Vinorelbine

Identification

Summary

Vinorelbine is a vinca alkaloid used in the treatment of metastatic non-small cell lung carcinoma (NSLC) and in conjunction with other drugs in locally advanced NSCLC.

Generic Name

Vinorelbine

DrugBank Accession Number

DB00361

Background

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.

Type

Small Molecule

Groups

Approved, Investigational

Structure

Similar Structures

Weight: Average: 778.947
Monoisotopic: 778.394164715
Chemical Formula: C₄₅H₅₄N₄O₈

Synonyms

5'-Noranhydrovinblastine
Vinorelbin
Vinorelbina
Vinorelbine
Vinorelbinum

External IDs

KW 2307 base

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Pharmacology

Indication

Vinorelbine tartrate is indicated for adults in the treatment of advanced non-small cell lung cancer (NSCLC), as a single therapy or in combination with other chemotherapeutic drugs ⁵.

Used in relapsed or refractory Hodgkin lymphoma, in combination with other chemotherapy agents ¹⁴.

For the treatment of desmoid tumor or aggressive fibromatosis, in combination with methotrexate ¹⁴.

For the treatment of recurrent or metastatic squamous cell head and neck cancer ¹⁴.

For the treatment of recurrent ovarian cancer ¹⁴.

For the treatment of metastatic breast cancer, in patients previously treated with anthracyline and/or taxane therapy ¹⁴.

For the treatment of HER2-positive, trastuzumab-resistant, advanced breast cancer in patients previously treated with a taxane, in combination with trastuzumab and everolimus ¹⁴.

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Associated Conditions

Indication Type	Indication	Combined Product Details	Approval Level	Patient Characteristics
Used in combination to treat	Locally advanced non-small cell lung cancer	Regimen in combination with: Cisplatin (DB00515)	••••••••••••	•••••••••• •••••••••
Treatment of	Metastatic breast cancer		••• •••••
Treatment of	Metastatic cervical cancer		••• •••••
Used in combination to treat	Metastatic non-small cell lung cancer	Regimen in combination with: Cisplatin (DB00515)	••••••••••••	•••••••••• •••••••••
Treatment of	Metastatic non-small cell lung cancer		••••••••••••	•••••••••••

Contraindications & Blackbox Warnings

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Pharmacodynamics

Vinorelbine is a semi-synthetic vinca-alkaloid with a wide spectrum of anti-tumor activity. The vinca-alkaloids are considered spindle poisons. They work by interfering with the polymerization of tubulin, a protein responsible for building the microtubule system which appears during cell division in proliferating cancer cells ¹¹.

Mechanism of action

Vinca alkaloids are structurally similar compounds composed of two multi-ringed units, vindoline, and catharanthine. Vinorelbine tartrate is a vinca alkaloid in which the catharanthine component is the target of structural modification ⁹, ¹⁰.

This structural modification contributes to unique pharmacologic properties.The antitumor activity of vinorelbine tartrate is believed to be owed to the inhibition of mitosis at metaphase via its interaction with tubulin ⁵.

Vinorelbine is a mitotic spindle poison that interferes with chromosomal segregation during mitosis, also known as cell division. It pauses cells at the G2/M phases, when present at concentrations close to the half maximal inhibitory concentration (IC50). Microtubules, which are derived from polymers of tubulin, are the main target of vinorelbine.

The chemical modification used to produce vinorelbine allows for the opening of the eight-member catharanthine ring with the formation of both a covalent and reversible bond with tubulin ¹¹.

The relative contribution of different microtubule-associated proteins in the production of tubulin vary between neural tissue and proliferating cells and this has important functional implications. The ability of vinorelbine to bind specifically to mitotic rather than other microtubules has been shown and may suggest that neurotoxicity is less likely to be a problem than with the molecular mechanism of action ¹¹.

As with other anti-microtubule agents, vinorelbine is known to contribute apoptosis in malignant cells. The exact mechanisms by which this process occurs are complex and many details are yet to be elucidated. The disarray of the microtubule structure has a number of effects, including the induction of tumor suppressor gene p53 and activation/inactivation of a number of protein kinases involved in essential signaling pathways, including p21 WAF1/CIP1 and Ras/Raf, PKC/PKA. These molecular changes lead to phosphorylation and consequently inactivation of the apoptosis inhibitor Bcl2. This, in turn, results in a decrease in the formation of heterodimers between Bcl2 and the pro-apoptotic gene BAX, stimulating the sequence of cell apoptosis ¹¹.

Vinorelbine tartrate also possibly interferes with amino acid, cyclic AMP and glutathione metabolism, calmodulin-dependent Ca++-transport ATPase activity, cellular respiration, and nucleic acid and lipid biosynthesis ⁵.

Target	Actions	Organism
ATubulin beta chain	antagonist inhibitor	Humans

Absorption

Vinorelbine is rapidly absorbed with peak serum concentration reached within 2 hours ⁵.

Vinorelbine is highly bound to platelets and lymphocytes and is also bound to alpha 1-acid glycoprotein, albumin, and lipoproteins ⁴.

Volume of distribution

The volume of distribution is large, indicating extensive extravascular distribution ⁴.

The steady-state volume of distribution values range from 25.4 to 40.1 L/kg, according to one study ⁷.

Widely distributed, with highest amounts found in elimination organs such as liver and kidneys, minimal in heart and brain ⁷.

Protein binding

80-90% ⁶

Metabolism

Vinorelbine undergoes substantial hepatic elimination in humans. Two metabolites of vinorelbine have been identified in human blood, plasma, and urine; vinorelbine N-oxide and deacetylvinorelbine. Deacetylvinorelbine has been demonstrated to be the primary metabolite of vinorelbine in humans, and has been shown to possess antitumor activity similar to vinorelbine ⁹, ¹⁰.

Vinorelbine is metabolized into two other minor metabolites, 20'-hydroxyvinorelbine and vinorelbine 6'-oxide ¹⁰.

Therapeutic doses of vinorelbine (30 mg/m2) yield very small, if any, quantifiable levels of either metabolite in blood or urine. The metabolism of vinorelbine is mediated by hepatic cytochrome P450 isoenzymes in the CYP3A subfamily ⁸, ⁴.

As the liver provides the main route for metabolism of the drug, patients with hepatic impairment may demonstrate increased toxicity with standard dosing, however, there are no available data on this. Likewise, the contribution of cytochrome P450 enzyme action to vinorelbine metabolism has potential implications in patients receiving other drugs metabolized by this route ¹¹.

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Vinorelbine
- 4-0-deacetyl Vinorelbine

Route of elimination

Vinorelbine undergoes substantial hepatic elimination in humans, with large amounts recovered in feces after intravenous administration to humans ⁵.

Urinary excretion of unchanged drug accounts for less than 20% of an intravenous dose, with fecal elimination accounting for an additional 30% to 60% ⁴.

After intravenous administration of radioactive vinorelbine, approximately 18% and 46% of administered radioactivity was recovered in urine and feces, respectively ⁷.

Half-life

The terminal phase half-life averaged 27.7 to 43.6 hours; the mean plasma clearances ranged from 0.97 to 1.26 L/hr/kg ⁴.

Clearance

The plasma clearance of vinorelbine is high, approaching the same as hepatic blood flow in humans, and its volume of distribution is large, indicating extensive extravascular distribution. In comparison to vinblastine or vincristine ⁴.

The clearance was found to be in the range of 0.29-1./26 L/ per kg in 4 clinical trials of patients receiving 30 mg/m2 of vinorelbine ¹².

Adverse Effects

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Toxicity

Due to the wide array of adverse effects of this drug, the toxicity of is categorized into organ systems ⁵.

Hematologic: Granulocytopenia was the primary dose-limiting toxicity with vinorelbine tartrate therapy; it is generally reversible and not cumulative. In one study, granulocytopenia resulted in hospitalizations for fever and/or sepsis in 8% of NSCLC and 9% of breast cancer patients ⁵. Infectious (septic) deaths occurred in about 1% of patients. Grade 3 or 4 anemia occurred in about 1% of lung cancer and approximately 14% of breast cancer patients. Blood transfusions were administered to 18% of patients who received vinorelbine tartrate therapy. The incidence of Grade 3 and 4 thrombocytopenia was found to be less than 1% ⁵.

Neurologic: Mild to moderate peripheral neuropathy may occur. Symptoms of paresthesia and hypesthesia are reported as the most commonly reported neurologic toxicities of this drug. The loss of deep tendon reflexes (DTR) occurs in less than 5% of patients, according to one study. The development of severe peripheral neuropathy is rare ⁵.

Dermatologic: Alopecia has been reported in only about 12% of patients and is usually reported as mild. Vinorelbine tartrate is a moderate vesicant, leading to injection site reactions. Symptoms include erythema, pain at the injection site and vein discoloration occurred in about 1/3 of all patients. Chemical phlebitis along the vein, near the site of injection, has been reported ⁵.

Respiratory: Shortness of breath was reported in 3% of NSCLC and 9% of breast cancer patients, and was severe in 2% of each patient population. Interstitial pulmonary changes have been documented in a few patients ⁵.

Gastrointestinal: Mild or moderate nausea symptoms occurred in 32% of NSCLC and 47% of breast cancer patients treated with vinorelbine tartrate. Severe nausea was occurred infrequently (1% and 3% in NSCLC and breast cancer patients, respectively). Prophylactic administration of anti-emetics was not routine in patients treated with single-agent vinorelbine tartrate. Constipation occurred in about 28% of NSCLC and 38% of breast cancer patients. The paralytic ileus incidence of less than 2% of patients. Vomiting, diarrhea, anorexia and stomatitis were found to be mild or moderate and occurred in less than 20% of study patients ⁵.

Hepatic: Transient elevations of liver enzymes were reported without clinical symptoms. Cardiovascular: Chest pain was reported in 5% of NSCLC and 8% of breast cancer patients. Most reports of chest pain were in patients who had either a history of cardiovascular disease or tumor within the chest. There have been rare reports of myocardial infarction; however, these have not been shown definitely attributable to vinorelbine tartrate ⁸.

Other: Muscle weakness (asthenia) occurred in about 25% of patients with NSCLC and 41% of patients with breast cancer. It was usually mild or moderate but showed a linear increase with cumulative doses ⁸.

Several other toxicities reported in approximately 5% of patients include jaw pain, myalgia, arthralgia, headache, dysphagia, and skin rash. Hemorrhagic cystitis (bladder inflammation with blood in urine) and the syndrome of inappropriate ADH secretion were both reported in less than 1% of patients. The treatment of these entities are mainly symptomatic ⁸.

The carcinogenic potential of Vinorelbine has not been adequately studied. Vinorelbine has been demonstrated to affect chromosome number and likely the chromosome structure in vivo (polyploidy in bone marrow cells from Chinese hamsters and a positive micronucleus test in mice were observed) ⁸.

Pathways

Pathway	Category
Vinorelbine Action Pathway	Drug action

Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">

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Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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Abametapir	The serum concentration of Vinorelbine can be increased when it is combined with Abametapir.
Abatacept	The metabolism of Vinorelbine can be increased when combined with Abatacept.
Abciximab	The risk or severity of bleeding can be increased when Abciximab is combined with Vinorelbine.
Acalabrutinib	The metabolism of Vinorelbine can be decreased when combined with Acalabrutinib.
Acebutolol	The metabolism of Acebutolol can be decreased when combined with Vinorelbine.

Food Interactions

Exercise caution with grapefruit products. Grapefruit inhibits CYP3A4 metabolism and may increase the serum levels of vinorelbine.
Exercise caution with St. John's Wort. This herb induces CYP3A4 metabolism and may reduce the serum levels of vinorelbine.

Products

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Product Ingredients

Ingredient	UNII	CAS	InChI Key
Vinorelbine tartrate	253GQW851Q	125317-39-7	CILBMBUYJCWATM-KRQCOKQWSA-N

International/Other Brands

Bendarelbin (Bendalis) / Eberelbin (Ebewe) / Eunexon (AC Farma) / Eurovinorelbin (Lapharm) / Filcrin (Filaxis) / Navelbin (Pierre Fabre) / Navildez (Cryopharma) / Navin (Cancernova) / Navirel (medac) / Neocitec (Sandoz) / Renovel (Mustafa Nevzat) / Riborelbin (Ribosepharm) / Vilne (Dosa) / Vinelbine (GP-Pharm) / Vinorayne (Hospira) / Vinorel (Eriochem) / Vinorgen (Bago) / Vinotel (Fresenius) / Zinavin (Novamed)

Brand Name Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Navelbine	Injection	10 mg/1mL	Intravenous	Pierre Fabre Pharmaceuticals, Inc.	2005-11-15	2021-10-31
Navelbine	Solution	10 mg / mL	Intravenous	Pierre Fabre Pharma Canada Inc	1994-12-31	2012-10-01
Vinorelbine Injection	Solution	10 mg / mL	Intravenous	Fresenius Kabi	2009-03-31	2021-07-20
Vinorelbine Injection, USP	Solution	10 mg / mL	Intravenous	Generic Medical Partners Inc	2017-08-01	Not applicable
Vinorelbine Injection, USP	Solution	10 mg / mL	Intravenous	Mylan Pharmaceuticals	Not applicable	Not applicable

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Aj-vinorelbine	Solution	10 mg / mL	Intravenous	Agila Jamp Canada Inc	Not applicable	Not applicable
Vinorelbine	Injection, solution	10 mg/1mL	Intravenous	Actavis Pharma, Inc.	2015-03-01	Not applicable
Vinorelbine	Injection	10 mg/1mL	Intravenous	Ingenus Pharmaceuticals, LLC	2019-08-08	Not applicable
Vinorelbine	Injection, solution, concentrate	10 mg/1mL	Intravenous	Teva Parenteral Medicines, Inc.	2003-03-01	2012-11-30
Vinorelbine	Injection, solution	10 mg/1mL	Intravenous	Sagent Pharmaceuticals	2014-09-15	Not applicable

Chemical Identifiers

UNII: Q6C979R91Y
CAS number: 71486-22-1
InChI Key: GBABOYUKABKIAF-IELIFDKJSA-N
InChI: InChI=1S/C45H54N4O8/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/h10-15,19-21,28,37-39,46,53H,8-9,16-18,22-25H2,1-7H3/t28-,37-,38+,39+,42+,43+,44-,45-/m0/s1
IUPAC Name: methyl (1R,9R,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@@]12N(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

References

General References

Marty M, Fumoleau P, Adenis A, Rousseau Y, Merrouche Y, Robinet G, Senac I, Puozzo C: Oral vinorelbine pharmacokinetics and absolute bioavailability study in patients with solid tumors. Ann Oncol. 2001 Nov;12(11):1643-9. [Article]
Piccirillo MC, Daniele G, Di Maio M, Bryce J, De Feo G, Del Giudice A, Perrone F, Morabito A: Vinorelbine for non-small cell lung cancer. Expert Opin Drug Saf. 2010 May;9(3):493-510. doi: 10.1517/14740331003774078. [Article]
Bahadori F, Topcu G, Eroglu MS, Onyuksel H: A new lipid-based nano formulation of vinorelbine. AAPS PharmSciTech. 2014 Oct;15(5):1138-48. doi: 10.1208/s12249-014-0146-3. Epub 2014 May 29. [Article]
Wargin WA, Lucas VS: The clinical pharmacokinetics of vinorelbine (Navelbine). Semin Oncol. 1994 Oct;21(5 Suppl 10):21-7. [Article]
Vinorelbine Tartrate [Link]
Ontario Cancer Care - Drug Formulary - vinorelbine monograph [Link]
Predictors of Vinorelbine Pharmacokinetics and Pharmacodynamics in Patients With Cancer [Link]
Vinorelbine injection, Daily Med [Link]
Metabolism pathway of vinorelbine (Navelbine®) in human: Characterisation of the metabolites by HPLC–MS/MS [Link]
Vinca Alkaloid Pharmacokinetics [Link]
Vinorelbine, a clinical review [Link]
Vinorelbine FDA pharmacology review [Link]
Drug Approval Package [Link]
Navelbine, PDR [Link]

External Links

Human Metabolome Database: HMDB0014505
KEGG Drug: D08680
PubChem Compound: 44424639
PubChem Substance: 46507772
ChemSpider: 4470974
RxNav: 39541
ChEBI: 480999
ChEMBL: CHEMBL553025
ZINC: ZINC000085536958
Therapeutic Targets Database: DAP000765
PharmGKB: PA451881
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Vinorelbine

FDA label

Download (102 KB)

MSDS

Download (155 KB)

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">

Phase	Status	Purpose	Conditions	Count
4	Completed	Treatment	Breast Cancer	1
4	Completed	Treatment	Metastatic Non-Small Cell Lung Cancer	1
4	Completed	Treatment	Non-Small Cell Lung Cancer (NSCLC)	2
4	Recruiting	Treatment	Metastatic Breast Cancer	2
4	Recruiting	Treatment	Non-Small Cell Lung Cancer (NSCLC)	1

Pharmacoeconomics

Manufacturers

Pierre fabre medicament
Actavis totowa llc
App pharmaceuticals llc
Baxter healthcare corp anesthesia and critical care
Bedford laboratories div ben venue laboratories inc
Ebewe pharma ges mbh nfg kg
Hospira inc
Teva parenteral medicines inc

Packagers

APP Pharmaceuticals
Bedford Labs
Ben Venue Laboratories Inc.
Ebewe Pharma
Hospira Inc.
Pierre Fabre
Sagent Pharmaceuticals
Sicor Pharmaceuticals
Teva Pharmaceutical Industries Ltd.
Wyeth Pharmaceuticals

Dosage Forms

Form	Route	Strength
Solution	Intravenous	13.85 mg
Injection, solution, concentrate	Intravenous	10 mg/ml
Solution	Parenteral	10 mg/ml
Capsule	Oral
Capsule	Oral	200 mg
Capsule	Oral	40 MG
Capsule	Oral	80 MG
Injection	Intravenous
Solution	Parenteral
Capsule	Oral	20 mg
Capsule	Oral	30 mg
Solution, concentrate	Intravenous	50 mg
Injection, solution	Intravenous	50 mg/5ml
Injection	Intravenous	10 mg/ml
Capsule, liquid filled	Oral	20 mg
Capsule, liquid filled	Oral	30 mg
Solution	Parenteral	10.000 mg
Capsule	Oral	20.000 mg
Capsule	Oral	27.700 mg
Injection, solution	Intravenous
Injection, solution	Intravenous	10 MG/ML
Injection, solution, concentrate	Intravenous; Parenteral	10 MG/ML
Injection, solution, concentrate	Intravenous
Solution	Intravenous	50 mg
Injection	Intravenous	50 mg/5mL
Injection, solution, concentrate	Intravenous	10 mg/1mL
Injection, solution, concentrate	Intravenous	50 mg/5mL
Capsule, liquid filled	Oral	20.00 mg
Capsule, liquid filled	Oral	30.00 mg
Injection	Intravenous	10 mg/1mL
Injection, solution	Intravenous	10 mg/1mL
Solution	Intravenous	10 mg / mL
Solution		10 mg/1ml

Prices

Unit description	Cost	Unit
Navelbine 50 mg/5 ml vial	42.0USD	ml
Vinorelbine 50 mg/5 ml vial	27.6USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

Solid

Experimental Properties

Property	Value	Source
melting point (°C)	181-183	MSDS
water solubility	10 mg/mL in water	MSDS
logP	4	Not Available

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	10	Chemaxon
Refractivity	216.99 m³·mol^-1	Chemaxon
Polarizability	84.31 Å³	Chemaxon
Number of Rings	9	Chemaxon
Bioavailability	1	Chemaxon
Rule of Five	No	Chemaxon
Ghose Filter	No	Chemaxon
Veber's Rule	No	Chemaxon
MDDR-like Rule	Yes	Chemaxon

Predicted ADMET Features

Property	Value	Probability
Human Intestinal Absorption	+	0.974
Blood Brain Barrier	-	0.8815
Caco-2 permeable	+	0.5602
P-glycoprotein substrate	Substrate	0.9283
P-glycoprotein inhibitor I	Inhibitor	0.7488
P-glycoprotein inhibitor II	Inhibitor	0.7388
Renal organic cation transporter	Non-inhibitor	0.6979
CYP450 2C9 substrate	Non-substrate	0.8513
CYP450 2D6 substrate	Substrate	0.6471
CYP450 3A4 substrate	Substrate	0.7247
CYP450 1A2 substrate	Non-inhibitor	0.8415
CYP450 2C9 inhibitor	Non-inhibitor	0.7863
CYP450 2D6 inhibitor	Non-inhibitor	0.8369
CYP450 2C19 inhibitor	Non-inhibitor	0.8381
CYP450 3A4 inhibitor	Non-inhibitor	0.8095
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.6672
Ames test	Non AMES toxic	0.8064
Carcinogenicity	Non-carcinogens	0.9299
Biodegradation	Not ready biodegradable	1.0
Rat acute toxicity	2.8350 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9014
hERG inhibition (predictor II)	Non-inhibitor	0.5171

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0000000900-dbcaea3871cd2e209ec2
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-8000008900-bcfcd38104da72f4f30e
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	splash10-004i-0000001900-9c09db7377d53f1fe53c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0a4i-9000006100-1af29a23f2493ea41add
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	splash10-0cdl-9050004400-d6434d10c7ded25a58e8
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	splash10-02t9-0190100200-ecc27a039bb4afb4858c

Chromatographic Properties

Collision Cross Sections (CCS)

Not Available

Targets

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Details1. Tubulin beta chain

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Antagonist
Inhibitor

General Function: Ubiquitin protein ligase binding
Specific Function: Tubulin is the major constituent of microtubules. It binds two moles of GTP, one at an exchangeable site on the beta chain and one at a non-exchangeable site on the alpha chain.
Gene Name: TUBB
Uniprot ID: P07437
Uniprot Name: Tubulin beta chain
Molecular Weight: 49670.515 Da

References

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
Kruczynski A, Barret JM, Etievant C, Colpaert F, Fahy J, Hill BT: Antimitotic and tubulin-interacting properties of vinflunine, a novel fluorinated Vinca alkaloid. Biochem Pharmacol. 1998 Mar 1;55(5):635-48. [Article]
Chang AY, Garrow GC: Pilot study of vinorelbine (Navelbine) and paclitaxel (Taxol) in patients with refractory breast cancer and lung cancer. Semin Oncol. 1995 Apr;22(2 Suppl 5):66-70; discussion 70-1. [Article]
Seve P, Dumontet C: [Class III beta tubulin expression in nonsmall cell lung cancer]. Rev Mal Respir. 2010 Apr;27(4):383-6. doi: 10.1016/j.rmr.2010.03.006. Epub 2010 Mar 25. [Article]

Enzymes

Details1. Cytochrome P450 2D6

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Inhibitor

General Function: Steroid hydroxylase activity
Specific Function: Responsible for the metabolism of many drugs and environmental chemicals that it oxidizes. It is involved in the metabolism of drugs such as antiarrhythmics, adrenoceptor antagonists, and tricyclic...
Gene Name: CYP2D6
Uniprot ID: P10635
Uniprot Name: Cytochrome P450 2D6
Molecular Weight: 55768.94 Da

References

Le Guellec C, Lacarelle B, Catalin J, Durand A: Inhibitory effects of anticancer drugs on dextromethorphan-O-demethylase activity in human liver microsomes. Cancer Chemother Pharmacol. 1993;32(6):491-5. [Article]

Details2. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Substrate

General Function: Vitamin d3 25-hydroxylase activity
Specific Function: Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name: CYP3A4
Uniprot ID: P08684
Uniprot Name: Cytochrome P450 3A4
Molecular Weight: 57342.67 Da

References

Leveque D, Wisniewski S, Renault C, Peter JD, Le Corre P, Monteil H, Jehl F: The effect of rifampin on the pharmacokinetics of vinorelbine in the micropig. Anticancer Res. 2003 May-Jun;23(3B):2741-4. [Article]
Beulz-Riche D, Grude P, Puozzo C, Sautel F, Filaquier C, Riche C, Ratanasavanh D: Characterization of human cytochrome P450 isoenzymes involved in the metabolism of vinorelbine. Fundam Clin Pharmacol. 2005 Oct;19(5):545-53. doi: 10.1111/j.1472-8206.2005.00367.x. [Article]

Drug created at June 13, 2005 13:24 / Updated at February 20, 2024 23:54

Vinorelbine

Identification

Structure for Vinorelbine (DB00361)

Pharmacology

Interactions

Products

Categories

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Clinical Trials

Pharmacoeconomics

Properties

Spectra

Collision Cross Sections (CCS)

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Enzymes

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References