Gimatecan

Names

[ Name ]:
Gimatecan

[Synonym ]:
trans-1-Hydroxy-7-phenyl-hepten-(2)-diin-(4,6)
7-Phenyl-hept-2t-en-4,6-diin-1-ol
7-tert-butoxyiminomethylcamptothecin
(E)-7-phenyl-2-hepten-4,6-diyn-1-ol
7-phenyl-hept-2t-ene-4,6-diyn-1-ol
ST-1481
1-Phenyl-hepten-(5)-trans-diin-(1.3)-ol-(7)
trans-7-Phenyl-hepten-(2)-diin-(4.6)-ol-(1)
2-Heptene-4,6-diyn-1-ol,7-phenyl-,(E)
(4S)-11-[(E)-(tert-butoxyimino)methyl]-4-ethyl-4-hydroxy-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
7-(t-butoxy)iminomethylcamptothecin
1H-Pyrano(3',4':6,7)indolizino(1,2-b)quinoline-11-carboxaldehyde, 4-ethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-, 11-(O-(1,1-dimethylethyl)oxime), (4S)-
(E)-7-tert-butoxyiminomethyl-camptothecin
7-hydroxy-1-phenyl-hept-5E-ene-1,3-diyne
(4S)-4-Ethyl-4-hydroxy-11-[(E)-{[(2-methyl-2-propanyl)oxy]imino}methyl]-1H-pyrano[3',4':6,7]indolizino[1,2-b]quinoline-3,14(4H,12H)-dione
1H-Pyrano[3',4':6,7]indolizino[1,2-b]quinoline-11-carboxaldehyde, 4-ethyl-3,4,12,14-tetrahydro-4-hydroxy-3,14-dioxo-, 11-[O-(1,1-dimethylethyl)oxime], (4S)-
Gimatecan

Biological Activity

[Description]:

Gimatecan (ST1481) is a potent topoisomerase I inhibitor. Gimatecan is an orally bioavailable camptothecin analogue with antitumor activity[1].

[Related Catalog]:

Research Areas >> Cancer

Signaling Pathways >> Cell Cycle/DNA Damage >> Topoisomerase

[Target]

Topoisomerase I

[In Vitro]

Gimatecan (3 to 300 ng/mL) significantly inhibits the growth of human bladder cancer models (HT1376 and MCR), thus reflecting antiproliferative potency[1]. Gimatecan causes a persistent S-phase arrest At 0.003 µg/mL and the number of S-phase cells increased after treatment with a higher concentration (0.03 µg/mL)[1]. Cell Proliferation Assay[1] Cell Line: HT1376 cells harbor a p53 mutation; MCR cells harbor two p53 mutations: one in exon 4 (CGC→CCC) and one in exon 9 (CAG→TAG) Concentration: 3 to 300 ng/mL Incubation Time: 1, 6, and 24 hours Result: IC50s of 90±3 and 9.0±0.4 ng/mL for MCR and HT1376 cells after treatment for 1 hours. IC50s of 5.0±0.2 and 2.8±0.1 ng/mL for MCR and HT1376 cells after treatment for 24 hours. The growth-inhibitory effect was dose-dependent and time-dependent. HT1376 cells were more sensitive than MCR cells at least following a short-term exposure.

[In Vivo]

Gimatecan (2 mg/kg; treatment per os, every fourth day for four times) is effective for inhibiting tumor growth[1]. Animal Model: Athymic Swiss nude mice bearing HT1376 model[1] Dosage: 2 mg/kg Administration: Treatment per os, every fourth day for four times Result: Caused a marked tumor growth inhibition during treatment.

[References]

[1]. Paola Ulivi, et al. Cellular Basis of Antiproliferative and Antitumor Activity of the Novel Camptothecin Derivative, Gimatecan, in Bladder Carcinoma Models. Neoplasia. 2005 Feb;7(2):152-61.

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
780.6±70.0 °C at 760 mmHg

[ Molecular Formula ]:
C₂₅H₂₅N₃O₅

[ Molecular Weight ]:
447.483

[ Flash Point ]:
425.9±35.7 °C

[ Exact Mass ]:
447.179413

[ PSA ]:
103.01000

[ LogP ]:
3.42

[ Vapour Pressure ]:
0.0±2.8 mmHg at 25°C

[ Index of Refraction ]:
1.667

Safety Information

[ Hazard Codes ]:
T+

Precursor & DownStream

Precursor

DownStream

Related Compounds

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