Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C43H53NO14.3H2O |
Molecular Weight | 861.9251 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 11 / 11 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.O.[H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](O)C4=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)C5=CC=CC=C5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C6=CC=CC=C6
InChI
InChIKey=XCDIRYDKECHIPE-QHEQPUDQSA-N
InChI=1S/C43H53NO14.3H2O/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);3*1H2/t26-,27-,28+,30-,31+,32+,33-,35-,41+,42-,43+;;;/m0.../s1
Molecular Formula | H2O |
Molecular Weight | 18.0153 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Molecular Formula | C43H53NO14 |
Molecular Weight | 807.8792 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 10 / 11 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Docetaxel was protected by patents (U.S. patent and European patent) which were owned by Sanofi-Aventis, and so was available only under the Taxotere brand name internationally. The European patent expired in 2010. Docetaxel is a clinically well-established anti-mitotic chemotherapy medication used for the treatment of patients with locally advanced or metastatic breast cancer after failure of prior chemotherapy. Also used as a single agent in the treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of prior platinum-based chemotherapy. It is also used in combination with prednisone, in the treatment of patients with androgen independent (hormone refractory) metastatic prostate cancer. Furthermore, docetaxel has uses in the treatment of gastric adenocarcinoma and head and neck cancer. Docetaxel interferes with the normal function of microtubule growth. Whereas drugs like colchicine cause the depolymerization of microtubules in vivo, docetaxel arrests their function by having the opposite effect; it hyper-stabilizes their structure. This destroys the cell's ability to use its cytoskeleton in a flexible manner. Specifically, docetaxel binds to the β-subunit of tubulin. Tubulin is the "building block" of mictotubules, and the binding of docetaxel locks these building blocks in place. The resulting microtubule/docetaxel complex does not have the ability to disassemble. This adversely affects cell function because the shortening and lengthening of microtubules (termed dynamic instability) is necessary for their function as a transportation highway for the cell. Chromosomes, for example, rely upon this property of microtubules during mitosis. Further research has indicated that docetaxel induces programmed cell death (apoptosis) in cancer cells by binding to an apoptosis stopping protein called Bcl-2 (B-cell leukemia 2) and thus arresting its function.
CNS Activity
Sources: http://www.medscape.com/viewarticle/776641
Curator's Comment: docetaxel cannot cross the blood–brain barrier and control metastatic foci
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18281755 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | TAXOTERE Approved UseINDICATIONS & USAGE Docetaxel injection concentrate is a microtubule inhibitor indicated for: Breast Cancer (BC): single agent for locally advanced or metastatic BC after chemotherapy failure; and with doxorubicin and cyclophosphamide as adjuvant treatment of operable node-positive BC (1.1) Non-Small Cell Lung Cancer (NSCLC): single agent for locally advanced or metastatic NSCLC after platinum therapy failure; and with cisplatin for unresectable, locally advanced or metastatic untreated NSCLC (1.2) Hormone Refractory Prostate Cancer (HRPC): with prednisone in androgen independent (hormone refractory) metastatic prostate cancer (1.3) Gastric Adenocarcinoma (GC): with cisplatin and fluorouracil for untreated, advanced GC, including the gastroesophageal junction (1.4) Squamous Cell Carcinoma of the Head and Neck Cancer (SCCHN): with cisplatin and fluorouracil for induction treatment of locally advanced SCCHN (1.5) 1.1 Breast Cancer Docetaxel injection concentrate is indicated for the treatment of patients with locally advanced or metastatic breast cancer after failure of prior chemotherapy. Docetaxel injection concentrate in combination with doxorubicin and cyclophosphamide is indicated for the adjuvant treatment of patients with operable node-positive breast cancer. 1.2 Non-Small Cell Lung Cancer Docetaxel injection concentrate as a single agent is indicated for the treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of prior platinum-based chemotherapy. Docetaxel injection concentrate in combination with cisplatin is indicated for the treatment of patients with unresectable, locally advanced or metastatic non-small cell lung cancer who have not previously received chemotherapy for this condition. 1.3 Prostate Cancer Docetaxel injection concentrate in combination with prednisone is indicated for the treatment of patients with androgen independent (hormone refractory) metastatic prostate cancer. 1.4 Gastric Adenocarcinoma Docetaxel injection concentrate in combination with cisplatin and fluorouracil is indicated for the treatment of patients with advanced gastric adenocarcinoma, including adenocarcinoma of the gastroesophageal junction, who have not received prior chemotherapy for advanced disease. 1.5 Head and Neck Cancer Docetaxel injection concentrate in combination with cisplatin and fluorouracil is indicated for the induction treatment of patients with locally advanced squamous cell carcinoma of the head and neck (SCCHN). Launch Date1996 |
|||
Primary | TAXOTERE Approved UseINDICATIONS & USAGE Docetaxel injection concentrate is a microtubule inhibitor indicated for: Breast Cancer (BC): single agent for locally advanced or metastatic BC after chemotherapy failure; and with doxorubicin and cyclophosphamide as adjuvant treatment of operable node-positive BC (1.1) Non-Small Cell Lung Cancer (NSCLC): single agent for locally advanced or metastatic NSCLC after platinum therapy failure; and with cisplatin for unresectable, locally advanced or metastatic untreated NSCLC (1.2) Hormone Refractory Prostate Cancer (HRPC): with prednisone in androgen independent (hormone refractory) metastatic prostate cancer (1.3) Gastric Adenocarcinoma (GC): with cisplatin and fluorouracil for untreated, advanced GC, including the gastroesophageal junction (1.4) Squamous Cell Carcinoma of the Head and Neck Cancer (SCCHN): with cisplatin and fluorouracil for induction treatment of locally advanced SCCHN (1.5) 1.1 Breast Cancer Docetaxel injection concentrate is indicated for the treatment of patients with locally advanced or metastatic breast cancer after failure of prior chemotherapy. Docetaxel injection concentrate in combination with doxorubicin and cyclophosphamide is indicated for the adjuvant treatment of patients with operable node-positive breast cancer. 1.2 Non-Small Cell Lung Cancer Docetaxel injection concentrate as a single agent is indicated for the treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of prior platinum-based chemotherapy. Docetaxel injection concentrate in combination with cisplatin is indicated for the treatment of patients with unresectable, locally advanced or metastatic non-small cell lung cancer who have not previously received chemotherapy for this condition. 1.3 Prostate Cancer Docetaxel injection concentrate in combination with prednisone is indicated for the treatment of patients with androgen independent (hormone refractory) metastatic prostate cancer. 1.4 Gastric Adenocarcinoma Docetaxel injection concentrate in combination with cisplatin and fluorouracil is indicated for the treatment of patients with advanced gastric adenocarcinoma, including adenocarcinoma of the gastroesophageal junction, who have not received prior chemotherapy for advanced disease. 1.5 Head and Neck Cancer Docetaxel injection concentrate in combination with cisplatin and fluorouracil is indicated for the induction treatment of patients with locally advanced squamous cell carcinoma of the head and neck (SCCHN). Launch Date1996 |
|||
Primary | TAXOTERE Approved UseINDICATIONS & USAGE Docetaxel injection concentrate is a microtubule inhibitor indicated for: Breast Cancer (BC): single agent for locally advanced or metastatic BC after chemotherapy failure; and with doxorubicin and cyclophosphamide as adjuvant treatment of operable node-positive BC (1.1) Non-Small Cell Lung Cancer (NSCLC): single agent for locally advanced or metastatic NSCLC after platinum therapy failure; and with cisplatin for unresectable, locally advanced or metastatic untreated NSCLC (1.2) Hormone Refractory Prostate Cancer (HRPC): with prednisone in androgen independent (hormone refractory) metastatic prostate cancer (1.3) Gastric Adenocarcinoma (GC): with cisplatin and fluorouracil for untreated, advanced GC, including the gastroesophageal junction (1.4) Squamous Cell Carcinoma of the Head and Neck Cancer (SCCHN): with cisplatin and fluorouracil for induction treatment of locally advanced SCCHN (1.5) 1.1 Breast Cancer Docetaxel injection concentrate is indicated for the treatment of patients with locally advanced or metastatic breast cancer after failure of prior chemotherapy. Docetaxel injection concentrate in combination with doxorubicin and cyclophosphamide is indicated for the adjuvant treatment of patients with operable node-positive breast cancer. 1.2 Non-Small Cell Lung Cancer Docetaxel injection concentrate as a single agent is indicated for the treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of prior platinum-based chemotherapy. Docetaxel injection concentrate in combination with cisplatin is indicated for the treatment of patients with unresectable, locally advanced or metastatic non-small cell lung cancer who have not previously received chemotherapy for this condition. 1.3 Prostate Cancer Docetaxel injection concentrate in combination with prednisone is indicated for the treatment of patients with androgen independent (hormone refractory) metastatic prostate cancer. 1.4 Gastric Adenocarcinoma Docetaxel injection concentrate in combination with cisplatin and fluorouracil is indicated for the treatment of patients with advanced gastric adenocarcinoma, including adenocarcinoma of the gastroesophageal junction, who have not received prior chemotherapy for advanced disease. 1.5 Head and Neck Cancer Docetaxel injection concentrate in combination with cisplatin and fluorouracil is indicated for the induction treatment of patients with locally advanced squamous cell carcinoma of the head and neck (SCCHN). Launch Date1996 |
|||
Primary | TAXOTERE Approved UseINDICATIONS & USAGE Docetaxel injection concentrate is a microtubule inhibitor indicated for: Breast Cancer (BC): single agent for locally advanced or metastatic BC after chemotherapy failure; and with doxorubicin and cyclophosphamide as adjuvant treatment of operable node-positive BC (1.1) Non-Small Cell Lung Cancer (NSCLC): single agent for locally advanced or metastatic NSCLC after platinum therapy failure; and with cisplatin for unresectable, locally advanced or metastatic untreated NSCLC (1.2) Hormone Refractory Prostate Cancer (HRPC): with prednisone in androgen independent (hormone refractory) metastatic prostate cancer (1.3) Gastric Adenocarcinoma (GC): with cisplatin and fluorouracil for untreated, advanced GC, including the gastroesophageal junction (1.4) Squamous Cell Carcinoma of the Head and Neck Cancer (SCCHN): with cisplatin and fluorouracil for induction treatment of locally advanced SCCHN (1.5) 1.1 Breast Cancer Docetaxel injection concentrate is indicated for the treatment of patients with locally advanced or metastatic breast cancer after failure of prior chemotherapy. Docetaxel injection concentrate in combination with doxorubicin and cyclophosphamide is indicated for the adjuvant treatment of patients with operable node-positive breast cancer. 1.2 Non-Small Cell Lung Cancer Docetaxel injection concentrate as a single agent is indicated for the treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of prior platinum-based chemotherapy. Docetaxel injection concentrate in combination with cisplatin is indicated for the treatment of patients with unresectable, locally advanced or metastatic non-small cell lung cancer who have not previously received chemotherapy for this condition. 1.3 Prostate Cancer Docetaxel injection concentrate in combination with prednisone is indicated for the treatment of patients with androgen independent (hormone refractory) metastatic prostate cancer. 1.4 Gastric Adenocarcinoma Docetaxel injection concentrate in combination with cisplatin and fluorouracil is indicated for the treatment of patients with advanced gastric adenocarcinoma, including adenocarcinoma of the gastroesophageal junction, who have not received prior chemotherapy for advanced disease. 1.5 Head and Neck Cancer Docetaxel injection concentrate in combination with cisplatin and fluorouracil is indicated for the induction treatment of patients with locally advanced squamous cell carcinoma of the head and neck (SCCHN). Launch Date1996 |
|||
Primary | TAXOTERE Approved UseINDICATIONS & USAGE Docetaxel injection concentrate is a microtubule inhibitor indicated for: Breast Cancer (BC): single agent for locally advanced or metastatic BC after chemotherapy failure; and with doxorubicin and cyclophosphamide as adjuvant treatment of operable node-positive BC (1.1) Non-Small Cell Lung Cancer (NSCLC): single agent for locally advanced or metastatic NSCLC after platinum therapy failure; and with cisplatin for unresectable, locally advanced or metastatic untreated NSCLC (1.2) Hormone Refractory Prostate Cancer (HRPC): with prednisone in androgen independent (hormone refractory) metastatic prostate cancer (1.3) Gastric Adenocarcinoma (GC): with cisplatin and fluorouracil for untreated, advanced GC, including the gastroesophageal junction (1.4) Squamous Cell Carcinoma of the Head and Neck Cancer (SCCHN): with cisplatin and fluorouracil for induction treatment of locally advanced SCCHN (1.5) 1.1 Breast Cancer Docetaxel injection concentrate is indicated for the treatment of patients with locally advanced or metastatic breast cancer after failure of prior chemotherapy. Docetaxel injection concentrate in combination with doxorubicin and cyclophosphamide is indicated for the adjuvant treatment of patients with operable node-positive breast cancer. 1.2 Non-Small Cell Lung Cancer Docetaxel injection concentrate as a single agent is indicated for the treatment of patients with locally advanced or metastatic non-small cell lung cancer after failure of prior platinum-based chemotherapy. Docetaxel injection concentrate in combination with cisplatin is indicated for the treatment of patients with unresectable, locally advanced or metastatic non-small cell lung cancer who have not previously received chemotherapy for this condition. 1.3 Prostate Cancer Docetaxel injection concentrate in combination with prednisone is indicated for the treatment of patients with androgen independent (hormone refractory) metastatic prostate cancer. 1.4 Gastric Adenocarcinoma Docetaxel injection concentrate in combination with cisplatin and fluorouracil is indicated for the treatment of patients with advanced gastric adenocarcinoma, including adenocarcinoma of the gastroesophageal junction, who have not received prior chemotherapy for advanced disease. 1.5 Head and Neck Cancer Docetaxel injection concentrate in combination with cisplatin and fluorouracil is indicated for the induction treatment of patients with locally advanced squamous cell carcinoma of the head and neck (SCCHN). Launch Date1996 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
742 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17956601 |
20 mg/m² 1 times / week multiple, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DOCETAXEL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3737 nM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17956601 |
100 mg/m² 1 times / 3 weeks multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DOCETAXEL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
1284 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17956601 |
20 mg/m² 1 times / week multiple, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DOCETAXEL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
5562 nM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17956601 |
100 mg/m² 1 times / 3 weeks multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DOCETAXEL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
0.99 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17956601 |
20 mg/m² 1 times / week multiple, intravenous dose: 20 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DOCETAXEL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
0.74 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/17956601 |
100 mg/m² 1 times / 3 weeks multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DOCETAXEL plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
11.1 h |
100 mg/m² 1 times / hour multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DOCETAXEL plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
3% |
100 mg/m² 1 times / hour multiple, intravenous dose: 100 mg/m² route of administration: Intravenous experiment type: MULTIPLE co-administered: |
DOCETAXEL plasma | Homo sapiens population: UNHEALTHY age: UNKNOWN sex: FEMALE / MALE food status: UNKNOWN |
Doses
Dose | Population | Adverse events |
---|---|---|
75 mg/m2 1 times / 3 weeks multiple, intravenous Dose: 75 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 75 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 51 years (range: 36 - 65 years) n = 39 Health Status: unhealthy Condition: advanced breast cancer: Age Group: 51 years (range: 36 - 65 years) Sex: F Population Size: 39 Sources: |
Disc. AE: Fluid retention... AEs leading to discontinuation/dose reduction: Fluid retention (16 patients) Sources: |
43 mg/m2 1 times / week multiple, intravenous MTD Dose: 43 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 43 mg/m2, 1 times / week Sources: |
unhealthy, 58 years (range: 41-81 years) n = 10 Health Status: unhealthy Condition: Advanced Refractory Cancer Age Group: 58 years (range: 41-81 years) Sex: M+F Population Size: 10 Sources: |
DLT: Fatigue, Asthenia... Other AEs: Nail toxicity, Alopecia... Dose limiting toxicities: Fatigue (grade 3-4, 2 patients) Other AEs:Asthenia (grade 3-4, 2 patients) Skin toxicity (grade 3-4, 1 patient) Diarrhea (grade 3-4, 1 patient) Nail toxicity (grade 3-4, 1 patient) Sources: Alopecia (grade 2, 1 patient) Leukopenia (grade 3, 2 patients) |
52 mg/m2 1 times / week multiple, intravenous Dose: 52 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 52 mg/m2, 1 times / week Sources: |
unhealthy, 58 years (range: 41-81 years) n = 3 Health Status: unhealthy Condition: Advanced Refractory Cancer Age Group: 58 years (range: 41-81 years) Sex: M+F Population Size: 3 Sources: |
DLT: Fatigue, Asthenia... Dose limiting toxicities: Fatigue (grade 3-4, 3 patients) Sources: Asthenia (grade 3-4, 3 patients) |
150 mg/m2 single, intravenous Overdose Dose: 150 mg/m2 Route: intravenous Route: single Dose: 150 mg/m2 Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Population Size: 1 Sources: |
Other AEs: Neutropenia, Asthenia... Other AEs: Neutropenia (severe) Sources: Asthenia (mild) Epidermal and dermal conditions Paresthesia (mild) |
200 mg/m2 single, intravenous Overdose Dose: 200 mg/m2 Route: intravenous Route: single Dose: 200 mg/m2 Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Population Size: 1 Sources: |
Other AEs: Neutropenia, Asthenia... Other AEs: Neutropenia (severe) Sources: Asthenia (mild) Epidermal and dermal conditions Paresthesia (mild) |
60 mg/m2 1 times / 3 weeks multiple, intravenous Recommended Dose: 60 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 60 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Disc. AE: Hypersensitivity... AEs leading to discontinuation/dose reduction: Hypersensitivity (severe) Sources: |
100 mg/m2 1 times / 3 weeks multiple, intravenous Dose: 100 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Other AEs: Hepatotoxicity... Other AEs: Hepatotoxicity (grade 5) Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Fluid retention | 16 patients Disc. AE |
75 mg/m2 1 times / 3 weeks multiple, intravenous Dose: 75 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 75 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, 51 years (range: 36 - 65 years) n = 39 Health Status: unhealthy Condition: advanced breast cancer: Age Group: 51 years (range: 36 - 65 years) Sex: F Population Size: 39 Sources: |
Alopecia | grade 2, 1 patient | 43 mg/m2 1 times / week multiple, intravenous MTD Dose: 43 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 43 mg/m2, 1 times / week Sources: |
unhealthy, 58 years (range: 41-81 years) n = 10 Health Status: unhealthy Condition: Advanced Refractory Cancer Age Group: 58 years (range: 41-81 years) Sex: M+F Population Size: 10 Sources: |
Leukopenia | grade 3, 2 patients | 43 mg/m2 1 times / week multiple, intravenous MTD Dose: 43 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 43 mg/m2, 1 times / week Sources: |
unhealthy, 58 years (range: 41-81 years) n = 10 Health Status: unhealthy Condition: Advanced Refractory Cancer Age Group: 58 years (range: 41-81 years) Sex: M+F Population Size: 10 Sources: |
Nail toxicity | grade 3-4, 1 patient | 43 mg/m2 1 times / week multiple, intravenous MTD Dose: 43 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 43 mg/m2, 1 times / week Sources: |
unhealthy, 58 years (range: 41-81 years) n = 10 Health Status: unhealthy Condition: Advanced Refractory Cancer Age Group: 58 years (range: 41-81 years) Sex: M+F Population Size: 10 Sources: |
Diarrhea | grade 3-4, 1 patient DLT |
43 mg/m2 1 times / week multiple, intravenous MTD Dose: 43 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 43 mg/m2, 1 times / week Sources: |
unhealthy, 58 years (range: 41-81 years) n = 10 Health Status: unhealthy Condition: Advanced Refractory Cancer Age Group: 58 years (range: 41-81 years) Sex: M+F Population Size: 10 Sources: |
Skin toxicity | grade 3-4, 1 patient DLT |
43 mg/m2 1 times / week multiple, intravenous MTD Dose: 43 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 43 mg/m2, 1 times / week Sources: |
unhealthy, 58 years (range: 41-81 years) n = 10 Health Status: unhealthy Condition: Advanced Refractory Cancer Age Group: 58 years (range: 41-81 years) Sex: M+F Population Size: 10 Sources: |
Asthenia | grade 3-4, 2 patients DLT |
43 mg/m2 1 times / week multiple, intravenous MTD Dose: 43 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 43 mg/m2, 1 times / week Sources: |
unhealthy, 58 years (range: 41-81 years) n = 10 Health Status: unhealthy Condition: Advanced Refractory Cancer Age Group: 58 years (range: 41-81 years) Sex: M+F Population Size: 10 Sources: |
Fatigue | grade 3-4, 2 patients DLT |
43 mg/m2 1 times / week multiple, intravenous MTD Dose: 43 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 43 mg/m2, 1 times / week Sources: |
unhealthy, 58 years (range: 41-81 years) n = 10 Health Status: unhealthy Condition: Advanced Refractory Cancer Age Group: 58 years (range: 41-81 years) Sex: M+F Population Size: 10 Sources: |
Asthenia | grade 3-4, 3 patients DLT |
52 mg/m2 1 times / week multiple, intravenous Dose: 52 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 52 mg/m2, 1 times / week Sources: |
unhealthy, 58 years (range: 41-81 years) n = 3 Health Status: unhealthy Condition: Advanced Refractory Cancer Age Group: 58 years (range: 41-81 years) Sex: M+F Population Size: 3 Sources: |
Fatigue | grade 3-4, 3 patients DLT |
52 mg/m2 1 times / week multiple, intravenous Dose: 52 mg/m2, 1 times / week Route: intravenous Route: multiple Dose: 52 mg/m2, 1 times / week Sources: |
unhealthy, 58 years (range: 41-81 years) n = 3 Health Status: unhealthy Condition: Advanced Refractory Cancer Age Group: 58 years (range: 41-81 years) Sex: M+F Population Size: 3 Sources: |
Epidermal and dermal conditions | 150 mg/m2 single, intravenous Overdose Dose: 150 mg/m2 Route: intravenous Route: single Dose: 150 mg/m2 Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Population Size: 1 Sources: |
|
Asthenia | mild | 150 mg/m2 single, intravenous Overdose Dose: 150 mg/m2 Route: intravenous Route: single Dose: 150 mg/m2 Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Population Size: 1 Sources: |
Paresthesia | mild | 150 mg/m2 single, intravenous Overdose Dose: 150 mg/m2 Route: intravenous Route: single Dose: 150 mg/m2 Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Population Size: 1 Sources: |
Neutropenia | severe | 150 mg/m2 single, intravenous Overdose Dose: 150 mg/m2 Route: intravenous Route: single Dose: 150 mg/m2 Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Population Size: 1 Sources: |
Epidermal and dermal conditions | 200 mg/m2 single, intravenous Overdose Dose: 200 mg/m2 Route: intravenous Route: single Dose: 200 mg/m2 Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Population Size: 1 Sources: |
|
Asthenia | mild | 200 mg/m2 single, intravenous Overdose Dose: 200 mg/m2 Route: intravenous Route: single Dose: 200 mg/m2 Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Population Size: 1 Sources: |
Paresthesia | mild | 200 mg/m2 single, intravenous Overdose Dose: 200 mg/m2 Route: intravenous Route: single Dose: 200 mg/m2 Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Population Size: 1 Sources: |
Neutropenia | severe | 200 mg/m2 single, intravenous Overdose Dose: 200 mg/m2 Route: intravenous Route: single Dose: 200 mg/m2 Sources: |
unhealthy, adult n = 1 Health Status: unhealthy Age Group: adult Population Size: 1 Sources: |
Hypersensitivity | severe Disc. AE |
60 mg/m2 1 times / 3 weeks multiple, intravenous Recommended Dose: 60 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 60 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Hepatotoxicity | grade 5 | 100 mg/m2 1 times / 3 weeks multiple, intravenous Dose: 100 mg/m2, 1 times / 3 weeks Route: intravenous Route: multiple Dose: 100 mg/m2, 1 times / 3 weeks Sources: |
unhealthy, adult Health Status: unhealthy Age Group: adult Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
---|---|---|---|
Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
---|---|---|---|---|
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022534Orig1s000ClinPhamR.pdf#page=12 Page: 12.0 |
major | likely Comment: In vivo studies showed that the exposure o f docetaxel increased 2.2-fold when it was coadministered with ketoconazole, a potent inhibitor o f CYP3A4. Protease inhibitors, particularly ritonavir, may increase the exposure o f docetaxe Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022534Orig1s000ClinPhamR.pdf#page=12 Page: 12.0 |
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Sources: https://pubmed.ncbi.nlm.nih.gov/18509327/ Page: - |
no | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/8640817/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18509327/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18509327/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18509327/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/18509327/ Page: - |
yes | |||
Sources: https://pubmed.ncbi.nlm.nih.gov/8736622/ Page: - |
yes | |||
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022534Orig1s000ClinPhamR.pdf#page=13 Page: 13.0 |
yes | yes (co-administration study) Comment: The effect o f ketoconazole (a strong CYP3A4 inhibitor) on the pharmacokinetics o f docetaxel was investigated in 7 cancer patients. Patients were randomized to receive either docetaxel (100 mg/m2 intravenous) alone or docetaxel (10 mg/m2 intravenous) in combination with ketoconazole (200 mg orally once daily for 3 days) in a crossover design with a 3-week washout period. The results o f this study indicated that the mean dose-normalized AUC o f docetaxel was increased 2.2-fold and its clearance was reduced by 49% when docetaxel was coadministration with ketoconazole Sources: https://www.accessdata.fda.gov/drugsatfda_docs/nda/2011/022534Orig1s000ClinPhamR.pdf#page=13 Page: 13.0 |
PubMed
Title | Date | PubMed |
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Severe syndrome of inappropriate antidiuretic hormone secretion with docetaxel treatment in metastatic breast cancer. | 2000 |
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[The mechanism of docetaxel-induced apoptosis in human lung cancer cells]. | 2000 May |
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Docetaxel induced cardiotoxicity. | 2001 Aug |
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Dissociation of Bax from a Bcl-2/Bax heterodimer triggered by phosphorylation of serine 70 of Bcl-2. | 2001 Dec |
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Reversible hepatic coma possibly induced by docetaxel treatment. | 2001 Feb-Mar |
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High incidence of central nervous system involvement in patients with metastatic or locally advanced breast cancer treated with epirubicin and docetaxel. | 2001 Mar |
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Pilot study of sequential vinorelbine and cisplatin followed by docetaxel for selected IIIB and stage IV non-small cell lung cancer. | 2001 Nov |
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Exisulind in combination with docetaxel inhibits growth and metastasis of human lung cancer and prolongs survival in athymic nude rats with orthotopic lung tumors. | 2002 Mar |
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Cystic maculopathy with normal capillary permeability secondary to docetaxel. | 2003 Apr |
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Bone pain associated with once-per-cycle pegfilgrastim is similar to daily filgrastim in patients with breast cancer. | 2003 Feb |
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Amelioration of docetaxel/cisplatin induced polyneuropathy by alpha-lipoic acid. | 2003 Feb |
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Docetaxel and epirubicin supported by granulocyte colony-stimulating factor first-line in advanced breast cancer. | 2003 May-Jun |
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[Combination chemotherapy with docetaxel+carboplatin in the treatment of cancer of the ovary and fallopian tube]. | 2004 Aug |
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Genome-wide discovery of loci influencing chemotherapy cytotoxicity. | 2004 Aug 10 |
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Down-regulation of intratumoral aromatase messenger RNA levels by docetaxel in human breast cancers. | 2004 Dec 15 |
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All-trans retinoic acid potentiates Taxotere-induced cell death mediated by Jun N-terminal kinase in breast cancer cells. | 2004 Jan 15 |
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Comparison of burst of reactive oxygen species and activation of caspase-3 in apoptosis of K562 and HL-60 cells induced by docetaxel. | 2004 Oct 8 |
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Concise prediction models of anticancer efficacy of 8 drugs using expression data from 12 selected genes. | 2004 Sep 10 |
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Focal adhesion kinase silencing augments docetaxel-mediated apoptosis in ovarian cancer cells. | 2005 Dec 15 |
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Enhanced Bax in oral SCC in relation to antitumor effects of chemotherapy. | 2005 Feb |
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Randomized phase II trial of the anti-angiogenic potential of doxorubicin and docetaxel; primary chemotherapy as Biomarker Discovery Laboratory. | 2005 Jan |
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HER-2/neu expression as a predictor of response to neoadjuvant docetaxel in patients with operable breast carcinoma. | 2005 Jun 1 |
|
Farnesyltransferase inhibitor R115777 (Zarnestra, Tipifarnib) synergizes with paclitaxel to induce apoptosis and mitotic arrest and to inhibit tumor growth of multiple myeloma cells. | 2005 Jun 15 |
|
Cyclooxygenase-2 inhibitor celecoxib augments chemotherapeutic drug-induced apoptosis by enhancing activation of caspase-3 and -9 in prostate cancer cells. | 2005 Jun 20 |
|
Differential effect of anti-apoptotic genes Bcl-xL and c-FLIP on sensitivity of MCF-7 breast cancer cells to paclitaxel and docetaxel. | 2005 May-Jun |
|
PAR1-mediated NFkappaB activation promotes survival of prostate cancer cells through a Bcl-xL-dependent mechanism. | 2005 Oct 15 |
|
MRP2 (ABCC2) transports taxanes and confers paclitaxel resistance and both processes are stimulated by probenecid. | 2005 Sep 20 |
|
Schedule dependent efficacy of gefitinib and docetaxel for bladder cancer. | 2006 Aug |
|
Adjuvant docetaxel or vinorelbine with or without trastuzumab for breast cancer. | 2006 Feb 23 |
|
Induction of tubulin by docetaxel is associated with p53 status in human non small cell lung cancer cell lines. | 2006 Jan 15 |
|
Enhancement of antitumor activity of docetaxel by celecoxib in lung tumors. | 2006 Jan 15 |
|
Vitamin D compounds: clinical development as cancer therapy and prevention agents. | 2006 Jul-Aug |
|
Small molecule, oligonucleotide-based telomerase template inhibition in combination with cytolytic therapy in an in vitro androgen-independent prostate cancer model. | 2006 Mar-Apr |
|
Sequential combinations of flavopiridol and docetaxel inhibit prostate tumors, induce apoptosis, and decrease angiogenesis in the Ggamma/T-15 transgenic mouse model of prostate cancer. | 2006 Oct 1 |
|
The in vitro anti-tumour activity of zoledronic acid and docetaxel at clinically achievable concentrations in prostate cancer. | 2007 |
|
Anticancer drugs and hyperthermia enhance cytotoxicity induced by polyamine enzymatic oxidation products. | 2007 Aug |
|
Gene amplification and expression in lung cancer cells with acquired paclitaxel resistance. | 2007 Feb |
|
Docetaxel-induced apoptosis of human melanoma is mediated by activation of c-Jun NH2-terminal kinase and inhibited by the mitogen-activated protein kinase extracellular signal-regulated kinase 1/2 pathway. | 2007 Feb 15 |
|
p-53 gene mutations as a predictive marker in a population of advanced breast cancer patients randomly treated with doxorubicin or docetaxel in the context of a phase III clinical trial. | 2007 Jun |
|
Diethylstilbestrol and docetaxel: a Phase II study of tubulin active agents in patients with metastatic, androgen-independent prostate cancer. | 2007 Sep 1 |
Patents
Sample Use Guides
Breast Cancer: 60 mg/m2 to 100 mg/m2 administered intravenously over 1 hour every 3 weeks.
Non-Small Cell Lung Cancer: 75 mg/m2 administered intravenously over 1 hour every 3 weeks.
Prostate Cancer: 75 mg/m2 every 3 weeks as a 1 hour intravenous infusion.
Gastric Adenocarcinoma: 75 mg/m2 as a 1 hour intravenous infusion, followed by cisplatin 75 mg/m2 , as a 1 to 3 hour intravenous infusion (both on day 1 only), followed by fluorouracil 750 mg/m2 per day given as a 24-hour continuous intravenous infusion for 5 days, starting at the end of the cisplatin infusion
Head and Neck Cancer: Induction chemotherapy followed by radiotherapy: For the induction treatment of locally advanced inoperable SCCHN, the recommended dose of TAXOTERE (docetaxel) is 75 mg/m2 as a 1 hour intravenous infusion followed by cisplatin 75 mg/m2 intravenously over 1 hour, on day one, followed by fluorouracil as a continuous intravenous infusion at 750 mg/m2 per day for five days. This regimen is administered every 3 weeks for 4 cycles. Following chemotherapy, patients should receive radiotherapy.
Route of Administration:
Intravenous
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7909419
The in vitro antiproliferative effect of docetaxel (Taxotere), paclitaxel (Taxol) and cisplatin was assessed in a range of human tumour types, including 25 tumour cell lines and 35 primary cultures. In all comparisons docetaxel and paclitaxel were much more potent than cisplatin with IC50 values of the taxoids being in the nanomolar range. Docetaxel generally was two- to four-fold more cytotoxic than paclitaxel. The sensitivity profile of the cell lines, which was based on the IC50 values, indicated a certain degree of cross-sensitivity between paclitaxel and docetaxel (linear regression analysis; r = 0.73, p < 0.001
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:26:50 GMT 2023
by
admin
on
Fri Dec 15 15:26:50 GMT 2023
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Record UNII |
15H5577CQD
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Record Status |
Validated (UNII)
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Record Version |
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C67437
Created by
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EMA ASSESSMENT REPORTS |
DOCEFREZ(WITHDRAWN: BREAST, PROSTETIC, HEAD AND NECK NEOPLASMS, CARCINOMA,NON-SMALL-CELL-LUNG, ADENOCARCINOMA)
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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EMA ASSESSMENT REPORTS |
DOCETAXEL TEVA (AUTHORIZED: BREAST, PROSTETIC, HEAD AND NECK NEOPLASMS, CARCINOMA,NON-SMALL-CELL-LUNG, ADENOCARCINOMA)
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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EMA ASSESSMENT REPORTS |
DOCETAXEL KABI (AUTHORIZED: BREAST, PROSTETIC, HEAD AND NECK NEOPLASMS, CARCINOMA,NON-SMALL-CELL-LUNG, ADENOCARCINOMA)
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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EMA ASSESSMENT REPORTS |
TAXESPIRA (AUTHORISED: CARCINOMA, NON-SMALL-CELL LUNG)
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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LIVERTOX |
NBK548899
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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NDF-RT |
N0000175592
Created by
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WHO-VATC |
QL01CD02
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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EMA ASSESSMENT REPORTS |
TAXOTERE (AUTHORIZED: STOMACH NEOPLASMS)
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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EMA ASSESSMENT REPORTS |
DOCETAXEL WINTHROP (AUTHORIZED: BREAST, PROSTETIC, HEAD AND NECK NEOPLASMS, CARCINOMA,NON-SMALL-CELL-LUNG, ADENOCARCINOMA)
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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EMA ASSESSMENT REPORTS |
DOCETAXEL MYLAN (AUTHORIZED: BREAST, PROSTETIC, HEAD AND NECK NEOPLASMS, CARCINOMA,NON-SMALL-CELL-LUNG, ADENOCARCINOMA)
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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EMA ASSESSMENT REPORTS |
DOCETAXEL TEVA PHARMA(AUTHORIZED: CARCINOMA, NON-SMALL-CELL LUNG)
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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EMA ASSESSMENT REPORTS |
DOCETAXEL ACCORD (AUTHORIZED: BREAST, PROSTETIC, HEAD AND NECK NEOPLASMS, CARCINOMA,NON-SMALL-CELL-LUNG, ADENOCARCINOMA)
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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EMA ASSESSMENT REPORTS |
TAXOTERE (AUTHORIZED: BREAST, PROSTETIC, STOMACH, HEAD AND NECK NEOPLASMS, CARCINOMA,NON-SMALL-CELL-LUNG, ADENOCARCINOMA)
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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WHO-ESSENTIAL MEDICINES LIST |
8.2
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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WHO-ATC |
L01CD02
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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FDA ORPHAN DRUG |
649918
Created by
admin on Fri Dec 15 15:26:50 GMT 2023 , Edited by admin on Fri Dec 15 15:26:50 GMT 2023
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NCI_THESAURUS |
C1490
Created by
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Code System | Code | Type | Description | ||
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4672
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PRIMARY | |||
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SUB25446
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PRIMARY | |||
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C067311
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PRIMARY | |||
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FF-68
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PRIMARY | |||
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DTXSID80872444
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PRIMARY | |||
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m4712
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PRIMARY | Merck Index | ||
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DOCETAXEL
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PRIMARY | |||
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148123
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PRIMARY | |||
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1224551
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PRIMARY | |||
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CHEMBL92
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PRIMARY | |||
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72962
Created by
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PRIMARY | RxNorm | ||
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Docetaxel
Created by
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PRIMARY | |||
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6809
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59809
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100000089469
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C1526
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939
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PRIMARY | |||
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15H5577CQD
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PRIMARY | |||
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148408-66-6
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PRIMARY | |||
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DB01248
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15H5577CQD
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PRIMARY |
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PARENT -> SALT/SOLVATE | |||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
USP
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ANHYDROUS->SOLVATE | |||
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TRANSPORTER -> SUBSTRATE |
Related Record | Type | Details | ||
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PRODRUG -> METABOLITE ACTIVE |
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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ACTIVE MOIETY |
Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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Volume of Distribution | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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