Belotecan free base

    WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 200461

CAS#: 256411-32-2 (free base)

Description: Belotecan, also known as CKD-602, is the semi-synthetic camptothecin analogue belotecan with potential antitumor activity. Belotecan binds to and inhibits the activity of topoisomerase I, stabilizing the cleavable complex of topoisomerase I-DNA, which inhibits the religation of single-stranded DNA breaks generated by topoisomerase I; lethal double-stranded DNA breaks occur when the top technicaloisomerase I-DNA complex is encountered by the DNA replication machinery, DNA replication is disrupted, and the tumor cell undergoes apoptosis. Topoisomerase I is an enzyme that mediates reversible single-strand breaks in DNA during DNA replication.


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Belotecan free, purity > 98%, is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 200461
Name: Belotecan free base
CAS#: 256411-32-2 (free base)
Chemical Formula: C25H27N3O4
Exact Mass: 433.2002
Molecular Weight: 433.51
Elemental Analysis: C, 69.27; H, 6.28; N, 9.69; O, 14.76


Related CAS #: 256411-32-2 (free base)   213819-48-8 (HCl)    

Synonym: Camtobell; CKD602; CKD-602; CKD 602; Belotecan free base

IUPAC/Chemical Name: (4S)-4-Ethyl-4-hydroxy-11-(2-(isopropylamino)ethyl)-1,12-dihydro-14H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H)-dione

InChi Key: LNHWXBUNXOXMRL-VWLOTQADSA-N

InChi Code: InChI=1S/C25H27N3O4/c1-4-25(31)19-11-21-22-17(12-28(21)23(29)18(19)13-32-24(25)30)15(9-10-26-14(2)3)16-7-5-6-8-20(16)27-22/h5-8,11,14,26,31H,4,9-10,12-13H2,1-3H3/t25-/m0/s1

SMILES Code: O=C1[C@](O)(CC)C2=C(CO1)C(N3CC4=C(CCNC(C)C)C5=CC=CC=C5N=C4C3=C2)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO, not in water

Shelf Life:
>5 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code:
293490


Additional Information

  
  
 
 
 
 


References

1: Kim HS, Park NH, Kang S, Seo SS, Chung HH, Kim JW, Song YS, Kang SB. Comparison of the efficacy between topotecan- and belotecan-, a new camptothecin analog, based chemotherapies for recurrent epithelial ovarian cancer: a single institutional experience. J Obstet Gynaecol Res. 2010 Feb;36(1):86-93. PubMed PMID: 20178532.

2: Jeong J, Cho BC, Sohn JH, Choi HJ, Kim SH, Lee YJ, Jung MK, Shin SJ, Park MS, Kim SK, Chang J, Kim JH. Belotecan for relapsing small-cell lung cancer patients initially treated with an irinotecan-containing chemotherapy: A phase II trial. Lung Cancer. 2010 Mar 16. [Epub ahead of print] PubMed PMID: 20138389.

3: Lee DH, Kim SW, Suh C, Lee JS, Ahn JS, Ahn MJ, Park K, Na II, Lee JC, Ryoo BY, Yang SH. Multicenter phase 2 study of belotecan, a new camptothecin analog, and cisplatin for chemotherapy-naive patients with extensive-disease small cell lung cancer. Cancer. 2010 Jan 1;116(1):132-6. Erratum in: Cancer. 2010 Jan 15;116(2):540. PubMed PMID: 19904804.

4: Nam EJ, Kim JW, Kim JH, Kim S, Kim SW, Jang SY, Lee DW, Jung YW, Kim YT. Efficacy and Toxicity of Belotecan With and Without Cisplatin in Patients With Recurrent Ovarian Cancer. Am J Clin Oncol. 2009 Sep 10. [Epub ahead of print] PubMed PMID: 19745693.

5: Kim SJ, Kim JS, Kim SC, Kim YK, Kim YK, Kang JY, Yoon HK, Song JS, Lee SH, Moon HS, Kim JW, Kim KH, Kim CH, Shim BY, Kim HK. A multicenter phase II study of belotecan, new camptothecin analogue, in patients with previously untreated extensive stage disease small cell lung cancer. Lung Cancer. 2010 Jun;68(3):446-9. Epub 2009 Aug 14. PubMed PMID: 19683359.

6: Kim HS, Kang SB, Seo SS, Han SS, Kim JW, Park NH, Kang SB, Lee HP, Song YS. Phase I/IIa study of combination chemotherapy with CKD-602 and cisplatin in patients with recurrent epithelial ovarian cancer. Ann N Y Acad Sci. 2009 Aug;1171:627-34. PubMed PMID: 19723113.

7: Zamboni WC, Strychor S, Maruca L, Ramalingam S, Zamboni BA, Wu H, Friedland DM, Edwards RP, Stoller RG, Belani CP, Ramanathan RK. Pharmacokinetic study of pegylated liposomal CKD-602 (S-CKD602) in patients with advanced malignancies. Clin Pharmacol Ther. 2009 Nov;86(5):519-26. Epub 2009 Aug 12. PubMed PMID: 19675541.

8: Jin QR, Shim WS, Choi MK, Tian GY, Song IS, Yang SG, Kim DD, Chung SJ, Shim CK. Decreased urinary secretion of belotecan in folic acid-induced acute renal failure rats due to down-regulation of Oat1 and Bcrp. Xenobiotica. 2009 Oct;39(10):711-21. PubMed PMID: 19552531.

9: Kim YY, Park CK, Kim SK, Phi JH, Kim JH, Kim CY, Wang KC, Cho BK. CKD-602, a camptothecin derivative, inhibits proliferation and induces apoptosis in glioma cell lines. Oncol Rep. 2009 Jun;21(6):1413-9. PubMed PMID: 19424618.

10: Zamboni WC, Ramalingam S, Friedland DM, Edwards RP, Stoller RG, Strychor S, Maruca L, Zamboni BA, Belani CP, Ramanathan RK. Phase I and pharmacokinetic study of pegylated liposomal CKD-602 in patients with advanced malignancies. Clin Cancer Res. 2009 Feb 15;15(4):1466-72. Epub 2009 Feb 3. Erratum in: Clin Cancer Res. 2009 Apr 15;15(8):2949-50. PubMed PMID: 19190127.

11: Ok YJ, Myoung H, Kim YK, Lee JH, Kim MJ, Yun PY. Apoptotic effect of CKD-602 (Camtobell) on oral squamous cell carcinoma cell lines. Oral Oncol. 2009 Mar;45(3):266-72. Epub 2008 Aug 19. PubMed PMID: 18715816.

12: Lee HP, Seo SS, Ryu SY, Kim JH, Bang YJ, Park SY, Nam JH, Kang SB, Lee KH, Song YS. Phase II evaluation of CKD-602, a camptothecin analog, administered on a 5-day schedule to patients with platinum-sensitive or -resistant ovarian cancer. Gynecol Oncol. 2008 Jun;109(3):359-63. Epub 2008 Apr 10. PubMed PMID: 18405948.

13: Zamboni WC, Strychor S, Joseph E, Walsh DR, Zamboni BA, Parise RA, Tonda ME, Yu NY, Engbers C, Eiseman JL. Plasma, tumor, and tissue disposition of STEALTH liposomal CKD-602 (S-CKD602) and nonliposomal CKD-602 in mice bearing A375 human melanoma xenografts. Clin Cancer Res. 2007 Dec 1;13(23):7217-23. PubMed PMID: 18056203.

14: Lee DH, Kim SW, Bae KS, Hong JS, Suh C, Kang YK, Lee JS. A phase I and pharmacologic study of belotecan in combination with cisplatin in patients with previously untreated extensive-stage disease small cell lung cancer. Clin Cancer Res. 2007 Oct 15;13(20):6182-6. PubMed PMID: 17947485.

15: Lee DH, Kim SW, Suh C, Lee JS, Lee JH, Lee SJ, Ryoo BY, Park K, Kim JS, Heo DS, Kim NK. Belotecan, new camptothecin analogue, is active in patients with small-cell lung cancer: results of a multicenter early phase II study. Ann Oncol. 2008 Jan;19(1):123-7. Epub 2007 Sep 6. PubMed PMID: 17823384.

16: Yu NY, Conway C, Pena RL, Chen JY. STEALTH liposomal CKD-602, a topoisomerase I inhibitor, improves the therapeutic index in human tumor xenograft models. Anticancer Res. 2007 Jul-Aug;27(4B):2541-5. PubMed PMID: 17695551.

17: Chung MK, Kim CY, Kim JC. Reproductive toxicity evaluation of a new camptothecin anticancer agent, CKD-602, in pregnant/lactating female rats and their offspring. Cancer Chemother Pharmacol. 2007 Feb;59(3):383-95. Epub 2006 Aug 1. PubMed PMID: 16896929.

18: Chung MK, Han SS, Kim JC. Evaluation of the toxic potentials of a new camptothecin anticancer agent CKD-602 on fertility and early embryonic development in rats. Regul Toxicol Pharmacol. 2006 Aug;45(3):273-81. Epub 2006 Jun 30. PubMed PMID: 16814440.

19: Chung MK, Kim JC, Han SS. Embryotoxic effects of CKD-602, a new camptothecin anticancer agent, in rats. Reprod Toxicol. 2005 May-Jun;20(1):165-73. PubMed PMID: 15808800.

20: Kim JC, Shin DH, Park SH, Park SC, Kim YB, Kim HC, Cha SW, Cho KH, Kang BH, Chung MK. 4-Week repeated intravenous dose toxicity study of a new camptothecin anticancer agent CKD-602 in dogs. Food Chem Toxicol. 2005 May;43(5):699-706. PubMed PMID: 15778009.

21: Chung MK, Kim JC, Han SS. Effects of CKD-602, a new camptothecin anticancer agent, on pregnant does and embryo-fetal development in rabbits. Drug Chem Toxicol. 2005;28(1):35-49. PubMed PMID: 15720034.

22: Kim JC, Shin DH, Kim SH, Kim JK, Park SC, Son WC, Lee HS, Suh JE, Kim CY, Ha CS, Chung MK. Subacute toxicity evaluation of a new camptothecin anticancer agent CKD-602 administered by intravenous injection to rats. Regul Toxicol Pharmacol. 2004 Dec;40(3):356-69. PubMed PMID: 15546689.

23: Crul M. CKD-602. Chong Kun Dang. Curr Opin Investig Drugs. 2003 Dec;4(12):1455-9. Review. PubMed PMID: 14763132.

24: Kim EJ, Lee RK, Suh JE, Han SS, Kim JK. Safety pharmacology of CKD-602, a novel anticancer agent. Arzneimittelforschung. 2003;53(4):272-9. PubMed PMID: 12785124.

25: Cho JY, Seo HB, Yu KS, Bae KS, Yi SY, Jang IJ, Shin SG. Simple and sensitive determination of the new antitumor drug CKD-602 in human plasma by liquid chromatography. J Chromatogr B Analyt Technol Biomed Life Sci. 2003 Jan 25;784(1):25-31. PubMed PMID: 12504179.

26: Park IS, Ahn MR, Suh SK, Choi HS, Sohn SJ, Yang JS, Yoo TM, Kuh HJ. In vitro pharmacodynamics of CKD-602 in HT-29 cells. Arch Pharm Res. 2002 Oct;25(5):718-23. Erratum in: Arch Pharm Res. 2002 Dec;25(6):989. PubMed PMID: 12433211.

27: Kim JH, Lee SK, Lim JL, Shin HJ, Hong CI. Preformulation studies of a novel camptothecin anticancer agent, CKD-602: physicochemical characterization and hydrolytic equilibrium kinetics. Int J Pharm. 2002 Jun 4;239(1-2):207-11. PubMed PMID: 12052706.

28: Lee JH, Lee JM, Lim KH, Kim JK, Ahn SK, Bang YJ, Hong CI. Preclinical and phase I clinical studies with Ckd-602, a novel camptothecin derivative. Ann N Y Acad Sci. 2000;922:324-5. PubMed PMID: 11193913.

29: Lee JH, Lee JM, Kim JK, Ahn SK, Lee SJ, Kim MY, Jew SS, Park JG, Hong CI. Antitumor activity of 7-[2-(N-isopropylamino)ethyl]-(20S)-camptothecin, CKD602, as a potent DNA topoisomerase I inhibitor. Arch Pharm Res. 1998 Oct;21(5):581-90. PubMed PMID: 9875499.