Compound: paclitaxel
SMILES: O=C1[C@]2([C@@H]([C@@]3(OC(=O)C)[C@H](OC3)C[C@@H]2O)[C@H](OC(=O)c4ccccc4)[C@]5(O)C[C@@H](C(=C([C@H]1OC(=O)C)C5(C)C)C)OC(=O)[C@H](O)[C@@H](NC(=O)c6ccccc6)c7ccccc7)C
InChIKey: RCINICONZNJXQF-MZXODVADSA-N
Synonyms: paclitaxel, TAXOL, 33069-62-4, Yewtaxan, Taxol A, Plaxicel, Genaxol, Genetaxyl, Ebetaxel, Capxol, OncoGel, Genexol, Intaxel, Mitotax, Pacliex, Paxene, Onxol, TaxAlbin, Cyclopax, Paxceed, Onxal, EmPAC, Taxus Liberte, Taxus stent, Zisu, Tocosol Paclitaxel, (-)-Paclitaxel, Padexol, Taxus, EndoTAG 1, LEP-ETU, NSC-125973, Nanoxel, Paclitaxol, Sindaxel, Coroflex Please, Cypher select, Taxus Express, DHP-107, MBT 0206, P88XT4IS4D, BMS-181339-01, Infinnium, DHP 107, Abraxane I.V. Suspension, BMS 181339-01, NK 105, NK-105, NSC125973, Paclitaxel (taxus canadensis), QW 8184, QW-8184, Liposome-entrapped paclitaxel easy-to-use, DTXSID9023413, IG 001, 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, DTXCID603413, (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, CHEBI:45863, 7 epi Taxol, ABRAXANE COMPONENT PACLITAXEL, ABI-007 COMPONENT PACLITAXEL, NAB-PACLITAXEL COMPONENT PACLITAXEL, NSC 125973, (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-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-, (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-, (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)-, paclitaxelum, Bris Taxol, Taxol, Bris, ((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, (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, PACITAXEL, RefChem:6096, Taxol 100, PACLITAXEL PACLITAXEL, L01CD01, PACLITAXEL PROTEIN BOUND PARTICLES ALBUMIN BOUND, Paclitaxel protein-bound particles for injectable suspension (albumin-bound), (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, 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,1-2alpha,12aalpha,12balpha))-, 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, Abraxane, LipoPac, Genexol-PM, ABI-007, MFCD00869953, HSDB 6839, ABI 007, DRG-0190, MBT-0206, Paclitaxel (Taxol), Paclitaxel, Taxus brevifolia, CHEMBL428647, (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, 7,11-Methano-1H-cyclodeca[3,4]benz[1,2-b]oxete, benzenepropanoic acid deriv., NCGC00164367-01, C47H51NO14, nab-paclitaxel, M02242, Cynviloq, Xorane, Taxol (Paclitaxel), (NAB)-Paclitaxel, SMR000857385, EndoTAG-1, SR-01000075350, UNII-P88XT4IS4D, Anzatax, Nanotaxel, Paclical, Pacligel, Paxoral, l diacetate, Paclitaxel?, CCRIS 8143, Anzatax;, Paclitaxel CRS, Paclitaxel HCL, Paclitaxel [USAN:USP:INN:BAN], Abraxane (TN), [diacetoxy-[(2R,3S)-3-benzamido-2-hydroxy-3-phenyl-propanoyl]oxy-dihydroxy-tetramethyl-oxo-[?]yl] benzoate, Paclitaxel; 5beta,20-Epoxy-1,7beta-dihydroxy-9-oxotax-11-ene-2alpha,4,10beta,13alpha-tetrayl 4,10-diacetate 2-benzoate 13-[(2R,3S)-3-(benzoylamino)-2-hydroxy-3-phenylpropanoate]; Taxol; Docetaxel Anhydrous Impurity F; Docetaxel Impurity F, Taxol A;, CAS-33069-62-4, Paclitaxel (natural), BMS-181339, Paclitaxel-SSMM-VIP, Paclitaxel (Standard), P-SSMM-VIP, PACLITAXEL [MI], PACLITAXEL [INN], PACLITAXEL [JAN], Prestwick3_000155, PACLITAXEL [HSDB], PACLITAXEL [USAN], TAXOL (TN), PACLITAXEL [VANDF], Paclitaxel (semi-synthetic), PACLITAXEL [MART.], SCHEMBL3976, Nova-12005, PACLITAXEL [USP-RS], PACLITAXEL [WHO-DD], 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, orb1310120, orb3140975, Taxol (TN) (Bristol Meyers), PACLITAXEL [GREEN BOOK], PACLITAXEL [ORANGE BOOK], ACon1_002231, HY-B0015R, KBio2_002509, KBio2_005077, KBio2_007645, KBio3_002987, ANX-513, DHP-208, DTS-301, PACLITAXEL [EP MONOGRAPH], PACLITAXEL [USP IMPURITY], SDP-013, cMAP_000068, ORAXOL COMPONENT PACLITAXEL, HMS2090D07, HMS2095O12, HMS2231A16, HMS3712O12, PACLITAXEL [USP MONOGRAPH], Abraxane (albumin-bound suspension), HY-B0015, MPI-5018, Tox21_112107, BDBM50001839, EBC-06097, MSK000431, NSC745099, Paclitaxel; Docetaxel EP Impurity F, ABI 007 COMPONENT PACLITAXEL, AKOS007930675, AKOS015969673, AKOS025312303, CCG-220155, CS-1145, DB01229, FP10637, GS-6554, NSC-745099, NCGC00164367-02, NCGC00164367-03, NCGC00164367-04, NCGC00164367-05, NCGC00164367-10, PACLITAXEL COMPONENT OF ABI-007, (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, NCI60_000601, SY016928, Paclitaxel, from Taxus yannanensis, powder, AB00513812, Paclitaxel natural for peak identification CRS, D00491, EN300-117275, N88686, AB00513812-02, AB00513812-03, Q423762, 7,4]benz[1,2-b]oxete,benzenepropanoic acid deriv., Paclitaxel semi-synthetic for system suitability CRS, 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 semi-synthetic for peak identification CRS, Paclitaxel, from semisynthetic (from Taxus sp.), >=97%, Paclitaxel Working Standard (Secondary Reference Standard), Paclitaxel, European Pharmacopoeia (EP) Reference Standard, Paclitaxel, from Taxus brevifolia, >=95% (HPLC), powder, H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b-diy, 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, (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 5Hcyclodeca(3,4)benz(1,2-b)oxet-5-one 6,12b-diacetate,, (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-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1, (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, (2beta,5beta,7alpha,8alpha,10alpha,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, ,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, ,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, (alphaR,betaS)- (9CI), -cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, [2aR-[2aalpha,4beta,4abeta,6beta,9alpha(aR*,betaS*),11alpha,12alpha,12aalpha,12balpha]]-, [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetoxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenyl-propanoyl]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, [(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, 4,10beta-Bis(acetyloxy)-13alpha-{[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy}-1,7beta-dihydroxy-9-oxo-4alpha,5beta-5,20-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, 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, 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)-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-, 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, 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))-, 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, 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,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
Theoretical properties:
molecular_formula: C47H51NO14
molecular_weight: 853.9 g/mol
exact_mass: 853.33095530 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 4
hydrogen_bond_acceptor_count: 14
rotatable_bond_count: 14
heavy_atom_count: 62
topological_polar_surface_area: 221 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: White to off-white crystalline powder
color: White to off-white crystalline powder
melting_point: 415 to 421 °F (NTP, 1992)
solubility: Insoluble
Descriptions:
pubchem: Paclitaxel can cause developmental toxicity, female reproductive toxicity and male reproductive toxicity according to state or federal government labeling requirements.
chebi: A tetracyclic diterpenoid isolated originally from the bark of the Pacific yew tree, <em>Taxus brevifolia</em>. 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.
chembl: PACLITAXEL is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Paclitaxel, sold under the brand name Taxol among others, is a chemotherapy medication used to treat ovarian cancer, esophageal cancer, breast cancer, lung cancer, Kaposi's sarcoma, cervical cancer, and pancreatic cancer. It is administered by intravenous injection. There is also an albumin-bound formulation.
Common side effects include hair loss, bone marrow suppression, numbness, allergic reactions, muscle pains, and diarrhea. Other side effects include heart problems, increased risk of infection, and lung inflammation. There are concerns that use during pregnancy may cause birth defects. Paclitaxel is in the taxane family of medications. It works by interference with the normal function of microtubules during cell division.
Paclitaxel was isolated in 1971 from the Pacific yew and approved for medical use in 1993. It is on the World Health Organization's List of Essential Medicines. It has been made from precursors, and through cell culture.