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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2016/01/23 00:31:49」(JST)

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Vinorelbine (NVB), sold under the trade name Navelbine, is a chemotherapy medication that is used to treatment a number of types of cancer, including breast cancer and non-small cell lung cancer.^[2]

It is on the World Health Organization's List of Essential Medicines, the most important medication needed in a basic health system.^[3] The wholesale price as of 2014 is between 8.60 and 42.80 USD a vial.^[4]^[5]

Medical uses

Vinorelbine is approved for the treatment of non-small-cell lung cancer. It is used off-label for other cancers such as metastatic breast cancer. It is also active in rhabdomyosarcoma.^[6]

Side effects

Vinorelbine has a number of side-effects that can limit its use:

Chemotherapy-induced peripheral neuropathy (a progressive, enduring and often irreversible tingling numbness, intense pain, and hypersensitivity to cold, beginning in the hands and feet and sometimes involving the arms and legs^[7]), lowered resistance to infection, bruising or bleeding, anaemia, constipation, diarrhea, nausea, tiredness and a general feeling of weakness (asthenia), inflammation of the vein into which it was injected (phlebitis). Seldom severe hyponatremia is seen.

Less common effects are hair loss and allergic reaction.

Pharmacology

The antitumor activity is due to inhibition of mitosis through interaction with tubulin.^[8] Vinorelbine is the first 5´NOR semi-synthetic vinca alkaloid. It is obtained by semi-synthesis from alkaloids extracted from the rosy periwinkle, Catharanthus roseus. It is marketed in India by Abbott Healthcare under the brand name Navelbine.

History

Vinorelbine was invented by the pharmacist Pierre Potier and his team from the CNRS in France in the 1980s and was licensed to the oncology department of the Pierre Fabre Group. It is a semi-synthetic vinca alkaloid. The drug was approved in France in 1989 under the brand name Navelbine for the treatment of non-small cell lung cancer. It gained approval to treat metastatic breast cancer in 1991. Vinorelbine received approval by the United States Food and Drug Administration (FDA) in December 1994 sponsored by Burroughs Wellcome Company. Pierre Fabre Group now markets Navelbine in the U.S., where the drug went generic in February 2003.

In most European countries, vinorelbine is approved to treat non-small cell lung cancer and breast cancer. In the United States it is approved only for non-small cell lung cancer.

Oral formulation

An oral formulation has been marketed and registered in most European countries. It has similar efficacy as the intravenous formulation, but it avoids venous toxicities of an infusion and is easier to take.^{[medical citation needed]} The oral form is not approved in the United States or Australia.^{[medical citation needed]}

References

^ Marty M, Fumoleau P, Adenis A, Rousseau Y, Merrouche Y, Robinet G, Senac I, Puozzo C (2001). "Oral vinorelbine pharmacokinetics and absolute bioavailability study in patients with solid tumors". Ann Oncol 12 (11): 1643–9. doi:10.1023/A:1013180903805. PMID 11822766.
^ "Navelbine". The American Society of Health-System Pharmacists. Retrieved Nov 28, 2015.
^ "19th WHO Model List of Essential Medicines (April 2015)" (PDF). WHO. April 2015. Retrieved May 10, 2015.
^ "Vinorelbine". International Drug Price Indicator Guide. Retrieved 28 November 2015.
^ "Vinorelbine". International Drug Price Indicator Guide. Retrieved 28 November 2015.
^ Casanova, M; Ferrari, A; Spreafico, F; Terenziani, M; Massimino, M; Luksch, R; Cefalo, G; Polastri, D; et al. (2002). "Vinorelbine in previously treated advanced childhood sarcomas: Evidence of activity in rhabdomyosarcoma". Cancer 94 (12): 3263–8. doi:10.1002/cncr.10600. PMID 12115359.
^ del Pino BM. Chemotherapy-induced Peripheral Neuropathy. NCI Cancer Bulletin. Feb 23, 2010;7(4):6.
^ Jordan, M.A.; Wilson, L. (2004). "Microtubules as a target for anticancer drugs.". Nature Reviews. Cancer 4 (4): 253–65. doi:10.1038/nrc1317. PMID 15057285.

UpToDate Contents

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1. 高齢患者およびperformance statusのスコアが低い患者における進行非小細胞肺癌に対する全身療法 systemic therapy for advanced non small cell lung cancer in elderly patients and patients with a poor performance status
2. 女性の転移性乳癌に対する全身療法：化学療法 systemic treatment of metastatic breast cancer in women chemotherapy
3. 高齢女性における転移性乳癌の治療 treatment of metastatic breast cancer in older women
4. ドライバー変異が認められない進行非小細胞肺癌の初期マネージメントのための全身療法 systemic therapy for the initial management of advanced non small cell lung cancer without a driver mutation
5. 難治性および再発性の小細胞肺癌の治療 treatment of refractory and relapsed small cell lung cancer

English Journal

Polymeric micelles for enhanced lymphatic drug delivery to treat metastatic tumors.

Qin L, Zhang F, Lu X, Wei X, Wang J, Fang X, Si D, Wang Y, Zhang C, Yang R, Liu C, Liang W.SourceProtein & Peptide Pharmaceutical Laboratory, Institute of Biophysics, Chinese Academy of Sciences, Beijing, China.
Journal of controlled release : official journal of the Controlled Release Society.J Control Release.2013 Oct 28;171(2):133-42. doi: 10.1016/j.jconrel.2013.07.005. Epub 2013 Jul 14.
Polymeric micelles have been proven to be a promising nano-sized system for drug delivery. Understanding its in vivo behaviors at the whole body, tissue and cellular levels is critical for translating this drug delivery system into clinical practice. In this study, the 14.5nm micelles made of polyet
PMID 23863448

Phase II study of lapatinib in combination with vinorelbine in patients with HER2 positive recurrent or metastatic breast cancer: A multicentric Turkish Oncology Group (TOG) trial.

Saip P, Eralp Y, Sen F, Karaca H, Ozkan M, Cetin B, Benekli M, Kucukoner M, Isikdogan A, Un O, Basaran G, Onur H.SourceDepartment of Medical Oncology, Institute of Oncology, Istanbul University, Capa, Istanbul 34390, Turkey. Electronic address: pinarsaip@gmail.com.
Breast (Edinburgh, Scotland).Breast.2013 Oct;22(5):628-33. doi: 10.1016/j.breast.2013.07.048. Epub 2013 Aug 16.
BACKGROUND: The aim of this explorative phase II study was to evaluate the activity and safety of lapatinib in combination with intravenous vinorelbine in women with HER2 positive metastatic or recurrent breast cancer.METHODS: Twenty-nine patients were enrolled. The primary objectives were response
PMID 23954396

Phase II study of docetaxel and vinorelbine as adjuvant chemotherapy for resected non-small cell lung cancers.

Chaft JE, Rekhtman N, Sima CS, Rusch V, Kris MG, Zakowski M, Azzoli CG.SourceThoracic Oncology Service, Division of Solid Tumor Oncology, Department of Medicine, Memorial Sloan-Kettering Cancer Center, 300 E, 66th Street, New York, NY, 10065, USA, chaftj@mskcc.org.
Cancer chemotherapy and pharmacology.Cancer Chemother Pharmacol.2013 Oct;72(4):931-4. doi: 10.1007/s00280-013-2263-1. Epub 2013 Aug 22.
PURPOSE: For patients with resected stage II-III non-small cell lung cancers (NSCLCs), adjuvant cisplatin-based chemotherapy improves survival over surgery alone. For cisplatin ineligible patients, there is no standard adjuvant option. We evaluated drug delivery and toxicity of docetaxel and vinorel
PMID 23975243

Japanese Journal

Rapid and sensitive determination of vinorelbine in human plasma by liquid chromatography-tandem mass spectrometry and its pharmacokinetic application

QIAN Jun,WANG Yixuan,CHANG Jianhua,ZHANG Jian,WANG Jialei,HU Xichun
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences 879(9), 662-668, 2011-03-15
NAID 10029518301

シスプラチン・ビノレルビン併用化学療法における肺癌治療クリニカルパス標準化の試み

柴田雅彦
日本クリニカルパス学会誌 13(2), 123-129, 2011
NAID 40019159707

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★リンクテーブル★

リンク元	「ビノレルビン」「ビンカアルカロイド」
拡張検索	「vinorelbine ditartrate」

「ビノレルビン」

Vinorelbine
Systematic (IUPAC) name
	4-(acetyloxy)- 6,7-didehydro- 15-((2R,6R,8S)-4-ethyl- 1,3,6,7,8,9-hexahydro- 8-(methoxycarbonyl)- 2,6-methano- 2H-azecino(4,3-b)indol-8-yl)- 3-hydroxy- 16-methoxy- 1-methyl- methyl ester,
Clinical data
Trade names	Navelbine
AHFS/Drugs.com	monograph
MedlinePlus	a695013
Pregnancy; category	AU: D; US: D (Evidence of risk); ;
Legal status	UK: POM (Prescription only); US: ℞-only;
Routes of; administration	intravenous, oral
Pharmacokinetic data
Bioavailability	43 ± 14% (oral)
Protein binding	79 to 91%
Metabolism	Hepatic (CYP3A4-mediated)
Biological half-life	27.7 to 43.6 hours
Excretion	Fecal (46%) and renal (18%)
Identifiers
CAS Number	71486-22-1
ATC code	L01CA04
PubChem	CID: 5311497
DrugBank	DB00361
ChemSpider	4470974
UNII	Q6C979R91Y
KEGG	D08680
ChEMBL	CHEMBL607994
Chemical data
Formula	C45H54N4O8
Molecular mass	778.932 g/mol
	SMILES O=C(OC)[C@]4(c2nc1ccccc1c2CN3CC(=C/[C@H](C3)C4)\CC)c5c(OC)cc6c(c5)[C@@]89[C@@H](N6C)[C@@](O)(C(=O)OC)[C@H](OC(=O)C)[C@@]7(/C=C\CN([C@@H]78)CC9)CC ;
	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 ; Key:GBABOYUKABKIAF-IELIFDKJSA-N ;
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