Product Name

Paclitaxel

CAS Number

33069-62-4

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Product Name:
Paclitaxel
CAS Number:
33069-62-4
Indication:
Used in the treatment of Kaposi's sarcoma and cancer of the lung, ovarian, and breast.
Mode 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 _ 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.

Pharmacodynamics:

Paclitaxel is a taxoid antineoplastic agent indicated as first-line and subsequent therapy for the treatment of advanced carcinoma of the ovary, and other various cancers including breast cancer. Paclitaxel is a novel antimicrotubule agent that promotes the assembly of microtubules from tubulin dimers and stabilizes microtubules by preventing depolymerization. This stability results in the inhibition of the normal dynamic reorganization of the microtubule network that is essential for vital interphase and mitotic cellular functions. In addition, paclitaxel induces abnormal arrays or "bundles" of microtubules throughout the cell cycle and multiple asters of microtubules during mitosis.

Metabolism:

Hepatic. In vitro studies with human liver microsomes and tissue slices showed that paclitaxel was metabolized primarily to 6a-hydrox-ypaclitaxel by the cytochrome P450 isozyme CYP2C8; and to two minor metabolites, 3ê-p-hydroxypaclitaxel and 6a, 3ê-p-dihydroxypaclitaxel, by CYP3A4.

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.

IUPAC:
(1S, 2S, 3R, 4S, 7R, 9S, 10S, 12R, 15S)-4, 12-bis(acetyloxy)-1, 9-dihydroxy-15-{[(2R, 3S)-2-hydroxy-3-phenyl-3-(phenylformamido)propanoyl]oxy}-10, 14, 17, 17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0, {3, 10}.0, {4, 7}]heptadec-13-en-2-yl benzoate
ATC:
L01CD01
PubChem:
36314
DrugBank:
DB01229 (APRD00259, DB05261, DB05927)
Formula:
C27H44O3
Molecular Mass:
853.9061
Synonyms:
Taxol 7-epi-Paclitaxel 7-epi-Taxol 7-Epipaclitaxel 7-Epitaxol ABI-007
SMILES:
CC(=O)O[C@@H]1C2=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)C3=CC=CC=C3)[C@@H]3[C@@]4(CO[C@@H]4C[C@H](O)[C@@]3(C)C1=O)OC(C)=O)C2(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)C1=CC=CC=C1)C1=CC=CC=C1
AHFS Code:
10:00.0
InChi:
RCINICONZNJXQF-MZXODVADSA-N
General Reference:
General Reference:

 

  1. Wall ME, Wani MC: Camptothecin and taxol: discovery to clinicãthirteenth Bruce F. Cain Memorial Award Lecture. Cancer Res. 1995 Feb 15;55(4):753-60. Pubmed
  2. 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
  3. 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
  4. 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 Kaposiês sarcoma with paclitaxel. Lancet. 1995 Jul 1;346(8966):26-8. Pubmed
  5. ABI 007. Drugs R D. 2004;5(3):155-9. Pubmed
  6. Gaitanis A, Staal S: Liposomal doxorubicin and nab-paclitaxel: nanoparticle cancer chemotherapy in current clinical use. Methods Mol Biol. 2010;624:385-92. Pubmed

 

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