Carboplatin

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Description:Carboplatin is a second-generation platinum compound with a broad spectrum of antineoplastic properties. Carboplatin contains a platinum atom complexed with two ammonia groups and a cyclobutane-dicarboxyl residue. This agent is activated intracellularly to form reactive platinum complexes that bind to nucleophilic groups such as GC-rich sites in DNA, thereby inducing intrastrand and interstrand DNA cross-links, as well as DNA-protein cross-links. These carboplatin-induced DNA and protein effects result in apoptosis and cell growth inhibition.

Price and Availability

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Chemical Structure

Theoretical Analysis

MedKoo Cat#: 100130Name: CarboplatinCAS#: 41575-94-4Chemical Formula: C6H12N2O4PtExact Mass: Molecular Weight: 371.25Elemental Analysis:C, 19.41; H, 3.26; N, 7.55; O, 17.24; Pt, 52.55

Synonym:Carboplatin Hexal; Carboplatino; US brand names: Paraplat; Paraplatin; Foreign brand names: Blastocarb; Carboplat; Carbosin; Carbosol; Carbotec; Displata; Ercar; Nealorin; Novoplatinum; Paraplatin AQ; Paraplatine; Platinwas; Ribocarbo; Abbreviation: CBDCA Code name: JM8

IUPAC/Chemical Name:platinum, diammine [1,1-cyclobutane-dicarboxylato(2-)-0,0’]-,(SP-4-2)

InChi Key:OLESAACUTLOWQZ-UHFFFAOYSA-L

InChi Code:InChI=1S/C6H8O4.2H3N.Pt/c7-4(8)6(5(9)10)2-1-3-6;;;/h1-3H2,(H,7,8)(H,9,10);2*1H3;/q;;;+2/p-2

SMILES Code:[O-]C(C1(CCC1)C([O-])=O)=O.[Pt+2].N.N

Technical Data

Additional Information

HistoryCarboplatin was discovered and developed at the Institute of Cancer Research in London. Bristol-Myers Squibb gained Food and Drug Administration (FDA) approval for carboplatin, under the brand name Paraplatin, in March 1989. Starting in October 2004, generic versions of the drug became available. From: http://en.wikipedia.org/wiki/Carboplatin . DRUG DESCRIPTIONPARAPLATIN® (carboplatin aqueous solution) INJECTION is supplied as a sterile, pyrogen-free, 10 mg/mL aqueous solution of carboplatin. Carboplatin is a platinum coordination compound. Carboplatin is a crystalline powder with the molecular formula of C6H12N2O4Pt and a molecular weight of 371.25. It is soluble in water at a rate of approximately 14 mg/mL, and the pH of a 1% solution is 5 to 7. It is virtually insoluble in ethanol, acetone, and dimethylacetamide. CLINICAL PHARMACOLOGYCarboplatin, like cisplatin, produces predominantly interstrand DNA cross-links rather than DNA-protein cross-links. This effect is apparently cell-cycle nonspecific. The aquation of carboplatin, which is thought to produce the active species, occurs at a slower rate than in the case of cisplatin. Despite this difference, it appears that both carboplatin and cisplatin induce equal numbers of drug-DNA cross-links, causing equivalent lesions and biological effects. The differences in potencies for carboplatin and cisplatin appear to be directly related to the difference in aquation rates. In patients with creatinine clearances of about 60 mL/min or greater, plasma levels of intact carboplatin decay in a biphasic manner after a 30-minute intravenous infusion of 300 mg/m2 to 500 mg/m2 of carboplatin. The initial plasma half-life (alpha) was found to be 1.1 to 2 hours (n=6), and the postdistribution plasma half-life (beta) was found to be 2.6 to 5.9 hours (n=6). The total body clearance, apparent volume of distribution and mean residence time for carboplatin are 4.4 L/hour, 16 L and 3.5 hours, respectively. The Cmax values and areas under the plasma concentration versus time curves from 0 to infinity (AUC inf) increase linearly with dose, although the increase was slightly more than dose proportional. Carboplatin, therefore, exhibits linear pharmacokinetics over the dosing range studied (300 mg/m2 to 500 mg/m2). Carboplatin is not bound to plasma proteins. No significant quantities of protein-free, ultrafilterable platinum-containing species other than carboplatin are present in plasma. However, platinum from carboplatin becomes irreversibly bound to plasma proteins and is slowly eliminated with a minimum half-life of 5 days. The major route of elimination of carboplatin is renal excretion. Patients with creatinine clearances of approximately 60 mL/min or greater excrete 65% of the dose in the urine within 12 hours and 71% of the dose within 24 hours. All of the platinum in the 24-hour urine is present as carboplatin. Only 3% to 5% of the administered platinum is excreted in the urine between 24 and 96 hours. There are insufficient data to determine whether biliary excretion occurs. Recent review papers on Carboplatin1: Ando Y, Shimokata T, Yasuda Y, Hasegawa Y. Carboplatin dosing for adult Japanese patients. Nagoya J Med Sci. 2014 Feb;76(1-2):1-9. Review. PubMed PMID: 25129986. 2: Pandey A, Bhosale B, Pandita V, Singh A, Ghosh J, Ghosh J, Bajpai J. Carboplatin hypersensitivity in relapsed ovarian carcinoma: A therapeutic challenge. Indian J Med Paediatr Oncol. 2014 Jan;35(1):17-20. doi: 10.4103/0971-5851.133705. Review. PubMed PMID: 25006278; PubMed Central PMCID: PMC4080656. 3: Kimura H, Uegaki M, Aoyama T, Kawai J, Hamano T, Hashimura T. [Carboplatin plus irinotecan induced partial response in a patient with small cell carcinoma of the prostate; a case report]. Hinyokika Kiyo. 2014 Jan;60(1):39-43. Review. Japanese. PubMed PMID: 24594772. 4: Lorusso D, Petrelli F, Coinu A, Raspagliesi F, Barni S. A systematic review comparing cisplatin and carboplatin plus paclitaxel-based chemotherapy for recurrent or metastatic cervical cancer. Gynecol Oncol. 2014 Apr;133(1):117-23. doi: 10.1016/j.ygyno.2014.01.042. Epub 2014 Jan 31. Review. PubMed PMID: 24486604. 5: Watanabe K, Shinkai M, Goto H, Yoshikawa S, Yamaguchi N, Hara Y, Shinoda M, Moriyama Y, Rubin BK, Ishigatsubo Y, Kaneko T. Chemotherapy with carboplatin and paclitaxel after failure of primary chemotherapy for advanced thymic carcinoma. A report of three cases and review of the literature. Tumori. 2013 Jul-Aug;99(4):e172-6. doi: 10.1700/1361.15119. Review. PubMed PMID: 24326856. 6: Otsuka I, Takaya H, Takagi K, Tanaka A, Kaseki H, Izuta C, Sato M, Matsuura T, Suzuki Y. [Carcinosarcoma of the ovary treated with paclitaxel and carboplatin chemotherapy - a report of 4 cases]. Gan To Kagaku Ryoho. 2013 Sep;40(9):1249-53. Review. Japanese. PubMed PMID: 24047791. 7: de Castria TB, da Silva EM, Gois AF, Riera R. Cisplatin versus carboplatin in combination with third-generation drugs for advanced non-small cell lung cancer. Cochrane Database Syst Rev. 2013 Aug 16;8:CD009256. doi: 10.1002/14651858.CD009256.pub2. Review. PubMed PMID: 23949842. 8: Ding Q, Zhan J. Amrubicin: potential in combination with cisplatin or carboplatin to treat small-cell lung cancer. Drug Des Devel Ther. 2013 Aug 1;7:681-9. doi: 10.2147/DDDT.S41910. eCollection 2013. Review. PubMed PMID: 23946645; PubMed Central PMCID: PMC3738252. 9: Ashur-Fabian O, Blumenthal DT, Bakon M, Nass D, Davis PJ, Hercbergs A. Long-term response in high-grade optic glioma treated with medically induced hypothyroidism and carboplatin: a case report and review of the literature. Anticancer Drugs. 2013 Mar;24(3):315-23. doi: 10.1097/CAD.0b013e32835c7a47. Review. PubMed PMID: 23348245. 10: Shaikh F, Nathan PC, Hale J, Uleryk E, Frazier L. Is there a role for carboplatin in the treatment of malignant germ cell tumors? A systematic review of adult and pediatric trials. Pediatr Blood Cancer. 2013 Apr;60(4):587-92. doi: 10.1002/pbc.24288. Epub 2012 Sep 13. Review. 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References

1: Schluckebier L, Garay OU, Zukin M, Ferreira CG. Carboplatin plus pemetrexed offers superior cost-effectiveness compared to pemetrexed in patients with advanced non-small cell lung cancer and performance status 2. Lung Cancer. 2015 Jun 22. pii: S0169-5002(15)00300-1. doi: 10.1016/j.lungcan.2015.06.015. [Epub ahead of print] PubMed PMID: 26143106.

2: Zhang NN, Zhang LG, Liu ZN, Huang GL, Zhang L, Yi J, Yao L, Hu XH. Therapeutic efficacy of paclitaxel and carboplatin via arterial or venous perfusion in rabbits with VX-2 tongue cancer. Int J Clin Exp Med. 2015 Apr 15;8(4):4979-88. eCollection 2015. PubMed PMID: 26131070; PubMed Central PMCID: PMC4483809.

3: Field KM, Simes J, Nowak AK, Cher L, Wheeler H, Hovey EJ, Brown CS, Barnes EH, Sawkins K, Livingstone A, Freilich R, Phal PM, Fitt G; CABARET/COGNO investigators, Rosenthal MA. Randomized phase 2 study of carboplatin and bevacizumab in recurrent glioblastoma. Neuro Oncol. 2015 Jun 30. pii: nov104. [Epub ahead of print] PubMed PMID: 26130744.

4: Enomoto Y, Kenmotsu H, Watanabe N, Baba T, Murakami H, Yoh K, Ogura T, Takahashi T, Goto K, Kato T. Efficacy and Safety of Combined Carboplatin, Paclitaxel, and Bevacizumab for Patients with Advanced Non-squamous Non-small Cell Lung Cancer with Pre-existing Interstitial Lung Disease: A Retrospective Multi-institutional Study. Anticancer Res. 2015 Jul;35(7):4259-63. PubMed PMID: 26124387.

5: Bertino EM, Williams TM, Nana-Sinkam SP, Shilo K, Chatterjee M, Mo X, RahmaniM, Phillips GS, Villalona-Calero MA, Otterson GA. Stromal Caveolin-1 Is Associated With Response and Survival in a Phase II Trial of nab-Paclitaxel WithCarboplatin for Advanced NSCLC Patients. Clin Lung Cancer. 2015 May 13. pii: S1525-7304(15)00122-9. doi: 10.1016/j.cllc.2015.05.004. [Epub ahead of print] PubMed PMID: 26123189.

6: Matulonis U, Berlin S, Lee H, Whalen C, Obermayer E, Penson R, Liu J, Campos S, Krasner C, Horowitz N. Phase I study of combination of vorinostat, carboplatin, and gemcitabine in women with recurrent, platinum-sensitive epithelial ovarian, fallopian tube, or peritoneal cancer. Cancer Chemother Pharmacol. 2015 Jun 29. [Epub ahead of print] PubMed PMID: 26119093.

7: Zhang S, Xu P, Yuan C, Ou W. [Safety of Neoadjuvant Bevacizumab plus Pemetrexed and Carboplatin 
in Patients with IIIa Lung Adenocarcinoma]. ZhongguoFei Ai Za Zhi. 2015 Jun 20;18(6):365-8. doi: 10.3779/j.issn.1009-3419.2015.06.06. Chinese. PubMed PMID: 26104893.

8: Valsecchi ME, Kimmey G, Bir A, Silbermins D. Role of Carboplatin in the Treatment of Triple Negative Early-Stage Breast Cancer. Rev Recent Clin Trials. 2015 Jun 23. [Epub ahead of print] PubMed PMID: 26104428.

9: Ishimoto O, Sugawara S, Inoue A, Maemondo M, Nukiwa T. Weekly irinotecan combined with carboplatin for patients with small-cell lung cancer: A phase I study. Respir Investig. 2015 Jul;53(4):156-60. doi: 10.1016/j.resinv.2015.02.006. Epub 2015 May 4. PubMed PMID: 26100175.

10: Hong CR, Kang HJ, Kim MS, Ju HY, Lee JW, Kim H, Kim HS, Park SH, Park KD, Park JD, Shin HY, Ahn HS. High-dose chemotherapy and autologous stem cell transplantation with melphalan, etoposide and carboplatin for high-risk osteosarcoma. Bone Marrow Transplant. 2015 Jun 22. doi: 10.1038/bmt.2015.145. [Epub ahead of print] PubMed PMID: 26098952.