Vinflunine

Modify Date: 2025-08-20 21:45:04

Vinflunine structure	Common Name	Vinflunine
	CAS Number	162652-95-1	Molecular Weight	816.92900
	Density	1.39 g/cm3	Boiling Point	N/A
	Molecular Formula	C₄₅H₅₄F₂N₄O₈	Melting Point	N/A
	MSDS	N/A	Flash Point	N/A

Use of Vinflunine

Vinflunine is a new vinca alkaloid uniquely fluorinated with the properties of mitotic-arresting and tubulin-interacting activity.Target: Microtubule/TubulinThe major effects of Vinflunine on dynamic instability are a slowing of the microtubule growth rate, an increase in growth duration, and a reduction in shortening duration. The effects of Vinflunine on the readmilling rate is examined by following [3H]GTP incorporation into MAP-rich microtubules, and the IC50 is 0.42 μM [1]. Vinflunine induced mitotic accumulation with IC50 with 18.8 nM, which decreases the centromere dynamicity by 44% and increases the time centromeres spent ina paused state by 63% [2]. Treatment of Vinflunine induces a rapid change in endothelial cell shape: cells retracts and assumes a rounded morphology. Mean IC50 values are 9.9 × 10-5 M × 10-5 M for fibronectin and 5.0× 10-5 M × 10-5 M for type IV collagen. A short 4 hours exposure of endothelial cells to Vinflunine at 10-8 0.05). An ID50 value (dose which inhibits 50% of bFGF-induced neovascularisation) is calculated as 1 mg/kg. Low doses of Vinflunine reduce the number of experimental liver metastases by human LS174T colon cancer cell. A slight overall decrease in liver metastatic foci is already observed at the very low dose of 0.16 mg/kg Vinflunine, although maximal overall inhibition is reached at the maximal tolerated dose (MTD) of 20 mg/kg [3].

Name	Vinflunine
Synonym	More Synonyms

Description	Vinflunine is a new vinca alkaloid uniquely fluorinated with the properties of mitotic-arresting and tubulin-interacting activity.Target: Microtubule/TubulinThe major effects of Vinflunine on dynamic instability are a slowing of the microtubule growth rate, an increase in growth duration, and a reduction in shortening duration. The effects of Vinflunine on the readmilling rate is examined by following [3H]GTP incorporation into MAP-rich microtubules, and the IC50 is 0.42 μM [1]. Vinflunine induced mitotic accumulation with IC50 with 18.8 nM, which decreases the centromere dynamicity by 44% and increases the time centromeres spent ina paused state by 63% [2]. Treatment of Vinflunine induces a rapid change in endothelial cell shape: cells retracts and assumes a rounded morphology. Mean IC50 values are 9.9 × 10-5 M × 10-5 M for fibronectin and 5.0× 10-5 M × 10-5 M for type IV collagen. A short 4 hours exposure of endothelial cells to Vinflunine at 10-8 0.05). An ID50 value (dose which inhibits 50% of bFGF-induced neovascularisation) is calculated as 1 mg/kg. Low doses of Vinflunine reduce the number of experimental liver metastases by human LS174T colon cancer cell. A slight overall decrease in liver metastatic foci is already observed at the very low dose of 0.16 mg/kg Vinflunine, although maximal overall inhibition is reached at the maximal tolerated dose (MTD) of 20 mg/kg [3].
Related Catalog	Signaling Pathways >> Cell Cycle/DNA Damage >> Microtubule/Tubulin Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin Natural Products >> Alkaloid Research Areas >> Cancer
References	[1]. Ngan, V.K., et al., Novel actions of the antitumor drugs vinflunine and vinorelbine on microtubules. Cancer Res, 2000. 60(18): p. 5045-51. [2]. Lobert, S., et al., Vinca alkaloid-induced tubulin spiral formation correlates with cytotoxicity in the leukemic L1210 cell line. Biochemistry, 2000. 39(39): p. 12053-62. [3]. Kruczynski, A., et al., Anti-angiogenic, vascular-disrupting and anti-metastatic activities of vinflunine, the latest vinca alkaloid in clinical development. Eur J Cancer, 2006. 42(16): p. 2821-32.

Description

Related Catalog

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

Signaling Pathways >> Cytoskeleton >> Microtubule/Tubulin

Natural Products >> Alkaloid

Research Areas >> Cancer

References

[1]. Ngan, V.K., et al., Novel actions of the antitumor drugs vinflunine and vinorelbine on microtubules. Cancer Res, 2000. 60(18): p. 5045-51.

[2]. Lobert, S., et al., Vinca alkaloid-induced tubulin spiral formation correlates with cytotoxicity in the leukemic L1210 cell line. Biochemistry, 2000. 39(39): p. 12053-62.

[3]. Kruczynski, A., et al., Anti-angiogenic, vascular-disrupting and anti-metastatic activities of vinflunine, the latest vinca alkaloid in clinical development. Eur J Cancer, 2006. 42(16): p. 2821-32.

Density	1.39 g/cm3
Molecular Formula	C₄₅H₅₄F₂N₄O₈
Molecular Weight	816.92900
Exact Mass	816.39100
PSA	133.87000
LogP	5.01950
Index of Refraction	1.652
InChIKey	NMDYYWFGPIMTKO-ACNJXBQRSA-N
SMILES	CCC12C=CCN3CCC4(c5cc(C6(C(=O)OC)CC7CC(C(C)(F)F)CN(Cc8c6[nH]c6ccccc86)C7)c(OC)cc5N(C)C4C(O)(C(=O)OC)C1OC(C)=O)C32

Vinorelbine

CAS#:71486-22-1

~34%

Vinflunine

CAS#:162652-95-1

Literature: Fahy; Duflos; Ribet; Jacquesy; Berrier; Jouannetaud; Zunino Journal of the American Chemical Society, 1997 , vol. 119, # 36 p. 8576 - 8577

Precursor 1
CAS#:71486-22-1 Vinorelbine
DownStream 0

4'-Deoxy-20'

Methyl (2β,3β,4β,5α,12β,19α)-4-acetoxy-15-[(12S,14R,16R)-16-(1,1-difluoroethyl)-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8-tetraen-12-yl]- 3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate

4'-Deoxy-20',20'-difluoro-8'-norvincaleukoblastine

MFCD00938122

C'-Norvincaleukoblastine,4'-deoxy-20',20'-difluoro

aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(4R,6R,8S)-4-(1,1-difluoroethyl)-1,3,4,5,6,7,8,9-octahydro-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)-

20',20'-difluoro-3',4'-dihydrovinorelbine

Methyl (2β,3β,4β,5α,12β,19α)-4-acetoxy-15-[(12S,14R,16R)-16-(1,1-difluoroethyl)-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0.0]octadeca-3(11),4,6,8-tetraen-12-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate

C45H54F2N4O8

Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(4R,6R,8S)-4-(1,1-difluoroethyl)-1,3,4,5,6,7,8,9-octahydro-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)-

methyl (2β,3β,4β,5α,12β,19α)-4-(acetyloxy)-15-[(4R,6R,8S)-4-(1,1-difluoroethyl)-8-(methoxycarbonyl)-1,3,4,5,6,7,8,9-octahydro-2,6-methanoazecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-6,7-didehydroaspidospermidine-3-carboxylate

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China
Product Name: Vinflunine
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China
Product Name: Vinflunine
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Henan Tianfu Chemical Co., Ltd.
China
Product Name: Vinflunine
Price: $Inquiry/1kg $Inquiry/25kg $Inquiry/1000kg $Inquiry/10ton
Purity: 99.0%
Delivery: Inquiry
Contact: Anson
Email: info@tianfuchem.com

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Vinflunine

Use of Vinflunine

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Vinflunine Biological Activity

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Precursor & DownStream

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