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Details

Stereochemistry ABSOLUTE
Molecular Formula C43H53NO14
Molecular Weight 807.8809
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOCETAXEL ANHYDROUS

SMILES

CC1=C2[C@]([H])(C(=O)[C@]3(C)[C@]([H])(C[C@]4([H])[C@@](CO4)([C@@]3([H])[C@@]([H])([C@](C[C@]1([H])OC(=O)[C@@]([H])([C@]([H])(c5ccccc5)N=C(O)OC(C)(C)C)O)(C2(C)C)O)OC(=O)c6ccccc6)OC(=O)C)O)O

InChI

InChIKey=ZDZOTLJHXYCWBA-VCVYQWHSSA-N
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

HIDE SMILES / InChI

Molecular Formula C43H53NO14
Molecular Weight 807.8809
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: description was created based on several sources, including

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

Curator's Comment:: docetaxel cannot cross the blood–brain barrier and control metastatic foci

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TAXOTERE

Approved Use

INDICATIONS & 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 Date

832032000000
Primary
TAXOTERE

Approved Use

INDICATIONS & 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 Date

832032000000
Primary
TAXOTERE

Approved Use

INDICATIONS & 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 Date

832032000000
Primary
TAXOTERE

Approved Use

INDICATIONS & 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 Date

832032000000
Primary
TAXOTERE

Approved Use

INDICATIONS & 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 Date

832032000000
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
742 nM
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
1284 nM × h
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
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

T1/2

ValueDoseCo-administeredAnalytePopulation
0.99 h
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
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

Funbound

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse 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)
Health Status: unhealthy
Age Group: 51 years (range: 36 - 65 years)
Sex: F
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)
Health Status: unhealthy
Age Group: 58 years (range: 41-81 years)
Sex: M+F
Sources:
DLT: Fatigue, Asthenia...
Other AEs: Nail toxicity, Alopecia...
Dose limiting toxicities:
Fatigue (grade 3-4, 2 patients)
Asthenia (grade 3-4, 2 patients)
Skin toxicity (grade 3-4, 1 patient)
Diarrhea (grade 3-4, 1 patient)
Other AEs:
Nail toxicity (grade 3-4, 1 patient)
Alopecia (grade 2, 1 patient)
Leukopenia (grade 3, 2 patients)
Sources:
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)
Health Status: unhealthy
Age Group: 58 years (range: 41-81 years)
Sex: M+F
Sources:
DLT: Fatigue, Asthenia...
Dose limiting toxicities:
Fatigue (grade 3-4, 3 patients)
Asthenia (grade 3-4, 3 patients)
Sources:
150 mg/m2 single, intravenous
Overdose
Dose: 150 mg/m2
Route: intravenous
Route: single
Dose: 150 mg/m2
Sources:
unhealthy, adult
Other AEs: Neutropenia, Asthenia...
Other AEs:
Neutropenia (severe)
Asthenia (mild)
Epidermal and dermal conditions
Paresthesia (mild)
Sources:
200 mg/m2 single, intravenous
Overdose
Dose: 200 mg/m2
Route: intravenous
Route: single
Dose: 200 mg/m2
Sources:
unhealthy, adult
Other AEs: Neutropenia, Asthenia...
Other AEs:
Neutropenia (severe)
Asthenia (mild)
Epidermal and dermal conditions
Paresthesia (mild)
Sources:
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
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
Other AEs: Hepatotoxicity...
AEs

AEs

AESignificanceDosePopulation
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)
Health Status: unhealthy
Age Group: 51 years (range: 36 - 65 years)
Sex: F
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)
Health Status: unhealthy
Age Group: 58 years (range: 41-81 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 58 years (range: 41-81 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 58 years (range: 41-81 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 58 years (range: 41-81 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 58 years (range: 41-81 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 58 years (range: 41-81 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 58 years (range: 41-81 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 58 years (range: 41-81 years)
Sex: M+F
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)
Health Status: unhealthy
Age Group: 58 years (range: 41-81 years)
Sex: M+F
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
Asthenia mild
150 mg/m2 single, intravenous
Overdose
Dose: 150 mg/m2
Route: intravenous
Route: single
Dose: 150 mg/m2
Sources:
unhealthy, adult
Paresthesia mild
150 mg/m2 single, intravenous
Overdose
Dose: 150 mg/m2
Route: intravenous
Route: single
Dose: 150 mg/m2
Sources:
unhealthy, adult
Neutropenia severe
150 mg/m2 single, intravenous
Overdose
Dose: 150 mg/m2
Route: intravenous
Route: single
Dose: 150 mg/m2
Sources:
unhealthy, adult
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
Asthenia mild
200 mg/m2 single, intravenous
Overdose
Dose: 200 mg/m2
Route: intravenous
Route: single
Dose: 200 mg/m2
Sources:
unhealthy, adult
Paresthesia mild
200 mg/m2 single, intravenous
Overdose
Dose: 200 mg/m2
Route: intravenous
Route: single
Dose: 200 mg/m2
Sources:
unhealthy, adult
Neutropenia severe
200 mg/m2 single, intravenous
Overdose
Dose: 200 mg/m2
Route: intravenous
Route: single
Dose: 200 mg/m2
Sources:
unhealthy, adult
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
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
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG



Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
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
Page: 12
no
no
no
no
no
no
no
no
no
no
no
no
no
yes
yes
yes
yes
yes
yes
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
Page: 13
PubMed

PubMed

TitleDatePubMed
HER-2/neu as a predictive marker in a population of advanced breast cancer patients randomly treated either with single-agent doxorubicin or single-agent docetaxel.
2004 Aug
[Combination chemotherapy with docetaxel+carboplatin in the treatment of cancer of the ovary and fallopian tube].
2004 Aug
Phase I trial of the cyclin-dependent kinase inhibitor flavopiridol in combination with docetaxel in patients with metastatic breast cancer.
2004 Aug 1
Genome-wide discovery of loci influencing chemotherapy cytotoxicity.
2004 Aug 10
Neoadjuvant and adjuvant chemotherapy with doxorubicin and docetaxel in locally advanced breast cancer.
2004 Dec
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
Concise prediction models of anticancer efficacy of 8 drugs using expression data from 12 selected genes.
2004 Sep 10
Docetaxel plus epirubicin as first-line chemotherapy in MBC (KCSG 01-10-05): phase II trial and the predictive values of circulating HER2 extracellular domain and vascular endothelial growth factor.
2005 Aug
Clinical response to neoadjuvant docetaxel predicts improved outcome in patients with large locally advanced breast cancers.
2005 Dec
Focal adhesion kinase silencing augments docetaxel-mediated apoptosis in ovarian cancer cells.
2005 Dec 15
Morphological and morphometric analysis of paclitaxel and docetaxel-induced peripheral neuropathy in rats.
2005 Jul
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
A phase I/II study of exisulind in combination with docetaxel/carboplatin in patients with metastatic non-small-cell lung cancer.
2005 May
A phase I/II dose-escalation study of exisulind and docetaxel in patients with hormone-refractory prostate cancer.
2005 May
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
Life-threatening complications from doxorubicin-docetaxel chemotherapy for breast cancer.
2005 Nov 2
PAR1-mediated NFkappaB activation promotes survival of prostate cancer cells through a Bcl-xL-dependent mechanism.
2005 Oct 15
[Antisense RNA targeting survivin enhances the chemosensitivity of LOVO/Adr cells to taxotere].
2005 Sep
Docetaxel induces p53-dependent apoptosis and synergizes with farnesyl transferase inhibitor r115777 in human epithelial cancer cells.
2005 Sep 1
Metronomic low-dose chemotherapy boosts CD95-dependent antiangiogenic effect of the thrombospondin peptide ABT-510: a complementation antiangiogenic strategy.
2005 Sep 15
MRP2 (ABCC2) transports taxanes and confers paclitaxel resistance and both processes are stimulated by probenecid.
2005 Sep 20
Phase I study of S-1 and biweekly docetaxel combination chemotherapy for advanced and recurrent gastric cancer.
2006 Apr
Bortezomib inhibits docetaxel-induced apoptosis via a p21-dependent mechanism in human prostate cancer cells.
2006 Aug
Schedule dependent efficacy of gefitinib and docetaxel for bladder cancer.
2006 Aug
Synergistic effects of docetaxel and S-1 by modulating the expression of metabolic enzymes of 5-fluorouracil in human gastric cancer cell lines.
2006 Aug 15
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
Docetaxel induces apoptosis in hormone refractory prostate carcinomas during multiple treatment cycles.
2006 Jun 5
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 combination of flavopiridol and docetaxel reduces the levels of X-linked inhibitor of apoptosis and AKT proteins and stimulates apoptosis in human LNCaP prostate cancer cells.
2006 May
Enhanced sensitivity to chemotherapy in esophageal cancer through inhibition of NF-kappaB.
2006 May
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
Toxicity of dose-dense docetaxel followed by doxorubicin with cyclophosphamide as adjuvant therapy for breast cancer in a phase II study.
2007 Aug
[Comparison of efficacy of docetaxel combined cisplatin (TP regimen) and cisplatin combined 5-fluorouracil (PF regimen) on locally advanced nasopharyngeal carcinoma].
2007 Aug
Anticancer drugs and hyperthermia enhance cytotoxicity induced by polyamine enzymatic oxidation products.
2007 Aug
Docetaxel-induced apoptosis in melanoma cells is dependent on activation of caspase-2.
2007 Feb
Gene amplification and expression in lung cancer cells with acquired paclitaxel resistance.
2007 Feb
Gene expression profiling of breast cancer patients treated with docetaxel, doxorubicin, and cyclophosphamide within the GEPARTRIO trial: HER-2, but not topoisomerase II alpha and microtubule-associated protein tau, is highly predictive of tumor response.
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
Down-regulation of inhibitor of apoptosis proteins by deguelin selectively induces apoptosis in breast cancer cells.
2007 Jan
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
Docetaxel-induced growth inhibition and apoptosis in androgen independent prostate cancer cells are enhanced by 1alpha,25-dihydroxyvitamin D3.
2007 Mar 8
Phase I/II trial of adjuvant dose-dense docetaxel/epirubicin/cyclophosphamide (TEC) in stage II and III breast cancer.
2007 May-Jun
Epigenetic inactivation of the CHFR gene in cervical cancer contributes to sensitivity to taxanes.
2007 Oct
Diethylstilbestrol and docetaxel: a Phase II study of tubulin active agents in patients with metastatic, androgen-independent prostate cancer.
2007 Sep 1
Weekly docetaxel, zoledronic acid and estramustine in hormone-refractory prostate cancer (HRPC).
2008 Feb
Pulmonary toxicity in patients treated with gemcitabine plus vinorelbine or docetaxel for advanced non-small cell lung cancer: outcome data on a randomized phase II study.
2008 Feb
Patents

Sample Use Guides

Breast Cancer: 60 mg/m2 to 100 mg/m2 administered intravenously over 1 hour every 3 weeks.
Route of Administration: Intravenous
In Vitro Use Guide
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 Fri Jun 25 22:56:17 UTC 2021
Edited
by admin
on Fri Jun 25 22:56:17 UTC 2021
Record UNII
699121PHCA
Record Status Validated (UNII)
Record Version
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Name Type Language
DOCETAXEL ANHYDROUS
WHO-DD  
Common Name English
DOCETAXEL TEVA
Brand Name English
BIND 014
Common Name English
DOCETAXEL [INN]
Common Name English
DOCETAXEL WINTHROP
Brand Name English
DOCETAXEL ANHYDROUS [WHO-DD]
Common Name English
DOCETAXEL KABI
Brand Name English
(2R,3S)-N-CARBOXY-3-PHENYLISOSERINE, N-TERT-BUTYL ESTER, 13-ESTER WITH 5.BETA.,20-EPOXY-1,2.ALPHA.,4,7.BETA.,10.BETA.,13.ALPHA.-HEXAHYDROXYTAX-11-EN-9-ONE 4-ACETATE 2-BENZOATE
Common Name English
DOCEFREZ
Brand Name English
DOCETAXEL [MI]
Common Name English
DOCETAXEL [HSDB]
Common Name English
CABAZITAXEL METABOLITE (RP56976)
Common Name English
DOCETAXEL [JAN]
Common Name English
NSC-628503
Code English
DOCETAXEL TEVA PHARMA
Brand Name English
DOCETAXEL, ANHYDROUS
Common Name English
BIND 014 [WHO-DD]
Common Name English
RP56976
Common Name English
CKD-810
Code English
DOCETAXEL MYLAN
Brand Name English
DOCETAXEL ACCORD
Brand Name English
Classification Tree Code System Code
EMA ASSESSMENT REPORTS DOCETAXEL WINTHROP (AUTHORIZED: STOMACH NEOPLASMS)
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
EMA ASSESSMENT REPORTS DOCEFREZ (WITHDRAWN: PROSTATIC NEOPLASMS)
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
EMA ASSESSMENT REPORTS DOCETAXEL WINTHROP (AUTHORIZED: PROSTATIC, NEOPLASMS)
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
EMA ASSESSMENT REPORTS DOCEFREEZ (WITHDRAWN: STOMACH NEOPLASMS)
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
NCI_THESAURUS C67437
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
NDF-RT N0000175085
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
EMA ASSESSMENT REPORTS DOCETAXEL TEVA (AUTHORIZED: PROSTATIC NEOPLASMS)
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
EMA ASSESSMENT REPORTS DOCTAXELL TEVA (AUTHORIZED: STOMACH NEOPLASMS)
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
EMA ASSESSMENT REPORTS DOCETAXEL TEVA PHARMA (WITHDRAWN: PROSTATIC, NEOPLASMS)
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
WHO-ATC L01CD02
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
EMA ASSESSMENT REPORTS DOCETAXEL MYLAN (WITHDRAWN: PROSTATIC NEOPLASMS)
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
NDF-RT N0000175592
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
EMA ASSESSMENT REPORTS DOCETAXEL ACCORD (PROSTATIC NEOPLASMS)
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
EMA ASSESSMENT REPORTS DOCETAXEL KABI (AUTHORIZED: PROSTATIC NEOPLASMS)
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
NCI_THESAURUS C1490
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
Code System Code Type Description
HSDB
6965
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
PRIMARY
EPA CompTox
114977-28-5
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
PRIMARY
INN
6621
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
PRIMARY
MERCK INDEX
M4712
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
PRIMARY Merck Index
EVMPD
SUB22289
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
PRIMARY
NCI_THESAURUS
C61734
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
PRIMARY
EVMPD
SUB12492MIG
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
PRIMARY
DRUG BANK
DB01248
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
PRIMARY
PUBCHEM
148124
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
PRIMARY
FDA UNII
699121PHCA
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
PRIMARY
CAS
114977-28-5
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
PRIMARY
RXCUI
1299922
Created by admin on Fri Jun 25 22:56:17 UTC 2021 , Edited by admin on Fri Jun 25 22:56:17 UTC 2021
PRIMARY RxNorm
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
In vitro studies showed that docetaxel is about 94% protein bound, mainly to ?1-acid glycoprotein, albumin, and lipoproteins. In three cancer patients, the in vitro binding to plasma proteins was found to be approximately 97%.
BINDING
SALT/SOLVATE -> PARENT
DERIVATIVE -> PARENT
METABOLIC ENZYME -> SUBSTRATE
SUBSTANCE->BASIS OF STRENGTH
EXCRETED UNCHANGED
FECAL
Related Record Type Details
PARENT -> METABOLITE ACTIVE
METABOLITE -> PARENT
In vitro drug interaction studies revealed that docetaxel is metabolized by the CYP3A4 isoenzyme
MINOR
FECAL
METABOLITE -> PARENT
In vitro drug interaction studies revealed that docetaxel is metabolized by the CYP3A4 isoenzyme
MINOR
FECAL
METABOLITE -> PARENT
In vitro drug interaction studies revealed that docetaxel is metabolized by the CYP3A4 isoenzyme
MINOR
FECAL
METABOLITE -> PARENT
In vitro drug interaction studies revealed that docetaxel is metabolized by the CYP3A4 isoenzyme
MAJOR
FECAL
Related Record Type Details
ACTIVE MOIETY