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417017 Sigma-Aldrich

Paclitaxel

From Taxus brevifolia, 95%

  • CAS Number 33069-62-4

  • Empirical Formula (Hill Notation) C47H51NO14

  • Molecular Weight 853.91

  •  Beilstein/REAXYS Number 1420457

  •  MDL number MFCD00869953

  •  PubChem Substance ID 329756140

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Properties

Related Categories Antibiotics, Antibiotics A to Z, Antibiotics N-S, Antibiotics by Application, Antibiotics by Mechanism of Action,
assay   95%
optical activity   [α]20/D −49°, c = 1 in methanol
impurities   ≤1% methyl alcohol and ethyl alcohol
mp   213 °C (dec.) (lit.)
Mode of action   DNA synthesis | interferes
antibiotic activity spectrum   viruses
SMILES string   [H][C@@]12C[C@H](O)[C@@]3(C)C(=O)[C@H](OC(C)=O)C4=C(C)[C@H](C[C@@](O)([C@@H](OC(=O)c5ccccc5)[C@]3([H])[C@@]1(CO2)OC(C)=O)C4(C)C)OC(=O)[C@H](O)[C@@H](NC(=O)c6ccccc6)c7ccccc7
InChI   1S/C47H51NO14/c1-25-31(60-43(56)36(52)35(28-16-10-7-11-17-28)48-41(54)29-18-12-8-13-19-29)23-47(57)40(61-42(55)30-20-14-9-15-21-30)38-45(6,32(51)22-33-46(38,24-58-33)62-27(3)50)39(53)37(59-26(2)49)34(25)44(47,4)5/h7-21,31-33,35-38,40,51-52,57H,22-24H2,1-6H3,(H,48,54)/t31-,32-,33+,35-,36+,37+,38-,40-,45+,46-,47+/m0/s1
InChI key   RCINICONZNJXQF-MZXODVADSA-N
Gene Information   human ... BCL2(596), TUBA1A(7846), TUBA1B(10376), TUBA1C(84790), TUBA3C(7278), TUBA3E(112714), TUBA4A(7277), TUBB(203068), TUBB1(81027), TUBB2A(7280), TUBB2B(347733), TUBB3(10381), TUBB4A(10382), TUBB4B(10383), TUBB6(84617), TUBB8(347688)

Description

General description

Chemical structure: taxoide

Biochem/physiol Actions

Paclitaxel is a potent anti-neoplastic and anti-mitotic taxane drug, which binds to the N-terminus of β-tubulin and and stabilizes microtubules arresting the cell cycle at the G2/M phase. The microtubule damage induces apoptosis through a JNK-dependent pathway followed by a JNK-independent pathway, perhaps related to the activation of protein kinase A (PKA) or of Raf-1 kinase, resulting in phosphorylation of Bcl-2. A major metabolite via CYP2CB is 6α-hydroxypaclitaxel (6α-OHP).

Caution

Paclitaxel undergoes transesterification in methanol and hydrolyzes in aqueous solutions.

Safety & Documentation

Safety Information

Symbol 
GHS08  GHS08
Signal word 
Danger
Hazard statements 
Precautionary statements 
RIDADR 
NONH for all modes of transport
WGK Germany 
3
RTECS 
DA8340700

Documents

Certificate of Analysis (COA)

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Protocols & Articles
Peer-Reviewed Papers
15

References

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T7402 Paclitaxel, from Taxus brevifolia, ≥95% (HPLC), powder

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