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MedKoo CAT#: 100544
Description: Lobaplatin (D-19466) is a diastereometric mixture of platinum(II) complexes containing a 1,2-bis(aminomethyl)cyclobutane stable ligand and lactic acid as the leaving group. Its antitumour activity results from the formation of DNA-drug adducts, mainly as GG and AG intra-strand cross-links. Lobaplatin influences the expression of the c-myc gene, which is involved in oncogenesis, apoptosis and cell proliferation. Lobaplatin has activity in a wide range of preclinical tumour models and appears to overcome tumour resistance to cisplatin and carboplatin in some of these models. In the body, lobaplatin remains largely intact until removed by glomerular filtration. (source: Expert Opin Investig Drugs. 2001 Jan;10(1):119-28.).
MedKoo Cat#: 100544
Chemical Formula: C9H18N2O3Pt
Molecular Weight: 397.33
Elemental Analysis: C, 27.21; H, 4.57; N, 7.05; O, 12.08; Pt, 49.10
Synonym: D19466; D-19466; Lobaplatin.
IUPAC/Chemical Name: cis-[(1R*,2R*)-1,2-Cyclobutanebis(methylamino)-N,N'][(2S)-2-hydroxypropanoato(2-)-O1,O2]platinum
InChi Key: RLXPIABKJFUYFG-UHFFFAOYSA-M
InChi Code: InChI=1S/C6H14N2.C3H5O3.Pt/c7-3-5-1-2-6(5)4-8;1-2(4)3(5)6;/h5-6H,1-4,7-8H2;2H,1H3,(H,5,6);/q;-1;+2/p-1
SMILES Code: CC([O-]1)C([O-][Pt]21[NH2+]CC(CC3)C3C[NH2+]2)=O.
Lobaplatin [D 19466] is a platinum complex with DNA alkylating activity that was developed by ASTA Medica (Degussa) for the treatment of cancer. ASTA Medica discontinued development of lobaplatin, and subsequent development of the compound became the responsibility of Zentaris AG (AEterna Laboratories), which was formed in 2001 from the biopharmaceutical, inhalation technology and gene therapy activities of ASTA Medica. On 30 December 2002, Zentaris was acquired by AEterna Laboratories. Cisplatin, one of the original platinum compounds, has had a major impact on the treatment of solid tumours such as germ cell cancer, ovarian cancer, bladder cancer and bronchial carcinoma, but its clinical usefulness is limited by renal, neurological and gastrointestinal toxicity. This has led to the development of second- and third-generation platinum analogues, such as lobaplatin, with reduced toxicity and a better therapeutic index. In January 2003, Zentaris AG and Hainan Tianwang International Pharmaceutical signed a contract for the manufacture and marketing of lobaplatin in China. The technology transfer agreement provides for Zentaris to receive a one-time payment to the amount of 4.5 million Canadian dollars. In addition, the contract foresees for Tianwang to manufacture and deliver lobaplatin to Zentaris or its partners for marketing in all other countries worldwide. Lobaplatin has been approved in China for the treatment of chronic myelogenous leukaemia (CML) and inoperable, metastatic breast and small cell lung cancer. However, it has not yet been launched there. In June 2003, AEterna reported that it expects lobaplatin to be launched in China by the end of 2003 at the 10th Annual Meeting of the Biotechnology Industry Organization (BIO-2003). Lobaplatin has also completed phase II clinical trials in the US, Australia, EU, Brazil and South Africa for the treatment of various cancers, including breast, oesophageal, lung and ovarian cancers as well as CML . see: Drugs R D. 2003;4(6):369-72. http://www.ncbi.nlm.nih.gov/pubmed/14584968 .
Phase I clinical trials of three quite different administration schedules found the same dose-limiting toxicity (thrombocytopoenia) and similar maximum tolerated doses (60 mg/m(2) per 3 - 4 weeks). In Phase II trials, lobaplatin showed activity in patients with a variety of tumour types. Many of the patients who responded to lobaplatin may also have responded to cisplatin and carboplatin because they had had no prior chemotherapy or had a prolonged remission after earlier treatment. In conclusion, lobaplatin is a new platinum drug, which overcomes some forms of cisplatin resistance in preclinical tumour models. Several potential clinical applications remain unexplored, such as its use in relapsed testicular cancer and in combination with other cancer chemotherapeutic agents and ionising radiation.
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2: Deng QQ, Huang XE, Ye LH, Lu YY, Liang Y, Xiang J. Phase II trial of LouboÂ® (Lobaplatin) and pemetrexed for patients with metastatic breast cancer not responding to anthracycline or taxanes. Asian Pac J Cancer Prev. 2013;14(1):413-7. PubMed PMID: 23534764.
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4: Xie CY, Xu YP, Jin W, Lou LG. Antitumor activity of lobaplatin alone or in combination with antitubulin agents in non-small-cell lung cancer. Anticancer Drugs. 2012 Aug;23(7):698-705. doi: 10.1097/CAD.0b013e328352cc10. PubMed PMID: 22441567.
5: Wang Z, Tang X, Zhang Y, Qi R, Li Z, Zhang K, Liu Z, Yang X. Lobaplatin induces apoptosis and arrests cell cycle progression in human cholangiocarcinoma cell line RBE. Biomed Pharmacother. 2012 Apr;66(3):161-6. doi: 10.1016/j.biopha.2011.09.008. Epub 2011 Dec 29. PubMed PMID: 22425181.
6: Engel JB, Martens T, Hahne JC, HÃ¤usler SF, Krockenberger M, Segerer S, Djakovic A, Meyer S, Dietl J, Wischhusen J, Honig A. Effects of lobaplatin as a single agent and in combination with TRAIL on the growth of triple-negative p53-mutated breast cancers in vitro. Anticancer Drugs. 2012 Apr;23(4):426-36. doi: 10.1097/CAD.0b013e32834fb8ce. PubMed PMID: 22314264.
7: Dai HY, Liu L, Qin SK, He XM, Li SY. Lobaplatin suppresses proliferation and induces apoptosis in the human colorectal carcinoma cell Line LOVO in vitro. Biomed Pharmacother. 2011 Jun;65(3):137-41. doi: 10.1016/j.biopha.2010.12.001. Epub 2010 Dec 30. PubMed PMID: 21612887.
8: Wu Q, Qin SK, Teng FM, Chen CJ, Wang R. Lobaplatin arrests cell cycle progression in human hepatocellular carcinoma cells. J Hematol Oncol. 2010 Oct 31;3:43. doi: 10.1186/1756-8722-3-43. PubMed PMID: 21034513; PubMed Central PMCID: PMC2988698.
9: Zhou B, Shan H, Zhu KS, Jiang ZB, Guan SH, Meng XC, Zeng XC. Chemoembolization with lobaplatin mixed with iodized oil for unresectable recurrent hepatocellular carcinoma after orthotopic liver transplantation. J Vasc Interv Radiol. 2010 Mar;21(3):333-8. doi: 10.1016/j.jvir.2009.11.006. Epub 2010 Feb 8. PubMed PMID: 20116286.
(Last updated: 4/18/2016).