Paclitaxel

Paclitaxel

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)-;Tax-11-en-9-one,5β,20-epoxy-1,2α,4,7β,10β,13α-hexahydroxy-,4,10-diacetate 2-benzoate 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine;Benzenepropanoic acid,β-(benzoylamino)-α-hydroxy-,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,[2aR-[2aα,4β,4aβ,6β,9α(αR*,βS*),11α,12α,12aα,12bα]]-;7,11-Methano-1H-cyclodeca[3,4]benz[1,2-b]oxete,benzenepropanoic acid deriv.;Taxol;NSC 125973;Taxol A;Paclitaxel;BMS 181339-01;Yewtaxan;Plaxicel;ABI 007;TaxAlbin;QW 8184;Ebetaxel;Capxol;MBT 0206;Abraxane;Genexol-PM;Pacliex;Genexol;Genetaxyl;NK 105;Mitotax;OncoGel;Onxal;DHP 107;EndoTAG 1;Genaxol;Intaxel;Taxus;TAXUS stent;(-)-Paclitaxel;Taxus Liberte;EmPAC;Tocosol Paclitaxel;Cyclopax;Zisu;LEP-ETU;Liposome-entrapped paclitaxel easy-to-use;Paxene;Infinnium;Padexol;Sindaxel;Nanoxel;5β,20-Epoxy-1,2a,4,7β,10β,13α-hexahydroxy-tax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine;PTX;Cypher select;Coroflex Please;Nab-paclitaxel;TAXUS Express;IG 001;Cynviloq;IG 002;157069-30-2;1203669-79-7;2376186-34-2

33069-62-4

C47H51NO14

RCINICONZNJXQF-MZXODVADSA-N

853.9

853.331

608-826-9

358882

2811

DTXSID9023413

White to off-white crystalline powder; Needles from aqueous methanol

2932999021

Bulk Drug Intermediates

221.29000

Taxol appears as needles (from aqueous methanol) or fine white powder. An anti-cancer drug.; Solid; [Merck Index] White to off-white solid; [HSDB] Powder; [Sigma-Aldrich MSDS]; Solid

3 Log10 unitless

Taxol appears as needles (from aqueous methanol) or fine white powder. An anti-cancer drug.

1.45003

216.5 °C

858.903

492.88

1.637

4e-07 mol/L

Commercially available albumin-bound paclitaxel for injectable suspension should be stored in unopened vials at 20-25 °C and retained in the original package for protection from bright light. Neither freezing nor refrigeration adversely affects albumin-bound paclitaxel for injectable suspension. When stored under recommended conditions, unopened vials of commercially available albumin-bound paclitaxel for injectable suspension are stable until the date indicated on the package. /Paclitaxel (albumin-bound)/; The manufacturer states that, when diluted as directed, paclitaxel solutions are stable for up to 27 hours when stored at approximately 25 °C under ambient lighting conditions.; Commercially available paclitaxel for injection concentrate should be stored in unopened vials at 20-25 °C and retained in the original package for protection from light. Neither freezing nor refrigeration adversely affects paclitaxel for injection concentrate. Refrigeration may result in precipitation of the drug or formulation vehicle; however, the precipitate typically will dissolve at room temperature without loss of potency. If freezing occurs, paclitaxel for injection concentrate may be thawed at room temperature until precipitate dissolves; the manufacturer states that the chemical or physical stability of the injection is not affected. If the solution remains cloudy or if an insoluble precipitate remains at room temperature, the vial should be discarded. When stored under recommended conditions, unopened vials of commercially available paclitaxel for injection concentrate are stable until the date indicated on the package.

2.06728e-15

Currently, no known antidote for paclitaxel overdosage exists. The primary expected complications of overdosage would typically involve bone marrow suppression, peripheral neurotoxicity, and mucositis. However, it is noteworthy that hyaluronidase is commonly utilized as an antidote for addressing paclitaxel extravasation. If the needle or cannula is still in place, it is advised to administer 1 to 6 mL of hyaluronidase into the existing IV line. If the needle or cannula is no longer inserted, healthcare providers may inject the hyaluronidase subcutaneously, encircling the area of extravasation clockwise. This procedure may be repeated several times over the next 3 to 4 hours. Paclitaxel interferes with the normal function of microtubule growth. Whereas drugs like colchicine cause the depolymerization of microtubules in vivo, paclitaxel arrests their function by having the opposite effect; it hyper-stabilizes their structure. This destroys the cell's ability to use its cytoskeleton in a flexible manner. Specifically, paclitaxel binds to the β subunit of tubulin. Tubulin is the 'building block' of mictotubules, and the binding of paclitaxel locks these building blocks in place. The resulting microtubule/paclitaxel complex does not have the ability to disassemble. This adversely affects cell function because the shortening and lengthening of microtubules (termed dynamic instability) is necessary for their function as a transportation highway for the cell. Chromosomes, for example, rely upon this property of microtubules during mitosis. Further research has indicated that paclitaxel induces programmed cell death (apoptosis) in cancer cells by binding to an apoptosis stopping protein called Bcl-2 (B-cell leukemia 2) and thus arresting its function. Paclitaxel has been associated with serum aminotransferase elevations in 7% to 26% of patients, but values greater than 5 times the upper limit of normal (ULN) in only 2% of those receiving the highest doses. Similar rates of alkaline phosphatase elevations and occasional mild bilirubin elevations also occur. The abnormalities are usually asymptomatic, mild and self-limited, rarely requiring dose modification or discontinuation. Paclitaxel has not been linked convincingly to instances of delayed, idiosyncratic clinically apparent liver injury with jaundice. However, the hypersensitivity reactions that occur with infusions of paclitaxel can be severe and accompanied by acute hepatic necrosis. The liver injury may be relatively mild and anicteric (Case 1), but can also be severe with rapid onset of multiorgan failure and death. At least one instance of acute liver failure following a hypersensitivity reaction to paclitaxel has been published in the literature and recent modifications of the product labels for paclitaxel and docetaxel mention the occurrence of toxic deaths following severe infusion reactions.

Specific optical rotation: -49 deg at 20 °C/D (methanol); UV max absorption 2 (methanol): 227, 273, nm (E= 29,800,1700)

pKa Acidic Apparent: 9.0885; pKa Basic Apparent: -2.203; pKa Acidic Apparent: 6.16 Log10 unitless; pKa Basic Apparent: -2.203 Log10 unitless

1.04713e-10 cm^3/molecule*sec

1.38038e-11

278.9 Ų [M+H]+ [CCS Type: TW, Method: calibrated with polyalanine and drug standards]

Clear colorless to slightly yellow viscous solution /Paclitxel Injection USP/

May be sensitive to prolonged exposure to moisture. (NTP, 1992).

Alcohols and Polyols