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MedKoo Cat#: 201410 | Name: Gimatecan

Description:

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

Gimatecan is an orally bioavailable, semi-synthetic lipophilic analogue of camptothecin, a quinoline alkaloid extracted from the Asian tree Camptotheca acuminate, with potential antineoplastic and antiangiogenic activities. Gimatecan 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 topoisomerase I-DNA complex is encountered by the DNA replication machinery, DNA replication is disrupted, and the tumor cell undergoes apoptosis.

Chemical Structure

Gimatecan
Gimatecan
CAS#292618-32-7

Theoretical Analysis

MedKoo Cat#: 201410

Name: Gimatecan

CAS#: 292618-32-7

Chemical Formula: C25H25N3O5

Exact Mass: 447.1794

Molecular Weight: 447.48

Elemental Analysis: C, 67.10; H, 5.63; N, 9.39; O, 17.88

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
LBQ707; LBQ 707; LB-Q707; ST1481; ST1481; ST-1481; CPT 1847; CPT-1847; CPT1847; Gimatecan;
IUPAC/Chemical Name
(4S)-11-((E)-((1,1-Dimethylethoxy)imino)methyl)-4-ethyl-4-hydroxy-1,12-dihydro-14H-pyrano(3',4':6,7)indolizino(1,2-b)quinoline-3,14(4H)-dione
InChi Key
UIVFUQKYVFCEKJ-OPTOVBNMSA-N
InChi Code
InChI=1S/C25H25N3O5/c1-5-25(31)18-10-20-21-16(12-28(20)22(29)17(18)13-32-23(25)30)15(11-26-33-24(2,3)4)14-8-6-7-9-19(14)27-21/h6-11,31H,5,12-13H2,1-4H3/b26-11+/t25-/m0/s1
SMILES Code
O=C1[C@](O)(CC)C2=C(CO1)C(N3CC4=C(/C=N/OC(C)(C)C)C5=CC=CC=C5N=C4C3=C2)=O
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. Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
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).
HS Tariff Code
2934.99.9001
More Info
Phase II study of Gimatecan: From June 2005 to December 2005, 69 assessable patients were enrolled. The best overall response to study treatment by combined CA-125 and RECIST criteria was partial response in 17 patients (24.6%) and disease stabilization in 22 patients (31.9%). The median time to progression and overall survival were 3.8 and 16.2 months, respectively. A total of 312 cycles were administered. Neutropenia grade 4 and thrombocytopenia grade 4 occurred in 17.4% and 7.2% of patients, respectively. Diarrhea grade 4 was never observed. Asthenia and fatigue were reported by 36.2% and 18.8% of patients, but were all grade 2 or less. CONCLUSION: Gimatecan is a new active agent in previously treated ovarian cancer with myelosuppression as main toxicity.   (source: Ann Oncol. 2010 Apr;21(4):759-65.). Phase II study of Gimatecan: From June 2005 to December 2005, 69 assessable patients were enrolled. The best overall response to study treatment by combined CA-125 and RECIST criteria was partial response in 17 patients (24.6%) and disease stabilization in 22 patients (31.9%). The median time to progression and overall survival were 3.8 and 16.2 months, respectively. A total of 312 cycles were administered. Neutropenia grade 4 and thrombocytopenia grade 4 occurred in 17.4% and 7.2% of patients, respectively. Diarrhea grade 4 was never observed. Asthenia and fatigue were reported by 36.2% and 18.8% of patients, but were all grade 2 or less. CONCLUSION: Gimatecan is a new active agent in previously treated ovarian cancer with myelosuppression as main toxicity.   (source: Ann Oncol. 2010 Apr;21(4):759-65.).    

Preparing Stock Solutions

The following data is based on the product molecular weight 447.48 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
This message contains search results from the National Center for Biotechnology Information (NCBI) at the U.S. National Library of Medicine (NLM). Do not reply directly to this message Sent On: Wed Oct 21 21:46:41 2020 Search: Gimatecan 20 selected items PubMed Results Items 1-20 of 20 (Display the 20 citations in PubMed) 1: DE Cesare M. High Efficacy of Intravenous Gimatecan on Human Tumor Xenografts. Anticancer Res. 2018 Oct;38(10):5783-5790. doi: 10.21873/anticanres.12917. PMID: 30275200. 2: Minenkova O, Vesci L, De Santis R, Santapaola D, Cincinelli R, Musso L, Dallavalle S, Giannini G. Growth inhibition of human ovarian carcinoma by a novel AvidinOX-anchored biotinylated camptothecin derivative. Bioorg Med Chem Lett. 2018 Nov 1;28(20):3312-3314. doi: 10.1016/j.bmcl.2018.09.017. Epub 2018 Sep 15. PMID: 30243588. 3: Zou J, Li S, Chen Z, Lu Z, Gao J, Zou J, Lin X, Li Y, Zhang C, Shen L. A novel oral camptothecin analog, gimatecan, exhibits superior antitumor efficacy than irinotecan toward esophageal squamous cell carcinoma in vitro and in vivo. Cell Death Dis. 2018 May 31;9(6):661. doi: 10.1038/s41419-018-0700-0. PMID: 29855512; PMCID: PMC5981453. 4: Chen Z, Liu Z, Huang W, Li Z, Zou J, Wang J, Lin X, Li B, Chen D, Hu Y, Ji J, Gao J, Shen L. Gimatecan exerts potent antitumor activity against gastric cancer in vitro and in vivo via AKT and MAPK signaling pathways. J Transl Med. 2017 Dec 13;15(1):253. doi: 10.1186/s12967-017-1360-z. PMID: 29237470; PMCID: PMC5729429. 5: Zhao Y, Lau LF, Dai X, Li B. In Vitro and In Vivo Anticancer Activity of Gimatecan against Hepatocellular Carcinoma. Asian Pac J Cancer Prev. 2016 Nov 1;17(11):4853-4856. doi: 10.22034/APJCP.2016.17.11.4853. PMID: 28030910; PMCID: PMC5454685. 6: Mulholland K, Wu C. Computational Study of Anticancer Drug Resistance Caused by 10 Topisomerase I Mutations, Including 7 Camptothecin Analogs and Lucanthone. J Chem Inf Model. 2016 Sep 26;56(9):1872-83. doi: 10.1021/acs.jcim.6b00317. Epub 2016 Sep 1. PMID: 27564845. 7: Prada CF, Alvarez-Velilla R, Balaña-Fouce R, Prieto C, Calvo-Álvarez E, Escudero-Martínez JM, Requena JM, Ordóñez C, Desideri A, Pérez-Pertejo Y, Reguera RM. Gimatecan and other camptothecin derivatives poison Leishmania DNA- topoisomerase IB leading to a strong leishmanicidal effect. Biochem Pharmacol. 2013 May 15;85(10):1433-40. doi: 10.1016/j.bcp.2013.02.024. Epub 2013 Mar 1. PMID: 23466420. 8: Lin F, Marchetti S, Pluim D, Iusuf D, Mazzanti R, Schellens JH, Beijnen JH, van Tellingen O. Abcc4 together with abcb1 and abcg2 form a robust cooperative drug efflux system that restricts the brain entry of camptothecin analogues. Clin Cancer Res. 2013 Apr 15;19(8):2084-95. doi: 10.1158/1078-0432.CCR-12-3105. Epub 2013 Mar 5. PMID: 23461902. 9: Hu J, Wen PY, Abrey LE, Fadul CE, Drappatz J, Salem N, Supko JG, Hochberg F. A phase II trial of oral gimatecan for recurrent glioblastoma. J Neurooncol. 2013 Feb;111(3):347-53. doi: 10.1007/s11060-012-1023-0. Epub 2012 Dec 12. PMID: 23232808. 10: Perego P, Cossa G, Tinelli S, Corna E, Carenini N, Gatti L, De Cesare M, Ciusani E, Zunino F, Luison E, Canevari S, Zaffaroni N, Beretta GL. Role of tyrosyl-DNA phosphodiesterase 1 and inter-players in regulation of tumor cell sensitivity to topoisomerase I inhibition. Biochem Pharmacol. 2012 Jan 1;83(1):27-36. doi: 10.1016/j.bcp.2011.09.021. Epub 2011 Sep 29. PMID: 21978643. 11: Biroccio A, Porru M, Rizzo A, Salvati E, D'Angelo C, Orlandi A, Passeri D, Franceschin M, Stevens MF, Gilson E, Beretta G, Zupi G, Pisano C, Zunino F, Leonetti C. DNA damage persistence as determinant of tumor sensitivity to the combination of Topo I inhibitors and telomere-targeting agents. Clin Cancer Res. 2011 Apr 15;17(8):2227-36. doi: 10.1158/1078-0432.CCR-10-3033. Epub 2011 Feb 25. PMID: 21355072. 12: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2010 Jan-Feb;32(1):47-86. PMID: 20383346. 13: Zucchetti M, Meco D, Di Francesco AM, Servidei T, Patriarca V, Cusano G, D'Incalci M, Forestieri D, Pisano C, Riccardi R. Antitumor activity and pharmacokinetics of oral gimatecan on pediatric cancer xenografts. Cancer Chemother Pharmacol. 2010 Sep;66(4):635-41. doi: 10.1007/s00280-009-1201-8. Epub 2009 Dec 20. PMID: 20091168. 14: Frapolli R, Zucchetti M, Sessa C, Marsoni S, Viganò L, Locatelli A, Rulli E, Compagnoni A, Bello E, Pisano C, Carminati P, D'Incalci M. Clinical pharmacokinetics of the new oral camptothecin gimatecan: the inter-patient variability is related to alpha1-acid glycoprotein plasma levels. Eur J Cancer. 2010 Feb;46(3):505-16. doi: 10.1016/j.ejca.2009.11.006. Epub 2009 Dec 16. PMID: 20007015. 15: Pecorelli S, Ray-Coquard I, Tredan O, Colombo N, Parma G, Tisi G, Katsaròs D, Lhommé C, Lissoni AA, Vermorken JB, du Bois A, Poveda A, Frigerio L, Barbieri P, Carminati P, Brienza S, Guastalla JP. Phase II of oral gimatecan in patients with recurrent epithelial ovarian, fallopian tube or peritoneal cancer, previously treated with platinum and taxanes. Ann Oncol. 2010 Apr;21(4):759-765. doi: 10.1093/annonc/mdp514. Epub 2009 Nov 11. PMID: 19906760; PMCID: PMC2844948. 16: Fabbri F, Brigliadori G, Carloni S, Ulivi P, Tesei A, Silvestrini R, Amadori D, Zoli W. Docetaxel-ST1481 sequence exerts a potent cytotoxic activity on hormone-resistant prostate cancer cells by reducing drug resistance-related gene expression. Prostate. 2010 Feb 1;70(2):219-27. doi: 10.1002/pros.21055. PMID: 19790230. 17: Zuco V, Supino R, Favini E, Tortoreto M, Cincinelli R, Croce AC, Bucci F, Pisano C, Zunino F. Efficacy of ST1968 (namitecan) on a topotecan-resistant squamous cell carcinoma. Biochem Pharmacol. 2010 Feb 15;79(4):535-41. doi: 10.1016/j.bcp.2009.09.012. PMID: 19765546. 18: Pace S, Capocasa F, Tallarico C, Frapolli R, Zucchetti M, Longo A. Determination of total and lactone form of a new camptothecin derivative gimatecan (ST1481) and its metabolite ST1698 in human plasma by high-performance liquid chromatography with fluorimetric detection. J Pharm Biomed Anal. 2009 Oct 15;50(3):507-14. doi: 10.1016/j.jpba.2009.05.019. Epub 2009 May 27. PMID: 19553057. 19: Vekhoff P, Halby L, Oussedik K, Dallavalle S, Merlini L, Mahieu C, Lansiaux A, Bailly C, Boutorine A, Pisano C, Giannini G, Alloatti D, Arimondo PB. Optimized synthesis and enhanced efficacy of novel triplex-forming camptothecin derivatives based on gimatecan. Bioconjug Chem. 2009 Apr;20(4):666-72. doi: 10.1021/bc800494y. PMID: 19309124. 20: Oostendorp RL, van de Steeg E, van der Kruijssen CM, Beijnen JH, Kenworthy KE, Schinkel AH, Schellens JH. Organic anion-transporting polypeptide 1B1 mediates transport of Gimatecan and BNP1350 and can be inhibited by several classic ATP-binding cassette (ABC) B1 and/or ABCG2 inhibitors. Drug Metab Dispos. 2009 Apr;37(4):917-23. doi: 10.1124/dmd.108.024901. Epub 2009 Jan 12. PMID: 19139163.