Vinorelbine

CAS# 71486-22-1

Vinorelbine

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Quality Control of Vinorelbine

Number of papers citing our products

Chemical structure

Vinorelbine

3D structure

Chemical Properties of Vinorelbine

Cas No. 71486-22-1 SDF Download SDF
PubChem ID 60780 Appearance Powder
Formula C45H54N4O8 M.Wt 778.93
Type of Compound Alkaloids Storage Desiccate at -20°C
Synonyms KW-2307 base
Solubility >25.9mg/mL in DMSO
SMILES CCC1=CC2CC(C3=C(CN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC
Standard InChIKey GBABOYUKABKIAF-BXZSYHTRSA-N
Standard InChI InChI=1S/C45H54N4O8/c1-8-27-19-28-22-44(40(51)55-6,36-30(25-48(23-27)24-28)29-13-10-11-14-33(29)46-36)32-20-31-34(21-35(32)54-5)47(4)38-43(31)16-18-49-17-12-15-42(9-2,37(43)49)39(57-26(3)50)45(38,53)41(52)56-7/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3/t28?,37-,38+,39+,42+,43+,44-,45-/m0/s1
General tips For obtaining a higher solubility , please warm the tube at 37 ℃ and shake it in the ultrasonic bath for a while.Stock solution can be stored below -20℃ for several months.
We recommend that you prepare and use the solution on the same day. However, if the test schedule requires, the stock solutions can be prepared in advance, and the stock solution must be sealed and stored below -20℃. In general, the stock solution can be kept for several months.
Before use, we recommend that you leave the vial at room temperature for at least an hour before opening it.
About Packaging 1. The packaging of the product may be reversed during transportation, cause the high purity compounds to adhere to the neck or cap of the vial.Take the vail out of its packaging and shake gently until the compounds fall to the bottom of the vial.
2. For liquid products, please centrifuge at 500xg to gather the liquid to the bottom of the vial.
3. Try to avoid loss or contamination during the experiment.
Shipping Condition Packaging according to customer requirements(5mg, 10mg, 20mg and more). Ship via FedEx, DHL, UPS, EMS or other couriers with RT, or blue ice upon request.

Source of Vinorelbine

The herbs of Catharanthus roseus

Biological Activity of Vinorelbine

DescriptionVinorelbine is a semi-synthetic Vinca alkaloid which is currently used in treatment of different cancer types mainly advanced breast cancer (ABC) and advanced/metastatic non-small cell lung cancer (NSCLC). Vinorelbine-loaded SSM can be developed as a new, safe, stable, and effective nanomedicine for the treatment of breast and lung cancers.
In vivo

Intravenous or oral administration of vinorelbine in adjuvant chemotherapy with cisplatin and vinorelbine for resected NSCLC.[Pubmed: 25769883 ]

Lung Cancer. 2015 May;88(2):167-73.

Cisplatin and Vinorelbine given intravenously is a well-established adjuvant chemotherapy regimen after surgery for early-stage NSCLC. Vinorelbine can also be administered orally. However, the efficacy of orally administrated Vinorelbine in adjuvant treatment of NSCLC is unknown. We assessed the overall survival (OS) and disease-free survival (DFS) of patients treated with adjuvant i.v. Vinorelbine or p.o. Vinorelbine, in combination with i.v. cisplatin.
METHODS AND RESULTS:
We reviewed two time-separated cohorts of patients referred to the Department of Oncology at Aarhus University Hospital (Denmark) from 2005 to 2012 for adjuvant chemotherapy after surgery for NSCLC. RESULTS AND Of the 265 patients included in this study, 126 patients received i.v. and 139 received p.o. Vinorelbine/cisplatin. The two groups were comparable with respect to important baseline characteristics. Median OS for all patients was 78.7 months and the median DFS was 35.7 months. No statistically significant difference in OS or DFS for patients treated with i.v. or oral Vinorelbine was detected. The DFS rates of the two groups were comparable across all variables in subgroup analysis.
CONCLUSIONS:
In conclusion we observed that intravenous or oral administration of Vinorelbine in combination with cisplatin after surgery for NSCLC appear equally effective in terms of overall and disease-free survival.

Oral vinorelbine in the treatment of non-small-cell lung cancer.[Pubmed: 24972635]

Expert Opin Pharmacother. 2014 Aug;15(11):1585-99.

Originally formulated as an intravenous (i.v.) agent, Vinorelbine is also currently available as an oral chemotherapeutic agent.
METHODS AND RESULTS:
Oral Vinorelbine has demonstrated significant activity in different settings for NSCLC, including adjuvant treatment for resected disease, concurrent chemoradiation for locally advanced NSCLC and palliative chemotherapy for recurrent/metastatic NSCLC, as part of combination schedules or as a single-agent treatment. AREAS COVERED: The authors explored the available data describing the use of oral Vinorelbine in NSCLC. PubMed articles and abstracts presented at international conferences were analysed, and relevant trials were reported and discussed. Specific settings, including the treatment of elderly and unfit patients and metronomic schedules including oral Vinorelbine, were evaluated. Available pharmacoeconomic data were also assessed.
CONCLUSIONS:
Oral Vinorelbine is an appealing agent, particularly as part of combination regimens containing platinum derivatives, although it can have a role as a single-agent treatment as well. Its safety profile is generally favourable and its route of administration is generally preferred by patients receiving chemotherapy. Compared to i.v. Vinorelbine and other antineoplastic agents, oral Vinorelbine has been reported to be advantageous in terms of cost savings.

Protocol of Vinorelbine

Structure Identification
AAPS PharmSciTech. 2014 Oct;15(5):1138-48.

A new lipid-based nano formulation of vinorelbine.[Pubmed: 24871553]

Vinorelbine (VLB) is a semi-synthetic Vinca alkaloid which is currently used in treatment of different cancer types mainly advanced breast cancer (ABC) and advanced/metastatic non-small cell lung cancer (NSCLC). However, its marketed formulation has been reported to have serious side effects, such as granulocytopenia, which is the major dose-limiting toxicity. Other unwanted effects include venous discoloration and phlebitis proximal to the site of injection, as well as localized rashes and urticaria, blistering, and skin sloughing.
METHODS AND RESULTS:
Our long-term aim in synthesizing a novel nanomicellar Vinorelbine formulation is to reduce or even eliminate these side effects and increase drug activity by formulating the drug in a lipid-based system as a nanomedicine targeted to the site of action. To this end, the purpose of this study was to prepare, characterize, and determine the in vitro efficacy of Vinorelbine-loaded sterically stabilized, biocompatible, and biodegradable phospholipid nanomicelles (SSM; size, ∼15 nm). Our results indicated that Vinorelbine incorporate at high quantities and within the interface between the core and palisade sections of the micelles. Incorporation ratio of drug within sterically stabilized micelles increased as the total amount of drug in the system increased, and no drug particles were formed at the highest drug concentrations tested. The nanomicellar formulation of Vinorelbine was ∼6.7-fold more potent than Vinorelbine dissolved in DMSO on MCF-7 cell line.
CONCLUSIONS:
Collectively, these data indicate that Vinorelbine-loaded SSM can be developed as a new, safe, stable, and effective nanomedicine for the treatment of breast and lung cancers.

Vinorelbine Dilution Calculator

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Vinorelbine Molarity Calculator

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Preparing Stock Solutions of Vinorelbine

1 mg 5 mg 10 mg 20 mg 25 mg
1 mM 1.2838 mL 6.4191 mL 12.8381 mL 25.6762 mL 32.0953 mL
5 mM 0.2568 mL 1.2838 mL 2.5676 mL 5.1352 mL 6.4191 mL
10 mM 0.1284 mL 0.6419 mL 1.2838 mL 2.5676 mL 3.2095 mL
50 mM 0.0257 mL 0.1284 mL 0.2568 mL 0.5135 mL 0.6419 mL
100 mM 0.0128 mL 0.0642 mL 0.1284 mL 0.2568 mL 0.321 mL
* Note: If you are in the process of experiment, it's necessary to make the dilution ratios of the samples. The dilution data above is only for reference. Normally, it's can get a better solubility within lower of Concentrations.

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Background on Vinorelbine

Vinorelbine is an anti-mitotic agent which inhibits the proliferation of Hela cells with IC50 of 1.25 nM.

In Vitro:Vinorelbine (0.5-5 nM) inhibits cell proliferation by 50% (IC50) at concentrations of 1.25 nM. At concentration of 8 nM vinorelbine, no cells are in anaphase[1]. Vinorelbine time-dependently induces the p53 and p21WAFI/CIP1 expression in androgen-dependent (AD) and- independent (AI) prostate cancer cell lines. Vinorelbine stimulates reporter genes in a concentration-dependent manner[2].

In Vivo:After vinorelbine treatment, the first neutropenicepisode occurred after the first (4 dogs), second (1), or sixth(1) vinorelbine treatment in the dogs[3]. Vinorelbine is tolerated at a weekly interval in tumor-bearing cats, with an MTD of 11.5 mg/m2[4].

References:
[1]. Ngan VK, et al. Mechanism of mitotic block and inhibition of cell proliferation by the semisynthetic Vinca alkaloids vinorelbine and its newer derivative vinflunine. Mol Pharmacol. 2001 Jul;60(1):225-32. [2]. Liu XM, et al. Unique induction of p21(WAF1/CIP1)expression by vinorelbine in androgen-independent prostate cancer cells. Br J Cancer. 2003 Oct 20;89(8):1566-73. [3]. Poirier VJ, et al. Toxicity, dosage, and efficacy of vinorelbine (Navelbine) in dogs with spontaneous neoplasia. J Vet Intern Med. 2004 Jul-Aug;18(4):536-9. [4]. Pierro JA, et al. Phase I clinical trial of vinorelbine in tumor-bearing cats. J Vet Intern Med. 2013 Jul-Aug;27(4):943-8.

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References on Vinorelbine

A new lipid-based nano formulation of vinorelbine.[Pubmed:24871553]

AAPS PharmSciTech. 2014 Oct;15(5):1138-48.

Vinorelbine (VLB) is a semi-synthetic Vinca alkaloid which is currently used in treatment of different cancer types mainly advanced breast cancer (ABC) and advanced/metastatic non-small cell lung cancer (NSCLC). However, its marketed formulation has been reported to have serious side effects, such as granulocytopenia, which is the major dose-limiting toxicity. Other unwanted effects include venous discoloration and phlebitis proximal to the site of injection, as well as localized rashes and urticaria, blistering, and skin sloughing. Our long-term aim in synthesizing a novel nanomicellar Vinorelbine formulation is to reduce or even eliminate these side effects and increase drug activity by formulating the drug in a lipid-based system as a nanomedicine targeted to the site of action. To this end, the purpose of this study was to prepare, characterize, and determine the in vitro efficacy of Vinorelbine-loaded sterically stabilized, biocompatible, and biodegradable phospholipid nanomicelles (SSM; size, approximately 15 nm). Our results indicated that Vinorelbine incorporate at high quantities and within the interface between the core and palisade sections of the micelles. Incorporation ratio of drug within sterically stabilized micelles increased as the total amount of drug in the system increased, and no drug particles were formed at the highest drug concentrations tested. The nanomicellar formulation of Vinorelbine was approximately 6.7-fold more potent than Vinorelbine dissolved in DMSO on MCF-7 cell line. Collectively, these data indicate that Vinorelbine-loaded SSM can be developed as a new, safe, stable, and effective nanomedicine for the treatment of breast and lung cancers.

Oral vinorelbine in the treatment of non-small-cell lung cancer.[Pubmed:24972635]

Expert Opin Pharmacother. 2014 Aug;15(11):1585-99.

INTRODUCTION: Originally formulated as an intravenous (i.v.) agent, Vinorelbine is also currently available as an oral chemotherapeutic agent. Oral Vinorelbine has demonstrated significant activity in different settings for NSCLC, including adjuvant treatment for resected disease, concurrent chemoradiation for locally advanced NSCLC and palliative chemotherapy for recurrent/metastatic NSCLC, as part of combination schedules or as a single-agent treatment. AREAS COVERED: The authors explored the available data describing the use of oral Vinorelbine in NSCLC. PubMed articles and abstracts presented at international conferences were analysed, and relevant trials were reported and discussed. Specific settings, including the treatment of elderly and unfit patients and metronomic schedules including oral Vinorelbine, were evaluated. Available pharmacoeconomic data were also assessed. EXPERT OPINION: Oral Vinorelbine is an appealing agent, particularly as part of combination regimens containing platinum derivatives, although it can have a role as a single-agent treatment as well. Its safety profile is generally favourable and its route of administration is generally preferred by patients receiving chemotherapy. Compared to i.v. Vinorelbine and other antineoplastic agents, oral Vinorelbine has been reported to be advantageous in terms of cost savings.

Intravenous or oral administration of vinorelbine in adjuvant chemotherapy with cisplatin and vinorelbine for resected NSCLC.[Pubmed:25769883]

Lung Cancer. 2015 May;88(2):167-73.

OBJECTIVES: Cisplatin and Vinorelbine given intravenously is a well-established adjuvant chemotherapy regimen after surgery for early-stage NSCLC. Vinorelbine can also be administered orally. However, the efficacy of orally administrated Vinorelbine in adjuvant treatment of NSCLC is unknown. We assessed the overall survival (OS) and disease-free survival (DFS) of patients treated with adjuvant i.v. Vinorelbine or p.o. Vinorelbine, in combination with i.v. cisplatin. MATERIALS AND METHODS: We reviewed two time-separated cohorts of patients referred to the Department of Oncology at Aarhus University Hospital (Denmark) from 2005 to 2012 for adjuvant chemotherapy after surgery for NSCLC. RESULTS AND CONCLUSION: Of the 265 patients included in this study, 126 patients received i.v. and 139 received p.o. Vinorelbine/cisplatin. The two groups were comparable with respect to important baseline characteristics. Median OS for all patients was 78.7 months and the median DFS was 35.7 months. No statistically significant difference in OS or DFS for patients treated with i.v. or oral Vinorelbine was detected. The DFS rates of the two groups were comparable across all variables in subgroup analysis. In conclusion we observed that intravenous or oral administration of Vinorelbine in combination with cisplatin after surgery for NSCLC appear equally effective in terms of overall and disease-free survival.

Description

Vinorelbine is an anti-mitotic agent which inhibits the proliferation of Hela cells with IC50 of 1.25 nM.

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