TXL

TAXOTERE

Created:	1999-07-08
Last modified:	2011-06-04

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2 entries where TXL is found as a standalone ligand

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Chemical Details
Formal Charge	0
Atom Count	111
Chiral Atom Count	11
Bond Count	116
Aromatic Bond Count	12

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Chemical Component Summary
Name	TAXOTERE
Systematic Name (OpenEye OEToolkits)	n/a
Formula	C₄₃ H₅₃ N O₁₄
Molecular Weight	807.879
Type	NON-POLYMER

Chemical Descriptors
Type	Program	Version	Descriptor
SMILES	ACDLabs	10.04	O=C(OC(C)(C)C)NC(c1ccccc1)C(O)C(=O)OC4C(=C3C(O)C(=O)C6(C(C(OC(=O)c2ccccc2)C(O)(C3(C)C)C4)C5(OC(=O)C)C(OC5)CC6O)C)C
SMILES	CACTVS	3.341	CC(=O)O[C]12CO[CH]1C[CH](O)[C]3(C)[CH]2[CH](OC(=O)c4ccccc4)[C]5(O)C[CH](OC(=O)[CH](O)[CH](NC(=O)OC(C)(C)C)c6ccccc6)C(=C([CH](O)C3=O)C5(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)OC(C)(C)C)O)O)OC(=O)c6ccccc6)(CO4)OC(=O)C)O)C)O
Canonical SMILES	CACTVS	3.341	CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@]3(C)[C@@H]2[C@H](OC(=O)c4ccccc4)[C@]5(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)c6ccccc6)C(=C([C@@H](O)C3=O)C5(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)OC(C)(C)C)O)O)OC(=O)c6ccccc6)(CO4)OC(=O)C)O)C)O
InChI	InChI	1.03	InChI=1S/C43H53NO14/c1-22-26(55-37(51)32(48)30(24-15-11-9-12-16-24)44-38(52)58-39(3,4)5)20-43(53)35(56-36(50)25-17-13-10-14-18-25)33-41(8,34(49)31(47)29(22)40(43,6)7)27(46)19-28-42(33,21-54-28)57-23(2)45/h9-18,26-28,30-33,35,46-48,53H,19-21H2,1-8H3,(H,44,52)/t26-,27-,28+,30-,31+,32+,33-,35-,41+,42-,43+/m0/s1
InChIKey	InChI	1.03	ZDZOTLJHXYCWBA-VCVYQWHSSA-N

Drug Info: DrugBank

DrugBank ID	DB01248 ?
Name	Docetaxel
Groups	approved investigational
Description	Docetaxel is a clinically well established anti-mitotic chemotherapy medication used for the treatment of different types of cancer, including breast, ovarian, and non-small cell lung cancer. Docetaxel is a complex diterpenoid molecule and a semisynthetic analogue of [paclitaxel].[A259676,L46466] Docetaxel reversibly binds to microtubulin with high affinity in a 1:1 stoichiometric ratio, allowing it to prevent cell division and promote to cell death.[A259676] Compared to paclitaxel, docetaxel is two times more potent as an inhibitor of microtubule depolymerization. Docetaxel binds to microtubules but does not interact with dimeric tubulin.[A259671] The use of docetaxel may lead to udesired outcomes such as hepatic impairment, hematologic effects, enterocolitis and neutropenic colitis, hypersensitivity reactions, fluid retention, second primary malignancies, embryo-fetal toxicity, and tumor lysis syndrome.[L46466] Docetaxel was approved by the FDA in 1996 and is available in solution for injection for intravenous or parenteral administration.[A259676]
Synonyms	N-Debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol N-Debenzoyl-N-(tert-butoxycarbonyl)-10-deacetylpaclitaxel TXL Docetaxel anhydrous Docetaxel trihydrate Docetaxel
Brand Names	Docetaxel Kabi Docivyx Docetaxel Accord Taro-docetaxel Docetaxel Teva Beizray Docetaxel anhydrous Docetaxel Taxespira Docetaxel Mylan Docetaxel Anhydrous Act Docetaxel 40 mg/ml Docetaxel Non-Alcohol Formula Docetaxel Injection Taxotere Docefrez Docetaxel Injection USP Docetaxel Teva Pharma Docetaxel Winthrop PMS-docetaxel
Indication	Docetaxel is indicated as a single agent for the treatment of locally advanced or metastatic breast cancer after chemotherapy failure; and with doxorubicin and cyclophosphamide as adjuvant treatment of operable node-positive BC. It is also indicated as a single agent for locally advanced or metastatic non-small cell lung cancer (NSCLC) after platinum therapy failure; and with cisplatin for unresectable, locally advanced or metastatic untreated NSCLC. For the treatment of metastatic castration-resistant prostate cancer, docetaxel is indicated with prednisone. Docetaxel is also indicated with cisplatin and fluorouracil for untreated, advanced gastric adenocarcinoma, including the gastroesophageal junction, and with cisplatin and fluorouracil for induction treatment of locally advanced squamous cell carcinoma of the head and neck (SCCHN).[L46466]
Categories	Agents Causing Muscle Toxicity Antimitotic Agents Antineoplastic Agents Antineoplastic and Immunomodulating Agents BCRP/ABCG2 Substrates Cardiotoxic antineoplastic agents Cyclodecanes Cycloparaffins Cytochrome P-450 CYP3A Inhibitors Cytochrome P-450 CYP3A Substrates Cytochrome P-450 CYP3A4 Inhibitors Cytochrome P-450 CYP3A4 Inhibitors (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 Inhibitors Cytochrome P-450 Substrates Diterpenes Hepatotoxic Agents Immunosuppressive Agents Microtubule Inhibition Microtubule Inhibitors Mitosis Modulators Myelosuppressive Agents Narrow Therapeutic Index Drugs OATP1B3 substrates P-glycoprotein substrates P-glycoprotein substrates with a Narrow Therapeutic Index Taxane Derivatives Taxoids Terpenes Tubulin Modulators
ATC-Code	L01CD02
CAS number	114977-28-5

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
Tubulin beta-1 chain	MREIVHIQIGQCGNQIGAKFWEMIGEEHGIDLAGSDRGASALQLERISVY...	unknown	inhibitor
Apoptosis regulator Bcl-2	MAHAGRTGYDNREIVMKYIHYKLSQRGYEWDAGDVGAAPPGAAPAPGIFS...	unknown
Nuclear receptor subfamily 1 group I member 2	MEVRPKESWNHADFVHCEDTESVPGKPSVNADEEVGGPQICRVCGDKATG...	unknown	binder
Cytochrome P450 3A4	MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...	unknown	substrate,inhibitor
Cytochrome P450 3A5	MDLIPNLAVETWLLLAVSLVLLYLYGTRTHGLFKRLGIPGPTPLPLLGNV...	unknown	substrate
Cytochrome P450 3A7	MDLIPNLAVETWLLLAVSLILLYLYGTRTHGLFKKLGIPGPTPLPFLGNA...	unknown	substrate
Cytochrome P450 1B1	MGTSLSPNDPWPLNPLSIQQTTLLLLLSVLATVHVGQRLLRQRRRQLRSA...	unknown	binder
ATP-dependent translocase ABCB1	MDLEGDRNGGAKKKNFFKLNNKSEKDKKEKKPTVSVFSMFRYSNWLDKLY...	unknown	substrate
ATP-binding cassette sub-family C member 10	MERLLAQLCGSSAAWPLPLWEGDTTGHCFTQLVLSALPHALLAVLSACYL...	unknown	substrate
Solute carrier organic anion transporter family member 1B3	MDQHQHLNKTAESASSEKKKTRRCNGFKMFLAALSFSYIAKALGGIIMKI...	unknown	substrate
Solute carrier family 22 member 7	MGFEELLEQVGGFGPFQLRNVALLALPRVLLPLHFLLPIFLAAVPAHRCA...	unknown	substrate
Broad substrate specificity ATP-binding cassette transporter ABCG2	MSSSNVEVFIPVSQGNTNGFPATASNDLKAFTEGAVLSFHNICYRVKLKS...	unknown	substrate
ATP-binding cassette sub-family C member 2	MLEKFCNSTFWNSSFLDSPEADLPLCFEQTVLVWIPLGYLWLLAPWQLLH...	unknown	substrate
Multidrug resistance-associated protein 1	MALRGFCSADGSDPLWDWNVTWNTSNPDFTKCFQNTVLVWVPCFYLWACF...	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