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
- External Links
- KEGG Drug
- D01935
- PubChem Compound
- 45358014
- ChemSpider
- 23089482
- Wikipedia
- Vinorelbine
- Predicted Properties
Property Value Source Water Solubility 0.0122 mg/mL ALOGPS logP 4.39 ALOGPS logP 4.65 Chemaxon logS -4.8 ALOGPS pKa (Strongest Acidic) 10.87 Chemaxon pKa (Strongest Basic) 8.66 Chemaxon Physiological Charge 2 Chemaxon Hydrogen Acceptor Count 8 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 133.87 Å2 Chemaxon Rotatable Bond Count 16 Chemaxon Refractivity 216.99 m3·mol-1 Chemaxon Polarizability 84.19 Å3 Chemaxon Number of Rings 9 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon