Home > Compound List > Product Information
Paclitaxel_Molecular_structure_CAS_33069-62-4)
Click picture or here to close

Paclitaxel

Catalog No. DB01229 Name DrugBank
CAS Number 33069-62-4 Website http://www.ualberta.ca/
M. F. C47H51NO14 Telephone (780) 492-3111
M. W. 853.90614 Fax (780) 492-1071
Purity Email david.wishart@ualberta.ca
Storage Chembase ID: 1098

SYNONYMS

IUPAC name
(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
IUPAC Traditional name
TAX
Brand Name
Xorane
Paxene
Paxceed
Abraxane
Epitaxol
LipoPac
Onxol
Taxol
Taxol A
Vascular Wrap
Synonyms
7-epi-Paclitaxel
7-epi-Taxol
7-Epipaclitaxel
7-Epitaxol
ABI-007

DATABASE IDS

PubChem CID 36314
PubChem SID 46506910
CAS Number 33069-62-4

PROPERTIES

Hydrophobicity(logP) 3
Solubility Insoluble

DETAILS

Description (English)
Item Information
Drug Groups approved
Description A cyclodecane isolated from the bark of the Pacific yew tree, TAXUS brevifolia. It stabilizes microtubules in their polymerized form leading to cell death. [PubChem] ABI-007 (Abraxane) is the latest attempt to improve upon paclitaxel, one of the leading chemotherapy treatments. Both drugs contain the same active agent, but Abraxane is delivered by a nanoparticle technology that binds to albumin, a natural protein, rather than the toxic solvent known as Cremophor. It is thought that delivering paclitaxel with this technology will cause fewer hypersensitivity reactions and possibly lead to greater drug uptake in tumors.
Indication Used in the treatment of Kaposi's sarcoma and cancer of the lung, ovarian, and breast.
Pharmacology 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.
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
Humans and other mammals
Biotransformation 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, 3’-p-hydroxypaclitaxel and 6a, 3’-p-dihydroxypaclitaxel, by CYP3A4.
Absorption I.V injected
Half Life Average distribution half-life of 0.34 hours and an average elimination half-life of 5.8 hours.
Protein Binding 89%-98%
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.
Distribution * 227 to 688 L/m2
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]
References
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]
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]
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]
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]
ABI 007. Drugs R D. 2004;5(3):155-9. [Pubmed]
Gaitanis A, Staal S: Liposomal doxorubicin and nab-paclitaxel: nanoparticle cancer chemotherapy in current clinical use. Methods Mol Biol. 2010;624:385-92. [Pubmed]
External Links
Wikipedia
RxList
Drugs.com

REFERENCES

  • ABI 007. Drugs R D. 2004;5(3):155-9. Pubmed
  • 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
  • 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
  • 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
  • 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
  • Gaitanis A, Staal S: Liposomal doxorubicin and nab-paclitaxel: nanoparticle cancer chemotherapy in current clinical use. Methods Mol Biol. 2010;624:385-92. Pubmed