TA1

TAXOL

Created:	2001-07-05
Last modified:	2024-09-27

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111 entries where TA1 is found as a standalone ligand2 entries where TA1 is covalently linked to polymer or other heterogen groups

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Chemical Details
Formal Charge	0
Atom Count	113
Chiral Atom Count	11
Bond Count	119
Aromatic Bond Count	18

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Chemical Component Summary
Name	TAXOL
Systematic Name (OpenEye OEToolkits)	n/a
Formula	C₄₇ H₅₁ N O₁₄
Molecular Weight	853.906
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(c1ccccc1)NC(c2ccccc2)C(O)C(=O)OC5C(=C4C(OC(=O)C)C(=O)C7(C(C(OC(=O)c3ccccc3)C(O)(C4(C)C)C5)C6(OC(=O)C)C(OC6)CC7O)C)C
SMILES	CACTVS	3.341	CC(=O)O[CH]1C(=O)[C]2(C)[CH](O)C[CH]3OC[C]3(OC(C)=O)[CH]2[CH](OC(=O)c4ccccc4)[C]5(O)C[CH](OC(=O)[CH](O)[CH](NC(=O)c6ccccc6)c7ccccc7)C(=C1C5(C)C)C
SMILES	OpenEye OEToolkits	1.5.0	CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(c5ccccc5)NC(=O)c6ccccc6)O)O)OC(=O)c7ccccc7)(CO4)OC(=O)C)O)C)OC(=O)C
Canonical SMILES	CACTVS	3.341	CC(=O)O[C@H]1C(=O)[C@]2(C)[C@@H](O)C[C@H]3OC[C@@]3(OC(C)=O)[C@H]2[C@H](OC(=O)c4ccccc4)[C@]5(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)c6ccccc6)c7ccccc7)C(=C1C5(C)C)C
Canonical SMILES	OpenEye OEToolkits	1.5.0	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](c5ccccc5)NC(=O)c6ccccc6)O)O)OC(=O)c7ccccc7)(CO4)OC(=O)C)O)C)OC(=O)C
InChI	InChI	1.03	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	InChI	1.03	RCINICONZNJXQF-MZXODVADSA-N

Drug Info: DrugBank

DrugBank ID	DB01229
Name	Paclitaxel
Groups	approved vet_approved
Description	Paclitaxel is a chemotherapeutic agent marketed under the brand name Taxol among others. Used as a treatment for various cancers, paclitaxel is a mitotic inhibitor that was first isolated in 1971 from the bark of the Pacific yew tree which contains endophytic fungi that synthesize paclitaxel. It is available as an intravenous solution for injection and the newer formulation contains albumin-bound paclitaxel marketed under the brand name Abraxane.
Synonyms	Taxol A paclitaxel protein-bound particles Paclitaxel protein-bound particles for injection suspension 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, Paclitaxel liposomal encapsulated paclitaxel Nanoparticulate paclitaxel NAB-PACLITAXEL COMPONENT PACLITAXEL 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 ABI-007 COMPONENT PACLITAXEL
Brand Names	Abraxane for Injectable Suspension Paclitaxel Protein-Bound Particles for Injectable Suspension (Albumin-Bound) Paclitaxel Injection, USP Paclitaxel for Injection Aj-paclitaxel Onxol Paclitaxel Powder for Injectable Suspension Nanoparticle, Albumin-bound Paclitaxel Paclitaxel for Injection USP Taxol Paclitaxel protein-bound particles for injectable suspension (albumin-bound) Pazenir Apealea Paxene Teva-paclitaxel for Injection Paclitaxel Injection USP Paclitaxel Paclitaxel Injection Paclitaxel Protein Bound Particles Albumin Bound Abraxane Paclitaxel NP Apo-paclitaxel Injectable Paclitaxel Paclitaxel
Indication	Used in the treatment of Kaposi's sarcoma and cancer of the lung, ovarian, and breast. Abraxane® is specfically indicated for the treatment of metastatic breast cancer and locally advanced or metastatic non-small cell lung cancer.
Categories	Agents Causing Muscle Toxicity Albumins Amino Acids, Peptides, and Proteins Antimitotic Agents Antineoplastic Agents Antineoplastic Agents, Phytogenic Antineoplastic and Immunomodulating Agents BSEP/ABCB11 Inhibitors BSEP/ABCB11 Substrates BSEP/ABCB11 Substrates with a Narrow Therapeutic Index Cardiotoxic antineoplastic agents Cyclodecanes Cycloparaffins Cytochrome P-450 CYP2C8 Substrates Cytochrome P-450 CYP2C8 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A Inducers Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inducers Cytochrome P-450 CYP3A4 Inducers (strength unknown) Cytochrome P-450 CYP3A4 Substrates Cytochrome P-450 CYP3A4 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A5 Substrates Cytochrome P-450 CYP3A5 Substrates with a Narrow Therapeutic Index Cytochrome P-450 CYP3A7 Substrates Cytochrome P-450 CYP3A7 Substrates with a Narrow Therapeutic Index Cytochrome P-450 Enzyme Inducers Cytochrome P-450 Substrates Diterpenes Hypotensive Agents Immunosuppressive Agents Microtubule Inhibition Microtubule Inhibitors Mitosis Modulators Myelosuppressive Agents Narrow Therapeutic Index Drugs Neurotoxic agents OATP1B3 substrates P-glycoprotein inhibitors P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Proteins Taxane Derivatives Taxoids Terpenes Tubulin Modulators
ATC-Code	L01CD01 L01CD51
CAS number	33069-62-4

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Tubulin beta-1 chain	MREIVHIQIGQCGNQIGAKFWEMIGEEHGIDLAGSDRGASALQLERISVY...	unknown	inhibitor
Apoptosis regulator Bcl-2	MAHAGRTGYDNREIVMKYIHYKLSQRGYEWDAGDVGAAPPGAAPAPGIFS...	unknown	inhibitor
Microtubule-associated protein 4	MADLSLADALTEPSPDIEGEIKRDFIATLEAEAFDDVVGETVGKTDYIPL...	unknown
Microtubule-associated protein 2	MADERKDEAKAPHWTSAPLTEASAHSHPPEIKDQGGAGEGLVRSANGFPY...	unknown
Microtubule-associated protein tau	MAEPRQEFEVMEDHAGTYGLGDRKDQGGYTMHQDQEGDTDAGLKESPLQT...	unknown
Nuclear receptor subfamily 1 group I member 2	MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATG...	unknown	inducer
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inducer
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
Cytochrome P450 3A7	MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...	unknown	substrate
Cytochrome P450 19A1	MVLEMLNPIHYNITSIVPEAMPAATMPVLLLTGLFLLVWNYEGTSSIPGP...	unknown	inhibitor
Cytochrome P450 1B1	MGTSLSPNDPWPLNPLSIQQTTLLLLLSVLATVHVGQRLLRQRRRQLRSA...	unknown	inhibitor
Cytochrome P450 2C8	MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...	unknown	substrate
Bile salt export pump	MSDSVILRSIKKFGEENDGFESDKSYNNDKKSRLQDEKKGDGVRVGFFQL...	unknown	substrate,inhibitor
P-glycoprotein 1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate,inhibitor
Multidrug resistance-associated protein 1	MALRGFCSADGSDPLWDWNVTWNTSNPDFTKCFQNTVLVWVPCFYLWACF...	unknown	inhibitor
Multidrug resistance-associated protein 7	MERLLAQLCGSSAAWPLPLWEGDTTGHCFTQLVLSALPHALLAVLSACYL...	unknown	substrate,inhibitor
Solute carrier organic anion transporter family member 1B3	MDQHQHLNKTAESASSEKKKTRRCNGFKMFLAALSFSYIAKALGGIIMKI...	unknown	substrate
Canalicular multispecific organic anion transporter 1	MLEKFCNSTFWNSSFLDSPEADLPLCFEQTVLVWIPLGYLWLLAPWQLLH...	unknown	substrate
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682