Paclitaxel

Names

[ Name ]:
Paclitaxel

[Synonym ]:
(2α,3ξ,5β,7β,10β,13α)-4,10-Diacetoxy-13-{[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy}-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
BMS 181339-01
Benzenepropanoic acid, β-(benzoylamino)-α-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13 ,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (αR,βS)-
Capxol
Plaxicel
Benzenepropanoic acid, β-(benzoylamino)-α-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-t etramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (αR,βS)-
taxal
benzenepropanoic acid, b-(benzoylamino)-a-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (aR,bS)-
benzenepropanoic acid, β-(benzoylamino)-α-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (αR,βS)-
Onxal
Paxceed
(2a,5b,7b,10b,13a)-4,10-bis(acetyloxy)-13-{[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy}-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
(2α,5β,7β,10β,13α)-4,10-Diacetoxy-13-{[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoyl]oxy}-1,7-dihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
5b,20-Epoxy-1,2a,4,7b,10b,13a-hexahydroxytax-11-en-9-one 4,10-Diacetate 2-Benzoate 13-Ester with (2R,3S)-N-Benzoyl-3-phenylisoserine
Yewtaxan
MFCD00869953
EINECS 205-285-7
Paclitaxel
TAXUS
NK 105
TaxAlbin
DHP 107
Peclitaxel
Taxol
(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-Bis(acetyloxy)-1,9-dihydroxy-15-({(2R,3S)-2-hydroxy-3-phenyl-3-[(phenylcarbonyl)amino]propanoyl}oxy)-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0.0]heptadec-13-en-2-ylbenzolcarboxylat
Paxene
Taxol A
LipoPac
Ebetaxel
ABI 007
(2α,5β,7β,10β,13α)-4,10-bis(acetyloxy)-1,7-dihydroxy-13-({(2R,3S)-2-hydroxy-3-phenyl-3-[(phenylcarbonyl)amino]propanoyl}oxy)-9-oxo-5,20-epoxytax-11-en-2-yl benzoate
Anzatax
UNII-P88XT4IS4D
(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-bis(acetyloxy)-1,9-dihydroxy-15-({(2R,3S)-2-hydroxy-3-phenyl-3-[(phenylcarbonyl)amino]propanoyl}oxy)-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0.0]heptadec-13-en-2-yl benzoate
EMPAC
Benzenepropanoic acid, β-(benzoylamino)-α-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-6,12b-bis(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (αR,βS)-
Onxol

Biological Activity

[Description]:

Paclitaxel is a potent anticancer medication which can promote microtubule (MT) assembly, inhibit MT depolymerization, and change MT dynamics required for mitosis and cell proliferation.

[Related Catalog]:

Signaling Pathways >> Antibody-drug Conjugate >> ADC Cytotoxin

Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin

Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

Research Areas >> Cancer

Natural Products >> Terpenoids and Glycosides

[Target]

IC50: 4 nM (MT)

[In Vitro]

Paclitaxel at 0.1, 0.5, and 1 μM reduces the proliferation and survival of CCRF-HSB-2 cells in a dose-dependent fashion and that the IC50 value of taxol is about 0.25 μM[1]. Paclitaxel directly associates with the endoplasmic reticulum to stimulate the release of calcium into the cytosol, contributing to the induction of apoptosis[2].

[In Vivo]

In a SCID mouse xenograft model, low dose metronomic Paclitaxel treatment decreases lung dissemination of EGI-1 cells without significantly affecting their local tumor growth[3]. Low doses of paclitaxel promot liver metastasis in mouse xenografts, which correlats with changes in estrogen metabolism in the host liver[4]. Paclitaxel (2 mg/kg per treatment, black circles) induces mechanical hypersensitivity in the glabrous skin of the hindpaw[5].

[Kinase Assay]

To determine which caspases are involved in apoptosis induced by taxol, caspase-3 inhibitor (DEVD-CHO), caspase-6 inhibitor (Z-VEID-FMK), caspase-8 inhibitor (Z-IETD-FMK or IETD-CHO), caspase-9 inhibitors (Z-LEHD-FMK or LEHD-CHO), and caspase-10 inhibitor (Z-AEVD-FMK) are used. These caspase inhibitors are dissolved in dimethyl sulfoxide (Me2SO); the final concentration of Me2SO is 0.1%. Cells (5×105) are preincubated in the presence or absence of 100 μM each of these inhibitors for 3 h at 37°C then treated with or without 0.1, 0.5, and 1 μM Paclitaxel for 48 h and processed for annexin V binding assay.

[Cell Assay]

1×104 cells are plated in 100 μL of the growth medium in the presence or absence of increasing concentrations (0.1-1 μM) of taxol in 96-well plates and cultured at 37°C in 5% CO2 for 12-48 h. The cells are then incubated with 25 μL of MTT (5 mg/mL) at 37°C for 4 h. After dissolving the crystals with 0.04 N HCl in isopropanol, the plates are read in a microplate reader at 570 nm. The concentration of drug that inhibits cell survival by 50% (IC50) is determined from cell survival plots.

[Animal admin]

Adult (250-320 g) male Sprague-Dawley rats are used for all experiments. Rats are housed two per cage in a temperature and humidity controlled, on a 12 h:12 h light:dark schedule with food and water available ad libitum. One week following the DiI injection, rats are anesthetized with isofluorane and injected into the tail vein with 2 mg/kg paclitaxel or its vehicle (1:1:23, cremophor EL:ethanol:0.9% saline). The tail vein injection is repeated three more times every other day for a total of four injections.

[References]

[1]. Park SJ, et al. Taxol induces caspase-10-dependent apoptosis. J Biol Chem. 2004 Dec 3;279(49):51057-67. Epub 2004 Sep 27.

[2]. Pan Z, et al. Paclitaxel attenuates Bcl-2 resistance to apoptosis in breast cancer cells through an endoplasmic reticulum-mediated calciumrelease in a dosage dependent manner. Biochem Biophys Res Commun. 2013 Feb 13. pii: S0006-291X(13)00259-3.

[3]. Cadamuro M, et al. Low dose paclitaxel reduces S100A4 nuclear import to inhibit invasion and hematogenous metastasis of cholangiocarcinoma. Cancer Res. 2016 Jun 21.

[4]. Li Q, et al. Low doses of paclitaxel enhance liver metastasis of breast cancer cells in the mouse model. FEBS J. 2016 Jun 16.

[5]. Yilmaz E, et al. Sensory neuron subpopulation-specific dysregulation of intracellular calcium in a rat model of chemotherapy-induced peripheral neuropathy. Neuroscience. 2015 Aug 6;300:210-8.

[6]. Jing C, et al. Lenvatinib enhances the antitumor effects of paclitaxel in anaplastic thyroid cancer. Am J Cancer Res. 2017 Apr 1;7(4):903-912.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
957.1±65.0 °C at 760 mmHg

[ Melting Point ]:
213 °C (dec.)(lit.)

[ Molecular Formula ]:
C₄₇H₅₁NO₁₄

[ Molecular Weight ]:
853.906

[ Flash Point ]:
532.6±34.3 °C

[ Exact Mass ]:
853.330933

[ PSA ]:
221.29000

[ LogP ]:
7.38

[ Vapour Pressure ]:
0.0±0.3 mmHg at 25°C

[ Index of Refraction ]:
1.637

[ Storage condition ]:
2-8°C

[ Stability ]:
Stable. Incompatible with strong oxidizing agents. Combustible.

[ Water Solubility ]:
methanol: 50 mg/mL, clear, colorless

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS05, GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H315-H317-H318-H334-H335-H341-H361

[ Precautionary Statements ]:
P261-P280-P284-P304 + P340-P305 + P351 + P338 + P310-P342 + P311

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
Xn:Harmful

[ Risk Phrases ]:
R40;R41

[ Safety Phrases ]:
22-26-36/37/39-45

[ RIDADR ]:
1544

[ WGK Germany ]:
3

[ RTECS ]:
DA8340700

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2932999021

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2932999021

Articles

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Cell-cell adhesions and cell contractility are upregulated upon desmosome disruption.

PLoS ONE 9(7) , e101824, (2014)

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Control of cytoplasmic dynein force production and processivity by its C-terminal domain.

Nat. Commun. 6 , 6206, (2015)

Cytoplasmic dynein is a microtubule motor involved in cargo transport, nuclear migration and cell division. Despite structural conservation of the dynein motor domain from yeast to higher eukaryotes, ...

Related Compounds

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