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Vinflunine

CAT: 0804-HY-B0628Size: InquireDry Ice: NoHazardous: No
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CAT#:0804-HY-B0628Size:Inquire
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CAS Number
162652-95-1
UNSPSC Description
Vinflunine is a type of fluorinated vinca alkaloid that has the ability to block mitosis and interact with tubulin[1][2][3].
Target Antigen
Microtubule/Tubulin
Type
Natural Products
Related Pathways
Cell Cycle/DNA Damage;Cytoskeleton
Applications
Cancer-programmed cell death
Field of Research
Cancer
Assay Protocol
https://www.medchemexpress.com/vinflunine.html
Solubility
10 mM in DMSO
Smiles
CC[C@@]12[C@@]3([H])[C@]4(CCN3CC=C2)[C@](N(C5=CC(OC)=C([C@@]6(C7=C(C[N@@]8C[C@](C[C@H](C8)C(F)(F)C)([H])C6)C9=CC=CC=C9N7)C(OC)=O)C=C54)C)([H])[C@](O)([C@@H]1OC(C)=O)C(OC)=O
Molecular Weight
816.93
References & Citations
[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.
Shipping Conditions
Room temperature
Clinical Information
Launched

Chemical Information

Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-((2R,4R,6S,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, (2beta,3beta,4beta,5alpha,12R,19alpha)-

Vinflunine is an organic heteropentacyclic compound and an organic heterotetracyclic compound that is vinorelbine in which the tetrahydropyridine moiety of the heterotetracyclic part of the molecule has been redced to the corresponding piperidine, and in which the ethyl group attached to this ring has been replaced by a 1,1-difluoroethyl group. It has a role as an antineoplastic agent. It is a methyl ester, a vinca alkaloid, an organic heterotetracyclic compound, an organic heteropentacyclic compound, an acetate ester and a semisynthetic derivative. It is functionally related to a vinorelbine.

CAS Number162652-95-1
PubChem CID10629256
IUPAC Namemethyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-4-[(12S,14S,16R)-16-(1,1-difluoroethyl)-12-methoxycarbonyl-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8-tetraen-12-yl]-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,13-tetraene-10-carboxylate
Molecular FormulaC45H54F2N4O8
Molecular Weight816.9
XLogP4.4
Topological Polar Surface Area134
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count13
Rotatable Bond Count10
Heavy Atom Count59
Formal Charge0
Complexity1720
SMILES
CC[C@@]12C=CCN3[C@@H]1[C@]4(CC3)[C@H]([C@]([C@@H]2OC(=O)C)(C(=O)OC)O)N(C5=CC(=C(C=C45)[C@]6(C[C@@H]7C[C@H](CN(C7)CC8=C6NC9=CC=CC=C89)C(C)(F)F)C(=O)OC)OC)C
InChI
InChI=1S/C45H54F2N4O8/c1-8-42-14-11-16-51-17-15-43(36(42)51)30-19-31(34(56-5)20-33(30)49(4)37(43)45(55,40(54)58-7)38(42)59-25(2)52)44(39(53)57-6)21-26-18-27(41(3,46)47)23-50(22-26)24-29-28-12-9-10-13-32(28)48-35(29)44/h9-14,19-20,26-27,36-38,48,55H,8,15-18,21-24H2,1-7H3/t26-,27+,36-,37+,38+,42+,43+,44-,45-/m0/s1
InChIKey
NMDYYWFGPIMTKO-KLCPSUAYSA-N
Chemical Structure
2D Structure
2D structure of Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-((2R,4R,6S,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, (2beta,3beta,4beta,5alpha,12R,19alpha)-
CAS: 162652-95-1
CID: 10629256
Formula: C45H54F2N4O8
MW: 816.9
Interactive 3D Structure
Loading 3D structure...
View on PubChemRaw 3D data
Computed Properties
PropertyValue
Molecular Weight816.9
XLogP34.4
Hydrogen Bond Donor Count2
Hydrogen Bond Acceptor Count13
Rotatable Bond Count10
Exact Mass816.39097102
Monoisotopic Mass816.39097102
Topological Polar Surface Area134 Ų
Heavy Atom Count59
Formal Charge0
Complexity1720
Isotope Atom Count0
Defined Atom Stereocenter Count9
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently-Bonded Unit Count1
Compound Is CanonicalizedYes

Alternative Products

CatalogName
MBS3611820-01Vinflunine
B2208-25Vinflunine tartrate
MBS6014769-01Vinflunine Ditartrate
291928-01Vinflunine Ditartrate discontinued

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