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| http://linked.open...gbank/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] (en)
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| http://linked.open...y/drugbank/dosage
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| http://linked.open...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 (en)
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| http://linked.open...gy/drugbank/group
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| http://linked.open...drugbank/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. (en)
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| http://linked.open...ugbank/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. (en)
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| sameAs
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| Title
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| adms:identifier
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| http://linked.open...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. (en)
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| http://linked.open...drugbank/packager
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| http://linked.open...y/drugbank/patent
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| http://linked.open...outeOfElimination
| - 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. (en)
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| http://linked.open.../drugbank/synonym
| - Paclitaxel (en)
- Taxol (en)
- Taxol A (en)
- (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 (en)
- 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 (en)
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| http://linked.open...drugbank/toxicity
| - Rat (ipr) LD<sub>50</sub>=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. (en)
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| http://linked.open...umeOfDistribution
| - * 227 to 688 L/m^2 [apparent volume of distribution at steady-state, 24 hour infusion] (en)
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| http://linked.open.../drug/hasAHFSCode
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| http://linked.open...k/foodInteraction
| - Avoid echinacea. (en)
- Avoid grapefruit and grapefruit juice due to potential increase of paclitaxel. (en)
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| http://linked.open...nk/proteinBinding
| - 89%-98% bound to plasma protein. The presence of cimetidine, ranitidine, dexamethasone, or diphenhydramine did not affect protein binding of paclitaxel. (en)
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| http://linked.open...ynthesisReference
| - 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. (en)
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| http://linked.open...y/mesh/hasConcept
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| foaf:page
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| http://linked.open...ugbank/IUPAC-Name
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| http://linked.open...gy/drugbank/InChI
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| http://linked.open...Molecular-Formula
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| http://linked.open.../Molecular-Weight
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| http://linked.open...noisotopic-Weight
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| http://linked.open...y/drugbank/SMILES
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| http://linked.open.../Water-Solubility
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| http://linked.open...ogy/drugbank/logP
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| http://linked.open...ogy/drugbank/logS
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| http://linked.open...l/drug/hasATCCode
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| http://linked.open...nd-Acceptor-Count
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| http://linked.open...-Bond-Donor-Count
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| http://linked.open...drugbank/InChIKey
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| http://linked.open...urface-Area--PSA-
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| http://linked.open...nk/Polarizability
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| http://linked.open...bank/Refractivity
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| http://linked.open...atable-Bond-Count
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| http://linked.open...ugbank/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. (en)
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| http://linked.open.../affectedOrganism
| - Humans and other mammals (en)
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| http://linked.open...casRegistryNumber
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| http://linked.open...drugbank/category
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| http://linked.open...rugbank/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] (en)
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| http://linked.open...gbank/containedIn
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| http://linked.open...k/Bioavailability
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