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Details

Stereochemistry ABSOLUTE
Molecular Formula C45H49NO13
Molecular Weight 811.8695
Optical Activity UNSPECIFIED
Defined Stereocenters 11 / 11
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of 10-DEACETYLPACLITAXEL

SMILES

[H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](O)C4=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)C5=CC=CC=C5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)C6=CC=CC=C6)C7=CC=CC=C7

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
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

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: CHEMBL2095182
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
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. Beginning on day 7 after birth, the entire litter of mice from selected matings were injected every other week interperitoneally with 5 ul of the selected taxane (10 mg/ml). After day 10, only mice with palpable polycystic kidneys continued to receive treatment. All polycystic mice were treated continually for the duration of their life. Animals similarly treated with dimethyl sulfoxide and untreated animals were used as controls.
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.
Name Type Language
10-DEACETYLPACLITAXEL
Common Name English
10-DESACETYLTAXOL
Common Name English
4-(acetyloxy)-13α-[[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy]-1,7β,10β-trihydroxy-9-oxo-5β,20-epoxytax-11-en-2α-yl benzoate
Systematic Name English
PACLITAXEL IMPURITY G [EP IMPURITY]
Common Name English
10-O-deacetylpaclitaxel
Common Name English
10-DESACETYLPACLITAXEL
Common Name English
10-DEACETYLTAXOL
Common Name English
Benzenepropanoic acid, β-(benzoylamino)-α-hydroxy-, 12b-(acetyloxy)-12-(benzoyloxy)-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-4,6,11-trihydroxy-4a,8,13,13-tetramethyl-5-oxo-7,11-methano-1H-cyclodeca[3,4]benz[1,2-b]oxet-9-yl ester, [2aR-[2aα,4β,4
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C1490
Created by admin on Fri Dec 15 15:33:32 GMT 2023 , Edited by admin on Fri Dec 15 15:33:32 GMT 2023
NCI_THESAURUS C67437
Created by admin on Fri Dec 15 15:33:32 GMT 2023 , Edited by admin on Fri Dec 15 15:33:32 GMT 2023
Code System Code Type Description
CAS
78432-77-6
Created by admin on Fri Dec 15 15:33:32 GMT 2023 , Edited by admin on Fri Dec 15 15:33:32 GMT 2023
PRIMARY
PUBCHEM
155831
Created by admin on Fri Dec 15 15:33:32 GMT 2023 , Edited by admin on Fri Dec 15 15:33:32 GMT 2023
PRIMARY
FDA UNII
B77R96LJLK
Created by admin on Fri Dec 15 15:33:32 GMT 2023 , Edited by admin on Fri Dec 15 15:33:32 GMT 2023
PRIMARY
NCI_THESAURUS
C957
Created by admin on Fri Dec 15 15:33:32 GMT 2023 , Edited by admin on Fri Dec 15 15:33:32 GMT 2023
PRIMARY NCIT
EPA CompTox
DTXSID00999763
Created by admin on Fri Dec 15 15:33:32 GMT 2023 , Edited by admin on Fri Dec 15 15:33:32 GMT 2023
PRIMARY