Paclitaxel
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MedKoo CAT#: 100690

CAS#: 33069-62-4 (free base)

Description: Paclitaxel is a compound with antineoplastic activity extracted from the Pacific yew tree Taxus brevifolia. Paclitaxel binds to tubulin and inhibits the disassembly of microtubules, thereby inhibiting 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).


Chemical Structure

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Paclitaxel
CAS# 33069-62-4 (free base)

Theoretical Analysis

MedKoo Cat#: 100690
Name: Paclitaxel
CAS#: 33069-62-4 (free base)
Chemical Formula: C47H51NO14
Exact Mass: 853.33
Molecular Weight: 853.910
Elemental Analysis: C, 66.11; H, 6.02; N, 1.64; O, 26.23

Price and Availability

Size Price Availability Quantity
1g USD 450 Ready to ship
2g USD 750 Ready to ship
10g USD 2950 Ready to ship
500mg USD 250 Ready to ship
200mg USD 150 Ready to ship
5g USD 1650 Ready to Ship
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Related CAS #: 186040-50-6 (ceribate); 33069-62-4 (free base)

Synonym: BMS 181339-01; BMS181339-01; BMS-181339-01; Brand name: Taxol; Anzatax; Asotax; Bristaxol; Praxel; Taxol Konzentrat. TAX.

IUPAC/Chemical Name: (2aR,4S,4aS,6R,9S,11S,12S,12aR,12bS)-9-(((2R,3S)-3-benzamido-2-hydroxy-3-phenylpropanoyl)oxy)-12-(benzoyloxy)-4,11-dihydroxy-4a,8,13,13-tetramethyl-5-oxo-2a,3,4,4a,5,6,9,10,11,12,12a,12b-dodecahydro-1H-7,11-methanocyclodeca[3,4]benzo[1,2-b]oxete-6,12b-diyl diacetate

InChi Key: RCINICONZNJXQF-MZXODVADSA-N

InChi Code: 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

SMILES Code: O=C1[C@H](OC(C)=O)C(C2(C)C)=C(C)[C@@H](OC([C@H](O)[C@@H](NC(C3=CC=CC=C3)=O)C4=CC=CC=C4)=O)C[C@@]2(O)[C@@H](OC(C5=CC=CC=C5)=O)[C@@]6([H])[C@@]1(C)[C@@H](O)C[C@@]7([H])OC[C@]76OC(C)=O

Appearance: white solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

Biological target: Antineoplastic agent that stabilizes tubulin polymerization.
In vitro activity: PTX (Paclitaxel) or PTX-Tf-NPs (Paclitaxel transferrin nanoparticles) reduce the viability of rat glioblastoma C6 cells in a dosedependent manner, but PTX-Tf-NPs exhibit a stronger inhibitory effect at higher concentrations compared with PTX. Rat glioblastoma C6 cells were treated with Tf-NPs, PTX or PTX-Tf-NPs for 48 h, and cell viability was detected using the MTT assay. The percentages of cell viability are presented in Fig. 1 and Table I. The results indicated that treatment with Tf-NPs at concentrations of 0.0032 or 0.016 µg/ml did not inhibit C6 cell viability, whereas Tf-NP treatment at concentrations of 0.08, 0.4, 2 and 10 µg/ml resulted in a cell viability of 92, 97, 97 and 88% in C6 cells, respectively, compared with control cells, indicating that Tf-NPs alone cause a low cytotoxicity in C6 cells. Both PTX and PTX-Tf-NPs exhibited a dose-dependent effect on cell viability in C6 cells. Following PTX treatment at concentrations of 0.0032, 0.016 and 0.08 µg/ml, C6 cell viability was 91, 87 and 83%, respectively, while following PTX-Tf-NP treatment, cell viability was 95, 91 and 83%, respectively. Statistical analysis revealed that at a concentration of ≤0.08 µg/ml, no significant difference in cell viability by treatment with either PTX or PTX-Tf-NPs was observed, indicating that PTX and PTX-Tf-NPs exhibit similar cell viability inhibitory effects at these concentrations. Nevertheless, at concentrations of 0.4, 2 and 10 µg/ml, C6 cells treated with PTX exhibited an average viability of 81, 74 and 62%, respectively, but C6 cells treated with PTX-Tf-NPs exhibited significantly lower viability compared with cells treated with PTX (78, 69 and 56%, respectively). This suggested that PTX-Tf-NPs were more potent compared with PTX in reducing the viability of C6 glioblastoma cells at higher concentrations. Reference: Exp Ther Med. 2021 Apr; 21(4): 292. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7885080/
In vivo activity: The blank and the PCX(Paclitxel)-loaded CD nanoparticles were administered to the tumor-bearing mice, and the change in tumor size was followed for 14 days (Figure 8 and Figure 9). On day 5, compared to the control groups that received physiological saline or blank CD nanoparticles, an approximately 25% reduction was observed in the tumor size of the mice treated with PCX-loaded nanoparticle or PCX solution (Figure 8). The most significant difference between the groups was achieved on day 8 in which the tumors continued to grow in the physiological saline control group; on the other hand, either the blank or the PCX-loaded CD nanoparticles reduced the tumor burden. In general, the PCX-loaded positively charged nanoparticles were the most efficient antitumor formulation, albeit not reaching the level of statistical significance (Figure 8). On day 14, the tumor size was reduced by 50% in all groups that were treated with blank or PCX-loaded CD formulations, or PCX solution. Collectively, the antitumor effect of the PCX-loaded amphiphilic CD nanoparticles was observed earlier than the PCX solution. Interestingly, in the long run, the blank CD nanoparticles were also capable of hindering the tumor growth (Figure 8 and Figure 9). Accordingly, Erdogar et al. showed that folatetargeted CD nanoparticles were better tolerated by animals and localized in the tumor area than PCX solution in Cremophor®EL. These results support that the CD nanoparticles can be a good candidate for increasing the efficacy and safety of PCX therapy in breast cancer. Reference: Nanomaterials (Basel). 2021 Feb; 11(2): 515. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7922126/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
Cloroform 1.0 1.17
DMF 5.0 5.86
DMSO 77.9 91.17
DMSO:PBS (pH 7.2) (1:10) 0.1 0.12
Ethanol 14.3 16.78
Methanol 5.0 5.86

Preparing Stock Solutions

The following data is based on the product molecular weight 853.910000000000000000000000000000 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Wang L, Liu C, Qiao F, Li M, Xin H, Chen N, Wu Y, Liu J. Analysis of the cytotoxic effects, cellular uptake and cellular distribution of paclitaxel-loaded nanoparticles in glioblastoma cells in vitro. Exp Ther Med. 2021 Apr;21(4):292. doi: 10.3892/etm.2021.9723. Epub 2021 Jan 27. PMID: 33717235; PMCID: PMC7885080. 2. Yang X, Qin J, Gong C, Yang J. Propofol enhanced the cell sensitivity to paclitaxel (PTX) in prostatic cancer (PC) through modulation of HOTAIR. Genes Genomics. 2021 Apr 23. doi: 10.1007/s13258-021-01093-0. Epub ahead of print. PMID: 33893626. 3. Varan G, Varan C, Öztürk SC, Benito JM, Esendağlı G, Bilensoy E. Therapeutic Efficacy and Biodistribution of Paclitaxel-Bound Amphiphilic Cyclodextrin Nanoparticles: Analyses in 3D Tumor Culture and Tumor-Bearing Animals In Vivo. Nanomaterials (Basel). 2021 Feb 18;11(2):515. doi: 10.3390/nano11020515. PMID: 33670527; PMCID: PMC7922126. 4. Gui G, Fan Z, Ning Y, Yuan C, Zhang B, Xu Q. Optimization, Characterization and in vivo Evaluation of Paclitaxel-Loaded FolateConjugated Superparamagnetic Iron Oxide Nanoparticles. Int J Nanomedicine. 2021 Mar 19;16:2283-2295. doi: 10.2147/IJN.S287434. PMID: 33776433; PMCID: PMC7992116.
In vitro protocol: 1. Wang L, Liu C, Qiao F, Li M, Xin H, Chen N, Wu Y, Liu J. Analysis of the cytotoxic effects, cellular uptake and cellular distribution of paclitaxel-loaded nanoparticles in glioblastoma cells in vitro. Exp Ther Med. 2021 Apr;21(4):292. doi: 10.3892/etm.2021.9723. Epub 2021 Jan 27. PMID: 33717235; PMCID: PMC7885080. 2. Yang X, Qin J, Gong C, Yang J. Propofol enhanced the cell sensitivity to paclitaxel (PTX) in prostatic cancer (PC) through modulation of HOTAIR. Genes Genomics. 2021 Apr 23. doi: 10.1007/s13258-021-01093-0. Epub ahead of print. PMID: 33893626.
In vivo protocol: 1. Varan G, Varan C, Öztürk SC, Benito JM, Esendağlı G, Bilensoy E. Therapeutic Efficacy and Biodistribution of Paclitaxel-Bound Amphiphilic Cyclodextrin Nanoparticles: Analyses in 3D Tumor Culture and Tumor-Bearing Animals In Vivo. Nanomaterials (Basel). 2021 Feb 18;11(2):515. doi: 10.3390/nano11020515. PMID: 33670527; PMCID: PMC7922126. 2. Gui G, Fan Z, Ning Y, Yuan C, Zhang B, Xu Q. Optimization, Characterization and in vivo Evaluation of Paclitaxel-Loaded FolateConjugated Superparamagnetic Iron Oxide Nanoparticles. Int J Nanomedicine. 2021 Mar 19;16:2283-2295. doi: 10.2147/IJN.S287434. PMID: 33776433; PMCID: PMC7992116.

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1: Carbognin L, Sperduti I, Nortilli R, Brunelli M, Vicentini C, Pellini F, Pollini GP, Giannarelli D, Tortora G, Bria E. Balancing activity and tolerability of neoadjuvant paclitaxel- and docetaxel-based chemotherapy for HER2-positive early stage breast cancer: sensitivity analysis of randomized trials. Cancer Treat Rev. 2015 Mar;41(3):262-70. doi: 10.1016/j.ctrv.2015.02.003. Epub 2015 Feb 9. Review. PubMed PMID: 25683304. 2: Onishi Y, Eshita Y, Ji RC, Onishi M, Kobayashi T, Mizuno M, Yoshida J, Kubota N. Anticancer efficacy of a supramolecular complex of a 2-diethylaminoethyl-dextran-MMA graft copolymer and paclitaxel used as an artificial enzyme. Beilstein J Nanotechnol. 2014 Dec 1;5:2293-307. doi: 10.3762/bjnano.5.238. eCollection 2014. Review. PubMed PMID: 25551057; PubMed Central PMCID: PMC4273266. 3: Liu H, Chen X, Sun J, Gao P, Song Y, Zhang N, Lu X, Xu H, Wang Z. The efficacy and toxicity of paclitaxel plus S-1 compared with paclitaxel plus 5-FU for advanced gastric cancer: a PRISMA systematic review and meta-analysis of randomized controlled trials. Medicine (Baltimore). 2014 Nov;93(25):e164. doi: 10.1097/MD.0000000000000164. Review. PubMed PMID: 25437030. 4: Slaughter KN, Moore KN, Mannel RS. Anti-angiogenic therapy versus dose-dense paclitaxel therapy for frontline treatment of epithelial ovarian cancer: review of phase III randomized clinical trials. Curr Oncol Rep. 2014 Nov;16(11):412. doi: 10.1007/s11912-014-0412-2. Review. PubMed PMID: 25292279. 5: Blais N, Hirsh V. Chemotherapy in Metastatic NSCLC - New Regimens (Pemetrexed, Nab-Paclitaxel). Front Oncol. 2014 Jul 21;4:177. doi: 10.3389/fonc.2014.00177. eCollection 2014. Review. Erratum in: Front Oncol. 2014;4:300. PubMed PMID: 25101242; PubMed Central PMCID: PMC4104641. 6: Tofthagen C, McAllister RD, Visovsky C. Peripheral neuropathy caused by Paclitaxel and docetaxel: an evaluation and comparison of symptoms. J Adv Pract Oncol. 2013 Jul;4(4):204-15. Review. PubMed PMID: 25032002; PubMed Central PMCID: PMC4093436. 7: Litsky J, Chanda A, Stilp E, Lansky A, Mena C. Critical evaluation of stents in the peripheral arterial disease of the superficial femoral artery - focus on the paclitaxel eluting stent. Med Devices (Auckl). 2014 May 28;7:149-56. doi: 10.2147/MDER.S45472. eCollection 2014. Review. PubMed PMID: 24920940; PubMed Central PMCID: PMC4045256. 8: Borazanci E, Von Hoff DD. Nab-paclitaxel and gemcitabine for the treatment of patients with metastatic pancreatic cancer. Expert Rev Gastroenterol Hepatol. 2014 Sep;8(7):739-47. doi: 10.1586/17474124.2014.925799. Epub 2014 May 31. Review. PubMed PMID: 24882381. 9: Li P, Liu JP. Long-term risk of late and very late stent thrombosis in patients treated with everolimus against paclitaxel-eluting stents: an updated meta-analysis. Coron Artery Dis. 2014 Aug;25(5):369-77. doi: 10.1097/MCA.0000000000000109. Review. PubMed PMID: 24818639. 10: Glück S. nab-Paclitaxel for the treatment of aggressive metastatic breast cancer. Clin Breast Cancer. 2014 Aug;14(4):221-7. doi: 10.1016/j.clbc.2014.02.001. Epub 2014 Feb 20. Review. PubMed PMID: 24806278. 11: Neesse A, Michl P, Tuveson DA, Ellenrieder V. nab-Paclitaxel: novel clinical and experimental evidence in pancreatic cancer. Z Gastroenterol. 2014 Apr;52(4):360-6. doi: 10.1055/s-0034-1366002. Epub 2014 Mar 31. Review. PubMed PMID: 24687799. 12: Al-Batran SE, Geissler M, Seufferlein T, Oettle H. Nab-paclitaxel for metastatic pancreatic cancer: clinical outcomes and potential mechanisms of action. Oncol Res Treat. 2014;37(3):128-34. doi: 10.1159/000358890. Epub 2014 Feb 7. Review. PubMed PMID: 24685917. 13: De Luca G, Wirianta J, Lee JH, Kaiser C, Di Lorenzo E, Suryapranata H. Sirolimus-eluting versus paclitaxel-eluting stent in primary angioplasty: a pooled patient-level meta-analysis of randomized trials. J Thromb Thrombolysis. 2014 Oct;38(3):355-63. Review. PubMed PMID: 24659172. 14: Roy A, Bhattacharyya M, Ernsting MJ, May JP, Li SD. Recent progress in the development of polysaccharide conjugates of docetaxel and paclitaxel. Wiley Interdiscip Rev Nanomed Nanobiotechnol. 2014 Jul-Aug;6(4):349-68. doi: 10.1002/wnan.1264. Epub 2014 Mar 20. Review. PubMed PMID: 24652678; PubMed Central PMCID: PMC4057951. 15: de Weger VA, Beijnen JH, Schellens JH. Cellular and clinical pharmacology of the taxanes docetaxel and paclitaxel--a review. Anticancer Drugs. 2014 May;25(5):488-94. doi: 10.1097/CAD.0000000000000093. Review. Erratum in: Anticancer Drugs. 2015 Feb;26(2):240. PubMed PMID: 24637579. 16: Howat S, Park B, Oh IS, Jin YW, Lee EK, Loake GJ. Paclitaxel: biosynthesis, production and future prospects. N Biotechnol. 2014 May 25;31(3):242-5. doi: 10.1016/j.nbt.2014.02.010. Epub 2014 Mar 11. Review. PubMed PMID: 24614567. 17: Zhang D, Yang R, Wang S, Dong Z. Paclitaxel: new uses for an old drug. Drug Des Devel Ther. 2014 Feb 20;8:279-84. doi: 10.2147/DDDT.S56801. eCollection 2014. Review. PubMed PMID: 24591817; PubMed Central PMCID: PMC3934593. 18: Megerdichian C, Olimpiadi Y, Hurvitz SA. nab-Paclitaxel in combination with biologically targeted agents for early and metastatic breast cancer. Cancer Treat Rev. 2014 Jun;40(5):614-25. doi: 10.1016/j.ctrv.2014.02.001. Epub 2014 Feb 12. Review. PubMed PMID: 24560997. 19: Cecco S, Aliberti M, Baldo P, Giacomin E, Leone R. Safety and efficacy evaluation of albumin-bound paclitaxel. Expert Opin Drug Saf. 2014 Apr;13(4):511-20. doi: 10.1517/14740338.2014.893293. Epub 2014 Feb 22. Review. PubMed PMID: 24559090. 20: Al-Hajeili M, Azmi AS, Choi M. Nab-paclitaxel: potential for the treatment of advanced pancreatic cancer. Onco Targets Ther. 2014 Feb 4;7:187-92. doi: 10.2147/OTT.S40705. eCollection 2014. Review. PubMed PMID: 24523592; PubMed Central PMCID: PMC3921002.