Paclitaxel

  • CAT Number: A000813
  • CAS Number: 33069-62-4
  • Molecular Formula: C₄₇H₅₁NO₁₄
  • Molecular Weight: 853.92
  • Purity: ≥95%
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Paclitaxel (CAS 33069-62-4) is a compound extracted from the Pacific yew tree Taxus brevifolia with antineoplastic activity. Paclitaxel binds to tubulin and inhibits the disassembly of microtubules, thereby resulting in the inhibition of cell division. This agent also induces apoptosis by binding to and blocking the function of the apoptosis inhibitor protein Bcl-2 (B-cell Leukemia 2).

Catalog Number A000813
CAS Number 33069-62-4
Synonyms

TAXOL; Taxol A; 33069-62-4; Abraxane; Paxene

Molecular Formula

C₄₇H₅₁NO₁₄

Purity 95%
Target Microtubule/Tubulin
Solubility >42.7mg/mL in DMSO
Storage -20°C
IUPAC Name [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4,12-diacetyloxy-15-[(2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl]oxy-1,9-dihydroxy-10,14,17,17-tetramethyl-11-oxo-6-oxatetracyclo[11.3.1.03,10.04,7]heptadec-13-en-2-yl] benzoate
InChI 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,22-24
InChIKey RCINICONZNJXQF-MZXODVADSA-N
SMILES CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)C6=CC=CC=C6)O)O)OC(=O)C7=CC=CC=C7)(CO4)OC(=O)C)O)C)OC(=O)C
Reference

1: Van Cutsem E, Bang YJ, Mansoor W, Petty RD, Chao Y, Cunningham D, Ferry DR, Smith NR, Frewer P, Ratnayake J, Stockman PK, Kilgour E, Landers D. A randomized, open-label study of the efficacy and safety of AZD4547 monotherapy versus paclitaxel for the treatment of advanced gastric adenocarcinoma with FGFR2 polysomy or gene amplification. Ann Oncol. 2017 Jun 1;28(6):1316-1324. doi: 10.1093/annonc/mdx107. PubMed PMID: 29177434.<br />
2: Lv KT, Gao LJ, Hua X, Li F, Gu Y, Wang W. The role of the globular heads of the C1q receptor in paclitaxel-induced human ovarian cancer cells apoptosis by a mitochondria-dependent pathway. Anticancer Drugs. 2017 Nov 23. doi: 10.1097/CAD.0000000000000567. [Epub ahead of print] PubMed PMID: 29176398.<br />
3: Bhatt P, Lalani R, Vhora I, Patil S, Amrutiya J, Misra A, Mashru R. Liposomes encapsulating native and cyclodextrin enclosed Paclitaxel: Enhanced loading efficiency and its pharmacokinetic evaluation. Int J Pharm. 2017 Nov 22. pii: S0378-5173(17)31103-1. doi: 10.1016/j.ijpharm.2017.11.048. [Epub ahead of print] PubMed PMID: 29175440.<br />
4: Saito S, Muneoka Y, Ishikawa T, Akazawa K. Cost-Effectiveness of Paclitaxel + Ramucirumab Combination Therapy for Advanced Gastric Cancer Progressing After First-Line Chemotherapy in Japan. Clin Ther. 2017 Nov 23. pii: S0149-2918(17)31057-3. doi: 10.1016/j.clinthera.2017.10.017. [Epub ahead of print] PubMed PMID: 29175097.<br />
5: Yamamoto E, Watanabe S, Bao B, Watanabe H, Nakatsuma K, Izuhara M, Ono K, Nakazawa G, Kimura T, Saito N. Preclinical evaluation of a paclitaxel-incorporated nanoparticle-coated balloon in rabbit and porcine models. Cardiovasc Revasc Med. 2017 Oct 19. pii: S1553-8389(17)30397-4. doi: 10.1016/j.carrev.2017.10.007. [Epub ahead of print] PubMed PMID: 29174499.<br />
6: Miles D, Cameron D, Hilton M, Garcia J, O/&#39;Shaughnessy J. Overall survival in MERiDiAN, a double-blind placebo-controlled randomised phase III trial evaluating first-line bevacizumab plus paclitaxel for HER2-negative metastatic breast cancer. Eur J Cancer. 2017 Nov 23. pii: S0959-8049(17)31358-8. doi: 10.1016/j.ejca.2017.10.018. [Epub ahead of print] PubMed PMID: 29174181.<br />
7: Wong YN, Manola J, Hudes GR, Roth BJ, Moul JW, Barsevick AM, Scher RM, Volk MJ, Vaughn DJ, Williams SD, Fisch MJ, Cella D, Carducci MA, Wilding G. Phase 2 Study of Weekly Paclitaxel Plus Estramustine in Metastatic Hormone-Refractory Prostate Carcinoma: ECOG-ACRIN Cancer Research Group (E1898) Trial. Clin Genitourin Cancer. 2017 Oct 16. pii: S1558-7673(17)30307-5. doi: 10.1016/j.clgc.2017.10.001. [Epub ahead of print] PubMed PMID: 29173976.<br />
8: Phan NH, Ly TT, Pham MN, Luu TD, Vo TV, Tran PH, Tran TT. A comparison of fucoidan conjugated to paclitaxel and curcumin for the dual delivery of cancer therapeutic agents. Anticancer Agents Med Chem. 2017 Nov 21. doi: 10.2174/1871520617666171121125845. [Epub ahead of print] PubMed PMID: 29173183.<br />
9: Steins A, Ebbing EA, Pistorius MCM, Waasdorp C, Krishnadath KK, Medema JP, Wilmink JW, Math&ocirc;t RAA, Bijlsma MF, van Laarhoven HWM. Systemic effects of angiogenesis inhibition alter pharmacokinetics and intratumoral delivery of nab-paclitaxel. Drug Deliv. 2017 Nov;24(1):1801-1810. doi: 10.1080/10717544.2017.1406559. PubMed PMID: 29172757.<br />
10: Herbst RS, Redman MW, Kim ES, Semrad TJ, Bazhenova L, Masters G, Oettel K, Guaglianone P, Reynolds C, Karnad A, Arnold SM, Varella-Garcia M, Moon J, Mack PC, Blanke CD, Hirsch FR, Kelly K, Gandara DR. Cetuximab plus carboplatin and paclitaxel with or without bevacizumab versus carboplatin and paclitaxel with or without bevacizumab in advanced NSCLC (SWOG S0819): a randomised, phase 3 study. Lancet Oncol. 2017 Nov 20. pii: S1470-2045(17)30694-0. doi: 10.1016/S1470-2045(17)30694-0. [Epub ahead of print] PubMed PMID: 29169877.

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