaliplatin-induced thrombotic thrombocytopenic purpura: case report and literature review. J Clin Oncol. 2012 Nov 1;30(31):e312-4. doi: 10.1200/JCO.2012.42.5082. Epub 2012 Sep 17. Review. PubMed PMID: 22987080.

5: Prochilo T, Abeni C, Bertocchi P, Zaniboni A. Oxaliplatin-induced lung toxicity. Case report and review of the literature. Curr Drug Saf. 2012 Apr;7(2):179-82. Review. PubMed PMID: 22873503.

6: Wu Z, Ouyang J, He Z, Zhang S. Infusion of calcium and magnesium for oxaliplatin-induced sensory neurotoxicity in colorectal cancer: a systematic review and meta-analysis. Eur J Cancer. 2012 Aug;48(12):1791-8. doi: 10.1016/j.ejca.2012.03.018. Epub 2012 Apr 28. Review. PubMed PMID: 22542974.

7: Jardim DL, Rodrigues CA, Novis YA, Rocha VG, Hoff PM. Oxaliplatin-related thrombocytopenia. Ann Oncol. 2012 Aug;23(8):1937-42. doi: 10.1093/annonc/mds074. Epub 2012 Apr 25. Review. PubMed PMID: 22534771.

8: Femia G, Hardy TA, Spies JM, Horvath LG. Posterior reversible encephalopathy syndrome following chemotherapy with oxaliplatin and a fluoropyrimidine: a case report and literature review. Asia Pac J Clin Oncol. 2012 Jun;8(2):115-22. doi: 10.1111/j.1743-7563.2012.01544.x. Review. PubMed PMID: 22524570.

9: Vietor NO, George BJ. Oxaliplatin-induced hepatocellular injury and ototoxicity: a review of the literature and report of unusual side effects of a commonly used chemotherapeutic agent. J Oncol Pharm Pract. 2012 Sep;18(3):355-9. doi: 10.1177/1078155212437901. Epub 2012 Feb 14. Review. PubMed PMID: 22333669.

10: Hill EJ, Nicolay NH, Middleton MR, Sharma RA. Oxaliplatin as a radiosensitiser for upper and lower gastrointestinal tract malignancies: what have we learned from a decade of translational research? Crit Rev Oncol Hematol. 2012 Sep;83(3):353-87. doi: 10.1016/j.critrevonc.2011.12.007. Epub 2012 Feb 5. Review. PubMed PMID: 22309673.



Additional Information

Oxaliplatin was discovered in 1976 at Nagoya City University by Professor Yoshinori Kidani, who was granted U.S. Patent 4,169,846 in 1979. Oxaliplatin was subsequently in-licensed by Debiopharm and developed as an advanced colorectal cancer treatment. Debio licensed the drug to Sanofi-Aventis in 1994. Eloxatin gained European approval in 1996 (firstly in France) and approval by the U.S. Food and Drug Administration (FDA) in 2002. The compound features a square planar platinum(II) center. In contrast to cisplatin and carboplatin, oxaliplatin features the bidentate ligand 1,2-diaminocyclohexane in place of the two monodentate ammine ligands. It also features a bidentate oxalate group. ( the above information was from: http://en.wikipedia.org/wiki/ Oxaliplatin ).
 
DRUG DESCRIPTION
ELOXATIN® (oxaliplatin for injection and oxaliplatin injection) is an antineoplastic agent with the molecular formula C8H14N2O4Pt and the chemical name of cis-[(1 R,2 R)-1,2cyclohexanediamine-N,N'] [oxalato(2-)-O,O'] platinum. 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. The molecular weight is 397.3. Oxaliplatin is slightly soluble in water at 6 mg/mL, very slightly soluble in methanol, and practically insoluble in ethanol and acetone. Powder for solution for infusion: ELOXATIN is supplied in vials containing 50 mg or 100 mg of oxaliplatin as a sterile, preservative-free lyophilized powder for reconstitution. Lactose monohydrate is present as an inactive ingredient at 450 mg and 900 mg in the 50 mg and 100 mg dosage strengths, respectively. Concentrate for solution for infusion: ELOXATIN is supplied in vials containing 50 mg, 100 mg or 200 mg of oxaliplatin as a sterile, preservative-free, aqueous solution at a concentration of 5 mg/ml. Water for Injection, USP is present as an inactive ingredient.
 
 
Mechanism of Action
Mechanism of Action
Oxaliplatin undergoes nonenzymatic conversion in physiologic solutions to active derivatives via displacement of the labile oxalate ligand. Several transient reactive species are formed, including monoaquo and diaquo DACH platinum, which covalently bind with macromolecules. Both inter-and intrastrand Pt-DNA crosslinks are formed. Crosslinks are formed between the N7 positions of two adjacent guanines (GG), adjacent adenine-guanines (AG), and guanines separated by an intervening nucleotide (GNG). These crosslinks inhibit DNA replication and transcription. Cytotoxicity is cell-cycle nonspecific. In vivo studies have shown antitumor activity of oxaliplatin against colon carcinoma. In combination with 5-fluorouracil , oxaliplatin exhibits in vitro and in vivo antiproliferative activity greater than either compound alone in several tumor models [HT29 (colon), GR (mammary), and L1210 (leukemia)].
Oxaliplatin undergoes nonenzymatic conversion in physiologic solutions to active derivatives via displacement of the labile oxalate ligand. Several transient reactive species are formed, including monoaquo and diaquo DACH platinum, which covalently bind with macromolecules. Both inter-and intrastrand Pt-DNA crosslinks are formed. Crosslinks are formed between the N7 positions of two adjacent guanines (GG), adjacent adenine-guanines (AG), and guanines separated by an intervening nucleotide (GNG). These crosslinks inhibit DNA replication and transcription. Cytotoxicity is cell-cycle nonspecific. In vivo studies have shown antitumor activity of oxaliplatin against colon carcinoma. In combination with 5-fluorouracil , oxaliplatin exhibits in vitro and in vivo antiproliferative activity greater than either compound alone in several tumor models [HT29 (colon), GR (mammary), and L1210 (leukemia)].