Vinorelbine

Names

[ Name ]:
Vinorelbine

[Synonym ]:
Methyl (2β,3β,4β,5α,12β,19α)-4-acetoxy-15-[(12S)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
8-methylsulfanyl-5-nonylsulfanyl-quinoline
aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(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, (2β,3β,4β,5α,12β,19α)-
vinorebline
3',4'-didehydro-4'-desoxy-8'-norvincaleucoblastine
5-Nonylthio-8-methylthio-chinolin
5'-noranhydrovinblastine
vinorelbene
Methyl (2β,3β,4β,5α,12β,19α)-4-acetoxy-15-[(12S)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8,15-pentaen-12-yl]-3-hydroxy-16-methox y-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate
Quinoline,8-(methylthio)-5-(nonylthio)
Vinorelbine
Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(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-, meth ;yl ester, (2β,3β,4β,5α,12β,19α)-

Biological Activity

[Description]:

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

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin

Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

Research Areas >> Cancer

[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].

[Animal admin]

As defined by the study, VRL1 is diluted in 0.9% NaCl to a concentration of 1.5 mg/mL, and given IV over 5 minutes. The intended treatment interval is 7 days for up to 4 treatments. After receiving 4 weekly doses, cats are eligible to continue VRL treatment every 2 weeks at the owner's expense.

[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.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Molecular Formula ]:
C₄₅H₅₄N₄O₈

[ Molecular Weight ]:
778.932

[ Exact Mass ]:
778.394165

[ PSA ]:
133.87000

[ LogP ]:
4.69

[ Index of Refraction ]:
1.676

[ Storage condition ]:
2-8C

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RD2530000

CHEMICAL NAME :: C'-Norvincaleukoblastine, 3',4'-didehydro-4'-deoxy-

CAS REGISTRY NUMBER :: 71486-22-1

LAST UPDATED :: 199706

DATA ITEMS CITED :: 1

MOLECULAR FORMULA :: C45-H54-N4-O8

MOLECULAR WEIGHT :: 779.03

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 26 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: GTKRDX Gan to Kagaku Ryoho. Cancer and Chemotherapy. (1-8-9 Yaesu, Chuo-ku, Tokyo 103, Japan) V.1- 1974- Volume(issue)/page/year: 10,1050,1983

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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