Vinorelbine Tartrate

Synopsis, Chemistry

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Also known as: Vinorelbine tartrate, 125317-39-7, Kw 2307, Navelbine (tn), Vinorelbine ditartrate (jan), Vinorelbine bitartarate

Molecular Formula

C₅₃H₆₆N₄O₂₀

Molecular Weight

1079.1 g/mol

InChI Key

CILBMBUYJCWATM-NPJYPKOYSA-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

Vinorelbine 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)-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-/m011/s1

2.1.3 InChI Key

CILBMBUYJCWATM-NPJYPKOYSA-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=CC2C[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. Kw 2307

4. Navelbine (tn)

5. Vinorelbine Ditartrate (jan)

6. Vinorelbine Bitartarate

7. Vinorelbine Tartrate (usp)

8. Schembl4334811

9. Schembl16766511

10. Amy22244

11. S4269

12. Akos037748842

13. Ccg-270632

14. As-75352

15. D01935

16. Bis((2r,3r)-2,3-dihydroxybutanedioic Acid); Methyl (1r,9r,10s,11r,12r,19r)-11-(acetyloxy)-12-ethyl-4-[(12s)-16-ethyl-12-(methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0(3),(1)(1).0?,?]octadeca-3(11),4,6,8,15-pentaen-12-yl]-10-hydroxy-5-methoxy-8-methyl-8,16-diazapentacyclo[10.6.1.0(1),?.0(2),?.0(1)?,(1)?]nonadeca-2(7),3,5,13-tetraene-10-carboxylate

2.3 Create Date

2005-06-24

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	11
Undefined Atom Stereocenter Count	1
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
Drug Label	Vinorelbine Tartrate Injection is for intravenous administration. Each vial contains vinorelbine tartrate equivalent to 10mg (1-mL vial) or 50 mg (5-mL vial) vinorelbine in Water for Injection, USP. No preservatives or other additives are present....
Active Ingredient	Vinorelbine tartrate
Dosage Form	Injectable
Route	Injection
Strength	eq 10mg base/ml
Market Status	Prescription
Company	Bedford; Hospira; Jiangsu Hansoh Pharm; Teva Pharms Usa; Actavis Elizabeth; Fresenius Kabi Usa; Hikma Maple; Ebewe Pharma; Dr Reddys Labs

2 of 2
Drug Name	Vinorelbine tartrate
Drug Label	Vinorelbine Tartrate Injection is for intravenous administration. Each vial contains vinorelbine tartrate equivalent to 10mg (1-mL vial) or 50 mg (5-mL vial) vinorelbine in Water for Injection, USP. No preservatives or other additives are present....
Active Ingredient	Vinorelbine tartrate
Dosage Form	Injectable
Route	Injection
Strength	eq 10mg base/ml
Market Status	Prescription
Company	Bedford; Hospira; Jiangsu Hansoh Pharm; Teva Pharms Usa; Actavis Elizabeth; Fresenius Kabi Usa; Hikma Maple; Ebewe Pharma; Dr Reddys Labs

5 Pharmacology and Biochemistry

5.1 MeSH Pharmacological Classification

Tubulin Modulators

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

Antineoplastic Agents, Phytogenic

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