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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H49NO13
Molecular Weight 811.8712
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 10-DEACETYLPACLITAXEL

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(c6ccccc6)O)O)(C2(C)C)O)OC(=O)c7ccccc7)OC(=O)C)O)O

InChI

InChIKey=TYLVGQKNNUHXIP-MHHARFCSSA-N
InChI=1S/C45H49NO13/c1-24-29(57-41(54)35(50)33(26-15-9-6-10-16-26)46-39(52)27-17-11-7-12-18-27)22-45(55)38(58-40(53)28-19-13-8-14-20-28)36-43(5,37(51)34(49)32(24)42(45,3)4)30(48)21-31-44(36,23-56-31)59-25(2)47/h6-20,29-31,33-36,38,48-50,55H,21-23H2,1-5H3,(H,46,52)/t29-,30-,31+,33-,34+,35+,36-,38-,43+,44-,45+/m0/s1

HIDE SMILES / InChI

Molecular Formula C45H49NO13
Molecular Weight 811.8712
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 10 / 11
E/Z Centers 0
Optical Activity UNSPECIFIED

10-deactyltaxol (10-deacetylpaclitaxel) is a naturally occurring taxane related to taxol (paclitaxel). Taxol is an antitumor drug with cytotoxic properties that correlate with its microtubule-stabilizing activities. When compared to paclitaxel 10-deacetyltaxol is 100% as active as paclitaxel in promoting in vitro microtubule assembly, but is only 30% as cytotoxic as paclitaxel. 10-deactyltaxol is a semi-synthetic precursor of paclitaxel and considered to be paclitaxel impurity. 10-deactyltaxol, isolated from the bark of Taxus brevifolia, was converted into paclitaxel in one composite step (trimethylsilylation, acetylation, and desilylation) and in an overall yield of 80-85%.

Approval Year

PubMed

PubMed

TitleDatePubMed
Microtubule active taxanes inhibit polycystic kidney disease progression in cpk mice.
1997 May
Patents

Patents

Sample Use Guides

All taxanes including 10-deactyltaxol (10-deacetylpaclitaxel) used in this study were dissolved at 10 mg/ml in dimethyl sulfoxide (DMSO) and were stored frozen at -20°C in aliquots until used.
Route of Administration: Intraperitoneal
The cytotoxic effects of taxol, 10-deacetyltaxol, and cephalomannine at concentrations of 0.1 ug/ml to 10.0 ug/ml for one and 24 hours exposure were determined in two human glioblastoma multiforme and two neuroblastoma cell lines using the MTT method. The neuroblastoma cell lines were established from previously treated patients, while the glioblastomas were from untreated patients. There was a proportionate concentration-toxicity relationship for all four cell lines. The neuroblastoma SK-N-FI was consistently the most resistant to all three drugs. The order of potency after a one hour exposure was taxol, 10-deacetyltaxol and cephalomannine.
Substance Class Chemical
Created
by admin
on Sat Jun 26 02:44:38 UTC 2021
Edited
by admin
on Sat Jun 26 02:44:38 UTC 2021
Record UNII
B77R96LJLK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
10-DEACETYLPACLITAXEL
Common Name English
10-DESACETYLTAXOL
Common Name English
10-DESACETYLPACLITAXEL
Common Name English
10-DEACETYLTAXOL
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1490
Created by admin on Sat Jun 26 02:44:38 UTC 2021 , Edited by admin on Sat Jun 26 02:44:38 UTC 2021
NCI_THESAURUS C67437
Created by admin on Sat Jun 26 02:44:38 UTC 2021 , Edited by admin on Sat Jun 26 02:44:38 UTC 2021
Code System Code Type Description
CAS
78432-77-6
Created by admin on Sat Jun 26 02:44:38 UTC 2021 , Edited by admin on Sat Jun 26 02:44:38 UTC 2021
PRIMARY
PUBCHEM
155831
Created by admin on Sat Jun 26 02:44:38 UTC 2021 , Edited by admin on Sat Jun 26 02:44:38 UTC 2021
PRIMARY
FDA UNII
B77R96LJLK
Created by admin on Sat Jun 26 02:44:38 UTC 2021 , Edited by admin on Sat Jun 26 02:44:38 UTC 2021
PRIMARY
NCI_THESAURUS
C957
Created by admin on Sat Jun 26 02:44:38 UTC 2021 , Edited by admin on Sat Jun 26 02:44:38 UTC 2021
PRIMARY NCIT
Related Record Type Details
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