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
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
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
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2095182 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7954398 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9150481
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21573554
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.
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NCI_THESAURUS |
C1490
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NCI_THESAURUS |
C67437
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78432-77-6
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155831
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B77R96LJLK
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C957
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DTXSID00999763
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SUBSTANCE RECORD