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Chemistry

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Also known as: Vinorelbine tartrate, 125317-39-7, Vinorelbine ditartrate, 5'-noranhydrovinoblastine tartrate, Vinorelbine ditartrate salt hydrate, Vinorelbinetartrate
Molecular Formula
C53H66N4O20
Molecular Weight
1079.1  g/mol
InChI Key
CILBMBUYJCWATM-LNLXBTRNSA-N

Navelbine Tartrate
A vinca alkaloid related to VINBLASTINE that is used as a first-line treatment for NON-SMALL CELL LUNG CANCER, or for advanced or metastatic BREAST CANCER refractory to treatment with ANTHRACYCLINES.
1 2D Structure

Navelbine Tartrate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2R,3R)-2,3-dihydroxybutanedioic acid;methyl (1R,9R,10S,11R,12R,19R)-11-acetyloxy-12-ethyl-4-[(12S,14S)-16-ethyl-12-methoxycarbonyl-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8,15-pentaen-12-yl]-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
2.1.2 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-/m111/s1
2.1.3 InChI Key
CILBMBUYJCWATM-LNLXBTRNSA-N
2.1.4 Canonical SMILES
CCC1=CC2CC(C3=C(CN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)C78CCN9C7C(C=CC9)(C(C(C8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC.C(C(C(=O)O)O)(C(=O)O)O.C(C(C(=O)O)O)(C(=O)O)O
2.1.5 Isomeric SMILES
CCC1=C[C@@H]2C[C@@](C3=C(CN(C2)C1)C4=CC=CC=C4N3)(C5=C(C=C6C(=C5)[C@]78CCN9[C@H]7[C@@](C=CC9)([C@H]([C@@]([C@@H]8N6C)(C(=O)OC)O)OC(=O)C)CC)OC)C(=O)OC.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O.[C@@H]([C@H](C(=O)O)O)(C(=O)O)O
2.2 Synonyms
2.2.1 MeSH Synonyms

1. 5' Nor Anhydrovinblastine

2. 5'-nor-anhydrovinblastine

3. Kw 2307

4. Kw-2307

5. Kw2307

6. Navelbine

7. Vinorelbine

8. Vinorelbine Tartrate

2.2.2 Depositor-Supplied Synonyms

1. Vinorelbine Tartrate

2. 125317-39-7

3. Vinorelbine Ditartrate

4. 5'-noranhydrovinoblastine Tartrate

5. Vinorelbine Ditartrate Salt Hydrate

6. Vinorelbinetartrate

7. 1217449-57-4

8. Vinorelbine, Ditartrate

9. Vinorelbine Ditartaric Acid

10. 317v397

11. Q-100110

12. (2r,3r)-2,3-dihydroxybutanedioic Acid;methyl (1r,9r,10s,11r,12r,19r)-11-acetyloxy-12-ethyl-4-[(12s,14s)-16-ethyl-12-methoxycarbonyl-1,10-diazatetracyclo[12.3.1.03,11.04,9]octadeca-3(11),4,6,8,15-pentaen-12-yl]-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

13. Methyl (3ar,3a1r,4r,5s,5ar,10br)-4-acetoxy-3a-ethyl-9-((6s,8s)-4-ethyl-8-(methoxycarbonyl)-1,3,6,7,8,9-hexahydro-2,6-methanoazecino[4,3-b]indol-8-yl)-5-hydroxy-8-methoxy-6-methyl-3a,3a1,4,5,5a,6,11,12-octahydro-1h-indolizino[8,1-cd]carbazole-5-carboxylate Bis((2r,3r)-2,3-dihydroxysuccinate)

2.3 Create Date
2010-03-29
3 Chemical and Physical Properties
Molecular Weight 1079.1 g/mol
Molecular Formula C53H66N4O20
Hydrogen Bond Donor Count10
Hydrogen Bond Acceptor Count23
Rotatable Bond Count16
Exact Mass1078.42704051 g/mol
Monoisotopic Mass1078.42704051 g/mol
Topological Polar Surface Area364 Ų
Heavy Atom Count77
Formal Charge0
Complexity1820
Isotope Atom Count0
Defined Atom Stereocenter Count12
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count3
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameVINORELBINE TARTRATE
Active IngredientVINORELBINE TARTRATE
CompanyACTAVIS TOTOWA (Application Number: A078011); DR REDDYS LABS LTD (Application Number: A202017); FRESENIUS KABI USA (Application Number: A076849); HOSPIRA (Application Number: A076827); JIANGSU HANSOH PHARM (Application Number: A091106); TEVA PHARMS USA (Application Number: A076028); WEST-WARD PHARMS INT (Application Number: A075992); WEST-WARD PHARMS INT (Application Number: A076461)

2 of 2  
Drug NameNAVELBINE
Active IngredientVINORELBINE TARTRATE
CompanyPIERRE FABRE (Application Number: N020388)

5 Pharmacology and Biochemistry
5.1 MeSH Pharmacological Classification

Antineoplastic Agents, Phytogenic

Agents obtained from higher plants that have demonstrable cytostatic or antineoplastic activity. (See all compounds classified as Antineoplastic Agents, Phytogenic.)


Tubulin Modulators

Agents that interact with TUBULIN to inhibit or promote polymerization of MICROTUBULES. (See all compounds classified as Tubulin Modulators.)


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