Detail

Paclitaxel

Description

Name: Paclitaxel
Type: small molecule
Groups: approved
Indication: Used in the treatment of Kaposi's sarcoma and cancer of the lung, ovarian, and breast. Abraxane® is specfically indicated for the treatment of metastatic breast cancer and locally advanced or metastatic non-small cell lung cancer.
Accession Number: DB01229 ( APRD00259, DB05261, DB05927)
Description: Paclitaxel is a mitotic inhibitor used in cancer chemotherapy. It was discovered in a US National Cancer Institute program at the Research Triangle Institute in 1967 when Monroe E. Wall and Mansukh C. Wani isolated it from the bark of the Pacific yew tree, Taxus brevifolia and named it taxol. Later it was discovered that endophytic fungi in the bark synthesize paclitaxel. When it was developed commercially by Bristol-Myers Squibb (BMS), the generic name was changed to paclitaxel and the BMS compound is sold under the trademark Taxol. In this formulation, paclitaxel is dissolved in Kolliphor EL and ethanol, as a delivery agent. A newer formulation, in which paclitaxel is bound to albumin, is sold under the trademark Abraxane. [Wikipedia]
Structure:
Prescription Products:
NameDosageStrengthRouteMarketing StartMarketing EndCountry
Abraxaneinjection, powder, lyophilized, for suspension100 mg/20mLintravenous10-02-2005US
Abraxane for Injectable Suspensionpowder for suspension100 mgintravenous31-08-2006Canada
Aj-paclitaxelsolution6 mgintravenous01-01-1970Canada
Paclitaxelinjection6 mg/mLintravenous11-07-2013US
Paclitaxelinjection6 mg/mLintravenous11-07-2013US
Paclitaxelinjection6 mg/mLintravenous11-07-2013US
Paclitaxelliquid6 mgintravenous01-01-1970Canada
Paclitaxel for Injectionsolution6 mgintravenous01-01-1970Canada
Paclitaxel for Injectionsolution6 mgintravenous31-10-2001Canada
Paclitaxel for Injectionsolution6 mgintravenous17-12-2007Canada
Paclitaxel for Injection USPsolution6 mgintravenous22-02-2011Canada
Paclitaxel Injectionliquid6 mgintravenous01-01-1970Canada
Paclitaxel Injectionliquid6 mgintravenous24-10-199706-12-2005Canada
Paclitaxel Injection USPsolution6 mgintravenous02-07-2014Canada
Paclitaxel Injection USPsolution6 mgintravenous31-03-2015Canada
Paclitaxel Injection, USPsolution6 mgintravenous01-01-1970Canada
Paxeneliquid6 mgintravenous01-01-1970Canada
Taxolsolution6 mgintravenous31-12-199320-07-2012Canada
Teva-paclitaxel for Injectionliquid6 mgintravenous01-01-1970Canada

Generic Prescription Products:
NameDosageStrengthRouteMarketing StartMarketing EndCountry
Apo-paclitaxel Injectablesolution6 mgintravenous07-02-2005Canada
Paclitaxelinjection, solution6 mg/mLintravenous20-03-2009US
Paclitaxelinjection300 mg/50mLintravenous30-09-2011US
Paclitaxelinjection100 mg/16.7mLintravenous30-09-2011US
Paclitaxelinjection, solution, concentrate6 mg/mLintravenous03-11-2009US
Paclitaxelinjection, solution, concentrate6 mg/mLintravenous24-09-2008US
Paclitaxelinjection, solution, concentrate6 mg/mLintravenous23-10-2008US
Paclitaxelinjection, solution, concentrate6 mg/mLintravenous16-09-2009US
Paclitaxelinjection30 mg/5mLintravenous30-09-2011US
Paclitaxelinjection100 mg/16.7mLintravenous30-09-2011US
Paclitaxelinjection300 mg/50mLintravenous30-09-2011US
Paclitaxelinjection30 mg/5mLintravenous30-09-2011US
Paclitaxelinjection, solution6 mg/mLintravenous27-09-2011US
Paclitaxelinjection, solution6 mg/mLintravenous05-01-2015US
Paclitaxelinjection, solution6 mg/mLintravenous02-01-2008US
Paclitaxelinjection, solution6 mg/mLintravenous08-05-2002US

Over the Counter Products: Not Available
International Brands
  • No Brands

Brand Names
  • No Brands

Brand Mixtures
Brand NameIngredients
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
PaclitaxelPaclitaxel
AbraxanePaclitaxel
Paclitaxel for InjectionPaclitaxel
Apo-paclitaxel InjectablePaclitaxel
Abraxane for Injectable SuspensionPaclitaxel
Paclitaxel for InjectionPaclitaxel
Paclitaxel for Injection USPPaclitaxel
Paclitaxel Injection USPPaclitaxel
Paclitaxel Injection USPPaclitaxel
TaxolPaclitaxel
Paclitaxel InjectionPaclitaxel
Paclitaxel InjectionPaclitaxel
PaxenePaclitaxel
Paclitaxel for InjectionPaclitaxel
Paclitaxel Injection, USPPaclitaxel
PaclitaxelPaclitaxel
Teva-paclitaxel for InjectionPaclitaxel
Aj-paclitaxelPaclitaxel

Categories
  • Antineoplastic Agents, Phytogenic
  • Tubulin Modulators
  • Taxane Derivatives

Pharmacology

Indication: Used in the treatment of Kaposi's sarcoma and cancer of the lung, ovarian, and breast. Abraxane® is specfically indicated for the treatment of metastatic breast cancer and locally advanced or metastatic non-small cell lung cancer.
Pharmacodynamics: Not Available
Mechanism of action: 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.
Absorption: When a 24 hour infusion of 135 mg/m^2 is given to ovarian cancer patients, the maximum plasma concentration (Cmax) is 195 ng/mL, while the AUC is 6300 ng•h/mL.
Volume of distribution:
  • 227 to 688 L/m^2 [apparent volume of distribution at steady-state, 24 hour infusion]

Protein binding: 89%-98% bound to plasma protein. The presence of cimetidine, ranitidine, dexamethasone, or diphenhydramine did not affect protein binding of paclitaxel.
Metabolism: Not Available
Route of elimination: In 5 patients administered a 225 or 250 mg/m2 dose of radiolabeled paclitaxel as a 3-hour infusion, a mean of 71% of the radioactivity was excreted in the feces in 120 hours, and 14% was recovered in the urine.
Half life: When a 24 hour infusion of 135 mg/m^2 is given to ovarian cancer patients, the elimination half=life is 52.7 hours.
Clearance: Not Available
Toxicity: Rat (ipr) LD50=32530 µg/kg. Symptoms of overdose include bone marrow suppression, peripheral neurotoxicity, and mucositis. Overdoses in pediatric patients may be associated with acute ethanol toxicity.
Affected organisms
  • Not Available

SNP Mediated Adverse Drug Reactions
  • Not Available

Pharmacoeconomics

Manufacturers:
  • Not Available

Packagers:
Dosage forms
FormRouteStrength
Injection, powder, lyophilized, for suspensionintravenous100 mg/20mL
Powder for suspensionintravenous100 mg
Injectionintravenous100 mg/16.7mL
Injectionintravenous30 mg/5mL
Injectionintravenous300 mg/50mL
Injectionintravenous6 mg/mL
Injection, solutionintravenous6 mg/mL
Injection, solution, concentrateintravenous6 mg/mL
Solutionintravenous6 mg
Liquidintravenous6 mg

Prices
Unit descriptionCostUnit
Paclitaxel 150 mg/25 ml vial$3.36ml
Paclitaxel 30 mg/5 ml vial$3.54ml
Paclitaxel 100 mg/16.7 ml vial$4.45ml
Paclitaxel 300 mg/50 ml vial$5.31ml
Onxol 30 mg/5 ml vial$34.54ml
Onxol 300 mg/50 ml vial$34.54ml
Taxol 30 mg/5 ml vial$35.06ml
Abraxane 100 mg vial$1119.6vial

Patents
CountryPatent NumberApprovedExpires (estimated)
2086874Canada1998-09-012013-01-07
2155947Canada2007-08-212014-02-22
5439686United States1993-02-222013-02-22
5498421United States1993-03-122013-03-12

Interactions

Drug Interactions
DrugInteraction
AbirateroneThe serum concentration of Paclitaxel can be increased when it is combined with Abiraterone.
AprepitantThe serum concentration of Paclitaxel can be increased when it is combined with Aprepitant.
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Paclitaxel.
AtazanavirThe serum concentration of Paclitaxel can be increased when it is combined with Atazanavir.
BexaroteneThe serum concentration of Bexarotene can be increased when it is combined with Paclitaxel.
BosentanThe serum concentration of Paclitaxel can be decreased when it is combined with Bosentan.
CarboplatinCarboplatin may increase the myelosuppressive activities of Paclitaxel.
CisplatinCisplatin may increase the myelosuppressive activities of Paclitaxel.
ClozapineThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Clozapine.
ConivaptanThe serum concentration of Paclitaxel can be increased when it is combined with Conivaptan.
DabrafenibThe serum concentration of Paclitaxel can be decreased when it is combined with Dabrafenib.
DasatinibThe serum concentration of Paclitaxel can be increased when it is combined with Dasatinib.
DaunorubicinThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Daunorubicin.
DeferasiroxThe serum concentration of Paclitaxel can be decreased when it is combined with Deferasirox.
DenosumabThe risk or severity of adverse effects can be increased when Denosumab is combined with Paclitaxel.
DoxorubicinThe metabolism of Doxorubicin can be decreased when combined with Paclitaxel.
EpirubicinThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Epirubicin.
FluconazoleThe metabolism of Paclitaxel can be decreased when combined with Fluconazole.
FosaprepitantThe serum concentration of Paclitaxel can be increased when it is combined with Fosaprepitant.
Fusidic AcidThe serum concentration of Paclitaxel can be increased when it is combined with Fusidic Acid.
HydrocodoneThe serum concentration of Hydrocodone can be decreased when it is combined with Paclitaxel.
IdarubicinThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Idarubicin.
IdelalisibThe serum concentration of Paclitaxel can be increased when it is combined with Idelalisib.
IvacaftorThe serum concentration of Paclitaxel can be increased when it is combined with Ivacaftor.
LeflunomideThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Leflunomide.
LuliconazoleThe serum concentration of Paclitaxel can be increased when it is combined with Luliconazole.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Paclitaxel.
MifepristoneThe serum concentration of Paclitaxel can be increased when it is combined with Mifepristone.
MitotaneThe serum concentration of Paclitaxel can be decreased when it is combined with Mitotane.
MitoxantroneThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Mitoxantrone.
NatalizumabThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Natalizumab.
NelfinavirThe metabolism of Paclitaxel can be decreased when combined with Nelfinavir.
NetupitantThe serum concentration of Paclitaxel can be increased when it is combined with Netupitant.
NimodipineThe serum concentration of Nimodipine can be decreased when it is combined with Paclitaxel.
OxaliplatinOxaliplatin may increase the myelosuppressive activities of Paclitaxel.
PalbociclibThe serum concentration of Paclitaxel can be increased when it is combined with Palbociclib.
PhenytoinThe metabolism of Paclitaxel can be increased when combined with Phenytoin.
PimecrolimusThe risk or severity of adverse effects can be increased when Pimecrolimus is combined with Paclitaxel.
RanolazineThe serum concentration of Paclitaxel can be increased when it is combined with Ranolazine.
RitonavirThe metabolism of Paclitaxel can be decreased when combined with Ritonavir.
RoflumilastRoflumilast may increase the immunosuppressive activities of Paclitaxel.
RosiglitazoneThe metabolism of Paclitaxel can be decreased when combined with Rosiglitazone.
SaquinavirThe serum concentration of Paclitaxel can be increased when it is combined with Saquinavir.
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Paclitaxel.
SiltuximabThe serum concentration of Paclitaxel can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Paclitaxel can be increased when it is combined with Simeprevir.
Sipuleucel-TThe therapeutic efficacy of Sipuleucel-T can be decreased when used in combination with Paclitaxel.
SorafenibThe risk or severity of adverse effects can be increased when Sorafenib is combined with Paclitaxel.
St. John's WortThe serum concentration of Paclitaxel can be decreased when it is combined with St. John's Wort.
StiripentolThe serum concentration of Paclitaxel can be increased when it is combined with Stiripentol.
TacrolimusThe risk or severity of adverse effects can be increased when Tacrolimus is combined with Paclitaxel.
TesmilifeneThe serum concentration of Paclitaxel can be decreased when it is combined with Tesmilifene.
TocilizumabThe serum concentration of Paclitaxel can be decreased when it is combined with Tocilizumab.
TofacitinibPaclitaxel may increase the immunosuppressive activities of Tofacitinib.
TrastuzumabThe serum concentration of Paclitaxel can be decreased when it is combined with Trastuzumab.
TrimethoprimThe metabolism of Paclitaxel can be decreased when combined with Trimethoprim.
VerapamilThe serum concentration of Paclitaxel can be increased when it is combined with Verapamil.
VinorelbinePaclitaxel may increase the neurotoxic activities of Vinorelbine.

Food Interactions:
  • Avoid echinacea.
  • Avoid grapefruit and grapefruit juice due to potential increase of paclitaxel.

Taxonomy

Kingdom: Organic compounds
Super Class: Not Available
Class: Not Available
Sub Class: Not Available
Direct Parent: Not Available
Alternative Parents:
  • Acetate salts
  • Alpha-acyloxy ketones
  • Benzoic acid esters
  • Benzoyl derivatives
  • Benzylethers
  • Beta amino acids and derivatives
  • Carboxylic acid esters
  • Cyclic alcohols and derivatives
  • Dialkyl ethers
  • Dicarboxylic acids and derivatives
  • Fatty acid esters
  • Hydrocarbon derivatives
  • Ketones
  • Monosaccharides
  • N-benzylbenzamides
  • Organonitrogen compounds
  • Oxacyclic compounds
  • Oxetanes
  • Phenylpropylamines
  • Secondary alcohols
  • Secondary carboxylic acid amides
  • Tertiary alcohols

substituent:
  • Acetate salt
  • Alcohol
  • Alpha-acyloxy ketone
  • Aromatic heteropolycyclic compound
  • Benzamide
  • Benzenoid
  • Benzoate ester
  • Benzoic acid or derivatives
  • Benzoyl
  • Benzylether
  • Beta amino acid or derivatives
  • Carbonyl group
  • Carboxamide group
  • Carboxylic acid derivative
  • Carboxylic acid ester
  • Cyclic alcohol
  • Dialkyl ether
  • Dicarboxylic acid or derivatives
  • Ether
  • Fatty acid ester
  • Fatty acyl
  • Hydrocarbon derivative
  • Ketone
  • Monocyclic benzene moiety
  • Monosaccharide
  • N-benzylbenzamide
  • Organoheterocyclic compound
  • Organonitrogen compound
  • Organooxygen compound
  • Oxacycle
  • Oxetane
  • Phenylpropylamine
  • Secondary alcohol
  • Secondary carboxylic acid amide
  • Taxane diterpenoid
  • Tertiary alcohol

References

Synthesis Reference: Hendricus B. A. de Bont, Ruben G. G. Leenders, Johan W. Scheeren, Hidde J. Haisma, Dick de Vos, "Paclitaxel prodrugs, method for preparation as well as their use in selective chemotherapy." U.S. Patent US5760072, issued September, 1989.
General Reference: # Wall ME, Wani MC: Camptothecin and taxol: discovery to clinic--thirteenth Bruce F. Cain Memorial Award Lecture. Cancer Res. 1995 Feb 15;55(4):753-60. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/7850785 # Wani MC, Taylor HL, Wall ME, Coggon P, McPhail AT: Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc. 1971 May 5;93(9):2325-7. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/5553076 # Fuchs DA, Johnson RK: Cytologic evidence that taxol, an antineoplastic agent from Taxus brevifolia, acts as a mitotic spindle poison. Cancer Treat Rep. 1978 Aug;62(8):1219-22. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/688258 # Saville MW, Lietzau J, Pluda JM, Feuerstein I, Odom J, Wilson WH, Humphrey RW, Feigal E, Steinberg SM, Broder S, et al.: Treatment of HIV-associated Kaposi's sarcoma with paclitaxel. Lancet. 1995 Jul 1;346(8966):26-8. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/7603142 # ABI 007. Drugs R D. 2004;5(3):155-9. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/15139776 # Gaitanis A, Staal S: Liposomal doxorubicin and nab-paclitaxel: nanoparticle cancer chemotherapy in current clinical use. Methods Mol Biol. 2010;624:385-92. "Pubmed":http://www.ncbi.nlm.nih.gov/pubmed/20217610
External Links:
ResourceLink
RxListhttp://www.rxlist.com/cgi/generic/paclitaxel.htm
Drugs.comhttp://www.drugs.com/cdi/paclitaxel.html

ATC Codes:
  • Array

AHFS Codes:
  • 10:00.00

MSDS: Download
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