(2R,3R)-2,3-dihydroxybutanedioic acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-4-[(12S,14S)-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

• ChemBase ID: 179511
• Molecular Formular: C49H60F2N4O14
• Molecular Mass: 967.0159064
• Monoisotopic Mass: 966.40740906
• SMILES: [C@H]([C@@H](O)C(=O)O)(O)C(=O)O.c1cc2c(cc1)c1c([nH]2)[C@@](C[C@H]2CN(C1)CC(C2)C(C)(F)F)(C(=O)OC)c1c(cc2c(c1)[C@@]13[C@@H](N2C)[C@]([C@@H]([C@]2([C@@H]1N(CC=C2)CC3)CC)OC(=O)C)(C(=O)OC)O)OC
• Canonical SMILES: OC(=O)[C@@H]([C@H](C(=O)O)O)O.COc1cc2N(C)[C@@H]3[C@@]4(c2cc1[C@]1(C[C@H]2CN(Cc5c1[nH]c1c5cccc1)CC(C2)C(F)(F)C)C(=O)OC)CCN1[C@H]4[C@@]([C@H]([C@]3(O)C(=O)OC)OC(=O)C)(CC)C=CC1
• InChI: InChI=1S/C45H54F2N4O8.C4H6O6/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;5-1(3(7)8)2(6)4(9)10/h9-14,19-20,26-27,36-38,48,55H,8,15-18,21-24H2,1-7H3;1-2,5-6H,(H,7,8)(H,9,10)/t26?,27?,36-,37+,38+,42+,43+,44-,45-;1-,2-/m01/s1
• InChIKey: TXONSEMUKVZUON-YJVRPKELSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3R)-2,3-dihydroxybutanedioic acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-4-[(12S,14S)-16-(1,1-difluoroethyl)-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0^3,^1^1.0^4,^9]octadeca-3(11),4,6,8-tetraen-12-yl]-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2,4,6,13-tetraene-10-carboxylate
• IUPAC Traditional name: L(+)-tartaric acid methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-4-[(1R,12S,14S)-16-(1,1-difluoroethyl)-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0^3,^1^1.0^4,^9]octadeca-3(11),4,6,8-tetraen-12-yl]-12-ethyl-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^1,^9.0^2,^7.0^1^6,^1^9]nonadeca-2,4,6,13-tetraene-10-carboxylate
• Synonyms: (2β,3β,4β,5α,12β,19α)-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-methylaspidospermidine-3-carboxylic Acid Methyl Ester (2R,3R)-2,3-Dihydroxybutanedioate; 4'-Deoxy-20',20'-difluoro-5'-nor-vincaleukoblastine Ditartrate; 20',20'-Difluoro-3',4'-dihydrovinorelbine Ditartrate; BMS 710485; F 12158; Javlor; Vinflunine Ditartrate

Database IDs

• CAS Number: 194468-36-5
• PubChem SID: 164235421
• PubChem CID: 71752957

CALCULATED PROPERTIES

• Acid pKa: 10.868424
• H Acceptors: 8
• H Donor: 2
• LogD (pH = 5.5): -0.8781617
• LogD (pH = 7.4): 2.6256256
• Log P: 4.6458116
• Molar Refractivity: 216.5265 cm^3
• Polarizability: 84.801506 Å^3
• Polar Surface Area: 133.87 Å^2
• Rotatable Bonds: 13
• Lipinski's Rule of Five: false

PROPERTIES

Physical Property

• Solubility: DMSO
• Apperance: White Solid
• Melting Point: 244-246°C (dec)

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - V314500

Vinflunine is a semisynthetic Vinca alkaloid with microtubule destabilizing and antiangiogenic activity. Vinflunine is a derivative of Vinorelbine. Vinflunine is used as an antineoplastic.

REFERENCES

• Kruczynski, A., et al.: Crit. Rev. Oncol. Hematol., 40, 159 (2001)
• Fabre, C., et al.: Biochem. Pharmacol., 64, 733 (2001)
• Bennouna, J. et al.: Ann. Oncol., 14, 630 (2001)
• Bennouna, J., et al.: Expert Opin. Invest. Drugs, 14, 1259 (2005).