Paclitaxel

Modify Date: 2024-01-02 19:49:07

Paclitaxel Structure
Paclitaxel structure
 Common Name Paclitaxel
CAS Number 33069-62-4 Molecular Weight 853.906
Density 1.4±0.1 g/cm3 Boiling Point 957.1±65.0 °C at 760 mmHg
Molecular Formula C47H51NO14 Melting Point 213 °C (dec.)(lit.)
MSDS Chinese USA Flash Point 532.6±34.3 °C
Symbol GHS05 GHS07 GHS08
GHS05, GHS07, GHS08		 Signal Word Danger

 Use of Paclitaxel


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.

 Names

Name paclitaxel
Synonym More Synonyms

 Paclitaxel 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
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.

 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

 Safety Information

Symbol GHS05 GHS07 GHS08
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

 Customs

HS Code 2932999021

 Articles350

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 Synonyms

(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
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Related Compounds: More...
Paclitaxel
105454-04-4
PACLITAXEL
23180-57-6
Paclitaxel C
153415-45-3
Paclitaxel-d5
1129540-33-5
Paclitaxel-d5
1261254-56-1
isopaclitaxel
307923-51-9
DHA-paclitaxel
199796-52-6
2'-Z-paclitaxel
148930-30-7
7-Epi Paclitaxel
7782-41-4
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