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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

CC(=O)O[C@@]12CO[C@@H]1C[C@H](O)[C@]3(C)[C@@H]2[C@H](OC(=O)C4=CC=CC=C4)[C@]5(O)C[C@H](OC(=O)[C@H](O)[C@@H](NC(=O)OC(C)(C)C)C6=CC=CC=C6)C(C)=C([C@@H](O)C3=O)C5(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
Defined Stereocenters 11 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

Sample Use Guides

In Vivo Use Guide
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 Tue Oct 22 00:14:16 UTC 2019
Edited
by admin
on Tue Oct 22 00:14:16 UTC 2019
Record UNII
699121PHCA
Record Status Validated (UNII)
Record Version
  • Download
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 Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
EMA ASSESSMENT REPORTS DOCEFREZ (WITHDRAWN: PROSTATIC NEOPLASMS)
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
EMA ASSESSMENT REPORTS DOCETAXEL WINTHROP (AUTHORIZED: PROSTATIC, NEOPLASMS)
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
EMA ASSESSMENT REPORTS DOCEFREEZ (WITHDRAWN: STOMACH NEOPLASMS)
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
NCI_THESAURUS C67437
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
NDF-RT N0000175085
Created by admin on Tue Oct 22 00:14:16 UTC 2019 , Edited by admin on Tue Oct 22 00:14:16 UTC 2019
EMA ASSESSMENT REPORTS DOCETAXEL TEVA (AUTHORIZED: PROSTATIC NEOPLASMS)
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
EMA ASSESSMENT REPORTS DOCTAXELL TEVA (AUTHORIZED: STOMACH NEOPLASMS)
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
EMA ASSESSMENT REPORTS DOCETAXEL TEVA PHARMA (WITHDRAWN: PROSTATIC, NEOPLASMS)
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
WHO-ATC L01CD02
Created by admin on Tue Oct 22 00:14:16 UTC 2019 , Edited by admin on Tue Oct 22 00:14:16 UTC 2019
EMA ASSESSMENT REPORTS DOCETAXEL MYLAN (WITHDRAWN: PROSTATIC NEOPLASMS)
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
NDF-RT N0000175592
Created by admin on Tue Oct 22 00:14:16 UTC 2019 , Edited by admin on Tue Oct 22 00:14:16 UTC 2019
EMA ASSESSMENT REPORTS DOCETAXEL ACCORD (PROSTATIC NEOPLASMS)
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
EMA ASSESSMENT REPORTS DOCETAXEL KABI (AUTHORIZED: PROSTATIC NEOPLASMS)
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
NCI_THESAURUS C1490
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
Code System Code Type Description
HSDB
114977-28-5
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
PRIMARY
EPA CompTox
114977-28-5
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
PRIMARY
INN
6621
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
PRIMARY
MERCK INDEX
M4712
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
PRIMARY Merck Index
EVMPD
SUB22289
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
PRIMARY
NCI_THESAURUS
C61734
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
PRIMARY
EVMPD
SUB12492MIG
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
PRIMARY
DRUG BANK
DB01248
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
PRIMARY
PUBCHEM
148124
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
PRIMARY
CAS
114977-28-5
Created by admin on Tue Oct 22 00:14:16 UTC 2019 , Edited by admin on Tue Oct 22 00:14:16 UTC 2019
PRIMARY
RXCUI
1299922
Created by admin on Tue Oct 22 00:14:17 UTC 2019 , Edited by admin on Tue Oct 22 00:14:17 UTC 2019
PRIMARY RxNorm
Related Record Type Details
SALT/SOLVATE -> PARENT
SUBSTANCE->BASIS OF STRENGTH
Related Record Type Details
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
PARENT -> METABOLITE ACTIVE
Related Record Type Details
ACTIVE MOIETY