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41575-94-4

41575-94-4 Structure

41575-94-4 Structure
IdentificationBack Directory
[Name]

Carboplatin
[CAS]

41575-94-4
[Synonyms]

JM-8
cbdca
Ercar
Carboplat
nsc-241240
PARAPLATIN
CARBOPLATIN
CARBONPLATIN
CARBOPLATINUM
Carboplatin99%
JM-8:NSC-241240
CarboplatinUsp24
CarboplatinUsp28
Carboplatin usp25
Carboplatin (100 mg)
PARAPLATIN (CARBOPLATIN)
1,1-CYCLOBUTANEDICARBOXYLATODIAMMINEPLATINUM
diammine(1,1-cyclobutanedicarboxylato)platinum
1,1-cyclobutanedicarboxylate diammine platinum
diammine-1,1-cyclobutanedicarboxylateplatinumi
1,1-cyclobutanedicarboxylatediammineplatinum(ii)
1,1-CYCLOBUTANEDICARBOXYLATODIAMMINEPLATINUM(II)
1,1-Cyclobutanedicarboxylate diamine platinum(II)
diammine(1,1-cyclobutanedicarboxylato)-platinum(I
CIS-DIAMINE(1,1-CYCLOBUTANEDICARBOXYLATO)PLATINUM
DIAMMINE(1,1-CYCLOBUTANEDICARBOXYLATO)PLATINUM(II)
CIS-DIAMMINE-[1,1-CYCLOBUTANE-DICARBOXYLATO]PLATIN
CIS-DIAMMINE[1,1-CYCLOBUTANE-DICARBOYLATO]PLATINUM
cis-(1,1-cyclobutanedicarboxylato)diammineplatinum
CIS-DIAMMINE[1,1-CYCLOBUTANE-DICARBOXYLATO] PLATINUM
1-cyclobutanedicarboxylato)diammine-(cis-platinum(ii
CIS-DIAMINE(1,1-CYCLOBUTANEDICARBOXYLATO)PLATINUM(II)
cis-(1,1-Cyclobutanedicarboxylato)diamineplatinum(II)
cis-(1,1-cyclobutanedicarboxylato)diammineplatinum(ii)
diammine[cyclobutane-1,1-dicarboxylato(2-)-O,O']platinum
CIS-DIAMMINE [1,1-CYCLOBUTANEDICARBOXYLATO] PLATINUM (II)
1,1-CYCLOBUTANEDICARBOXYLATODIAMMINEPLATINUM(II) CARBOPLATIN
1-cyclobutanedicarboxylato(2-)-o,o’)-diammine((sp-4-2)-platinu
1,1-Cyclobutanedicarboxylatodiammineplatinum(II),99%CARBOPLATIN
SP-4-2)-Diammine[1,1-cyclobutanedicar-boxylato-(2-)O,O’]platinum
CARBOPLATIN (DIAMMINE(1,1-CYCLOBUTANEDICARBOXYLATO)PLATINUM(II))
(SP-4-2)-Diamimine[1,1-cyclobutanedi(carboxylato-kO)(2-)]platinum
(SP-4-2)-Diamrnine[1,1-cyclobutanedicarboxylato(2-)-O,O’]platinuln
Carboplatin/cis-DiaMMine[1,1 cyclobutane dicarboxylato] platinuM
Platinum, diamine(1,1-cyclobutanedicarboxylato(2-)-O,O')-, (SP-4-2)-
1,1-CYCLOBUTANEDICARBOXYLATODIAMMINEPLATINUM(II), 99% USP CARBOPLATIN
Platinum, diammine1,1-cyclobutanedi(carboxylato-.kappa.O)(2-)-, (SP-4-2)-
[EINECS(EC#)]

255-446-0
[Molecular Formula]

C6H12N2O4Pt
[MDL Number]

MFCD00070464
[MOL File]

41575-94-4.mol
[Molecular Weight]

371.25
Chemical PropertiesBack Directory
[Appearance]

White Crystals
[Melting point ]

228-230°C
[mp ]

228-230°C
[storage temp. ]

Store at RT
[solubility ]

Sparingly soluble in water, very slightly soluble in acetone and in ethanol (96 per cent).
[form ]

crystal
[color ]

white
[Stability:]

Stable. Incompatible with strong oxidizing agents.
[Water Solubility ]

Soluble in water.
[Merck ]

1822
[EPA Substance Registry System]

Platinum, diammine[1,1-cyclobutanedi( carboxylato-.kappa.O)(2-)]-, (SP-4-2)-(41575-94-4)
Hazard InformationBack Directory
[Chemical Properties]

White Crystals
[Usage]

Analog of Cisplatin with reduced nephrotoxicity. Antineoplastic
[Usage]

anthelmintic
[Usage]

antitumor agent,
[Biological Activity]

Antitumor agent that forms platinum-DNA adducts. Causes intra-and interstrand DNA crosslinks blocking DNA replication and transcription. Enhances radiation-induced single-strand DNA breakage and displays lower nephrotoxicity than analog cisplatin (cis-Diaminodichloroplatinum ).
[Originator]

Johnson Matthey (United Kingdom)
[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.
[Manufacturing Process]

cis-Diammine platinum diiodide was reacted with silver sulfate to give cis-diaquodiammine platinum sulfate. This was reacted with the barium salt of 1,1-cyclobutanedicarboxylic acid to yield Carboplatin.
[Brand name]

Paraplatin (Bristol-Myers Squibb).
[Therapeutic Function]

Antitumor
[General Description]

Carboplatin is available in 50-, 150-, and 450-mg vials for IVadministration in the treatment of ovarian cancer, bladdercancer, germ cell tumors, head and neck cancers, small celllung cancer, and NSCLC. Activation of the agent occurs byaquation in a manner similar to that seen for cisplatin. Thepresence of the chelating 1,1-cyclobutane-dicarboxylateslows this reaction 100-fold and reduces the toxicity of theagent. The sites of alkylation and mechanisms of resistanceare like those seen for cisplatin, and the two agents showcross-resistance. The agent is widely distributed upon IV administration but, because of its greater stability, it bindsslowly to plasma proteins, requiring 24 hours to reach 90%bound drug compared with 4 hours for cisplatin. The agent iseliminated in the urine with a terminal elimination half-lifeof 2 to 6 hours. Adverse effects include myelosuppression,which is dose limiting. Other adverse effects include renaltoxicity, nausea, vomiting, and peripheral neuropathy, butthese occur much less frequently than with cisplatin.
[Pharmaceutical Applications]

Carboplatin, cis-diammine(1,1-cyclobutanedicarboxylato)platinum(II), is a second-generation platinum drug. Its structure is based on cisplatin with the difference that the chloride ligands are exchanged for a bidentate chelating ligand. A consequence is that carboplatin is less reactive than cisplatin and therefore is less nephrotoxic and orthotoxic than the parent compound. Unfortunately, it is more myelosuppressive than cisplatin, which reduces the patients’ white blood cell count and makes them susceptible to infections. Carboplatin was licensed by the FDA in 1989 under the brand name Paraplatin and has since then gained worldwide recognition. Carboplatin on its own or in combination with other anticancer agents is used in the treatment of a variety of cancer types including head and neck, ovarian, small-cell lung, testicular cancer and others.
Carboplatin is a pale-white solid showing good aqueous solubility. The synthesis starts with potassium tetrachloroplatinate, which is reacted to the orange [PtI4]2- anion.
[Biochem/physiol Actions]

Carboplatin is a platinum-based antineoplastic drug that damages DNA by forming intrastrand cross-links with neighboring guanine residues. Tumors acquire resistance to these drugs through the loss of DNA-mismatch repair (MMR) activity and the resultant decrease in the induction of programmed cell death.
[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.
[Side effects]

The ultimate damage done to cells as a result of carboplatin use, however, approaches that of cisplatin. The plasma half-life of carboplatin is 3 hours, and the drug is less extensively bound to serum proteins. Excretion is predominantly renal, and doses must be reduced in patients with kidney disease. Suppression of platelets and white blood cells is the most significant toxic reaction of carboplatin use.
[Chemical Synthesis]

Carboplatin, cis-diamino-(1,1-cyclobutandicarboxylate)platinum(II), is made from cisplatin by reacting it with a solution of silver nitrate, and then with cyclobutan-1,1-dicarboxylic acid to form the desired carboplatin (30.2.5.2).

[Veterinary Drugs and Treatments]

Like cisplatin, carboplatin may be useful in a variety of veterinary neoplastic diseases including squamous cell carcinomas, ovarian carcinomas, mediastinal carcinomas, pleural adenocarcinomas, nasal carcinomas and thyroid adenocarcinomas. Carboplatin’s primary use currently in small animal medicine is in the adjunctive treatment (post amputation) of osteogenic sarcomas. Its effectiveness in treating transitional cell carcinoma of the bladder has been disappointing; however, carboplatin may have more efficacy against melanomas than does cisplatin.
Carboplatin, unlike cisplatin, appears to be relatively safe to use in cats.
Carboplatin may be considered for intralesional use in conditions such as equine sarcoids or in treating adenocarcinoma in birds.
Whether carboplatin is more efficacious than cisplatin for certain cancers does not appear to be decided at this point, but the drug does appear to have fewer adverse effects (less renal toxicity and reduced vomiting) in dogs.
Safety DataBack Directory
[Hazard Codes ]

T
[Risk Statements ]

46-61-20/21/22-42/43-20/21
[Safety Statements ]

53-22-26-36/37/39-45
[RIDADR ]

2811
[WGK Germany ]

3
[RTECS ]

TP2300000
[HS Code ]

28439090
[Hazardous Substances Data]

41575-94-4(Hazardous Substances Data)
[Toxicity]

LD50 in mice (mg/kg): 150 i.p., 140 i.v.; in rats (mg/kg): 85 i.v. (Lelieveld)
Raw materials And Preparation ProductsBack Directory
【Raw materials】

Ethanol-->Potassium iodide-->Barium hydroxide-->Hydrazine monohydrochloride-->Barium hydroxide octahydrate-->1,1-Cyclobutanedicarboxylic acid-->Silver sulfate-->Potassium chloroplatinate
Questions And AnswerBack Directory
[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.
[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.

[Mechanism of action]

Once carboplatin penetrates the cell membrane, carboplatin is subjected to hydrolysis becoming positively charged. The hydrolyzed product is capable of reacting with any nucleophile, such as the sulfhydryl groups on proteins and nitrogen donor atoms on nucleic acids. Carboplatin connects to the N7 reactive center on purine bases, which elicits DNA injury that blocks replicative machinery and directs cancer cells towards apoptosis. The spectrum of chemical changes induced by carboplatin within DNA is wide, however, the most prominent is the formation of the 1,2-intrastrand [d(GpG)and d(ApG)] adducts of purines.

Spectrum DetailBack Directory
[Spectrum Detail]

Carboplatin(41575-94-4)1HNMR
Carboplatin(41575-94-4)13CNMR
Carboplatin(41575-94-4)IR1
Carboplatin(41575-94-4)IR2
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