Navelbine Tartrate

Synopsis, 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

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 Formula	C₅₃H₆₆N₄O₂₀
Molecular Weight	1079.1 g/mol
Hydrogen Bond Donor Count	10
Hydrogen Bond Acceptor Count	23
Rotatable Bond Count	16
Exact Mass	1078.42704051 g/mol
Monoisotopic Mass	1078.42704051 g/mol
Topological Polar Surface Area	364 Å²
Heavy Atom Count	77
Formal Charge	0
Complexity	1820
Isotope Atom Count	0
Defined Atom Stereocenter Count	12
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	3

4 Drug and Medication Information

4.1 Drug Information

1 of 2
Drug Name	VINORELBINE TARTRATE
Active Ingredient	VINORELBINE TARTRATE
Company	ACTAVIS 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 Name	NAVELBINE
Active Ingredient	VINORELBINE TARTRATE
Company	PIERRE 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.)