Oxaliplatin | CAS#61825-94-3 | DNA crosslinker

MedKoo Cat#: 100680 | Name: Oxaliplatin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

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

Oxaliplatin

CAS#61825-94-3

Theoretical Analysis

MedKoo Cat#: 100680

Name: Oxaliplatin

CAS#: 61825-94-3

Chemical Formula: C8H14N2O4Pt

Exact Mass: 0.0000

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
100mg	USD 110.00	Ready to ship
200mg	USD 140.00	Ready to ship
500mg	USD 160.00	Ready to ship
1g	USD 210.00	Ready to ship
2g	USD 390.00	Ready to ship
5g	USD 680.00	Ready to ship
10g	USD 1,250.00	Ready to ship

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Related CAS #

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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

More Info

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 ELOXATINÂ® (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)].

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#EOS50622

QC Data

View QC data: current batch, Lot#EOS50622

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Oxaliplatin (NSC 266046, L-OHP, Eloxatin) is a DNA alkylating agent that activates autophagy.

In vitro activity:

To investigate the cytotoxicity of oxaliplatin in HCC, HCCLM3 and Hep3B cells were treated with various concentrations of oxaliplatin for 24, 48 and 72 h. As shown in Figure 1, oxaliplatin (over 8 μM) caused significant growth inhibition and marked decrease in cell viability in a dose- and time-dependent manner. To determine whether the growth inhibition induced by oxaliplatin was caused by induction of apoptosis, two-color flow cytometric analysis of HCCLM3 and Hep3B cells stained with Annexin V-FITC and PI was carried out. Oxaliplatin treatment was found to increase the percentage of apoptotic cells (4.71 ± 1.13% for untreated HCCLM3 cells versus 17.70 ± 1.87% for oxaliplatin-treated HCCLM3 cells, p = 0.000; 2.51 ± 0.71% for untreated Hep3B cells versus 21.19 ± 2.21% for oxaliplatin-treated Hep3B cells, p = 0.000; Figure 2). After treatment with oxaliplatin, TEM detected an increased number of cells that were crenulated, karyopycnotic, and had swollen mitochondria, disrupted cristae, and floccular material in the cytoplasm, a large Golgi apparatus containing immature granules, and a reduced number of free ribosomes (Figure 3). Reference: Expert Opin Investig Drugs. 2009 Nov;18(11):1595-604. https://www.tandfonline.com/doi/full/10.1517/13543780903292626

In vivo activity:

With sham treatment, TTc transport causes fluorescent signal intensity over the thoracic spine to increase from 0 to 60 minutes after injection. On average, fluorescence signal increased 722%+/-117% (Mean+/-SD) from 0 to 60 minutes. Oxaliplatin treated animals had comparable transport at baseline (787%+/-140%), but transport rapidly decreased through the course of the study, falling to 363%+/-88%, 269%+/-96%, 191%+/-58%, 121%+/-39%, 75%+/-21% with each successive week and stabilizing around 57% (+/-15%) at 7 weeks. Statistically significant divergence occurred at approximately 3 weeks (p≤0.05, linear mixed-effects regression model). Quantitative immuno-fluorescence histology with a constant cutoff threshold showed reduced TTc in the spinal cord at 7 weeks for treated animals versus controls (5.2 Arbitrary Units +/-0.52 vs 7.1 AU +/-1.38, p<0.0004, T-test). There was no significant difference in neural cell mass between the two groups as shown with NeuN staining (10.2+/-1.21 vs 10.5 AU +/-1.53, p>0.56, T-test). Reference: PLoS One. 2012;7(9):e45776. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3447809/

	Solvent	mg/mL	mM
Solubility
	H2O	4.0	10.10

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

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.

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

Formulation protocol:

In vitro protocol:

1. Wang Z, Zhou J, Fan J, Qiu SJ, Yu Y, Huang XW, Sun J, Tan CJ, Dai Z. Oxaliplatin induces apoptosis in hepatocellular carcinoma cells and inhibits tumor growth. Expert Opin Investig Drugs. 2009 Nov;18(11):1595-604. doi: 10.1517/13543780903292626. PMID: 19780708.

In vivo protocol:

1. Schellingerhout D, LeRoux LG, Hobbs BP, Bredow S. 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. PMID: 23029238; PMCID: PMC3447809. 2. Wang Z, Zhou J, Fan J, Qiu SJ, Yu Y, Huang XW, Sun J, Tan CJ, Dai Z. Oxaliplatin induces apoptosis in hepatocellular carcinoma cells and inhibits tumor growth. Expert Opin Investig Drugs. 2009 Nov;18(11):1595-604. doi: 10.1517/13543780903292626. PMID: 19780708.

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PMID: 39143546. 4: Nakatsumi H, Komatsu Y, Harada K, Kawamoto Y, Yuki S, Sawada K, Ishiguro A, Sogabe S, Ando T, Sasaki Y, Yoshikawa A, Nakamura M, Dazai M, Tateyama M, Muto O, Kotaka M, Sagawa T, Muranaka T, Hatanaka K, Takagi R, Sakata Y. A multicenter, prospective, phase II trial of second-line aflibercept plus FOLFIRI in patients with metastatic colorectal cancer refractory to an anti-EGFR antibody: HGCSG1801. Int J Cancer. 2024 Aug 14. doi: 10.1002/ijc.35116. Epub ahead of print. PMID: 39143041. 5: Baltussen JC, van den Bos F, Slingerland M, Binda TRR, Liefers GJ, van den Hout WB, Fiocco M, Verschoor AJ, Cloos-van Balen M, Holterhues C, Houtsma D, Jochems A, Spierings LEAMM, van Bodegom-Vos L, Mooijaart SP, Gelderblom H, Speetjens FM, de Glas NA, Portielje JEA. DOSAGE study: protocol for a phase III non-inferiority randomised trial investigating dose-reduced chemotherapy for advanced colorectal cancer in older patients. BMJ Open. 2024 Aug 13;14(8):e089882. doi: 10.1136/bmjopen-2024-089882. PMID: 39142680. 6: Dai C, Zhen F, Yu L, Xin S. Puerarin alleviates oxaliplatin-induced neuropathic pain by promoting Nrf2/GPX4-mediated antioxidative response. PLoS One. 2024 Aug 14;19(8):e0308872. doi: 10.1371/journal.pone.0308872. PMID: 39141625. 7: Ye M, Hu J, Han L, Zhang H, Xue P, Kang Y, Bai S, Xu Z. Neighboring Effect- Initiated Supramolecular Nanocomplex with Sequential Infiltration as Irreversible Apoptosis Inducer for Synergetic Chemo-Immunotherapy. Adv Sci (Weinh). 2024 Aug 13:e2402809. doi: 10.1002/advs.202402809. Epub ahead of print. PMID: 39137339. 8: Hasik P, Thomas C, Hazarika M, Undela K. Ocular adverse events associated with Platins: a disproportionality analysis of pharmacovigilance data and extensive systematic review of case reports. Expert Opin Drug Saf. 2024 Aug 13. doi: 10.1080/14740338.2024.2392860. Epub ahead of print. PMID: 39137273. 9: Adagrasib (Krazati) for colorectal cancer. 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Phase IB Study of Oral Selinexor in Combination with Rituximab and Platinum Chemotherapy in Patients with Relapsed/Refractory B-Cell Lymphoma-Final Analysis. Cancers (Basel). 2024 Jul 26;16(15):2672. doi: 10.3390/cancers16152672. PMID: 39123400; PMCID: PMC11311764. 13: Singh H, Lowder KE, Kapner K, Kelly RJ, Zheng H, McCleary NJ, Abrams TA, Chan JA, Regan EM, Klempner SJ, Hannigan AM, Remland J, Brais LK, Andrews E, Yurgelun M, Cleary JM, Rubinson DA, Ritterhouse LL, Maron G, Aguirre AJ, Meyerhardt JA, Gardecki E, Lennerz JK, Wolpin BM, Enzinger PC. Clinical outcomes and ctDNA correlates for CAPOX BETR: a phase II trial of capecitabine, oxaliplatin, bevacizumab, trastuzumab in previously untreated advanced HER2+ gastroesophageal adenocarcinoma. Nat Commun. 2024 Aug 9;15(1):6833. doi: 10.1038/s41467-024-51271-3. PMID: 39122726; PMCID: PMC11316091. 14: Ahuja S, Joseph KA, Zaheer S. Incidental detection of an appendiceal neuroendocrine tumor in a right hemicolectomy specimen for colonic adenocarcinoma: A case report. Int J Surg Case Rep. 2024 Aug 3;122:110121. doi: 10.1016/j.ijscr.2024.110121. Epub ahead of print. PMID: 39121720. 15: Ni JY, Sun HL, Guo GF, Zhou X, Wei JX, Xu LF. Hepatic arterial infusion of GEMOX plus systemic gemcitabine chemotherapy combined with lenvatinib and PD-1 inhibitor in large unresectable intrahepatic cholangiocarcinoma. Int Immunopharmacol. 2024 Aug 8;140:112872. doi: 10.1016/j.intimp.2024.112872. Epub ahead of print. PMID: 39121605. 16: Di Y, Zhang X, Wen X, Qin J, Ye L, Wang Y, Song M, Wang Z, He W. MAPK Signaling-Mediated RFNG Phosphorylation and Nuclear Translocation Restrain Oxaliplatin-Induced Apoptosis and Ferroptosis. Adv Sci (Weinh). 2024 Aug 9:e2402795. doi: 10.1002/advs.202402795. Epub ahead of print. PMID: 39120977. 17: Swierz MJ, Storman D, Mitus JW, Hetnal M, Kukielka A, Szlauer-Stefanska A, Pedziwiatr M, Wolff R, Kleijnen J, Bala MM. Transarterial (chemo)embolisation versus systemic chemotherapy for colorectal cancer liver metastases. Cochrane Database Syst Rev. 2024 Aug 9;8(8):CD012757. doi: 10.1002/14651858.CD012757.pub2. PMID: 39119869; PMCID: PMC11311242. 18: Fu Z, Zhou Y, Zhang Y, Zhou Z, Yu Y, Yuan C, Dong J, Duan S. MicroRNA‑325: A comprehensive exploration of its multifaceted roles in cancer pathogenesis and therapeutic implications (Review). Oncol Lett. 2024 Jul 26;28(4):459. doi: 10.3892/ol.2024.14592. PMID: 39119235; PMCID: PMC11307554. 19: Cui Z, Le Y, Liu H, Feng L, Zhang S. Comprehensive treatment of gallbladder cancer: a case report. Ann Med Surg (Lond). 2024 May 28;86(8):4811-4815. doi: 10.1097/MS9.0000000000002206. PMID: 39118674; PMCID: PMC11305716. 20: Si X, Ji G, Ma S, Huang Z, Liu T, Shi Z, Zhang Y, Li J, Song W, Chen X. Minimally Invasive Injectable Gel for Local Immunotherapy of Liver and Gastric Cancer. Adv Sci (Weinh). 2024 Aug 8:e2405935. doi: 10.1002/advs.202405935. Epub ahead of print. PMID: 39116306.