Drug Details

General Information of the Drug (ID: DR7626)
Name
Docetaxel
Synonyms
Taxotere; 114977-28-5; Docetaxel anhydrous; Docetaxol; RP-56976; EmDOC; RP 56976; NSC 628503; N-debenzoyl-N-tert-butoxycarbonyl-10-deacetyltaxol; UNII-699121PHCA; TXL; Taxotere (TN); MFCD00800737; N-debenzoyl-N-Boc-10-deacetyl taxol; Docetaxolum; N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetyltaxol; CHEBI:4672; 699121PHCA; Docetaxel, 98%; NSC628503; NSC-628503; N-debenzoyl-N-(tert-butoxycarbonyl)-10-deacetylpaclitaxel; DSSTox_CID_20464; DSSTox_RID_79497; DSSTox_GSID_40464; (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; Docetaxel, Trihydrate; Taxoel; Taxotere(R); Docetaxel Winthrop; Docetaxel [INN]; (1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-(acetyloxy)-15-{[(2R,3S)-3-{[(tert-butoxy)carbonyl]amino}-2-hydroxy-3-phenylpropanoyl]oxy}-1,9,12-trihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.0^{3,10}.0^{4,7}]heptadec-13-en-2-yl benzoate; (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-acetoxy-9-(((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-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]oxet-12-yl benzoate; CAS-114977-28-5; Docetaxolum [INN-Latin]; Docecad; Docefrez; docetaxel 114977-28-5; HSDB 6965; XRP-6976L; ANX-514; SDP-014; SID 530; Docetaxel (TN); NCGC00181306-01; NCGC00181306-02; 5?,20-Epoxy-1,7?,10?-trihydroxy-9-oxotax-11-ene-2?,4,13?-triyl 4-acetate 2-benzoate 13-[(2R,3S)-3-[[(1,1-dimethylethoxy)carbonyl]amino]-2-hydroxy-3-phenylpropanoate]; Taxotere (Aventis); CID148124; Docetaxel - Taxotere; bind-014; Docetaxel (JAN/INN); CHEMBL92; SCHEMBL4419; docetaxel anhydrous derivatives; GTPL6809; DTXSID0040464; BDBM36351; SYP-0704A; ZDZOTLJHXYCWBA-VCVYQWHSSA-; AMY4356; 114977-28-5, Docetaxel; HMS2089K08; EX-A1206; HY-B0011; Tox21_112781; Tox21_113088; AC-383; CD0182; ZINC85537053; AKOS015960718; AKOS024457953; Tox21_112781_1; CS-1144; DB01248; KS-1452; MCULE-1930158681; ISOCYANATOETHYLMETHACRYLATEPOLYMER; Docetaxel, purum, >=97.0% (HPLC); NCGC00181306-04; NCGC00242509-01; 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; Benzenepropanoic acid, beta-(((1,1-dimethylethoxy)carbonyl)amino)-alpha-hydroxy-, 12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca(3,4)benz(1,2-b)oxet-9-yl ester; AB0072965; D4102; C11231; D07866; W-1428; AB01273941-01; AB01273941-02; Q420436; SR-01000003023; W-60384; Q-100074; SR-01000003023-5; BRD-K30577245-001-04-3; BRD-K30577245-341-01-9; Z1551429742; Anhydrous Docetaxel, European Pharmacopoeia (EP) Reference Standard; (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl (aR,bS)-b-[[(1,1-dimethylethoxy)carbonyl]amino]-a-hydroxybenzenepropanoate; (2beta,5beta,7alpha,8alpha,10alpha,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; [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,9,12-trihydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate; [2aR-[2a?,4?,4a?,6?,9?(?R*,?S*),11?,12?,12a?,12b?]]-?-[[(1,1-Dimethylethoxy)carbonyl]amino]-?-hydroxy-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester benzenepropanoic acid; [acetoxy-[(2R,3S)-3-(tert-butoxycarbonylamino)-2-hydroxy-3-phenyl-propanoyl]oxy-trihydroxy-tetramethyl-oxo-[?]yl] benzoate; 114915-20-7; Benzenepropanoic acid, beta-(((1,1-dimethylethoxy)carbonyl)amino)-alpha-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-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,1-dimethylethoxy)carbonyl]amino]-.alpha.-hydroxy-, (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-12b-(acetyloxy)-12-(benzyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-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)
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Molecular Type
Small molecule
Disease Solid tumour/cancer [ICD-11: 2A00-2F9Z] Approved [1]
Structure
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2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability
Clearance
The drug present in the plasma can be removed from the body at the rate of 14 mL/min/kg
Elimination
5% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 4 minutes (alpha), 36 minutes (beta), and 11.1 hours (gamma)
Metabolism
The drug is metabolized via the hepatic
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.1457 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.04%
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 2.1 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 0.0065 mg/mL
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Formula
C43H53NO14
PubChem CID
148124
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
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
ZDZOTLJHXYCWBA-VCVYQWHSSA-N
CAS Number
CAS 114977-28-5
GDSC
Docetaxel
TTD Drug ID
D0O5WP
DrugBank ID
DB01248
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Ceramide      Ananas comosus     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Induction Apoptosis
Induction Cell cycle arrest in S and G2/M phase
                    In-vitro Model B16 CVCL_F936 Mouse melanoma Mus musculus
MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
                    In-vivo Model B16 tumor-bearing mice. Kunming mice (18-22 g) was inoculated with B16 melanoma cells (3 * 105) by subcutaneously injection at the right axillary space.
                    Experimental
                    Result(s)		 Ceramide could enhance the antitumor activity of Docetaxel in a synergistic manner, which suggest promising application prospects of Ceramide + Docetaxel combination treatment.
          Curcumin      Hellenia speciosa     Click to Show/Hide the Molecular Data of This NP
                 Augmenting Drug Sensitivity     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Down-regulation Expression MMP-2  Molecule Info 
Pathway MAP
Down-regulation Expression MMP-9  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
Up-regulation Expression TIMP1  Molecule Info 
Pathway MAP
                    In-vitro Model PANC-1 CVCL_0480 Pancreatic ductal adenocarcinoma Homo sapiens
HPAF-II CVCL_0313 Pancreatic ductal adenocarcinoma Homo sapiens
MIA PaCa-2 CVCL_0428 Pancreatic ductal adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Curcumin showed synergistic anti-cancer effects with edocetaxel on PC cells by upregulation of TIMP1/TIMP2 with concomitant downregulation of MMP2/MMP9/N-cadherin proteins.
          Cyclopamine      Veratrum californicum     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [4]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression EGFR  Molecule Info 
Pathway MAP
                    In-vitro Model LNCaP CVCL_0395 Prostate carcinoma Homo sapiens
DU145 CVCL_0105 Prostate carcinoma Homo sapiens
PC-3 CVCL_0035 Prostate carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Combined use of inhibitors of EGF-EGFR and hedgehog signaling with docetaxel could represent a more promising strategy for treatment in patients with metastatic and androgen-independent prostate cancer.
          Estramustine      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [5]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model PC-3 CVCL_0035 Prostate carcinoma Homo sapiens
LNCaP CVCL_0395 Prostate carcinoma Homo sapiens
                    Experimental
                    Result(s)		 These results provide novel molecular targets of docetaxel and estramustine combination treatment in prostate cancer cells.
          Farnesol      Mosla chinensis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [6]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model LNCaP CVCL_0395 Prostate carcinoma Homo sapiens
PC-3 CVCL_0035 Prostate carcinoma Homo sapiens
                    Experimental
                    Result(s)		 Ibandronate effectively inhibits growth of prostate cancer cell lines via inhibition of the farnesyl-IPP-synthase and exhibits synergistic effects with docetaxel.
          Schisandrol B      Schisandra chinensis     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [7]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Up-regulation Cleavage CASP3  Molecule Info 
Pathway MAP
Down-regulation Expression CDH2  Molecule Info 
Pathway MAP
                    In-vitro Model Ca Ski CVCL_1100 Cervical squamous cell carcinoma Homo sapiens
                    In-vivo Model Mice were subcutaneously implanted with cell suspension holding 1*106 Caski cells in the right flank.
                    Experimental
                    Result(s)		 Sch B enhanced the anti-tumor effects of DTX in vitro and in vivo via growth, invasion, and apoptosis regulating.
          Selenium      Soil     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [8]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Biological
                    Regulation		 Induction Cell cycle arrest in G2/M phase
                    In-vitro Model MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
MCF-7 CVCL_0031 Invasive breast carcinoma Homo sapiens
                    Experimental
                    Result(s)		 The combination of selenium with docetaxel inhibits cell proliferation through apoptosis and cell arrest in the G2/M phase in MDA-MB-231 breast cancer cells.
          Vinblastine      Catharanthus roseus     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [9]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vitro Model NCI-H1299 CVCL_0060 Lung large cell carcinoma Homo sapiens
MDA-MB-231 CVCL_0062 Breast adenocarcinoma Homo sapiens
                    Experimental
                    Result(s)		 Combination therapy of breast and lung cancer cell lines using docetaxel or vinblastine with tamoxifen synergistically increases the anti-proliferative affect of single agents.
Target and Pathway
Target(s) Tubulin (TUB)  Molecule Info  [10]
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6809).
Reference 2 Synergistic enhancement of cancer therapy using a combination of ceramide and docetaxel. Int J Mol Sci. 2014 Mar 10;15(3):4201-20.
Reference 3 Curcumin enhances anti?cancer efficacy of either gemcitabine or docetaxel on pancreatic cancer cells. Oncol Rep. 2020 Oct;44(4):1393-1402.
Reference 4 Combined targeting of epidermal growth factor receptor and hedgehog signaling by gefitinib and cyclopamine cooperatively improves the cytotoxic effects of docetaxel on metastatic prostate cancer cells. Mol Cancer Ther. 2007 Mar;6(3):967-78.
Reference 5 Gene expression profiling revealed novel molecular targets of docetaxel and estramustine combination treatment in prostate cancer cells. Mol Cancer Ther. 2005 Mar;4(3):389-98.
Reference 6 Differential effects of ibandronate, docetaxel and farnesol treatment alone and in combination on the growth of prostate cancer cell lines. Acta Oncol. 2011 Jan;50(1):127-33.
Reference 7 Schisandrin B synergizes docetaxel-induced restriction of growth and invasion of cervical cancer cells in vitro and in vivo. Ann Transl Med. 2020 Sep;8(18):1157.
Reference 8 Effects of combination therapy of docetaxel with selenium on the human breast cancer cell lines MDA-MB-231 and MCF-7. Ann Surg Treat Res. 2015 Feb;88(2):55-62.
Reference 9 Combination therapy increases the efficacy of docetaxel, vinblastine and tamoxifen in cancer cells. J Cancer Res Ther. Jul-Sep 2014;10(3):715-21.
Reference 10 Docetaxel: a review of its use in metastatic breast cancer. Drugs. 2005;65(17):2513-31.
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