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Namespace Prefixes

PrefixIRI
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Statements

Subject Item
n2:DB01229
rdf:type
n3:Drug
n3: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]
n3:dosage
n32:271B5A98-363D-11E5-9242-09173F13E4C5 n32:271B5A99-363D-11E5-9242-09173F13E4C5 n32:271B5A9A-363D-11E5-9242-09173F13E4C5 n32:271B5A95-363D-11E5-9242-09173F13E4C5 n32:271B5A96-363D-11E5-9242-09173F13E4C5 n32:271B5A97-363D-11E5-9242-09173F13E4C5
n3:generalReferences
# 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
n3:group
approved
n3:halfLife
When a 24 hour infusion of 135 mg/m^2 is given to ovarian cancer patients, the elimination half=life is 52.7 hours.
n3: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.
owl:sameAs
n27:DB01229 n28:DB01229
dcterms:title
Paclitaxel
adms:identifier
n10:7887 n13:46506910 n14:PA450761 n15:36314 n16:2770 n18:33395 n19:DB01229 n20:D00491 n21:0703-4764-01 n22:2770 n23:C07394 n31:Paclitaxel
n3:mechanismOfAction
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.
n3:packager
n30:271B5A8B-363D-11E5-9242-09173F13E4C5 n30:271B5A8C-363D-11E5-9242-09173F13E4C5 n30:271B5A89-363D-11E5-9242-09173F13E4C5 n30:271B5A8A-363D-11E5-9242-09173F13E4C5 n30:271B5A87-363D-11E5-9242-09173F13E4C5 n30:271B5A88-363D-11E5-9242-09173F13E4C5 n30:271B5A7D-363D-11E5-9242-09173F13E4C5 n30:271B5A7E-363D-11E5-9242-09173F13E4C5 n30:271B5A7B-363D-11E5-9242-09173F13E4C5 n30:271B5A7C-363D-11E5-9242-09173F13E4C5 n30:271B5A85-363D-11E5-9242-09173F13E4C5 n30:271B5A86-363D-11E5-9242-09173F13E4C5 n30:271B5A83-363D-11E5-9242-09173F13E4C5 n30:271B5A84-363D-11E5-9242-09173F13E4C5 n30:271B5A81-363D-11E5-9242-09173F13E4C5 n30:271B5A82-363D-11E5-9242-09173F13E4C5 n30:271B5A7F-363D-11E5-9242-09173F13E4C5 n30:271B5A80-363D-11E5-9242-09173F13E4C5
n3:patent
n11:5498421 n11:5439686 n11:2086874 n11:2155947
n3:routeOfElimination
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.
n3:synonym
5beta,20-Epoxy-1,2-alpha,4,7beta,10beta,13alpha-hexahydroxytax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine Paclitaxel (2AR-(2aalpha,4beta,4abeta,6beta,9alpha(alpha r*,betas*),11alpha,12alpha,12balpha))-beta-(benzoylamino)-alpha-hydroxybenzenepropanoic acid 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 Taxol A Taxol
n3:toxicity
Rat (ipr) LD<sub>50</sub>=32530 &micro;g/kg. Symptoms of overdose include bone marrow suppression, peripheral neurotoxicity, and mucositis. Overdoses in pediatric patients may be associated with acute ethanol toxicity.
n3:volumeOfDistribution
* 227 to 688 L/m^2 [apparent volume of distribution at steady-state, 24 hour infusion]
n24:hasAHFSCode
n25:10-00-00
n3:foodInteraction
Avoid echinacea. Avoid grapefruit and grapefruit juice due to potential increase of paclitaxel.
n3:proteinBinding
89%-98% bound to plasma protein. The presence of cimetidine, ranitidine, dexamethasone, or diphenhydramine did not affect protein binding of paclitaxel.
n3:synthesisReference
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.
n7:hasConcept
n8:M0026156
foaf:page
n6:paclitaxel.htm n17:paclitaxel.html
n3:IUPAC-Name
n4:271B5A9F-363D-11E5-9242-09173F13E4C5
n3:InChI
n4:271B5AA5-363D-11E5-9242-09173F13E4C5
n3:Molecular-Formula
n4:271B5AA4-363D-11E5-9242-09173F13E4C5
n3:Molecular-Weight
n4:271B5AA1-363D-11E5-9242-09173F13E4C5
n3:Monoisotopic-Weight
n4:271B5AA2-363D-11E5-9242-09173F13E4C5
n3:SMILES
n4:271B5AA3-363D-11E5-9242-09173F13E4C5
n3:Water-Solubility
n4:271B5AB5-363D-11E5-9242-09173F13E4C5 n4:271B5A9D-363D-11E5-9242-09173F13E4C5
n3:logP
n4:271B5A9B-363D-11E5-9242-09173F13E4C5 n4:271B5AB7-363D-11E5-9242-09173F13E4C5 n4:271B5A9E-363D-11E5-9242-09173F13E4C5
n3:logS
n4:271B5A9C-363D-11E5-9242-09173F13E4C5
n24:hasATCCode
n33:L01CD01
n3:H-Bond-Acceptor-Count
n4:271B5AAB-363D-11E5-9242-09173F13E4C5
n3:H-Bond-Donor-Count
n4:271B5AAC-363D-11E5-9242-09173F13E4C5
n3:InChIKey
n4:271B5AA6-363D-11E5-9242-09173F13E4C5
n3:Polar-Surface-Area--PSA-
n4:271B5AA7-363D-11E5-9242-09173F13E4C5
n3:Polarizability
n4:271B5AA9-363D-11E5-9242-09173F13E4C5
n3:Refractivity
n4:271B5AA8-363D-11E5-9242-09173F13E4C5
n3:Rotatable-Bond-Count
n4:271B5AAA-363D-11E5-9242-09173F13E4C5
n3: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.
n3:affectedOrganism
Humans and other mammals
n3:casRegistryNumber
33069-62-4
n3:category
n3:clearance
* 21.7 L/h/m2 [Dose 135 mg/m2, infusion duration 24 h] * 23.8 L/h/m2 [Dose 175 mg/m2, infusion duration 24 h] * 7 L/h/m2 [Dose 135 mg/m2, infusion duration 3 h] * 12.2 L/h/m2 [Dose 175 mg/m2, infusion duration 3 h]
n3:containedIn
n12:271B5A91-363D-11E5-9242-09173F13E4C5 n12:271B5A94-363D-11E5-9242-09173F13E4C5 n12:271B5A92-363D-11E5-9242-09173F13E4C5 n12:271B5A93-363D-11E5-9242-09173F13E4C5 n12:271B5A8F-363D-11E5-9242-09173F13E4C5 n12:271B5A90-363D-11E5-9242-09173F13E4C5 n12:271B5A8D-363D-11E5-9242-09173F13E4C5 n12:271B5A8E-363D-11E5-9242-09173F13E4C5
n3:Bioavailability
n4:271B5AB1-363D-11E5-9242-09173F13E4C5
n3:Ghose-Filter
n4:271B5AB3-363D-11E5-9242-09173F13E4C5
n3:MDDR-Like-Rule
n4:271B5AB4-363D-11E5-9242-09173F13E4C5
n3:Melting-Point
n4:271B5AB6-363D-11E5-9242-09173F13E4C5
n3:Number-of-Rings
n4:271B5AB0-363D-11E5-9242-09173F13E4C5
n3:Physiological-Charge
n4:271B5AAF-363D-11E5-9242-09173F13E4C5
n3:Rule-of-Five
n4:271B5AB2-363D-11E5-9242-09173F13E4C5
n3:Traditional-IUPAC-Name
n4:271B5AA0-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-acidic-
n4:271B5AAD-363D-11E5-9242-09173F13E4C5
n3:pKa--strongest-basic-
n4:271B5AAE-363D-11E5-9242-09173F13E4C5