cis-Diammine(1,1-cyclobutanedicarboxylato)platinum(II)

Base Information

• Chemical Name: cis-Diammine(1,1-cyclobutanedicarboxylato)platinum(II)
• CAS No.: 41575-94-4
• Molecular Formula: C6H12N2O4Pt
• Molecular Weight: 371.252
• Hs Code.: 28439000
• European Community (EC) Number: 255-446-0
• Mol file: 41575-94-4.mol

Synonyms:Blastocarb;Carboplat;Carboplatin;Carbosin;Carbotec;CBDCA;cis-Diammine(cyclobutanedicarboxylato)platinum II;Ercar;JM 8;JM-8;JM8;Nealorin;Neocarbo;NSC 241240;NSC-241240;NSC241240;Paraplatin;Paraplatine;Platinwas;Ribocarbo

Chemical Property of cis-Diammine(1,1-cyclobutanedicarboxylato)platinum(II)

Chemical Property:

• Appearance/Colour: White Crystals
• Melting Point: 228-230 °C
• Boiling Point: 366.4oCat 760 mmHg
• Flash Point: 189.6oC
• PSA: 59.08000
• LogP: 0.81700
• Storage Temp.: Store at RT
• Solubility.: Sparingly soluble in water, very slightly soluble in acetone and in ethanol (96 per cent).
• Water Solubility.: Soluble in water.
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 0
• Exact Mass: 373.060151
• Heavy Atom Count: 13
• Complexity: 169

Purity/Quality:

98.0%-102.0%, ^*data from raw suppliers

Carboplatin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 46-61-20/21/22-42/43-20/21
• Safety Statements: 53-22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(C1)(C(=O)O)C(=O)O.N.N.[Pt]
• Description: Carboplatin (Brand name: Paraplatin) is a kind of chemotherapy medication used for the treatment of a series of cancers. It can be used for the treatment of various kinds of cancers including ovarian cancer, lung cancer, head and neck cancer, brain cancer, and neuroblastoma. Moreover, it may also be used for treating some types of testicular cancer. Carboplatin belongs to a kind of alkylating agent. It takes effect through three major mechanisms: (1) Attach the alkyl groups to the DNA bases, further causing DNA fragmentation so that DNA replication is inhibited; (2) Cause DNA damage through inducing the formation of cross-links which prevents DNA from being separated for synthesis or transcription; (3) Induce mispairing of the nucleotides leading to mutations. Carboplatin is a second generation, platinum-containing antineoplastic agent with significantly reduced nephro-, neuro-, and ototoxicity in comparison to cisplatin. It is effective in the treatment of advanced ovarian carcinoma of epithelial origin and small cell carcinoma of the lung.
• Uses: Carboplatin is a second-generation platinum compound analog with established activity against a broad spectrum of solid tumors including brain tumors, neuroblastoma, rhabdomyosarcoma, and germ cell tumors. It is commonly used for pediatric cancer and approximately one-third of children with solid tumor are estimated to receive carboplatin at some point during their treatment. anthelmintic antitumor agent, Data on carboplatin production have not been found. Carboplatin is used in chemotherapy to treat cancer, and more particularly to treat cancer of ovary, embryonal carcinoma of the testis, microcellular carcinoma of the lung, neuroblastoma, and squamous cell carcinomas of the head and neck. Analog of Cisplatin with reduced nephrotoxicity. Antineoplastic
• Indications: Carboplatin (Paraplatin) is an analogue of cisplatin. Its plasma half-life is 3 to 5 hours, and it has no significant protein binding. Renal excretion is the major route of drug elimination. Despite its lower chemical reactivity, carboplatin has antitumor activity that is similar to that of cisplatin against ovarian carcinomas, small cell lung cancers, and germ cell cancers of the testis. Most tumors that are resistant to cisplatin are cross-resistant to carboplatin. The major advantage of carboplatin over cisplatin is a markedly reduced risk of toxicity to the kidneys, peripheral nerves, and hearing; additionally, it produces less nausea and vomiting. It is, however, more myelosuppressive than cisplatin. Other adverse effects include anemia, abnormal liver function tests, and occasional allergic reactions.
• Therapeutic Function: Antitumor
• Clinical Use: This drug induces fewer nonhematological toxicities (e.g., emesis, nephrotoxicity, and ototoxicity) compared to cisplatin, and it is approved for use only in the treatment of ovarian cancer. Unlabeled uses include combination therapy in lung, testicular, and head and neck cancers.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: increased risk of nephrotoxicity and possibly ototoxicity with aminoglycosides, capreomycin, polymyxins or vancomycin. Antipsychotics: avoid with clozapine, increased risk of agranulocytosis.

Technology Process of cis-Diammine(1,1-cyclobutanedicarboxylato)platinum(II)

There total 15 articles about cis-Diammine(1,1-cyclobutanedicarboxylato)platinum(II) which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 88.0%

cis-diaminediiodoplatinum(II) + cyclobutane-1,1'-dicarboxylic acid (5445-51-2) → carboplatinum (41575-94-4)

Guidance literature:

With barium dihydroxide; silver sulfate; In water; byproducts: AgI, BaSO4; addn. of Ag2SO4 to slight excess of Pt-complex, stirring (4 h), filtration off of AgI, concn., addn. of soln. of ligand (neutralized with Ba(OH)2); filtration off of BaSO4, concn. (crystn.), washing (EtOH, Et2O), drying(vac.); elem. anal.;

DOI:10.1016/S0020-1693(00)84123-7

Reference yield: 80.0%

cis-diamminediiodoplatinum (II) (13841-96-8,15978-93-5,15978-94-6) → carboplatinum (41575-94-4)

Guidance literature:

In water; at 20 ℃; for 48h; Darkness;

DOI:10.1021/acs.molpharmaceut.6b00466

Reference yield: 70.0%

cisplatin (15663-27-1) + cyclobutane-1,1'-dicarboxylic acid (5445-51-2) → carboplatinum (41575-94-4)

Guidance literature:

With potassium hydroxide; In water; N,N-dimethyl-formamide; Pt-compd. dissolved in DMF with heating, addn. of the acid and aq. KOH, heated in an unstoppered flask at 60°C for 20 h; cooled, filtered, addn. of ether;

DOI:10.1016/S0020-1693(00)83478-7

upstream raw materials:

water

1,1-cyclobutanedicarboxylic acid disodium salt

cisplatin

cyclobutane-1,1'-dicarboxylic acid

Downstream raw materials:

cisplatin

bis(N,N-diethyldithiocarbamate)platinum(II)

(OC-6-33)-diammine(cyclobutane-1,1-dicarboxylato)dihydroxidoplatinum(IV)

Refernces

• 1、 Harrison, R. C.,McAuliffe, C. A.,Zaki, A. M.. "". . p. L15 - L16. Retrieved 1980.
• 2、 Chen, Shu,Deng, Zhiqin,Hirao, Hajime,Li, Cai,Wang, Zhigang,Xu, Zoufeng,Yao, Houzong,Zhou, Qiyuan,Zhu, Guangyu. "An intramolecular photoswitch can significantly promote photoactivation of Pt(iv) prodrugs". . p. 6536 - 6542. Retrieved 2021.
• 3、 Tolan, Dina A.,Abdel-Monem, Yasser K.,El-Nagar, Mohamed A.. "Anti-tumor platinum (IV) complexes bearing the anti-inflammatory drug naproxen in the axial position". . . Retrieved 2019/01/16.