Molecule

ID:1098

General Information
Structure
MolImage
Molecular Formula
C₄₇H₅₁NO₁₄
Molecular Mass
853.90614
Exact Mass
853.33095532
Charge
0
InChI
InChI=1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
InChIKey
RCINICONZNJXQF-MZXODVADSA-N
Canonic Smiles
CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)C[C@@H]3[C@]([C@H]2[C@@H]([C@]2(C(C1=C(C)[C@@H](OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C2)(C)C)O)OC(=O)c1ccccc1)(CO3)OC(=O)C
Isomeric Smiles
[C@H]1(OC(=O)c2ccccc2)[C@@H]2[C@@]3(CO[C@@H]3C[C@@H]([C@]2(C(=O)[C@@H](C2=C([C@H](C[C@]1(O)C2(C)C)OC(=O)[C@@H]([C@H](c1ccccc1)NC(=O)c1ccccc1)O)C)OC(=O)C)C)O)OC(=O)C
Calculated Properties
JChem
LogD (pH = 7.4)
3.54
LogD (pH = 5.5)
3.54
Log P
3.54
Rotatable Bonds
14
H Donor
4
H Acceptors
10
Lipinski's Rule of Five
false
Acid pKa
11.93
Polar Surface Area
221.29
Polarizability
87.13
Molar Refractivity
218.29
LOG S
-6.77
Names and Identifiers
Brand Name
LipoPacOnxolAbraxaneTaxolVascular WrapEpitaxolPaxceedTaxol AXoranePaxene
Synonyms
7-EpitaxolABI-0077-epi-Taxol7-epi-PaclitaxelPaclitaxel7-EpipaclitaxelTaxol®YewtaxanOncoGelNSC 125973(-)-PaclitaxelGenetaxylTaxolPacliexOnxalAbraxaneGenaxolPaclitaxelTaxol AAnzataxTAXOLtaxol5beta,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-phenylisoserinePaclitaxel(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 esterTaxol Apaclitaxel
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 (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[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate (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[11.3.1.0³,¹⁰.0⁴,⁷]heptadec-13-en-2-yl benzoate
IUPAC Traditional name
TAX taxol paclitaxel (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[11.3.1.03,10.04,7]heptadec-13-en-2-yl benzoate (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
API Name
Paclitaxel
Registration numbers
PubChem CID
36314
IUPHAR ligand ID
2770
Chemspider ID
10368587
Unique Ingredient Identifier
P88XT4IS4D
DrugBank ID
DB01229
CAS Number
33069-62-4
Wikipedia Title
Paclitaxel
MDL Number
MFCD00869953
Patent number
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KNApSAcK Database
C00002365
PDBeChem Database
TA1
CompTox Database
DTXSID9023413
SureChEMBL Database
SCHEMBL3976
VirtualMetabolicHuman Database
taxol
Reactom Database
R-HSA-211910
BindingDB Database
50001839
ACToR Database
33069-62-4
ArrayExpress (Repository of Microarray data)
E-TOXM-9
KEGG DRUG Database
D00491
SABIO-RK Database
14410
Rhea Database
RHEA:33687
ArrayExpress (Gene Expression Altlas)
E-GEOD-28784E-GEOD-12791
Drug Central Database
2,044
Properties
Physical Property
Solubility
Insoluble
Methanol
Hydrophobicity(logP)
3
Melting Point
213-223°C
214-216°C
Vapor Pressure
< 1.12 x 10-7 Torr
Apperance
White Solid
Powder
Pharmacology Properties
Excretion
Fecal and urinary
Metabolism
Hepatic (CYP2C8 and CYP3A4)
Admin Routes
iv
Half Life
5.8 hours
Pregnancy Category
D (US)
Bioavailability
6.5% (oral)
Legal Status
Rx-only (US)
Protein Bound
89 to 98%
Mechanism of Action
Binds to the beta subunit of tubulin
Interferes with the normal function of microtubule growth by hyper-stabilisation of their structure
Safety Information
Australian Hazchem
2X
Emergency Response Guidebook(ERG) Number
154
RTECS
DA8340700
Hazard Class
6.1
European Hazard Symbols
Toxic Toxic (T)
Safety Statements 
S:28-36/37/39-45-53
Packing Group
III
MSDS Link
EU Hazard Identification Number
6.1B
EU Classification
T2
Risk Statements 
R:25
UN Number
2811
Storage Condition
Room Temperature (15-30°C)
-20°C Freezer
Product Information
Purity
>98%
95+%
Certificate of Analysis
Application(s)
Biochemical tool extensively used to study cellular shape and function.
Use limited by low solubility and scarce availability of Taxus brevifolia bark
Antileukaemic and antineoplastic agent, esp. against melanoma and ovarian tumours
Also shown to be active against oomycete fungi
Biological Source
Isol. from the stem bark of Taxus brevifolia and Taxus cuspidata (Taxaceae)
Molecular Spectra
No Data Available
Click here to submit data
Molecule Details
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]
(Taxol?) From the Pacific Yew Tree Taxus brevifolia Antitumor agent which lowers the critical concentration for tubulin polymerization and reversibly binds to tubulin prohibiting depolymerization. Purity: >98%
An antineoplastic. Used in the study of structure and function of microtubles into tubulin. Paclitaxel is now used to treat patients with lung, ovarian, breast cancer, head and neck cancer, and advanced forms of Kaposi's sarcoma. Paclitaxel is a mitotic i
A tetracyclic diterpenoid isolated originally from the bark of the Pacific yew tree, Taxus brevifolia. It is a mitotic inhibitor used in cancer chemotherapy. Note that the use of the former generic name 'taxol' is now limited, as Taxol is a registered trade mark.
References
PubChem Literature
From Data Sources
• 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
• Gaitanis A, Staal S: Liposomal doxorubicin and nab-paclitaxel: nanoparticle cancer chemotherapy in current clinical use. Methods Mol Biol. 2010;624:385-92. 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
• 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
• 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
• Danesi, R., et al.: Mol. Pharmacol., 47, 1106 (1984)
• Markman, M., et al.: Expert. Opin. Pharmacother., 3, 755 (1984)
• Letourneau, P.C., et al.: J. Cell Biol., 98, 1355 (1984)
• Manfredi, J.J., et al.: Pharmacol. Ther., 25, 83 (1984)
• Stone, G.W., et al.:
• Winkler, J.D. et al., Tetrahedron, 1992, 48, 6953, (rev)
• Kingston, D.G.I. et al., J. Nat. Prod., 1982, 45, 466-470, (2',7-di-Ac)
• Horwitz, S.B. et al., Ann. N.Y. Acad. Sci., 1986, 466, 733, (rev, pharmacol)
• Ojima, I. et al., Tetrahedron, 1992, 48, 6985, (synth)
• Wall, M.E., Chron. Drug Discovery, 1993, 3, 327, (rev)
• Kingston, D.G.I. et al., J. Nat. Prod., 1990, 53, 1; 802, (bibl, rev)
• Chmurny, G.N. et al., J. Nat. Prod., 1992, 55, 414, (pmr, cmr)
• Wani, M.S. et al., J.A.C.S., 1971, 93, 2325, (isol, nmr, ms, ir, uv)
• Young, D.H. et al., Experientia, 1992, 48, 882, (antifungal activity)
• Hilton, B.D. et al., J. Nat. Prod., 1992, 55, 1157, (pmr)
• Huang, C.H.O. et al., J. Nat. Prod., 1986, 49, 665, (isol, deriv)
• Wheeler, N.C. et al., J. Nat. Prod., 1992, 55, 432, (occur)
• Nicolaou, K.C. et al., Angew. Chem., Int. Ed., 1994, 33, 15, (rev)
• Hongjie, Z. et al., Heterocycles, 1994, 38, 975
• Williams, H.J. et al., Tetrahedron, 1993, 49, 6545, (pmr, conformn)
• Slichenmyer, W.J. et al., Anti-Cancer Drugs, 1991, 2, 519, (rev)
• Zhang, H. et al., Yunnan Zhiwu Yanjiu, 1993, 15, 424; CA, 121, 78282e
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