Docetaxel | CAS#114977-28-5 | VEGF inhibitor

MedKoo Cat#: 100270 | Name: Docetaxel

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Docetaxel, 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.

Chemical Structure

Docetaxel

CAS#114977-28-5 (anhydrous)

Theoretical Analysis

MedKoo Cat#: 100270

Name: Docetaxel

CAS#: 114977-28-5 (anhydrous)

Chemical Formula: C43H53NO14

Exact Mass: 807.3466

Molecular Weight: 807.80

Elemental Analysis: C, 63.93; H, 6.61; N, 1.73; O, 27.73.

Price and Availability

Size	Price	Availability
50mg	USD 90.00	Ready to ship
100mg	USD 150.00	Ready to ship
200mg	USD 225.00	Ready to ship
500mg	USD 450.00	Ready to ship
1g	USD 750.00	Ready to ship
2g	USD 1,250.00	Ready to ship
5g	USD 2,650.00	Ready to ship

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Related CAS #

148408-66-6 (hydrate) 114977-28-5 (anhydrous)

Synonym

RP56976; RP 56976; RP-56976. Docetaxel hydrate, brand name: Taxotere.

IUPAC/Chemical Name

(2aR,4S,4aS,6R,9S,11S,12S,12bS)-12b-acetoxy-9-(((2R,3S)-3-((tert-butoxycarbonyl)amino)-2-hydroxy-3-phenylpropanoyl)oxy)-4,6,11-trihydroxy-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]oxet-12-yl benzoate.

InChi Key

ZDZOTLJHXYCWBA-JXHJHTFNSA-N

InChi Code

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,44,52)/t26-,27-,28+,30-,31+,32+,33?,35-,41+,42-,43+/m0/s1

SMILES Code

O=C(O[C@@H](C1[C@@]2(C)[C@@H](O)C[C@@]3([H])OC[C@]31OC(C)=O)[C@]4(O)C[C@H](OC([C@H](O)[C@@H](NC(OC(C)(C)C)=O)C5=CC=CC=C5)=O)C(C)=C(C4(C)C)[C@@H](O)C2=O)C6=CC=CC=C6

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 for in vitro study.

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

More Info

Product Data

Product Data

Certificate of Analysis

View CoA: current batch, Lot#T9Z03C19

View CoA: current batch, Lot#T8Z09C11

QC Data

View QC data: current batch, Lot#T8Z09C11

View QC data: current batch, Lot#T9Z03C19

Safety Data Sheet (SDS)

View Safety Data Sheet (SDS)

Instruction

View handling instruction

Biological target:

Docetaxel (RP-56976) is a microtubule depolymerization inhibitor with an IC50 of 0.2 μM.

In vitro activity:

Docetaxel-loaded nanomicelles were prepared in this study to improve the solubility and tumor targeting effect of docetaxel(DTX),and further evaluate their anticancer effects in vitro. PBAE-DTX nanomicelles were prepared by film-hydration method with amphiphilic block copolymer polyethyleneglycol methoxy-polylactide(PELA) and pH sensitive triblock copolymer polyethyleneglycol methoxy-polylactide-poly-β-aminoester(PBAE) were used respectively to prepare PELA-DTX nanomicelles and PBAE-DTX nanomicelles. The nanomicelles were characterized by physicochemical properties and the activity of mice Lewis lung cancer cells was studied. The DTX micelles also showed significant inhibitory effects on Lewis lung cancer cells by MTT assay, and pH-sensitive PBAE-DTX showed better cytotoxicity. The results of flow cytometry indicated that,the apoptosis rate of lung cancer Lewis cells was(20.72±1.47)%,(29.71±2.38)%,and(40.91±1.90)%(P<0.05) at 48 h after treatment in DTX,PELA-DTX,and PBAE-DTX groups. The results showed that different docetaxel preparations could promote the apoptosis of Lewis cells, and PBAE-DTX had stronger apoptotic-promoting effect. The pH-sensitive DTX-loaded micelles are promising candidates in developing stimuli triggered drug delivery systems in acidic tumor micro-environments with improved inhibitory effects of tumor growth on Lewis lung cancer. Reference: Zhongguo Zhong Yao Za Zhi. 2019 Jun;44(11):2251-2259. https://pubmed.ncbi.nlm.nih.gov/31359650/

In vivo activity:

Docetaxel (DTX) has poor solubility, low specificity, and severe side effects. For efficient targeting of DTX to hepsin-overexpressing SKOV3 ovarian cancer cells, PEGylated and RIPL peptide (IPLVVPLRRRRRRRRC)-conjugated nanostructured lipid carriers (PEG-RIPL-NLCs) were examined for in vivo antitumor efficacy. Experiments in male Sprague-Dawley rats revealed that DTX-PEG-RIPL-NLCs increased the mean residence time of DTX but reduced total body clearance and volume of distribution. In a SKOV3-bearing xenograft Balb/c athymic mouse model, DTX-PEG-RIPL-NLCs suppressed tumors, evidenced by tumor volume change and histopathological examination. Thus, it can be concluded that PEG-RIPL-NLCs have an advantage of high payload of poorly water-soluble drugs and are a good candidate for drug targeting to SKOV3-derived ovarian cancer. Reference: Int J Pharm. 2020 Jun 15;583:119393. https://www.sciencedirect.com/science/article/abs/pii/S037851732030377X?via%3Dihub

	Solvent	mg/mL	mM
Solubility
	DMSO	55.2	68.33
	Ethanol	60.8	75.22
	DMF	5.0	6.20
	DMSO:PBS (pH 7.2) (1:10)	0.1	0.12

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 807.80 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.

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 YJ, Wang J, Hao DL, Yue QX, Xie R, DE GJ, Yi H, Zang C, Zhao QH, Chen YJ. [Preparation of docetaxel-loaded nanomicelles and their anti-Lewis lung cancer effect in vitro]. Zhongguo Zhong Yao Za Zhi. 2019 Jun;44(11):2251-2259. Chinese. doi: 10.19540/j.cnki.cjcmm.20190326.305. PMID: 31359650. 2. Kim CH, Kang TH, Kim BD, Lee TH, Yoon HY, Goo YT, Choi YS, Kang MJ, Choi YW. Enhanced docetaxel delivery using sterically stabilized RIPL peptide-conjugated nanostructured lipid carriers: In vitro and in vivo antitumor efficacy against SKOV3 ovarian cancer cells. Int J Pharm. 2020 Jun 15;583:119393. doi: 10.1016/j.ijpharm.2020.119393. Epub 2020 May 4. PMID: 32376445.

In vitro protocol:

In vivo protocol:

1. Kim CH, Kang TH, Kim BD, Lee TH, Yoon HY, Goo YT, Choi YS, Kang MJ, Choi YW. Enhanced docetaxel delivery using sterically stabilized RIPL peptide-conjugated nanostructured lipid carriers: In vitro and in vivo antitumor efficacy against SKOV3 ovarian cancer cells. Int J Pharm. 2020 Jun 15;583:119393. doi: 10.1016/j.ijpharm.2020.119393. Epub 2020 May 4. PMID: 32376445.

1: Conry RM. Response of follicular dendritic cell sarcoma to gemcitabine and docetaxel: report of two cases and literature review. Clin Sarcoma Res. 2014 Jun 28;4:6. doi: 10.1186/2045-3329-4-6. eCollection 2014. PubMed PMID: 25009738. 2: Park JC, Pratz CF, Tesfaye A, Brodsky RA, Antonarakis ES. The Effect of Therapeutic Anticoagulation on Overall Survival in Men Receiving First-Line Docetaxel Chemotherapy for Metastatic Castration-Resistant Prostate Cancer. Clin Genitourin Cancer. 2014 Jun 11. pii: S1558-7673(14)00118-9. doi: 10.1016/j.clgc.2014.04.008. [Epub ahead of print] PubMed PMID: 24999166. 3: Shiota M, Yokomizo A, Takeuchi A, Kiyoshima K, Inokuchi J, Tatsugami K, Naito S. Risk factors for febrile neutropenia in patients receiving docetaxel chemotherapy for castration-resistant prostate cancer. Support Care Cancer. 2014 Jul 5. [Epub ahead of print] PubMed PMID: 24996830. 4: Pan B, Chen D, Huang J, Wang R, Feng B, Song H, Chen L. HMGB1-mediated autophagy promotes docetaxel resistance in human lung adenocarcinoma. Mol Cancer. 2014 Jul 5;13(1):165. [Epub ahead of print] PubMed PMID: 24996221. 5: Mizumachi T, Homma A, Kakizaki T, Sakashita T, Kano S, Hatakeyama H, Tsuchiya K, Yasuda K, Onimaru R, Shirato H, Taguchi J, Shimizu Y, Kinoshita I, Akita H, Fukuda S. Feasibility and efficacy of induction docetaxel, cisplatin, and 5-fluorouracil chemotherapy combined with concurrent weekly cisplatin chemoradiotherapy for locally advanced head and neck squamous cell carcinoma. Int J Clin Oncol. 2014 Jul 5. [Epub ahead of print] PubMed PMID: 24993675. 6: Palma G, Conte C, Barbieri A, Bimonte S, Luciano A, Rea D, Ungaro F, Tirino P, Quaglia F, Arra C. Antitumor activity of PEGylated biodegradable nanoparticles for sustained release of docetaxel in triple-negative breast cancer. Int J Pharm. 2014 Jun 30;473(1-2):55-63. doi: 10.1016/j.ijpharm.2014.06.058. [Epub ahead of print] PubMed PMID: 24992317. 7: Tuxen MK, Cold S, Tange UB, Balslev E, Nielsen DL. Phase II study of neoadjuvant pegylated liposomal doxorubicin and cyclophosphamide Â± trastuzumab followed by docetaxel in locally advanced breast cancer. Acta Oncol. 2014 Jul 3:1-6. [Epub ahead of print] PubMed PMID: 24991893. 8: Caffo O, De Giorgi U, Fratino L, Lo Re G, Basso U, D Angelo A, Donini M, Verderame F, Ratta R, Procopio G, Campadelli E, Massari F, Gasparro D, Macrini S, Messina C, Giordano M, Alesini D, Zustovich F, Fraccon AP, Vicario G, Conteduca V, Maines F, Galligioni E. Safety and Clinical Outcomes of Patients Treated with Abiraterone Acetate After Docetaxel: Results of the Italian Named Patient Programme. BJU Int. 2014 Jul 2. doi: 10.1111/bju.12857. [Epub ahead of print] PubMed PMID: 24988879. 9: Yang WC, Chen CH, Tang JY, Wu CF, Liu YC, Sun Y, Lin SF. Induction chemotherapy with docetaxel, Cisplatin and Fluorouracil followed by surgery and concurrent chemoradiotherapy improves outcome of recurrent advanced head and neck squamous cell carcinoma. Anticancer Res. 2014 Jul;34(7):3765-73. PubMed PMID: 24982400. 10: Matsumoto H, Kubota H, Higashida M, Yoden E, Hiratsuka J, Haruma K, Nakamura M, Hirai T. Docetaxel/ TS-1 with Radiation for Unresectable Squamous Cell Carcinoma of the Esophagus - A Phase II Trial. Anticancer Res. 2014 Jul;34(7):3759-63. PubMed PMID: 24982399.

1. Soylu H, Kırca M, Avcı S, Ozpolat B, Ustunel I. Antiandrogen abiraterone and docetaxel treatments affect Notch1, Jagged1 and Hes1 expressions in metastatic prostate cancer cells. Exp Mol Pathol. 2021 Apr;119:104607. doi: 10.1016/j.yexmp.2021.104607. Epub 2021 Jan 19. PMID: 33482170.