Docetaxel

  • CAT Number: A000806
  • CAS Number: 114977-28-5
  • Molecular Formula: C₄₃H₅₃NO₁₄
  • Molecular Weight: 807.88
  • Purity: ≥95%
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Docetaxel (CAS 114977-28-5), also known as RP-56976, is a semi-synthetic, second-generation taxane derived from a compound found in the European yew tree Taxus baccata. Docetaxel displays potent and broad antineoplastic properties; it binds to and stabilizes tubulin, thereby inhibiting microtubule disassembly which results in cell- cycle arrest at the G2/M phase and cell death. This agent also inhibits pro-angiogenic factors such as vascular endothelial growth factor (VEGF) and displays immunomodulatory and pro-inflammatory properties by inducing various mediators of the inflammatory response. Docetaxel has been studied for use as a radiation-sensitizing agent.

Catalog Number A000806
CAS Number 114977-28-5
Synonyms

RP56976, NSC 628503

Molecular Formula

C₄₃H₅₃NO₁₄

Purity 95%
Target Microtubule/Tubulin
Solubility >40.4mg/mL in DMSO
Storage -20°C
IUPAC Name [(1S,2S,3R,4S,7R,9S,10S,12R,15S)-4-acetyloxy-1,9,12-trihydroxy-15-[(2R,3S)-2-hydroxy-3-[(2-methylpropan-2-yl)oxycarbonylamino]-3-phenylpropanoyl]oxy-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/C43H53NO14/c1-22-26(55-37(51)32(48)30(24-15-11-9-12-16-24)44-38(52)58-39(3,4)5)20-43(53)35(56-36(50)25-17-13-10-14-18-25)33-41(8,34(49)31(47)29(22)40(43,6)7)27(46)19-28-42(33,21-54-28)57-23(2)45/h9-18,26-28,30-33,35,46-48,53H,19-21H2,1-8H3,(H,44,
InChIKey ZDZOTLJHXYCWBA-VCVYQWHSSA-N
SMILES CC1=C2C(C(=O)C3(C(CC4C(C3C(C(C2(C)C)(CC1OC(=O)C(C(C5=CC=CC=C5)NC(=O)OC(C)(C)C)O)O)OC(=O)C6=CC=CC=C6)(CO4)OC(=O)C)O)C)O
Reference

1: Enteshari S, Varshosaz J, Minayian M, Hassanzadeh F. Antitumor activity of raloxifene-targeted poly(styrene maleic acid)-poly (amide-ether-ester-imide) co-polymeric nanomicelles loaded with docetaxel in breast cancer-bearing mice. Invest New Drugs. 2017 Nov 27. doi: 10.1007/s10637-017-0533-1. [Epub ahead of print] PubMed PMID: 29177974.<br />
2: Miyake H, Matsushita Y, Tamura K, Motoyama D, Ito T, Sugiyama T, Otsuka A. Impact of prior androgen receptor-axis-targeted agents on the clinical activity of subsequent docetaxel in patients with metastatic castration-resistant prostate cancer: comparative assessment between abiraterone acetate and enzalutamide. Med Oncol. 2017 Nov 21;34(12):200. doi: 10.1007/s12032-017-1060-9. PubMed PMID: 29164346.<br />
3: Doddapaneni R, Patel K, Chowdhury N, Singh M. Reversal of drug-resistance by noscapine chemo-sensitization in docetaxel resistant triple negative breast cancer. Sci Rep. 2017 Nov 20;7(1):15824. doi: 10.1038/s41598-017-15531-1. PubMed PMID: 29158480.<br />
4: Ren G, Chen P, Tang J, Wang R, Duan S, Wang R, Xie Y, Zhang S. Construction and cellular uptake evaluation of redox-responsitive docetaxel prodrug self-assembled nanoparticles. Drug Dev Ind Pharm. 2017 Nov 21:1-30. doi: 10.1080/03639045.2017.1405435. [Epub ahead of print] PubMed PMID: 29157014.<br />
5: Su CY, Liu JJ, Ho YS, Huang YY, Hung-Shu Chang V, Liu DZ, Chen LC, Ho HO, Sheu MT. Development and Characterization of Docetaxel-Loaded Lecithin-Stabilized Micellar Drug Delivery System (L(sb)MDDs) for Improving the Therapeutic Efficacy and Reducing Systemic Toxicity. Eur J Pharm Biopharm. 2017 Nov 14. pii: S0939-6411(17)30945-1. doi: 10.1016/j.ejpb.2017.11.006. [Epub ahead of print] PubMed PMID: 29154834.<br />
6: Milbar N, Kates M, Chappidi MR, Pederzoli F, Yoshida T, Sankin A, Pierorazio PM, Schoenberg MP, Bivalacqua TJ. Oncological Outcomes of Sequential Intravesical Gemcitabine and Docetaxel in Patients with Non-Muscle Invasive Bladder Cancer. Bladder Cancer. 2017 Oct 27;3(4):293-303. doi: 10.3233/BLC-170126. PubMed PMID: 29152553; PubMed Central PMCID: PMC5676758.<br />
7: Zhu Y, Zhang W, Li Q, Li Q, Qiu B, Liu H, Liu M, Hu Y. A Phase II Randomized Controlled Trial: Definitive Concurrent Chemoradiotherapy with Docetaxel Plus Cisplatin versus 5-Fluorouracil plus Cisplatin in Patients with Oesophageal Squamous Cell Carcinoma. J Cancer. 2017 Oct 10;8(18):3657-3666. doi: 10.7150/jca.20053. eCollection 2017. PubMed PMID: 29151952; PubMed Central PMCID: PMC5688918.<br />
8: Tsuchiya Y, Ushijima K, Noguchi T, Okada N, Hayasaka JI, Jinbu Y, Ando H, Mori Y, Kusama M, Fujimura A. Influence of a dosing-time on toxicities induced by docetaxel, cisplatin and 5-fluorouracil in patients with oral squamous cell carcinoma; a cross-over pilot study. Chronobiol Int. 2017 Nov 16:1-6. doi: 10.1080/07420528.2017.1392551. [Epub ahead of print] PubMed PMID: 29144178.<br />
9: Tsai CH, Tzeng SF, Hsieh SC, Yang YC, Hsiao YW, Tsai MH, Hsiao PW. A standardized herbal extract mitigates tumor inflammation and augments chemotherapy effect of docetaxel in prostate cancer. Sci Rep. 2017 Nov 15;7(1):15624. doi: 10.1038/s41598-017-15934-0. PubMed PMID: 29142311; PubMed Central PMCID: PMC5688072.<br />
10: Kawasaki K, Takeuchi D, Kaneko T, Miura S, Kamiya J, Miyahara Y, Yoshimura K, Ogata A. [A Case of Advanced Gastric Cancer Responding to Neoadjuvant Chemotherapy with Docetaxel, Cisplatin, and 5-Fluorouracil, Leading to a Pathological Complete Response]. Gan To Kagaku Ryoho. 2017 Nov;44(11):1017-1020. Japanese. PubMed PMID: 29138379.

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