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33069-62-4 molecular structure
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(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

ChemBase ID: 1098
Molecular Formular: C47H51NO14
Molecular Mass: 853.90614
Monoisotopic Mass: 853.33095532
SMILES and InChIs

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
Canonical 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
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

Cite this record

CBID:1098 http://www.chembase.cn/molecule-1098.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
IUPAC Traditional name
TAX
paclitaxel
taxol
(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
Brand Name
Epitaxol
LipoPac
Onxol
Paxceed
Paxene
Taxol
Taxol A
Xorane
Vascular Wrap
Abraxane
Synonyms
7-epi-Paclitaxel
7-epi-Taxol
7-Epipaclitaxel
7-Epitaxol
ABI-007
Paclitaxel
Taxol®
Taxol A
Anzatax
Paclitaxel
Abraxane
Genaxol
Genetaxyl
OncoGel
Onxal
Pacliex
(-)-Paclitaxel
Taxol
Yewtaxan
NSC 125973
CAS Number
33069-62-4
MDL Number
MFCD00869953
PubChem SID
46506910
160964561
PubChem CID
36314
CHEBI ID
45863
ATC CODE
L01CD01
L01CD03
CHEMBL
48
Chemspider ID
10368587
DrugBank ID
DB01229
IUPHAR ligand ID
2770
KEGG ID
D00491
Unique Ingredient Identifier
P88XT4IS4D
Wikipedia Title
Paclitaxel

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 10.364198  H Acceptors 10 
H Donor LogD (pH = 5.5) 3.538834 
LogD (pH = 7.4) 3.538369  Log P 3.53884 
Molar Refractivity 218.2945 cm3 Polarizability 86.54275 Å3
Polar Surface Area 221.29 Å2 Rotatable Bonds 14 
Lipinski's Rule of Five false 
Log P 3.2  LOG S -5.19 
Solubility (Water) 5.56e-03 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
Insoluble expand Show data source
Methanol expand Show data source
Apperance
Powder expand Show data source
White Solid expand Show data source
Melting Point
213-223°C expand Show data source
214-216°C expand Show data source
Vapor Pressure
< 1.12 x 10-7 Torr expand Show data source
Hydrophobicity(logP)
3 expand Show data source
Storage Condition
-20°C Freezer expand Show data source
Room Temperature (15-30°C) expand Show data source
RTECS
DA8340700 expand Show data source
European Hazard Symbols
Toxic Toxic (T) expand Show data source
UN Number
2811 expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Hazard Class
6.1 expand Show data source
Packing Group
III expand Show data source
Australian Hazchem
2X expand Show data source
Risk Statements
R:25 expand Show data source
Safety Statements
S:28-36/37/39-45-53 expand Show data source
EU Classification
T2 expand Show data source
EU Hazard Identification Number
6.1B expand Show data source
Emergency Response Guidebook(ERG) Number
154 expand Show data source
Admin Routes
iv expand Show data source
Bioavailability
6.5% (oral) expand Show data source
Excretion
Fecal and urinary expand Show data source
Half Life
5.8 hours expand Show data source
Metabolism
Hepatic (CYP2C8 and CYP3A4) expand Show data source
Protein Bound
89 to 98% expand Show data source
Legal Status
Rx-only (US) expand Show data source
Pregnancy Category
D (US) expand Show data source
Mechanism of Action
Binds to the beta subunit of tubulin expand Show data source
Interferes with the normal function of microtubule growth by hyper-stabilisation of their structure expand Show data source
Purity
>98% expand Show data source
95+% expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Biological Source
Isol. from the stem bark of Taxus brevifolia and Taxus cuspidata (Taxaceae) expand Show data source
Application(s)
Also shown to be active against oomycete fungi expand Show data source
Antileukaemic and antineoplastic agent, esp. against melanoma and ovarian tumours expand Show data source
Biochemical tool extensively used to study cellular shape and function. expand Show data source
Use limited by low solubility and scarce availability of Taxus brevifolia bark expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals DrugBank DrugBank Wikipedia Wikipedia TRC TRC
MP Biomedicals - 02193532 external link
(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%
DrugBank - DB01229 external link
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
Toronto Research Chemicals - P132500 external link
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

REFERENCES

REFERENCES

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