3D Mol Similar

Oxaliplatin

: Iupac Name：[(1R,2R)-2-azanidylcyclohexyl]azanide;oxalic acid;platinum(2+); CAS No.: 61825-94-3; Molecular Weight：395.28; Modify Date.: 2022-12-07 13:27

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1. Names and Identifiers

: 1.1 Name; Oxaliplatin; 1.2 Synonyms; (1,2-cyclohexanediamine-n,n’)(ethanedioato(2-)-o,o’)-platinu(sp-4-2-(1r-tr [SP-4-2-(1R-TRANS)]-(1,2-CYCLOHEXANEDIAMINE-N,N')[ETHANEDIOATA(2-)-O,O']PLATINUM [SP-4-2-(1R-trans)]-(1，2-Cyclohexanediamine-N，N，)[ethanedioato(2-)-O，O’Jplatinum 1-ohp oxalato(1r,2r-cyclohexanediammine)platinum(ii) oxalatoplatin trans-l-diaminocyclohexane oxalatoplatinum; View all

1.3 CAS No.: 61825-94-3

1.4 EINECS(EC#): 621-248-1

1.5 Molecular Formula: C8H12N2O4Pt (isomer)

1.6 Inchi: InChI=1/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;;+4/p-2/t5-,6-;;/s2

1.7 InChIkey: DWAFYCQODLXJNR-WHMNLBETNA-L

1.8 Canonical Smiles: [H][C@@]12CCCC[C@@]1([H])N[Pt++]1(N2)[O-]C(=O)C(=O)[O-]1

1.9 Isomers Smiles: C1CC[C@H]([C@@H](C1)[NH-])[NH-].C(=O)(C(=O)O)O.[Pt+2]

2. Properties

2.1 StorageTemp: 2-8°C

3. Safety and Handling

3.1 Hazard Codes: Xn,Xi

3.1 Risk Statements: 36/37/38-40-42/43

3.1 Safety Statements: 26-36

3.1 RIDADR: 2811

3.1 WGK Germany: 3

3.1 RTECS: TP2275850

4. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Skin irritation, Category 2

Skin sensitization, Category 1

Eye irritation, Category 2

Specific target organ toxicity \u2013 single exposure, Category 3

Carcinogenicity, Category 2

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H315 Causes skin irritation H317 May cause an allergic skin reaction H319 Causes serious eye irritation H335 May cause respiratory irritation H351 Suspected of causing cancer
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P280 Wear protective gloves/protective clothing/eye protection/face protection. P261 Avoid breathing dust/fume/gas/mist/vapours/spray. P272 Contaminated work clothing should not be allowed out of the workplace. P271 Use only outdoors or in a well-ventilated area. P201 Obtain special instructions before use. P202 Do not handle until all safety precautions have been read and understood.
Response	P302+P352 IF ON SKIN: Wash with plenty of water/... P321 Specific treatment (see ... on this label). P332+P313 If skin irritation occurs: Get medical advice/attention. P362+P364 Take off contaminated clothing and wash it before reuse. P333+P313 If skin irritation or rash occurs: Get medical advice/attention. P305+P351+P338 IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. P337+P313 If eye irritation persists: Get medical advice/attention. P304+P340 IF INHALED: Remove person to fresh air and keep comfortable for breathing. P312 Call a POISON CENTER/doctor/\u2026if you feel unwell. P308+P313 IF exposed or concerned: Get medical advice/ attention.
Storage	P403+P233 Store in a well-ventilated place. Keep container tightly closed. P405 Store locked up.
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

View all

5. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

6. Synthesis Route

61825-94-3Total: 6 Synthesis Route

144-62-7 1285 Suppliers

61825-94-3 402 Suppliers

Literatures:
WO2007/140804 A1, ; Page/Page column 14-16 ;
Yield: ~61%

61848-66-6 4 Suppliers

61825-94-3 402 Suppliers

Literatures:
Inorganic Chemistry, , vol. 27, p. 4106 - 4113
Yield: null

61848-66-6 4 Suppliers

144-62-7 1285 Suppliers

61825-94-3 402 Suppliers

Literatures:
US2008/207935 A1, ; Page/Page column 7 ;
Yield: ~39%

View all

7. Precursor and Product

precursor:

20439-47-8

15843-43-3

61848-66-6

10025-99-7

33081-83-3

144-62-7

8. Other Information

8.0 Merck: 14,6912

8.1 Indications and Usage: Oxaliplatin, also called Eloxatin or Eloxatine, is a platinum derivative.
Used clinically to treat patients with metastatic colorectal cancer after failure of fluorouracil treatment, can be used alone or in combination with 5-fluorouracil. It is the third-generation platinum antitumor compound after cisplatin and carboplatin, and so far the only platinum-based drug with significant effectiveness against colorectal cancer. It also inhibits proliferation of ovarian cancer and melanoma cell lines.

8.2 Mechanisms of Action: Acts on DNA through production of alkylating conjugates, inhibiting its synthesis and reproduction by forming interchain and intrachain cross-links.

8.3 Adverse Effects

Hematopoietec system: Oxaliplatin has a certain blood toxicity. When used alone, it can cause the following adverse effects: anemia, leukopenia, neutropenia, thrombocytopenia, sometimes reaching grade 3 or 4. Increases hematologic toxicities such as neutropenia and thrombocytopenia when combined with 5-fluorouracil.
Digestive system: can cause nausea, vomiting, and diarrhea when used alone. These symptoms can sometimes be very serious. These side effects are significantly exacerbated when used in combination with 5-fluorouacil. Use of prophylactic and/or therapeutic antiemetic drugs is recommended.
Nervous system: Peripheral sensory neuropathy characterized by peripheral neuritis. Sometimes associated with convulsions and sensory disturbances in the mouth, upper respiratory tract, and upper GI tract.

8.4 Description: Oxaliplatin is a platinum-containing DNA-crosslinking agent. It induces the formation of DNA inter- and intrastrand crosslinks and DNA-protein crosslinks, inhibits DNA and RNA synthesis, and induces apoptosis in cancer cells. Oxaliplatin is cytotoxic to cisplatin-sensitive A2780(1A9) and KB-3-1 cells and cisplatin-resistant A2780-E(80) and KB-CP20 cells (IC₅₀s = 0.12, 0.39, 4.7, and 2.7 μM, respectively). It reduces tumor growth in an HCCLM3 mouse xenograft model when administered at doses of 5 or 10 mg/kg once per week. Formulations containing oxaliplatin have been used in the treatment of advanced colorectal cancer and as an adjuvant in stage III colon cancer.

8.5 Description: Eloxatin was launched in France for second-line treatment of metastatic colorectal cancer. Oxaliplatin is a second generation platinum drug prepared in three steps from either k₂tCl₄ or K₂Ptl₄. It has an antitumor spectrum similar to cisplatin, however, it is more effective against L1210 leukemia and cisplatin resistant L1210. It is also effective against B16 melanoma but has a dose limiting toxicity of peripheral sensory neuropathy that is reversible upon cessation of the drug. The (R,R)- enantiomer has greater activity than the (S,S)-isomer but this is tumor line dependent, e.g., there was no difference found for P-388 or Sarcoma 180. Clinical drug administration based on circadium timing showed it was better tolerated when given 16 h after the onset of light. Oxaliplatin binds to guanineN7 and can lead to bidentate chelation that results in the bending of DNA. This feature is recognized by high mobility group proteins (HMG) which impedes repair reactions and stops replication and transcription.; View all

8.6 Chemical Properties: White Crystalline Solid

8.7 Originator: Bebiopharm (Switzerland)

8.8 Uses: Third generation platinum complex. An antitumor agent with activity against colorectal cancer. Cytotoxicity follows the formation of adducts with DNA. Antineoplastic.

8.9 Uses: vasodilator

8.10 Uses: A potent anti-neoplastic agent that binds to DNA and shows efficacy in Cisplatin resistant cell lines

8.11 Uses: Oxaliplatin is a platinum-based antineoplastic agent that functions by forming DNA adducts specifically in cancer cells, preventing DNA replication and transcription which leads to cell death. Oxaliplatin has cytotoxic effects in a broad range of cell lines, including colon, ovarian, and lung cancer, with IC50 values ranging from 0.5-240, 0.12-19.8, and 2.6-6.1 μM, respectively. Through its general cytotoxic effects, oxaliplatin has anti-tumor activity against advanced colorectal cancer and is typically administered with fluorouracil and leucovorin in a combination known as FOLFOX.

8.12 Uses: A antitumor agent with activity against colorectal cancer. Cytotoxicity follows the formation of adducts with DNA

8.13 Brand name: Eloxatin (Sanofi Aventis).

8.14 General Description: Oxaliplatin is available in 50- and 100-mg vials for IV administrationin the treatment of ovarian cancer, metastaticcolorectal cancer, and early stage colon cancer in combinationwith 5-fluorouracil/leucovorin. The activation of theagent occurs in low-chloride environments to give theaquated species, which subsequently reacts with DNA in amanner similar to cisplatin. The mechanisms of resistance aresimilar for the two agents; however, oxaliplatin is not recognizedby MMR enzymes and does not show cross-resistancewith cisplatin. The agent is widely distributed, highly proteinbound (85%–88%), and irreversibly binds to erythrocytes.Numerous metabolites have been identified many of whichare produced as a result of nonenzymatic processes and includechloro-, dichloro-, monoaquo-, and diaquo-species.The parent and metabolites are eliminated primarily in theurine with a long terminal elimination half-life of 240 hours.Neurotoxicity is dose limiting and normally presents as peripheralneuropathy, which may be exacerbated by exposureto low temperatures. The neurotoxicity is normally reversiblein contrast to that seen with cisplatin, which may be irreversible.Other adverse effects include nausea, vomiting, diarrhea,myelosuppression, and hypersensitivity reactions.Ototoxicity and renal toxicity occur only rarely in contrast tocisplatin.; View all

8.15 Biological Activity: Antitumor agent that forms platinum-DNA adducts. Causes intra- and interstrand DNA crosslinks blocking DNA replication and transcription. Displays higher cytotoxicity and lower nephrotoxicity than analog cisplatin (cis-Diaminodichloroplatinum ) and shows antitumor activity in cell lines with acquired cisplatin resistance.

8.16 Biochem/physiol Actions: Oxaliplatin a platinum analogue, causes DNA damage and cell death by binding to DNA and forming inter and intrastrand crosslinks preventing replication and transcription. Oxaliplatin is an anti-tumor agent with activity against colorectal cancer; cytotoxicity follows the formation of adducts with DNA. Oxaliplatin is an approved drug for treating colorectal cancer. It is an active ingredient in FOLFOX (Folinic acid:5-FU:oxaliplatin in the ratio 1:10:1 of micromolar concentrations respectively). Oxaliplatin causes both acute and chronic neurotoxicity in patients in a dose dependent manner and is reversible either by reducing or stopping the drug.

8.17 Safety Profile: A poison by intraperitoneal route. When heated to decomposition it emits toxic vapors of NOx and Pt.

8.18 in vitro: oxaliplatin is active against human melanoma cell lines c32 and g361 with the ic50 values of 0.98 mm and 0.14 mm, respectively. oxaliplatin effectively inhibited bladder carcinoma cell lines rt4 and tccsup, ovarian carcinoma cell line a2780, colon carcinoma cell line ht-29, glioblastoma cell lines u-87mg and u-373mg, and melanoma cell lines sk-mel-2 and ht-144 with the ic50 values of 11 μm, 15 μm, 0.17 μm, 0.97 μm, 17.6 μm, 2.95 μm, 30.9 μm and 7.85 μm, respectively.

8.19 in vivo: a weekly injection of oxaliplatin (10 mg/kg, i.p.) to nude mice bearing hepatocellular hcclm3 tumors significantly reduces tumor volume and apoptotic index. oxaliplatin (5 mg/kg, i.v. on days 1, 5 and 9) was active on t-leukemia-lymphoma l40 akr with t/c of 1.77. oxaliplatin was also efficient on intracerebrally grafted l1210 leukemia, b16 melanoma xenografts, ma 16-c xenografts, lewis lung xenografts and c26 colon carcinoma xenografts. oxaliplatin induced impairment of retrograde neuronal transport in mice.

8.20 references: [1]. culy cr, clemett d, wiseman lr. oxaliplatin.a review of its pharmacological properties and clinical efficacy in metastatic colorectal cancer and its potential in other malignancies.drugs. 2000 oct;60(4):895-924.
[2]. raymond e, faivre s, chaney s et al. cellular and molecular pharmacology of oxaliplatin. mol cancer ther. 2002 jan;1(3):227-35.
[3]. stein a, arnold d. oxaliplatin: a review of approved uses. expert opin pharmacother. 2012 jan;13(1):125-37.
[4]. hoff pm, saad ed, costa f et al. literature review and practical aspects on the management of oxaliplatin-associated toxicity. clin colorectal cancer. 2012 jun;11(2):93-100.
[5]. hall md, et al. say no to dmso: dimethylsulfoxide inactivates cisplatin, carboplatin, and other platinum complexes. cancer res. 2014 jul 15;74(14):3913-22.

9. Question & Answer

What are the effects and side effects of Oxaliplatin? Feb 22 2023
Oxaliplatin is a highly valuable product with good effects in treating gastrointestinal diseases and tumors. However, some individuals may experience adverse reactions or side effects after using Oxa..
Does Sequential Treatment with Fluoropyrimidine and Bevacizumab followed by Oxaliplatin Improve Therapeutic Duration in Metastatic Colorectal Cancer? Jan 17 2023
Oxaliplatin-induced neurotoxicity has always been a challenging issue for oncologists. The European Journal of Cancer (EJC) has published a study by Japanese scholars from the C-cubed research, aiming..
Does Oxaliplatin Cause Gastrointestinal Irritation? Nov 22 2022
Oxaliplatin is a third-generation platinum-based anticancer drug that is primarily used for colorectal and ovarian cancer, with good efficacy. It can also be used for gastric cancer, non-small cell lu..
What should we know about Oxaliplatin? Sep 19 2022
In the field of medicine, we often come across various drugs, some of which have powerful effects and can bring surprising results. Oxaliplatin is one such drug that is indispensable in the fight agai..

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Anti-tumor drugs Oxaliplatin