化合物信息

ID:1098

基本信息
化学结构
MolImage
分子式
C₄₇H₅₁NO₁₄
分子量
853.90614
精确质量
853.33095532
电荷
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
计算属性
JChem
LogD (pH = 7.4)
3.54
LogD (pH = 5.5)
3.54
Log P
3.54
可自由旋转的化学键
14
质子供体
4
质子受体
10
里宾斯基五规则
false
Acid pKa
11.93
极化表面积
221.29
极化性
87.13
摩尔折射率
218.29
LOG S
-6.77
名称和标识
商标名
LipoPacOnxolAbraxaneTaxolVascular WrapEpitaxolPaxceedTaxol AXoranePaxene
别名
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标准名
(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传统名
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名称
Paclitaxel
数据登录号
Chemspider ID
10368587
PubChem CID
36314
IUPHAR配体索引
2770
DrugBank ID
DB01229
美国药典/FDA物质标识码
P88XT4IS4D
维基百科标题
Paclitaxel
专利号
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PDBeChem数据库
TA1
SureChEMBL数据库
SCHEMBL3976
VirtualMetabolicHuman数据库
taxol
CompTox数据库
DTXSID9023413
KNApSAcK数据库
C00002365
Reactom Database
R-HSA-211910
KEGG DRUG Database
D00491
BindingDB数据库
50001839
ACToR数据库
33069-62-4
ArrayExpress (Repository of Microarray data)
E-TOXM-9
SABIO-RK数据库
14410
ArrayExpress (Gene Expression Altlas)
E-GEOD-28784E-GEOD-12791
Rhea数据库
RHEA:33687
Drug Central Database
2,044
化合物性质
理化性质
溶解度
Insoluble
Methanol
疏水性(logP)
3
熔点
213-223°C
214-216°C
蒸汽压
< 1.12 x 10-7 Torr
外观
White Solid
Powder
药理学性质
排泄
Fecal and urinary
代谢
Hepatic (CYP2C8 and CYP3A4)
给药途径
iv
半衰期
5.8 hours
妊娠期药物分类
D (US)
生物利用度
6.5% (oral)
法定药品分级
Rx-only (US)
蛋白结合率
89 to 98%
生物活性机理
Binds to the beta subunit of tubulin
Interferes with the normal function of microtubule growth by hyper-stabilisation of their structure
安全信息
澳大利亚Hazchem
2X
美国ERG指导号
154
RTECS编号
DA8340700
联合国危险货物等级
6.1
欧盟危险性物质标志
有毒 有毒 (T)
安全公开号 
S:28-36/37/39-45-53
联合国危险货物包装类别(PG)
III
MSDS下载
欧盟危险识别号(EUHIN)
6.1B
欧盟危险货物分类
T2
危险公开号 
R:25
联合国危险货物编号
2811
保存条件
Room Temperature (15-30°C)
-20°C Freezer
产品相关信息
纯度
>98%
95+%
质检报告
应用领域
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
生物来源
Isol. from the stem bark of Taxus brevifolia and Taxus cuspidata (Taxaceae)
分子图谱
暂无数据
点击上传数据
描述信息
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.
参考文献
PubChem文献
数据源提供
• 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)
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