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MedKoo product information:

 Lobaplatin

MedKoo Code#:  100544

Name:  Lobaplatin

CAS#:  135558-11-1, 131374-93-1 ([cis-(1R*,2R*)]-isomer)

 

Synonym:  Lobaplatin, D-19466

 

IUPAC/Chemical name:

cis-[(1R*,2R*)-1,2-Cyclobutanebis(methylamino)-N,N'][(2S)-2-hydroxypropanoato(2-)-O1,O2]platinum

 

Chemical structure:

Theoretical analysis :

 

Chemical Formula: C9H18N2O3Pt

Molecular Weight: 397.33

Elemental Analysis: C, 27.21; H, 4.57; N, 7.05; O, 12.08; Pt, 49.10

 

 

Availability and price:

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Quality control data:

Product will be shipped with supporting analytical data.

 

 

Information about this agent

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.

 

 

 

References

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3: 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. Epub 2010 Feb 8. PubMed PMID: 20116286.

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13: Sternberg CN, de Mulder P, Fossa S, Kaye S, Roberts T, Pawinsky A, Daamen S. Lobaplatin in advanced urothelial tract tumors. The Genitourinary Group of the European Organization for Research and Treatment of Cancer (EORTC). Ann Oncol. 1997 Jul;8(7):695-6. PubMed PMID: 9296225.

14: Harstrick A, Vanhoefer U, Heidemann A, Druyen H, Wilke H, Seeber S. Drug interactions of 5-fluorouracil with either cisplatin or lobaplatin--a new, clinically active platinum analog in established human cancer cell lines. Anticancer Drugs. 1997 Apr;8(4):391-5. PubMed PMID: 9180394.

15: Rietbroek RC, van de Vaart PJ, Haveman J, Blommaert FA, Geerdink A, Bakker PJ, Veenhof CH. Hyperthermia enhances the cytotoxicity and platinum-DNA adduct formation of lobaplatin and oxaliplatin in cultured SW 1573 cells. J Cancer Res Clin Oncol. 1997;123(1):6-12. PubMed PMID: 8996534.

16: Saris CP, van de Vaart PJ, Rietbroek RC, Blommaert FA. In vitro formation of DNA adducts by cisplatin, lobaplatin and oxaliplatin in calf thymus DNA in solution and in cultured human cells. Carcinogenesis. 1996 Dec;17(12):2763-9. PubMed PMID: 9006117.

17: Jain N, Lam YM, Pym J, Campling BG. Mechanisms of resistance of human small cell lung cancer lines selected in VP-16 and cisplatin. Cancer. 1996 May 1;77(9):1797-808. PubMed PMID: 8646677.

18: Welink J, Pechstein B, van der Vijgh WJ. Determination of the two diastereoisomers of lobaplatin (D-19466) in plasma ultrafiltrate of cancer patients with a normal or an impaired kidney or liver function by high-performance liquid chromatography with ultraviolet detection. J Chromatogr B Biomed Appl. 1996 Jan 12;675(1):107-11. PubMed PMID: 8634751.

19: Jung P, Bachmann P, Burk K, Jakse G. Lobaplatin in combination with methotrexate and vinblastine in patients with transitional cell carcinoma of the urinary tract--a pilot phase I/(II) study. Eur J Cancer. 1995 Oct;31A(11):1891-2. PubMed PMID: 8541125.

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21: Eliopoulos AG, Kerr DJ, Maurer HR, Hilgard P, Spandidos DA. Induction of the c-myc but not the cH-ras promoter by platinum compounds. Biochem Pharmacol. 1995 Jun 29;50(1):33-8. PubMed PMID: 7605342.

22: Gietema JA, Veldhuis GJ, Guchelaar HJ, Willemse PH, Uges DR, Cats A, Boonstra H, van der Graaf WT, Sleijfer DT, de Vries EG, et al. Phase II and pharmacokinetic study of lobaplatin in patients with relapsed ovarian cancer. Br J Cancer. 1995 Jun;71(6):1302-7. PubMed PMID: 7779728; PubMed Central PMCID: PMC2033845.

23: Degardin M, Armand JP, Chevallier B, Cappelaere P, Lentz MA, David M, Roché H. A clinical screening cooperative group phase II evaluation of lobaplatin (ASTA D-19466) in advanced head and neck cancer. Invest New Drugs. 1995;13(3):253-5. PubMed PMID: 8729955.

24: Weiss RB, Christian MC. New cisplatin analogues in development. A review. Drugs. 1993 Sep;46(3):360-77. Review. Erratum in: Drugs. 1993 Sep;46(3):377. PubMed PMID: 7693428.

25: Gietema JA, Guchelaar HJ, de Vries EG, Aulenbacher P, Sleijfer DT, Mulder NH. A phase I study of lobaplatin (D-19466) administered by 72 h continuous infusion. Anticancer Drugs. 1993 Feb;4(1):51-5. PubMed PMID: 8457715.

26: Gietema JA, de Vries EG, Sleijfer DT, Willemse PH, Guchelaar HJ, Uges DR, Aulenbacher P, Voegeli R, Mulder NH. A phase I study of 1,2-diamminomethyl-cyclobutane-platinum (II)-lactate (D-19466; lobaplatin) administered daily for 5 days. Br J Cancer. 1993 Feb;67(2):396-401. PubMed PMID: 8431374; PubMed Central PMCID: PMC1968188.

27: Harstrick A, Bokemeyer C, Scharnofkse M, Hapke G, Reile D, Schmoll HJ. Preclinical activity of a new platinum analogue, lobaplatin, in cisplatin-sensitive and -resistant human testicular, ovarian, and gastric carcinoma cell lines. Cancer Chemother Pharmacol. 1993;33(1):43-7. PubMed PMID: 8269588.

28: Meijer C, Mulder NH, Timmer-Bosscha H, Sluiter WJ, Meersma GJ, de Vries EG. Relationship of cellular glutathione to the cytotoxicity and resistance of seven platinum compounds. Cancer Res. 1992 Dec 15;52(24):6885-9. PubMed PMID: 1458477.

29: Christian MC. The current status of new platinum analogs. Semin Oncol. 1992 Dec;19(6):720-33. Review. PubMed PMID: 1462169.

30: Guchelaar HJ, Uges DR, Aulenbacher P, de Vries EG, Mulder NH. Stability of the new anticancer platinum analogue 1,2-diaminomethyl-cyclobutane-platinum(II)-lactate (lobaplatin; D19466) in intravenous solutions. Pharm Res. 1992 Jun;9(6):808-11. PubMed PMID: 1409365.

31: Voegeli R, Schumacher W, Engel J, Respondek J, Hilgard P. D-19466, a new cyclobutane-platinum complex with antitumor activity. J Cancer Res Clin Oncol. 1990;116(5):439-42. PubMed PMID: 2229133.
 

 

 

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