Drug Information
| General Information | ||||||
|---|---|---|---|---|---|---|
| Drug ID |
DR00251
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| Drug Name |
Docetaxel
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| Synonyms |
(2alpha,5beta,7beta,10beta,13alpha)-4-(acetyloxy)-13-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1,7,10-trihydroxy-9-oxo-5,20-epoxytax-11-en-2-yl benzoate; 4-(acetyloxy)-13alpha-({(2R,3S)-3-[(tert-butoxycarbonyl)amino]-2-hydroxy-3-phenylpropanoyl}oxy)-1,7beta,10beta-trihydroxy-9-oxo-5beta,20-epoxytax-11-en-2alpha-yl benzoate; ANX-514; Docetaxel (INN); Docetaxel 114977-28-5; Docetaxel anhydrous; Docetaxel, Trihydrate; EmDOC; N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetylpaclitaxel; N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol; N-debenzoyl-N-Boc-10-deacetyl taxol; RP-56976; SDP-014; TXL; Taxotere; Taxotere (TN); Taxotere(R); XRP-6976L
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| Drug Type |
Small molecular drug
|
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| Indication | Breast cancer [ICD11:2C60-2C6Z] | Approved | [1] | |||
| Lung cancer [ICD11:2C25] | Approved | [1] | ||||
| Prostate cancer [ICD11:2C82] | Approved | [1] | ||||
| Gastric cancer [ICD11:2B72] | Approved | [1] | ||||
| Head and neck cancer [ICD11:2B60-2B6E] | Approved | [1] | ||||
| Ovarian cancer [ICD11:2C73] | Approved | [1] | ||||
| Therapeutic Class |
Anticancer Agents
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| Structure |
|
 |
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| 3D MOL | 2D MOL | |||||
| Formula |
C43H53NO14
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| Canonical SMILES |
CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)O)C)O
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| InChI |
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
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| InChIKey |
ZDZOTLJHXYCWBA-VCVYQWHSSA-N
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| CAS Number |
CAS 114977-28-5
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| Pharmaceutical Properties | Molecular Weight | 807.9 | Topological Polar Surface Area | 224 | ||
| Heavy Atom Count | 58 | Rotatable Bond Count | 13 | |||
| Hydrogen Bond Donor Count | 5 | Hydrogen Bond Acceptor Count | 14 | |||
| XLogP |
1.6
|
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| PubChem CID | ||||||
| PubChem SID |
10249812
,103172104
,104418276
,117664410
,117682515
,12014196
,124950708
,126606827
,126630894
,126657365
,13410
,134337881
,136340291
,136375539
,14791415
,14815974
,17424977
,24845209
,26683886
,46225079
,46506766
,494081
,53790583
,56310805
,56310954
,56311107
,56311313
,56311574
,56312625
,56312880
,56312940
,56312941
,56313207
,56313989
,56314033
,56314070
,56314178
,56314280
,57346703
,78743198
,7890914
,7979114
,81044598
,822539
,833094
,87678200
,92308884
,92711403
,96024562
,99319097
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| ChEBI ID |
ChEBI:4672
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| TTD Drug ID | ||||||
| DT(s) Transporting This Drug | BCRP | Transporter Info | Breast cancer resistance protein | Substrate | [2] | |
| MRP1 | Transporter Info | Multidrug resistance-associated protein 1 | Substrate | [3] | ||
| MRP2 | Transporter Info | Multidrug resistance-associated protein 2 | Substrate | [4] | ||
| MRP7 | Transporter Info | Multidrug resistance-associated protein 7 | Substrate | [5] | ||
| OATP1B1 | Transporter Info | Organic anion transporting polypeptide 1B1 | Substrate | [6] | ||
| OATP1B3 | Transporter Info | Organic anion transporting polypeptide 1B3 | Substrate | [7] | ||
| P-GP | Transporter Info | P-glycoprotein 1 | Substrate | [8] | ||
| TAPL | Transporter Info | TAP-like protein | Substrate | [9] | ||
| References | ||||||
| 1 | Docetaxel was approved by FDA. The official website of the U.S. Food and Drug Administration. (2019) | |||||
| 2 | Ixabepilone, a novel microtubule-targeting agent for breast cancer, is a substrate for P-glycoprotein (P-gp/MDR1/ABCB1) but not breast cancer resistance protein (BCRP/ABCG2). J Pharmacol Exp Ther. 2011 May;337(2):423-32. | |||||
| 3 | Human intestinal transporter database: QSAR modeling and virtual profiling of drug uptake, efflux and interactions. Pharm Res. 2013 Apr;30(4):996-1007. | |||||
| 4 | Transport of diclofenac by breast cancer resistance protein (ABCG2) and stimulation of multidrug resistance protein 2 (ABCC2)-mediated drug transport by diclofenac and benzbromarone. Drug Metab Dispos. 2009 Jan;37(1):129-36. | |||||
| 5 | Modulation of the ATPase and transport activities of broad-acting multidrug resistance factor ABCC10 (MRP7). Cancer Res. 2012 Dec 15;72(24):6457-67. | |||||
| 6 | FDA Drug Development and Drug Interactions | |||||
| 7 | Rapid screening of antineoplastic candidates for the human organic anion transporter OATP1B3 substrates using fluorescent probes. Cancer Lett. 2008 Feb 18;260(1-2):163-9. | |||||
| 8 | Effect of ABCB1 C3435T polymorphism on docetaxel pharmacokinetics according to menopausal status in breast cancer patients. Br J Cancer. 2010 Aug 10;103(4):560-6. | |||||
| 9 | RNA-sequencing dissects the transcriptome of polyploid cancer cells that are resistant to combined treatments of cisplatin with paclitaxel and docetaxel. Mol Biosyst. 2017 Sep 26;13(10):2125-2134. | |||||
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