Overview Pharmacological effects Clinical evaluation Adverse reactions Chemical properties Application
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Vinorelbine tartrate

Overview Pharmacological effects Clinical evaluation Adverse reactions Chemical properties Application
Product Name
Vinorelbine tartrate
CAS No.
125317-39-7
Chemical Name
Vinorelbine tartrate
Synonyms
NAVELBINE;VINORELBINE DITARTRATE;NVB;VINORELBINE BITARTRATE;c’-norvincaleukoblastine,3’,4’-didehydro-4’-dioxy-,(r-(r*,r*))-2,3-dihydroxy;Vinorelbin Tartrate;VINORELBINE TARTRATE USP STANDARD;3′,4′-Didehydro-4′-deoxy-C′-norvincaleukoblastine [R-(R*,R*)-2-3-dihydroxybutanedioate (1:2)salt], 5′-Noranhydrovinoblastine tartrate, KW-2307, NVB, Navelbine tartrate;(2β,3β,4β,5α,12R,19α)-4-(Acetyloxy)-6,7-didehydro-15-[(2R,6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylicacidmethylester;KW-2307
CBNumber
CB8761554
Molecular Formula
C53H66N4O20
Formula Weight
1079.11
MOL File
125317-39-7.mol
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Vinorelbine tartrate Property

Melting point:
181-183°C
storage temp. 
2-8°C
solubility 
H2O: 10 mg/mL
form 
powder
color 
off-white
Stability:
Light Sensitive, Temperature Sensitive
InChI
InChI=1/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-/s3
InChIKey
PMDHUNWDGZSEMN-WTUOTUPFSA-N
SMILES
[C@]123CCN4CC=C[C@@](CC)([C@@H](OC(=O)C)[C@](O)(C(=O)OC)[C@@H]1N(C)C1=CC(OC)=C([C@@]5(C(OC)=O)C[C@H]6C=C(C[N@](C6)CC6C7=C(C=CC=C7)NC5=6)CC)C=C21)[C@@H]34.[C@H](O)(C(=O)O)[C@@H](O)C(=O)O.[C@H](O)(C(=O)O)[C@@H](O)C(=O)O |&1:0,7,10,15,21,30,36,40,56,57,62,67,72,r|
CAS DataBase Reference
125317-39-7(CAS DataBase Reference)
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Safety

Hazard Codes 
Xi
Risk Statements 
43
Safety Statements 
26-36
RIDADR 
UN 1544PSN1 6.1 / PGII
WGK Germany 
3
HS Code 
29339900
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H317May cause an allergic skin reaction

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
Y0001939
Product name
Vinorelbine for peak identification B
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
Y0001939
Price
$150
Updated
2024/03/01
Sigma-Aldrich
Product number
Y0001938
Product name
Vinorelbine for peak identification A
Purity
European Pharmacopoeia (EP) Reference Standard
Packaging
Y0001938
Price
$176
Updated
2024/03/01
Sigma-Aldrich
Product number
V2264
Product name
Vinorelbine ditartrate salt hydrate
Purity
≥98% (HPLC), powder
Packaging
5mg
Price
$114
Updated
2024/03/01
Sigma-Aldrich
Product number
PHR3160
Product name
Vinorelbine Tartrate
Purity
pharmaceutical secondary standard, certified reference material
Packaging
500MG
Price
$936
Updated
2024/03/01
Sigma-Aldrich
Product number
1714506
Product name
Vinorelbine tartrate
Packaging
200mg
Price
$4200
Updated
2024/03/01
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Vinorelbine tartrate Chemical Properties,Usage,Production

Overview

Vinorelbine belongs to vinblastine derivatives, its action is similar to vincristine. It is first marketed in 1989 in France. The main role is to combine tubulin, consequently, it causes microtubule formation disorder during cells mitosis.
Vinorelbine belongs to cycle specific drugs, it is used clinically in the treatment of non-small cell lung cancer (NSCLC) and breast cancer, ovarian cancer, head and neck squamous cell carcinoma, leukemia. In addition,it also has a strong inhibitory effect on small cell lung cancer, colon cancer, brain tumors, malignant melanoma.

Pharmacological effects

Vinorelbine tartrate is the tartrate form of vinorelbine ,it is a semi-synthetic  vincristine compound, it belongs to M phase specific drugs, mechanism of action is similar to vincristine . Mainly it , by selectively blocking mitotic cell tubulin polymerization to form microtubule and  inducing tubulin depolymerization , impedes spindle microtubules,and it makes cell division stop  in the middle, and it has few effect on the synthetic tubulin in the shaft of nerve cells. Since NVB affinity for axonal microtubules is poor, only when there is a high concentration of it ,it has effect on axonal , so it has the lower neurotoxicity than other vincristine drugs,and it  has a greater therapeutic index. Human pharmacokinetics of vinorelbine show that after intravenous administration there is a three-compartment model, the volume  of distribution is large , PPB is up to 50% to 80%, plasma clearance rate is high, the terminal elimination phase T1/2 is 40 h, it has a rapid tissue distribution, concentration in tissues is significantly higher than vincristine (VCR), vindesine (VDS). Plasma clearance is 0.8 L/(kg • h),it is mainly through biliary secretion, and it is excreted with the feces, urine excretion accounts for 10% to 15%.It has a higher efficacy and less adverse reactions of the nervous system.

Clinical evaluation

Numerous clinical studies have shown that vinorelbine is one of the most effective drugs for the treatment of non-small cell lung cancer and breast cancer, single agent response rate is 14% to 35% and 30% to 60% respectively. And DDP combination chemotherapy in NSCLC and with doxorubicin combination therapy of breast cancer, efficiency is up to 30% to 50% and 50% to 77%, respectively. It has a good effect on ovarian cancer, malignant lymphoma, head and neck cancer, esophageal cancer.

Adverse reactions

  • Vinorelbine hematologic toxicity is dose-limiting , mainly it is neutropenia, which mostly restore  within 7d, it has a certain influence on red blood cells , thrombocytopenia and anemia incidence is less than 2%.
  • Neurotoxicity mainly performs as tendon reflexes (about 25%), occasional paresthesia, few patients may have gastrointestinal autonomic nerve paralysis induced constipation (17%~41%),  paralytic ileus is rare  , 2% 6% of the patients suffer finger (toe) numb, but the incidence is much lower than the VCR and VDS.
  • Incidence of gastrointestinal side effects is less than 10%. Occasionally, nausea, vomiting, dyspnea, and bronchospasm, often occur in a few minutes or several hours after treatment . Alopecia incidence is less than 10%.
  • Vinorelbine drug extravasation into the surrounding tissue can cause burning, injection site phlebitis, local tissue necrosis, ulceration, cellulitis.
  • Myelosuppression is dose-limiting toxicity. 3 to 5 days after the medication, transient myelosuppression can occur, usually it can recover within 10 days, attention should be paid to prevent infection. Neurotoxicity is visible.

Chemical properties

White or almost white powder or crystalline powder, odorless.

Application

Antineoplastic agents

Chemical Properties

Pale Yellow Powder

Uses

Vinorelbine Bitartrate is an antineoplastic.

Definition

ChEBI: The L-(+)-tartrate salt of vinorelbine.

brand name

Navelbine (Pierre).

General Description

Vinorelbine ditartrate is available in 1- and 5-mL vials at aconcentration of 10 mg/mL for IV use. It is FDA approvedfor the treatment of NSCLC. The agent has also been usedin treating metastatic breast cancer, cervical cancer, uterinecancer, and lung cancer especially in older patients or thosewith physical difficulties. Vinorelbine is the most lipophilicof the vinca alkaloids because of modifications of thecatharanthine ring system and dehydration of the piperidinering. This allows the agent to be quickly taken up into cellsincluding lung tissue where concentrations are 300-foldhigher than plasma concentrations. This is 3 to 13 timeshigher than the lung concentrations seen with vincristine.The agent is highly protein bound (80%–91%) and metabolizedby CYP3A. The major metabolite seen is the 4-Odesacetylderivative, which is equally active with the parentbut only formed in small quantities. The agent is eliminatedprimarily (33%–88%) in the bile with some appearing inthe urine (16%–30%). The elimination half-life is 27 to43 hours. The toxicities seen for vinorelbine includemyelosuppression, which is dose limiting but ceases upondiscontinuation of drug. This is most commonly seen as aneutropenia, and patient’s neutrophil count should be monitoredprior to and during therapy to decrease the chanceof infection. Additional toxicities include nausea/vomiting,elevation of liver function tests, alopecia, generalized fatigue，and inappropriate secretion of antidiuretic hormone.Neurotoxicity is seen with vinorelbine but occurs to a lesserdegree compared with other vinca alkaloids because of itsdecreased affinity for axonal microtubules.

Biological Activity

Selective mitotic microtubule antagonist that exhibits > 20 fold selectivity over axonal microtubules. Inhibits proliferation of multiple human tumor cell lines (IC 50 = 1.25 nM in HeLa cells) and blocks metaphase/anaphase transition by suppression of microtubule dynamics (IC 50 = 3.8 nM). Reduces spindle length by 29% and inhibits microtubule polymerization at micromolar concentrations.

Biochem/physiol Actions

Vinorelbine is a potent anti-mitotic, anti-tumor agent. Vinorelbine inhibits microtubule assembly. Low neurotoxicity is related to its higher affinity for mitotic microtubules than for axonal microtubules.

Vinorelbine tartrate Preparation Products And Raw materials

Raw materials

Preparation Products

Vinorelbine
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View Lastest Price from Vinorelbine tartrate manufacturers

WUHAN FORTUNA CHEMICAL CO., LTD
Product
Vinorelbine tartrate 125317-39-7
Price
US $0.00/g
Min. Order
1g
Purity
98%-102%; USP
Supply Ability
1000g
Release date
2021-09-17
S&Y Biochem Co.,Ltd
Product
Vinorelbine tartrate 125317-39-7
Price
US $1.00/G
Min. Order
1G
Purity
99
Supply Ability
1000
Release date
2024-09-23
Baoji Guokang Bio-Technology Co., Ltd.
Product
Vinorelbine tartrate 125317-39-7
Price
US $1556.00/g/Bag
Min. Order
10g
Purity
99%
Supply Ability
1kg
Release date
2021-06-03

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  • 3′,4′-Didehydro-4′-deoxy-C′-norvincaleukoblastine [R-(R*,R*)-2-3-dihydroxybutanedioate (1:2)salt], 5′-Noranhydrovinoblastine tartrate, KW-2307, NVB, Navelbine tartrate
  • VINORELBINEDITARTRATE SALT HYDRATE
  • VINORELBINE TARTRATE USP STANDARD
  • VINORELBINE TARTRATE, NAVELBINE
  • VINORELBINE RELATED COMPOUND A4-O-DEACETYLVINORELBINE TARTRATE USP STANDARD
  • VINORELBINE TARTRATE, USP
  • VinorelbineTartrateUsp28
  • butanedioate(1:2)
  • c’-norvincaleukoblastine,3’,4’-didehydro-4’-dioxy-,(r-(r*,r*))-2,3-dihydroxy
  • NVB
  • NAVELBINE
  • NAVELBINE TARTRATE
  • VINORELBINE BITARTRATE
  • VINORELBINE DITARTARIC ACID
  • VINORELBINE DITARTRATE
  • VINORELBINE DITARTRATE SALT
  • VINORELBINE TARTRATE
  • VINORELBINE(RG)
  • Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(2R,6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2b,3b,4b,5a,12b,19a)-, (2R,3R)-2,3-dihydroxybutanedioate (1:2) (salt)
  • Aspidospermidine-3-carboxylic acid, 4-(acetyloxy)-6,7-didehydro-15-[(2R,6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methyl-, methyl ester, (2b,3b,4b,5a,12R,19a)-, (2R,3R)-2,3-dih
  • C'-Norvincaleukoblastine, 3',4'-didehydro-4'-deoxy-, [R-(R*,R*)]-2,3-dihydroxybutanedioate (1:2) (salt)
  • Navelbine ditartrate
  • Nor-5'-anhydrovinblastine ditartrate
  • Vinorelbin Tartrate
  • 5'-NORANHYDROVINOBLASTINE TARTRATE
  • 3',4'-DIDEHYDRO-4'-DEOXY-C'-NORVINCALEUKOBLASTINE [R-(R*,R*)-2-3-DIHYDROXYBUTANEDIOATE (1:2) SALT]
  • Pacilitaxel
  • Vinorelbine ditartrate, Vinorelbine bitartrate, VRLB,KW – 2307 NVB
  • Vinorelbine Ditartrate salt hydrate, ≥98%(HPLC)
  • KW-2307
  • Vinorelbine Bitartarate
  • (2β,3β,4β,5α,12R,19α)-4-(Acetyloxy)-6,7-didehydro-15-[(2R,6R,8S)-4-ethyl-1,3,6,7,8,9-hexahydro-8-(methoxycarbonyl)-2,6-methano-2H-azecino[4,3-b]indol-8-yl]-3-hydroxy-16-methoxy-1-methylaspidospermidine-3-carboxylicacidmethylester
  • Vinorelbine ditartrate salt hydrate,3′,4′-Didehydro-4′-deoxy-C′-norvincaleukoblastine [R-(R*,R*)-2-3-dihydroxybutanedioate (1:2)salt], 5′-Noranhydrovinoblastine tartrate, KW-2307, NVB, Navelbine tartr
  • Vinorelbine Tartrate (200 mg)
  • Methyl (1R,9R,10S,11R,12R,19R)-11-(acetyloxy)-12-ethyl-4-[(1R,12S,14R)-16-ethyl-12-(Methoxycarbonyl)-1,10-diazatetracyclo[12.3.1.0^{3,11}.0^{4,9}]octadeca-3(11),4(9),5,7,15-pentaen-12-yl]-10-hydroxy-5-Methoxy-8-Methyl-8,16-diazapentacyclo[10.6.1.0^{1,9}.0
  • Vinorelbine ditartate
  • lbine Ditartrate
  • Vinoreline Tartrate
  • 5μ-Noranhydrovinoblastine tartrate, KW-2307, Navelbine tartrate, NVB, 3μ,4μ-Didehydro-4μ-deoxy-Cμ-norvincaleukoblastine [R-(R*,R*)-2-3-dihydroxybutanedioate (1:2)salt]
  • Vinorelbine hydrate ditartrate salt
  • Vinorelbine Tartrate USP/EP
  • 3',4'-Didehydro-4'-deoxy-C'-norvincaleukoblastine Ditartrate
  • Eunades
  • Vinorelbin artrate
  • vinorelbine L-tartrate
  • Vinorelbine tartrate CRS
  • Vinorelbine tartrate cas 125317-39-7
  • inorelbine tartrate
  • Vinorelbine tartrate USP/EP/BP
  • Vinorelbine Bitartrate (10mM in DMSO)
  • Vinorelbine ditartrate (KW-2307)
  • Vinorelbine DitartrateQ: What is Vinorelbine Ditartrate Q: What is the CAS Number of Vinorelbine Ditartrate Q: What is the storage condition of Vinorelbine Ditartrate Q: What are the applications of Vinorelbine Ditartrate
  • Vinorelbine-D3 DitartrateQ: What is Vinorelbine-D3 Ditartrate Q: What is the CAS Number of Vinorelbine-D3 Ditartrate
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  • Methyl (3aR,3a1R,4R,5S,5aR,10bR)-4-acetoxy-3a-ethyl-9-((8R)-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)
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