Paclitaxel

Base Information

• Chemical Name: Paclitaxel
• CAS No.: 33069-62-4
• Deprecated CAS: 157069-30-2,1203669-79-7
• Molecular Formula: C47H51NO14
• Molecular Weight: 853.92
• Hs Code.: 2939.90
• European Community (EC) Number: 608-826-9
• NSC Number: 745099,125973
• UN Number: 2811
• UNII: P88XT4IS4D,3PPC5TL76P
• DSSTox Substance ID: DTXSID9023413
• Nikkaji Number: J17.834I
• Wikipedia: Paclitaxel
• Wikidata: Q423762
• NCI Thesaurus Code: C1411
• RXCUI: 56946
• Pharos Ligand ID: F6F6DK8FGGAH
• Metabolomics Workbench ID: 43441
• ChEMBL ID: CHEMBL428647
• Mol file: 33069-62-4.mol

Synonyms:33069-62-4;P88XT4IS4D;Paclitaxel;Taxol;Taxol A;Yewtaxan;Genaxol;Plaxicel;Abraxane;Ebetaxel;Genetaxyl;Capxol;Paxene;Onxol;Cyclopax;Genexol;Intaxel;Mitotax;Pacliex;TaxAlbin;OncoGel;Paxceed;EmPAC;Onxal;Zisu;Taxus stent;Taxus Liberte;ABI-007;Padexol;nab-paclitaxel;EndoTAG 1;LipoPac;Tocosol Paclitaxel;(-)-Paclitaxel;Nanoxel;Paclitaxol;Sindaxel;NSC-125973;Coroflex Please;Cypher select;Taxus Express;LEP-ETU;Genexol-PM;(NAB)-Paclitaxel;MBT 0206;BMS 181339-01;Cynviloq;Infinnium;HSDB 6839;ABI 007;DHP 107;DHP-107;Abraxane I.V. Suspension;BMS-181339-01;UNII-P88XT4IS4D;DRG-0190;Paclitaxel (Taxol);NK 105;Paclitaxel (taxus canadensis);NSC 125973;QW 8184;EndoTAG-1;CCRIS 8143;Liposome-entrapped paclitaxel easy-to-use;DTXSID9023413;CHEBI:45863;ABI-007 COMPONENT PACLITAXEL;IG 001;NK-105;NSC125973;5beta,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-phenylisoserine;QW-8184;nabpaclitaxel;CHEMBL428647;DTXCID603413;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-9-(((2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b-diyl diacetate;ORAXOL COMPONENT PACLITAXEL;Paclitaxel [USAN:USP:INN:BAN];Abraxane (albumin-bound suspension);ABRAXANE COMPONENT PACLITAXEL;MBT-0206;ABI 007 COMPONENT PACLITAXEL;(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 ester;NCGC00164367-01;NAB-PACLITAXEL COMPONENT PACLITAXEL;MFCD00869953;PACLITAXEL (MART.);PACLITAXEL [MART.];PACLITAXEL (USP-RS);PACLITAXEL [USP-RS];(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;PACLITAXEL (EP MONOGRAPH);PACLITAXEL (USP IMPURITY);PACLITAXEL [EP MONOGRAPH];PACLITAXEL [USP IMPURITY];PACLITAXEL (USP MONOGRAPH);PACLITAXEL [USP MONOGRAPH];Xorane;7,11-Methano-1H-cyclodeca[3,4]benz[1,2-b]oxete, benzenepropanoic acid deriv.;SMR000857385;SR-01000075350;Paclitaxel [USAN:BAN:INN];paclitaxelum;Anzatax;Nanotaxel;Paclical;Pacligel;Paxoral;Bris Taxol;C47-H51-N-O14;Taxol, Bris;Paclitaxel,(S);Abraxane (TN);(2alpha,5beta,7beta,10beta,13alpha)-4,10-bis(acetyloxy)-1,7-dihydroxy-13-({(2R,3S)-2-hydroxy-3-phenyl-3-[(phenylcarbonyl)amino]propanoyl}oxy)-9-oxo-5,20-epoxytax-11-en-2-yl benzoate;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-Dodecahydro-4,6,9,11,12,12b-hexahydroxy-4a,8,13,13-tetramethyl-7,11-methano-5H-cyclodeca(3,4)benz(1,2-b)oxet-5-one 6,12b-diacetate, 12-benzoate, 9-ester with (2R,3S)-N-benzoyl-3-phenylisoserine;[diacetoxy-[(2R,3S)-3-benzamido-2-hydroxy-3-phenyl-propanoyl]oxy-dihydroxy-tetramethyl-oxo-[?]yl] benzoate;4alpha,10beta-bis(acetyloxy)-13alpha-((2S,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyloxy)-1,7beta-dihydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate;4alpha,10beta-bis(acetyloxy)-13alpha-[(2S,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyloxy]-1,7beta-dihydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate;5?,20-Epoxy-1,7?-dihydroxy-9-oxotax-11-ene-2?,4,10?,13?-tetrayl 4,10-diacetate 2-benzoate 13-[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate];BENZENEPROPANOIC ACID, .BETA.-(BENZOYLAMINO)-.ALPHA.-HYDROXY-, (2AR,4S,4AS,6R,9S,11S,12S,12AR,12BS)-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 ESTER, (.ALPHA.R,.BETA.S)-;Benzenepropanoic acid, .beta.-(benzoylamino)-.alpha.-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-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 ester, (.alpha.R,.beta.S)-;Taxol (Paclitaxel);CAS-33069-62-4;PACITAXEL;BMS-181339;Paclitaxel-SSMM-VIP;P-SSMM-VIP;PACLITAXEL [MI];PACLITAXEL [INN];PACLITAXEL [JAN];Prestwick3_000155;PACLITAXEL [HSDB];PACLITAXEL [USAN];TAXOL (TN);PACLITAXEL [VANDF];SCHEMBL3976;3PPC5TL76P;Nova-12005;PACLITAXEL [WHO-DD];Paclitaxel, Taxus brevifolia;BIDD:PXR0046;BSPBio_000290;KBioGR_002509;KBioSS_002517;Paclitaxel (JAN/USP/INN);MLS002154218;MLS002695976;OAS-PAC-100;PACLITAXEL [EMA EPAR];BPBio1_000320;GTPL2770;MEGxp0_001940;Taxol (TN) (Bristol Meyers);PACLITAXEL [GREEN BOOK];PACLITAXEL [ORANGE BOOK];ACon1_002231;KBio2_002509;KBio2_005077;KBio2_007645;KBio3_002987;ANX-513;DHP-208;DTS-301;L01CD01;SDP-013;cMAP_000068;HMS2090D07;HMS2095O12;HMS2231A16;HMS3712O12;[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 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 ester, (2aR-(2a-alpha,4-beta,4a-beta,6-beta,9-alpha(alpha-R*,beta-S*),11-alpha,12-alpha,12a-alpha, 12b-alpha))-;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 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 ester, (2aR-(2aalpha,4beta,4abeta,6beta,9alpha(alphaR*,betaS*),11alpha,12alpha,12aalpha,12balpha))-;HY-B0015;MPI-5018;Tax-11-en-9-one, 5beta,20-epoxy-1,2alpha,4,7beta,10beta,13alpha- hexahydroxy-, 4,10-diacetate 2-benzoate, 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine;Tox21_112107;BDBM50001839;NSC745099;AKOS007930675;AKOS015969673;AKOS025312303;CCG-220155;CS-1145;DB01229;GS-6554;NSC-745099;NCGC00164367-02;NCGC00164367-03;NCGC00164367-04;NCGC00164367-05;NCGC00164367-10;Paclitaxel, From Taxus brevifolia, 95%;NCI60_000601;Paclitaxel, from Taxus yannanensis, powder;PACLITAXEL IMPURITY L [EP IMPURITY];AB00513812;D00491;EN300-117275;M02242;N88686;AB00513812-02;AB00513812-03;Paclitaxel, Antibiotic for Culture Media Use Only;Q423762;7,4]benz[1,2-b]oxete,benzenepropanoic acid deriv.;Q-201533;SR-01000075350-1;SR-01000075350-3;SR-01000075350-6;SR-01000075350-7;SR-01000075350-9;BRD-K62008436-001-03-1;BRD-K62008436-001-05-6;BRD-K62008436-001-22-1;Paclitaxel, from semisynthetic (from Taxus sp.), >=97%;Paclitaxel, European Pharmacopoeia (EP) Reference Standard;Paclitaxel, from Taxus brevifolia, >=95% (HPLC), powder;Paclitaxel, United States Pharmacopeia (USP) Reference Standard;12-benzoate, 9-ester with (2R,3S)-N-benzoyl-3-phenylisoserine;Paclitaxel, Pharmaceutical Secondary Standard;Certified Reference Material;Paclitaxel natural for peak identification, European Pharmacopoeia (EP) Reference Standard;(1S,2S,3R,4S,5R,7S,8S,10R,13S)-4,10-Diacetoxy-2-benzoyloxy-5,20-epoxy-1,7-dihydroxy-9-oxotax-11-en-13-yl (2R,3S)-3-benzoylamino-2-hydroxy-3-phenylpropionate;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-1,2a,3,4,4a,6,9,10,11,12,12a,12b-Dodecahydro 4,6,9,11,12,12b-hexahydroxy-4a,8,13,13-tetramethyl-7,11-methano 5Hcyclodeca(3,4)benz(1,2-b)oxet-5-one 6,12b-diacetate,;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-4,6,12b-Tris(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl (alphaR,betaS)-beta-(benzoylamino)-alpha-hydroxybenzenepropanoate;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-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 (aR,bS)-b-(benzoylamino)-a-hydroxybenzenepropanoate;(2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-9-(((2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-3,4,4a,5,6,9,10,11,12,12a-decahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b(2aH)-diyl diacetate;(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;[(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl]benzoate;1203669-79-7;4,7beta,10beta-tris(acetyloxy)-13alpha-[[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy]-1-hydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate;5-BETA,20-EPOXY-1,2-ALPHA,4,7-BETA,10-BETA,13-ALPHA-HEXAHYDROXY-TAX-11-EN-9-ONE 4,10-DIACETATE 2-BENZOATE 13-ESTER WITH (2R,3S)-N-BENZOYL-3-PHENYL-ISOSERINE;5beta,20-Epoxy-1,2 alpha, 4,7beta, 10beta, 13alpha-hexahydroxy tax-11-en-9-one 4,10-diacetate 2-benzoate 13-ester with (2R, 3S)-N-benzoyl-3-phenylisoserine;Benzenepropanoic acid, 6,12b-bis(acetyl oxy)-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 ester, [2aR- [2a.alpha.,4.beta.,4a.beta.,6.beta.,9.alpha.(alpha. R*,.beta.S*),11.alpha.,12.alpha.,12a.alpha.,12b.alpha.]]-;Benzenepropanoic acid, b-(benzoylamino)-.alpha.-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-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 ester, (aR,bS)-;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-4,6,12b-tris(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (alphaR,betaS)-;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-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;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-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 ester, (alphaR,betaS)-;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 4,6,12b-tris(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-11-hydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, [2aR-[2aalpha,4beta,4abeta,6beta,9alpha(alphaR*,betaS*),11alpha,12alpha,12aalpha,12balpha]]-;Benzenepropanoic acid, beta-(benzoylamino)-alpha-hydroxy-, 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;Paclitaxel semi-synthetic for peak identification, European Pharmacopoeia (EP) Reference Standard;Paclitaxel semi-synthetic for system suitability, European Pharmacopoeia (EP) Reference Standard;TAX-11-EN-9-ONE, 5-BETA,20-EPOXY-1,2-ALPHA,4,7-BETA,10-BETA,13-ALPHA-HEXA-HYDROXY-, 4,10-DIACETATE 2-BENZOATE 13-ESTER WITH (2R,3S)-N-BENZOYL-3-PHENYLISOSERINE;TAX-11-EN-9-ONE, 5BETA,20-EPOXY-1,2ALPHA,4,7BETA,10BETA,13ALPHA-HEXAHYDROXY-, 4,10-DIACETATE 2-BENZOATE 13-ESTER WITH (2R,3S)-N-BENZOYL-3-PHENYLISOSERINE;Tax-11-en-9-one, 5beta,20-epoxy-1,2alpha,4,7beta,10beta,13alpha-hexahydroxy-, 4,10-diacetate 2-benzoate 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine (8CI);Tax-11-en-9-one, 5beta,20-epoxy-1,2alpha,4,7beta,10beta,13alpha-hexahydroxy-, 4,10-diacetate 2-benzoate, 13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine;Tax-11-en-9-one,20-epoxy-1,2.alpha.,4,7.beta., 10.beta.,13.alpha.- hexahydroxy-, 4,10-diacetate 2- benzoate,13-ester with (2R,3S)-N-benzoyl-3-phenylisoserine

Chemical Property of Paclitaxel

Chemical Property:

• Appearance/Colour: white powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 213 °C
• Refractive Index: -49 ° (C=1, MeOH)
• Boiling Point: 957.115 °C at 760 mmHg
• PKA: 11.90±0.20(Predicted)
• Flash Point: 532.644 °C
• PSA: 221.29000
• Density: 1.39 g/cm³
• LogP: 4.12660
• Storage Temp.: 2-8°C
• Solubility.: methanol: 50 mg/mL, clear, colorless
• Water Solubility.: 0.3mg/L(37 oC)
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 4
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 14
• Exact Mass: 853.33095530
• Heavy Atom Count: 62
• Complexity: 1790
• Transport DOT Label: Poison

Purity/Quality:

99% ^*data from raw suppliers

Paclitaxel ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R40:; R41:
• Hazard Codes: Xn
• Statements: 37/38-41-42/43-62-68-40-48-20/21/22-68/20/21/22
• Safety Statements: 22-26-36/37/39-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Chemical Classes: Other Uses -> Biochemical Research
• Drug Classes: Antineoplastic Agents
• Canonical SMILES: CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
• Isomeric SMILES: CC1=C2[C@H](C(=O)[C@@]3([C@H](C[C@@H]4[C@]([C@H]3[C@@H]([C@@](C2(C)C)(C[C@@H]1OC(=O)[C@@H]([C@H](C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
• Recent ClinicalTrials: Paclitaxel and Carboplatin With or Without Bevacizumab in Treating Patients With Stage II, Stage III, or Stage IV Ovarian Epithelial Cancer, Primary Peritoneal Cancer, or Fallopian Tube Cancer
• Recent EU Clinical Trials: A Phase 1/2 Open-Label, Umbrella Platform Design Study of Investigational Agents With Pembrolizumab (MK-3475) in Participants With Advanced Esophageal Cancer Previously Exposed to PD-1/PD-L1 Treatment (KEYMARKER-U06): Substudy 06B.
• Recent NIPH Clinical Trials: Phase 3 study of pembrolizumab vs chemotherapy in dMMR advanced or recurrent endometrial carcinoma
• Description: Paclitaxel, a natural product isolated from the bark of the Pacific yew, is effective in treating refractory metastatic ovarian cancer. Unlike any other antineoplastic agents, paclitaxel appears to have several possible mechanisms of action, including an antimicrotubule action through the promotion of tubulin polymerization and stabilization of microtubules, thereby, halting mitosis and promoting cell death. The supply of paclitaxel is limited by its low natural abundance and currently it is being manufactured by a semi-synthetic route from deacetylbaccatin Ⅲ that is isolated from the needles of the yew tree. Recent completion of two total syntheses of taxol conquered the structural complexity of the title compound and may be useful in obtaining certain closely related analogs, some of which have been found to have antitumor activity. Paclitaxel has potential uses in the treatment of metastatic breast cancer, lung cancer, head and neck cancer, and malignant melanoma.
• Physical properties: Appearance: Odorless and tasteless white or kind of white crystal powder. Solubility: Poorly soluble in water but slightly soluble in ether. Soluble in methanol, acetonitrile, chloroform, acetone, and other organic solvents. Melting point: 213–216?°C. Specific optical rotation: ?49° (C?=?1, MeOH); Curl: 20° to D?=?49.0–55.0° (10?mg/mL of methanol solution) in anhydrous dry goods without solvents.
• Uses: Paclitaxel is an antineoplastic that used to treat patients with lung, ovarian, breast cancer, head and neck cancer, and advanc ed forms of Kaposi's sarcoma. Paclitaxel is a mitotic inhibitor used in cancer chemotherapy. It is also used in the study of structure and function of microtubles into tubulin.
• Indications: Paclitaxel (Taxol) is a highly complex, organic compound isolated from the bark of the Pacific yew tree. It binds to tubulin dimers and microtubulin filaments, promoting the assembly of filaments and preventing their depolymerization. This increase in the stability of microfilaments results in disruption of mitosis and cytotoxicity and disrupts other normal microtubular functions, such as axonal transport in nerve fibers. The major mechanism of resistance that has been identified for paclitaxel is transport out of tumor cells, which leads to decreased intracellular drug accumulation. This form of resistance is mediated by the multidrug transporter P-glycoprotein.
• Therapeutic Function: Antineoplastic
• Clinical Use: Paclitaxel is among the most active of all anticancer drugs, with significant efficacy against carcinomas of the breast, ovary, lung, head, and neck. It is combined with cisplatin in the therapy of ovarian and lung carcinomas and with doxorubicin in treating breast cancer.
• Drug interactions: Potentially hazardous interactions with other drugs Antipsychotics: avoid with clozapine (increased risk of agranulocytosis). Cytotoxics: increased risk of neutropenia with lapatinib.

Technology Process of Paclitaxel

There total 352 articles about Paclitaxel which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

dmap (1122-58-3) → taxol (33069-62-4)

Guidance literature:

With hydrogenchloride; water; In ethanol; at 0 - 20 ℃; for 2.41667h;

Reference yield: 100.0%

7-O-(triethylsilyl)paclitaxel (148930-55-6) → taxol (33069-62-4)

Guidance literature:

With pyridine hydrogenfluoride; In tetrahydrofuran; Ambient temperature;

DOI:10.1246/cl.1998.3

Reference yield: 99.0%

(2'R,3S)-2'-(2-methoxy-2-propyloxy)-7-triethylsilyl taxol → taxol (33069-62-4)

Guidance literature:

With pyridine; hydrogen fluoride; In water; acetonitrile; at 0 - 25 ℃; for 18h;

upstream raw materials:

acetic anhydride

C₅₀H₅₂Cl₃NO₁₆

7-(triethylsilyl)baccatin III

(4S,5S)-3-benzoyl-2,2-dimethyl-4-phenyl-1,3-oxazolidine-5-carboxylic acid

Downstream raw materials:

2'-t-BOC-L-phenylalanyltaxol

2'-<3-(N,N-diethylamino)propionyl>taxol hydrochloride

2'-O-(methoxyacetyl)paclitaxel

2'-(tert-butyldimethylsilyl)-7-(triethylsilyl)paclitaxel

Refernces

• 1、 Nawarathne, Irosha N.,Sullivan, Sean A.,Walker, Kevin D.. "CoA recycling by a benzoate coenzyme A ligase in cascade reactions with aroyltransferases to biocatalyze paclitaxel analogs". . . Retrieved 2020.
• 2、 -. "Intermediate compound for preparing paclitaxel, synthetic method of intermediate compound and synthetic method of paclitaxel". . . Retrieved 2022/01/12.
• 3、 Hu, Ya-Jian,Gu, Chen-Chen,Wang, Xin-Feng,Min, Long,Li, Chuang-Chuang. "Asymmetric Total Synthesis of Taxol". . p. 17862 - 17870. Retrieved 2021/11/04.