Vinorelbine tartrateProduct ingredient for Vinorelbine

Name
Vinorelbine tartrate
Drug Entry
Vinorelbine

Vinorelbine is an anti-mitotic chemotherapy drug that is used in the treatment of several types of malignancies, including breast cancer and non-small cell lung cancer (NSCLC) 5. It was initially approved in the USA in 1990's for the treatment of NSCLC 13.

It is a third-generation vinca alkaloid. The introduction of third-generation drugs (vinorelbine, gemcitabine, taxanes) in platinum combination improved survival of patients with advanced NSCLC, with very similar results from the various drugs. Treatment toxicities are considerable in the combination treatment setting 2.

A study was done on the clearance rate of vinorelbine on individuals with various single polymorphonuclear mutations. It was found that there was 4.3-fold variation in vinorelbine clearance across the cohort, suggesting a strong influence of genetics on the clearance of this drug 7.

Accession Number
DBSALT000447  (DBSALT001060)
Structure
Synonyms
Nor-5'-anhydrovinblastine ditartrate / Vinorelbine ditartarate
External IDs
KW 2307 / KW-2307
UNII
253GQW851Q
CAS Number
125317-39-7
Weight
Average: 1079.1059
Monoisotopic: 1078.427040572
Chemical Formula
C53H66N4O20
InChI Key
CILBMBUYJCWATM-KRQCOKQWSA-N
InChI
InChI=1S/C45H54N4O8.2C4H6O6/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;2*5-1(3(7)8)2(6)4(9)10/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3;2*1-2,5-6H,(H,7,8)(H,9,10)/t28-,37-,38?,39+,42+,43+,44-,45-;2*1-,2-/m011/s1
IUPAC Name
bis((2R,3R)-2,3-dihydroxybutanedioic acid); methyl (1R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(12S,14R)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4,6,8,15-pentaen-12-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0^{2,7}.0^{16,19}]nonadeca-2,4,6,13-tetraene-10-carboxylate
SMILES
[H][C@](O)(C(O)=O)[C@@]([H])(O)C(O)=O.[H][C@](O)(C(O)=O)[C@@]([H])(O)C(O)=O.[H]C12N(C)C3=CC(OC)=C(C=C3[C@@]11CCN3CC=C[C@](CC)([C@@]13[H])[C@@]([H])(OC(C)=O)[C@]2(O)C(=O)OC)[C@]1(C[C@@]2([H])CN(CC(CC)=C2)CC2=C1NC1=CC=CC=C21)C(=O)OC
KEGG Drug
D01935
PubChem Compound
45358014
ChemSpider
23089482
Wikipedia
Vinorelbine
Predicted Properties
PropertyValueSource
Water Solubility0.0122 mg/mLALOGPS
logP4.39ALOGPS
logP4.65Chemaxon
logS-4.8ALOGPS
pKa (Strongest Acidic)10.87Chemaxon
pKa (Strongest Basic)8.66Chemaxon
Physiological Charge2Chemaxon
Hydrogen Acceptor Count8Chemaxon
Hydrogen Donor Count2Chemaxon
Polar Surface Area133.87 Å2Chemaxon
Rotatable Bond Count16Chemaxon
Refractivity216.99 m3·mol-1Chemaxon
Polarizability84.19 Å3Chemaxon
Number of Rings9Chemaxon
Bioavailability0Chemaxon
Rule of FiveNoChemaxon
Ghose FilterNoChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon