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Details

Stereochemistry ABSOLUTE
Molecular Formula C43H53NO14
Molecular Weight 807.8792
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DOCETAXEL ANHYDROUS

SMILES

[H][C@]12[C@H](OC(=O)C3=CC=CC=C3)[C@]4(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C5=CC=CC=C5)C(C)=C([C@@H](O)C(=O)[C@]1(C)[C@@H](O)C[C@H]6OC[C@@]26OC(C)=O)C4(C)C

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 807.8792
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

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

1996
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

1996
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

1996
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

1996
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

1996
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)
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)
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)
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)
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
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
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
n = 1
Health Status: unhealthy
Age Group: adult
Population Size: 1
Sources:
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)
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
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: 12.0
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: 13.0
PubMed

PubMed

TitleDatePubMed
Docetaxel neuropathy: a distal axonopathy.
1999 Dec
Use of gabapentin to treat taxane-induced myalgias.
1999 Jan
Dose-finding study of docetaxel and doxorubicin in first-line treatment of patients with metastatic breast cancer.
1999 May
Severe syndrome of inappropriate antidiuretic hormone secretion with docetaxel treatment in metastatic breast cancer.
2000
Mesenteric venous thrombosis attributed to docetaxel.
2000 Aug
[The mechanism of docetaxel-induced apoptosis in human lung cancer cells].
2000 May
Cell cycle status and apoptosis of hematopoietic progenitor cells released into the peripheral blood after taxanes and granulocyte colony-stimulating factor in breast cancer patients.
2000 May-Jun
Comparison of 2-methoxyestradiol-induced, docetaxel-induced, and paclitaxel-induced apoptosis in hepatoma cells and its correlation with reactive oxygen species.
2000 Sep 1
Docetaxel induced cardiotoxicity.
2001 Aug
Dissociation of Bax from a Bcl-2/Bax heterodimer triggered by phosphorylation of serine 70 of Bcl-2.
2001 Dec
Reversible hepatic coma possibly induced by docetaxel treatment.
2001 Feb-Mar
Pretreatment with paclitaxel enhances apo-2 ligand/tumor necrosis factor-related apoptosis-inducing ligand-induced apoptosis of prostate cancer cells by inducing death receptors 4 and 5 protein levels.
2001 Jan 15
Doxorubicin followed by docetaxel versus docetaxel followed by doxorubicin in the adjuvant treatment of node positive breast cancer: results of a feasibility study.
2001 Jan-Feb
High incidence of central nervous system involvement in patients with metastatic or locally advanced breast cancer treated with epirubicin and docetaxel.
2001 Mar
Scleroderma in association with the use of docetaxel (taxotere) for breast cancer.
2001 Mar-Apr
Pilot study of sequential vinorelbine and cisplatin followed by docetaxel for selected IIIB and stage IV non-small cell lung cancer.
2001 Nov
A phase II trial of docetaxel and CPT-11 in patients with metastatic adenocarcinoma of the esophagus, gastroesophageal junction, and gastric cardia.
2002
Docetaxel in combination with dacarbazine in patients with advanced melanoma.
2002
Preclinical and clinical studies of docetaxel and exisulind in the treatment of human lung cancer.
2002 Feb
Atrial fibrillation during adjuvant chemotherapy with docetaxel: a case report.
2002 Nov-Dec
Amelioration of docetaxel/cisplatin induced polyneuropathy by alpha-lipoic acid.
2003 Feb
Phase II clinical trial of carboplatin and docetaxel in patients with metastatic ovarian cancer: active combination with low incidence of peripheral neuropathy.
2003 May-Jun
ERK inhibitor PD98059 enhances docetaxel-induced apoptosis of androgen-independent human prostate cancer cells.
2003 Nov 10
Neoadjuvant and adjuvant chemotherapy with doxorubicin and docetaxel in locally advanced breast cancer.
2004 Dec
Down-regulation of intratumoral aromatase messenger RNA levels by docetaxel in human breast cancers.
2004 Dec 15
Docetaxel versus paclitaxel for adjuvant treatment of ovarian cancer: case-control analysis of toxicity.
2004 Feb
The proteasome inhibitor bortezomib enhances the activity of docetaxel in orthotopic human pancreatic tumor xenografts.
2004 Jan
Modulation of thymidine phosphorylase by neoadjuvant chemotherapy in primary breast cancer.
2004 Jun 14
Use of gabapentin in the prevention of taxane-induced arthralgias and myalgias.
2004 May 1
Primary systemic chemotherapy with sequential, dose-dense epirubicin and docetaxel for inoperable, locally advanced inflammatory breast cancer: a phase II study.
2005
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
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
MRP2 (ABCC2) transports taxanes and confers paclitaxel resistance and both processes are stimulated by probenecid.
2005 Sep 20
Enhancement of antitumor activity of docetaxel by celecoxib in lung tumors.
2006 Jan 15
Small molecule, oligonucleotide-based telomerase template inhibition in combination with cytolytic therapy in an in vitro androgen-independent prostate cancer model.
2006 Mar-Apr
Enhanced sensitivity to chemotherapy in esophageal cancer through inhibition of NF-kappaB.
2006 May
[Comparison of efficacy of docetaxel combined cisplatin (TP regimen) and cisplatin combined 5-fluorouracil (PF regimen) on locally advanced nasopharyngeal carcinoma].
2007 Aug
Docetaxel-induced apoptosis in melanoma cells is dependent on activation of caspase-2.
2007 Feb
Docetaxel-induced growth inhibition and apoptosis in androgen independent prostate cancer cells are enhanced by 1alpha,25-dihydroxyvitamin D3.
2007 Mar 8
Weekly docetaxel, zoledronic acid and estramustine in hormone-refractory prostate cancer (HRPC).
2008 Feb
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
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 Dec 15 15:38:30 GMT 2023
Edited
by admin
on Fri Dec 15 15:38:30 GMT 2023
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
BIND 014 [WHO-DD]
Common Name English
DOCETAXEL WINTHROP
Brand 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 anhydrous [WHO-DD]
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
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 Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
EMA ASSESSMENT REPORTS DOCEFREZ (WITHDRAWN: PROSTATIC NEOPLASMS)
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
EMA ASSESSMENT REPORTS DOCETAXEL WINTHROP (AUTHORIZED: PROSTATIC, NEOPLASMS)
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
EMA ASSESSMENT REPORTS DOCEFREEZ (WITHDRAWN: STOMACH NEOPLASMS)
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
NCI_THESAURUS C67437
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
NDF-RT N0000175085
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
EMA ASSESSMENT REPORTS DOCETAXEL TEVA (AUTHORIZED: PROSTATIC NEOPLASMS)
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
EMA ASSESSMENT REPORTS DOCTAXELL TEVA (AUTHORIZED: STOMACH NEOPLASMS)
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
EMA ASSESSMENT REPORTS DOCETAXEL TEVA PHARMA (WITHDRAWN: PROSTATIC, NEOPLASMS)
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
WHO-ATC L01CD02
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
EMA ASSESSMENT REPORTS DOCETAXEL MYLAN (WITHDRAWN: PROSTATIC NEOPLASMS)
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
NDF-RT N0000175592
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
EMA ASSESSMENT REPORTS DOCETAXEL ACCORD (PROSTATIC NEOPLASMS)
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
EMA ASSESSMENT REPORTS DOCETAXEL KABI (AUTHORIZED: PROSTATIC NEOPLASMS)
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
NCI_THESAURUS C1490
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
Code System Code Type Description
HSDB
6965
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
EPA CompTox
DTXSID0040464
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
INN
6621
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
SMS_ID
100000090616
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
MERCK INDEX
m4712
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY Merck Index
EVMPD
SUB22289
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
DAILYMED
699121PHCA
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
NCI_THESAURUS
C61734
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
EVMPD
SUB12492MIG
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
NSC
628503
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
CHEBI
4672
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
DRUG BANK
DB01248
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
PUBCHEM
148124
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
FDA UNII
699121PHCA
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
CAS
114977-28-5
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY
RXCUI
1299922
Created by admin on Fri Dec 15 15:38:30 GMT 2023 , Edited by admin on Fri Dec 15 15:38:30 GMT 2023
PRIMARY RxNorm
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
BINDER->LIGAND
In vitro studies showed that docetaxel is about 94% protein bound, mainly to α1-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
SOLVATE->ANHYDROUS
METABOLIC ENZYME -> SUBSTRATE
SUBSTANCE->BASIS OF STRENGTH
EXCRETED UNCHANGED
FECAL
Related Record Type Details
PARENT -> METABOLITE ACTIVE
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
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC