Oxaliplatin

Modify Date: 2024-01-02 16:52:36

Oxaliplatin Structure
Oxaliplatin structure
 Common Name Oxaliplatin
CAS Number 61825-94-3 Molecular Weight 395.28
Density N/A Boiling Point 193.6ºC at 760 mmHg
Molecular Formula C8H12N2O4Pt Melting Point N/A
MSDS Chinese USA Flash Point N/A
Symbol GHS07 GHS08
GHS07, GHS08		 Signal Word Warning

 Use of Oxaliplatin


Oxaliplatin is a DNA synthesis inhibitor. It causes DNA crosslinking damage, prevents DNA replication and transcription and causes cell death.

 Names

Name oxaliplatin
Synonym More Synonyms

 Oxaliplatin Biological Activity

Description Oxaliplatin is a DNA synthesis inhibitor. It causes DNA crosslinking damage, prevents DNA replication and transcription and causes cell death.
Related Catalog
In Vitro Oxaliplatin acts through the formation of DNA-adducts. Oxaliplatin induces primary and secondary DNA lesions leading to cell apoptosis[1]. Oxaliplatin inhibits human melanoma cell lines C32 and G361 with IC50 values of 0.98 mM and 0.14 mM, respectively[2]. Oxaliplatin potently inhibits 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 with IC50 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[3].
In Vivo Oxaliplatin (10 mg/kg, i.p.) significantly reduces tumor volume and apoptotic index in the nude mice bearing hepatocellular HCCLM3 tumors[4]. Oxaliplatin (5 mg/kg, i.v.) is effective on T-leukemia-lymphoma L40 AKR with T/C of 1.77. Oxaliplatin is efficient on intracerebrally grafted L1210 leukemia, MA 16-C xenografts, B16 melanoma xenografts, Lewis lung xenografts and C26 colon carcinoma xenografts[5]. Oxaliplatin induces impairment of retrograde neuronal transport in mice[6].
Cell Assay Typically, cells are plated into 96-well plates on day 0 and exposed to Oxaliplatin on day 1; the sulforhodamine-B assay is carried out 48 h after Oxaliplatin exposure. The plates are incubated at 37°C in 5% CO2 and 100% relative humidity at all times except when adding Oxaliplatin and during the final assay period. The initial number of cells plated for the assay ranged from 2-20×103 cells/50/nL/well. The numbers of cells for plating and the drug exposure time are based on pilot studies using the criteria that (a) the cells in control wells are still in the log phase of growth on the day of the assay; (b) the maximum absorbance for the untreated controls on the day of the assay is in the range of 1.0 to 1.5; and (c) cells go through > 2 doublings during the drug exposure. Eight wells are used per concentration. The plates are read at 570 and/or 540 nm using a Biotek Instruments model EL309 microplate reader interfaced with an IBM PC-compatible computer.
Animal Admin HCC tumor models produced by HCCLM3 are established in nude mice by subcutaneous injection of 5×105 HCCLM3 cells in 0.2 mL of serum-free culture medium into the left upper flank region. Three days later, the mice are randomLy assigned to receive one of the following three treatments: i) a weekly intraperitoneal (i.p.) injection of distilled water (control group, n=8); ii) a weekly i.p. injection of oxaliplatin at 5 mg/kg (low dose group, n=7); or iii) a weekly i.p. injection of oxaliplatin at 10 mg/kg (high dose group, n=7). Tumor growth is monitored by measuring two bisecting diameters of each tumor with a caliper every 5 days. The tumor volume is calculated using the formula (V=a×b2/2), with a as the larger diameter and b as the smaller diameter. Mice are euthanized by day 32 after oxaliplatin administration. Tumors of each group are completely removed, weighed, photographed, and fixed in 10% formalin/PBS or stored in liquid nitrogen for histological examination.
References

[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 cisplatin and carboplatin. 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 and carboplatinum. 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]. Romero HK, et al. Inhibition of α9α10 nicotinic acetylcholine receptors prevents chemotherapy-induced neuropathic pain. Proc Natl Acad Sci U S A. 2017 Mar 7;114(10):E1825-E1832.

 Chemical & Physical Properties

Boiling Point 193.6ºC at 760 mmHg
Molecular Formula C8H12N2O4Pt
Molecular Weight 395.28
PSA 104.64000
LogP 0.61450
Appearance of Characters solid
Storage condition Store at +4°C
Stability Stable. Store cool. Incompatible with oxidizing agents.
Water Solubility Slightly soluble in water, very slightly soluble in methanol, practically insoluble in anhydrous ethanol. | Soluble in water with heating and/or sonication

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TP2275850
CHEMICAL NAME :
Platinum, (1,2-cyclohexanediamine-N,N')(ethanedioato(2-)-O,O')- , (SP-4-2-(1R-trans))-
CAS REGISTRY NUMBER :
61825-94-3
LAST UPDATED :
199706
DATA ITEMS CITED :
2
MOLECULAR FORMULA :
C8-H14-N2-O4-Pt
MOLECULAR WEIGHT :
397.33

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
14300 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 14,529,1989
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
19800 ug/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
DRFUD4 Drugs of the Future. (J.R. Prous, S.A., Apartado de Correos 540, 08080 Barcelona, Spain) V.1- 1975/76- Volume(issue)/page/year: 14,529,1989

 Safety Information

Symbol GHS07 GHS08
GHS07, GHS08
Signal Word Warning
Hazard Statements H315-H317-H319-H335-H351
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
Hazard Codes Xn:Harmful;
Risk Phrases R36/37/38;R40;R42/43
Safety Phrases S26-S36
RIDADR UN 2811 6.1/PG 2
WGK Germany 3
RTECS TP2275850
Packaging Group II
HS Code 28439000

 Synthetic Route

Potassium tetrachloroplatinate(II) structure

Potassium tetra...

CAS#:10025-99-7
(1R,2R)-(-)-1,2-Diaminocyclohexane structure

(1R,2R)-(-)-1,2...

CAS#:20439-47-8
Oxalic acid structure

Oxalic acid

CAS#:144-62-7

~20%

Oxaliplatin Structure

Oxaliplatin

CAS#:61825-94-3
Literature: US2008/207935 A1, ; Page/Page column 7 ;
Oxalic acid structure

Oxalic acid

CAS#:144-62-7

~61%

Oxaliplatin Structure

Oxaliplatin

CAS#:61825-94-3
Literature: WO2007/140804 A1, ; Page/Page column 14-16 ;
trans(−)-DDCP structure

trans(−)-DDCP

CAS#:61848-66-6
disilver(I) oxalate structure

disilver(I) oxalate

CAS#:15843-43-3

~40%

Oxaliplatin Structure

Oxaliplatin

CAS#:61825-94-3
Literature: Inorganica Chimica Acta, , vol. 401, p. 64 - 69
trans(−)-DDCP structure

trans(−)-DDCP

CAS#:61848-66-6
Oxalic acid structure

Oxalic acid

CAS#:144-62-7

~39%

Oxaliplatin Structure

Oxaliplatin

CAS#:61825-94-3
Literature: US2008/207935 A1, ; Page/Page column 7 ;
trans(−)-DDCP structure

trans(−)-DDCP

CAS#:61848-66-6
ditetrabutylammonium oxolate structure

ditetrabutylamm...

CAS#:33081-83-3

~49%

Oxaliplatin Structure

Oxaliplatin

CAS#:61825-94-3
Literature: WO2007/85957 A1, ; Page/Page column 13-16 ;
trans(−)-DDCP structure

trans(−)-DDCP

CAS#:61848-66-6

~%

Oxaliplatin Structure

Oxaliplatin

CAS#:61825-94-3
Literature: Inorganic Chemistry, , vol. 27, p. 4106 - 4113

 Articles260

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PKM2 Subcellular Localization Is Involved in Oxaliplatin Resistance Acquisition in HT29 Human Colorectal Cancer Cell Lines.

PLoS ONE 10 , e0123830, (2015)

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 Synonyms

Dacplat
Oxaliplatin
MFCD00866327
platinum, [ethanedioato(2-)-κO,κO]-, compd. with (1R,2R)-1,2-cyclohexanediamine (1:1)
Platinum(2+) ethanedioate - (1R,2R)-1,2-cyclohexanediamine (1:1)
Platinum(2+) ethanedioate (1R,2R)-1,2-cyclohexanediamine (1:1)
[Ethanedioato(2-)-κO,O]platinum - (1R,2R)-cyclohexane-1,2-diamine (1:1)
Platinum(2+) ethanedioate (1R,2R)-1,2-cyclohexanediamine (1:1:1)
Elocatin
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Related Compounds: More...
Oxaliplatin
63121-00-6
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61758-77-8
Oxaliplatin impurity C
111321-67-6
Dihydroxy Oxaliplatin-Pt(IV)
56270-79-2
Oxaliplatin mixture with capecitabine
930113-49-8
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