Identification

Name
Vandetanib
Accession Number
DB05294
Description

Vandetanib is an oral once-daily kinase inhibitor of tumour angiogenesis and tumour cell proliferation with the potential for use in a broad range of tumour types.

On April 6 2011, vandetanib was approved by the FDA to treat nonresectable, locally advanced, or metastatic medullary thyroid cancer in adult patients.

Type
Small Molecule
Groups
Approved
Structure
Thumb
Weight
Average: 475.354
Monoisotopic: 474.106666884
Chemical Formula
C22H24BrFN4O2
Synonyms
  • N-(4-Bromo-2-fluorophenyl)-6-methoxy-7-((1-methyl-4-piperidinyl)methoxy)-4-quinazolinamine
  • N-(4-Bromo-2-fluorophenyl)-6-methoxy-7-((1-methylpiperidin-4-yl)methoxy)quinazolin-4-amine
  • Vandetanib
External IDs
  • GNF-PF-2188
  • HSDB 8198
  • ZD 6474
  • ZD-6474
  • ZD6474

Pharmacology

Indication

Vandetanib is currently approved as an alternative to local therapies for both unresectable and disseminated disease. Because Vandetanib can prolong the Q-T interval, it is contraindicated for use in patients with serious cardiac complications such as congenital long QT syndrome and uncompensated heart failure.

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More
Pharmacodynamics

Mean IC50 of approximately 2.1 μg/mL.

Mechanism of action

ZD-6474 is a potent and selective inhibitor of VEGFR (vascular endothelial growth factor receptor), EGFR (epidermal growth factor receptor) and RET (REarranged during Transfection) tyrosine kinases.

VEGFR- and EGFR-dependent signalling are both clinically validated pathways in cancer, including non-small-cell lung cancer (NSCLC). RET activity is important in some types of thyroid cancer, and early data with vandetanib in medullary thyroid cancer has led to orphan-drug designation by the regulatory authorities in the USA and EU.

TargetActionsOrganism
UVascular endothelial growth factor A
inhibitor
Humans
UEpidermal growth factor receptor
inhibitor
Humans
UProtein-tyrosine kinase 6
inhibitor
Humans
UAngiopoietin-1 receptor
inhibitor
Humans
UProto-oncogene tyrosine-protein kinase receptor RetNot AvailableHumans
Absorption

Slow- peak plasma concentrations reached at a median 6 hours. On multiple dosing, Vandetanib accumulates about 8 fold with steady state reached after around 3 months.

Volume of distribution

Vd of about 7450 L.

Protein binding

Protein binding of about 90%.

Metabolism

Unchanged vandentanib and metabolites vandetanib N-oxide and N-desmethyl vandetanib were detected in plasma, urine and feces. N-desmethyl-vandetanib is primarily produced by CYP3A4, and vandetanib-N-oxide is primarily produced by flavin–containing monooxygenase enzymes FMO1 and FMO3.

Hover over products below to view reaction partners

Route of elimination

About 69% was recovered following 21 days after a single dose of vandentanib. 44% was found in feces and 25% in urine.

Half-life

Median half life of 19 days.

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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.
DrugInteraction
AbaloparatideThe therapeutic efficacy of Abaloparatide can be decreased when used in combination with Vandetanib.
AbametapirThe serum concentration of Vandetanib can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Vandetanib can be increased when combined with Abatacept.
AbemaciclibVandetanib may decrease the excretion rate of Abemaciclib which could result in a higher serum level.
AcalabrutinibThe metabolism of Vandetanib can be decreased when combined with Acalabrutinib.
AcebutololThe risk or severity of QTc prolongation can be increased when Acebutolol is combined with Vandetanib.
AcetaminophenThe metabolism of Acetaminophen can be increased when combined with Vandetanib.
AcetazolamideThe metabolism of Vandetanib can be decreased when combined with Acetazolamide.
AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Vandetanib.
AdalimumabThe metabolism of Vandetanib can be increased when combined with Adalimumab.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

    Learn more
  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

    Learn more
Food Interactions
  • Avoid grapefruit products. Grapefruit inhibits CYP3A4 metabolism, which may increase the serum levels of vandetanib.
  • Avoid St. John's Wort. This herb induces CYP3A4 metabolism, which may reduce the serum levels of vandetanib.
  • Take with or without food.

Products

International/Other Brands
Zactima (AstraZeneca ) / Zictifa (AstraZeneca )
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
CaprelsaTablet100 mgOralSanofi Genzyme, a Division of Sanofi Aventis Canada Inc2012-02-23Not applicableCanada flag
CaprelsaTablet, film coated100 mgOralGenzyme Europe Bv2012-02-17Not applicableEU flag
CaprelsaTablet300 mg/1OralAstraZeneca Pharmaceuticals LP2011-07-252020-05-31US flag
CaprelsaTablet, film coated300 mg/1OralGenzyme Corporation2011-07-25Not applicableUS flag
CaprelsaTablet300 mgOralSanofi Genzyme, a Division of Sanofi Aventis Canada Inc2012-02-23Not applicableCanada flag
CaprelsaTablet100 mg/1OralAstraZeneca Pharmaceuticals LP2011-07-252020-05-31US flag
CaprelsaTablet, film coated300 mgOralGenzyme Europe Bv2012-02-17Not applicableEU flag
CaprelsaTablet, film coated100 mg/1OralGenzyme Corporation2011-07-25Not applicableUS flag
VandetanibTablet100 mg/1OralAstra Zeneca Lp2011-04-212013-06-22US flag
VandetanibTablet300 mg/1OralAstra Zeneca Lp2011-04-212014-08-17US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

ATC Codes
L01XE12 — Vandetanib
Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as quinazolinamines. These are heterocyclic aromatic compounds containing a quianazoline moiety substituted by one or more amine groups.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazanaphthalenes
Sub Class
Benzodiazines
Direct Parent
Quinazolinamines
Alternative Parents
Aniline and substituted anilines / Anisoles / Alkyl aryl ethers / Aminopyrimidines and derivatives / Bromobenzenes / Fluorobenzenes / Piperidines / Aryl bromides / Imidolactams / Aryl fluorides
show 8 more
Substituents
Alkyl aryl ether / Amine / Aminopyrimidine / Aniline or substituted anilines / Anisole / Aromatic heteropolycyclic compound / Aryl bromide / Aryl fluoride / Aryl halide / Azacycle
show 23 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
piperidines, organofluorine compound, organobromine compound, aromatic ether, secondary amine, quinazolines (CHEBI:49960)

Chemical Identifiers

UNII
YO460OQ37K
CAS number
443913-73-3
InChI Key
UHTHHESEBZOYNR-UHFFFAOYSA-N
InChI
InChI=1S/C22H24BrFN4O2/c1-28-7-5-14(6-8-28)12-30-21-11-19-16(10-20(21)29-2)22(26-13-25-19)27-18-4-3-15(23)9-17(18)24/h3-4,9-11,13-14H,5-8,12H2,1-2H3,(H,25,26,27)
IUPAC Name
N-(4-bromo-2-fluorophenyl)-6-methoxy-7-[(1-methylpiperidin-4-yl)methoxy]quinazolin-4-amine
SMILES
COC1=C(OCC2CCN(C)CC2)C=C2N=CN=C(NC3=C(F)C=C(Br)C=C3)C2=C1

References

General References
  1. Bates D: ZD-6474. AstraZeneca. Curr Opin Investig Drugs. 2003 Dec;4(12):1468-72. [PubMed:14763134]
  2. Ton GN, Banaszynski ME, Kolesar JM: Vandetanib: a novel targeted therapy for the treatment of metastatic or locally advanced medullary thyroid cancer. Am J Health Syst Pharm. 2013 May 15;70(10):849-55. doi: 10.2146/ajhp120253. [PubMed:23640345]
  3. Andriamanana I, Gana I, Duretz B, Hulin A: Simultaneous analysis of anticancer agents bortezomib, imatinib, nilotinib, dasatinib, erlotinib, lapatinib, sorafenib, sunitinib and vandetanib in human plasma using LC/MS/MS. J Chromatogr B Analyt Technol Biomed Life Sci. 2013 May 1;926:83-91. doi: 10.1016/j.jchromb.2013.01.037. Epub 2013 Mar 16. [PubMed:23562906]
KEGG Drug
D06407
PubChem Compound
3081361
PubChem Substance
175426969
ChemSpider
2338979
BindingDB
21
RxNav
1098413
ChEBI
49960
ChEMBL
CHEMBL24828
ZINC
ZINC000053683345
PharmGKB
PA166118341
PDBe Ligand
ZD6
Wikipedia
Vandetanib
AHFS Codes
  • 10:00.00 — Antineoplastic Agents
PDB Entries
2ivu
FDA label
Download (220 KB)
MSDS
Download (220 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
4Active Not RecruitingTreatmentThyroid Cancers1
3Active Not RecruitingTreatmentDifferentiated Thyroid Cancer (DTC)1
3Active Not RecruitingTreatmentLocally Advanced or Metastatic Medullary Thyroid Cancer / Medullary Thyroid Cancer (MTC)1
3Active Not RecruitingTreatmentLung Cancers / Non-Small Cell Lung Carcinoma (NSCLC)1
3Active Not RecruitingTreatmentThyroid Cancers1
3CompletedTreatmentLung Cancers / Non-Small Cell Lung Carcinoma (NSCLC)1
3CompletedTreatmentNon-Small Cell Lung Carcinoma (NSCLC)2
3RecruitingTreatmentMedullary Thyroid Cancer (MTC)1
2Active Not RecruitingTreatmentDifferentiated Thyroid Cancer (DTC) / Follicular Thyroid Cancer / Poorly Differentiated Thyroid Gland Carcinoma / Thyroid Cancer, Medullary / Thyroid Cancers / Thyroid Papillary Carcinoma1
2Active Not RecruitingTreatmentMetastatic Breast Cancer1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
FormRouteStrength
TabletOral100 mg
TabletOral300 mg
Tablet, film coatedOral100 mg/1
Tablet, film coatedOral100 mg
Tablet, film coatedOral300 mg
Tablet, film coatedOral300 mg/1
TabletOral100 mg/1
TabletOral300 mg/1
Prices
Not Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)Region
US8642608No2014-02-042022-02-06US flag
US8067427No2011-11-292028-08-08US flag
US7173038No2007-02-062021-08-14US flag
USRE42353No2011-05-102017-09-23US flag
Additional Data Available
  • Filed On
    Filed On

    The date on which a patent was filed with the relevant government.

    Learn more

Properties

State
Solid
Experimental Properties
PropertyValueSource
water solubility0.008 mg/mL at 25°C (77°F )FDA Label
Predicted Properties
PropertyValueSource
Water Solubility0.0102 mg/mLALOGPS
logP5.01ALOGPS
logP4.54ChemAxon
logS-4.7ALOGPS
pKa (Strongest Acidic)13.8ChemAxon
pKa (Strongest Basic)9.13ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area59.51 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity118.63 m3·mol-1ChemAxon
Polarizability47.1 Å3ChemAxon
Number of Rings4ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9961
Blood Brain Barrier+0.9596
Caco-2 permeable+0.611
P-glycoprotein substrateSubstrate0.7412
P-glycoprotein inhibitor IInhibitor0.7327
P-glycoprotein inhibitor IIInhibitor0.9501
Renal organic cation transporterInhibitor0.6556
CYP450 2C9 substrateNon-substrate0.8419
CYP450 2D6 substrateNon-substrate0.5827
CYP450 3A4 substrateSubstrate0.6006
CYP450 1A2 substrateInhibitor0.7333
CYP450 2C9 inhibitorNon-inhibitor0.7749
CYP450 2D6 inhibitorInhibitor0.5867
CYP450 2C19 inhibitorInhibitor0.5077
CYP450 3A4 inhibitorInhibitor0.5288
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.8009
Ames testAMES toxic0.5693
CarcinogenicityNon-carcinogens0.9322
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.5482 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.5
hERG inhibition (predictor II)Inhibitor0.8342
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (103 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available
MS/MS Spectrum - , positiveLC-MS/MSsplash10-000i-0293000000-9037b32a179af5e7ba9a

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Vascular endothelial growth factor receptor binding
Specific Function
Growth factor active in angiogenesis, vasculogenesis and endothelial cell growth. Induces endothelial cell proliferation, promotes cell migration, inhibits apoptosis and induces permeabilization of...
Gene Name
VEGFA
Uniprot ID
P15692
Uniprot Name
Vascular endothelial growth factor A
Molecular Weight
27042.205 Da
References
  1. Link [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Ubiquitin protein ligase binding
Specific Function
Receptor tyrosine kinase binding ligands of the EGF family and activating several signaling cascades to convert extracellular cues into appropriate cellular responses. Known ligands include EGF, TG...
Gene Name
EGFR
Uniprot ID
P00533
Uniprot Name
Epidermal growth factor receptor
Molecular Weight
134276.185 Da
References
  1. Link [Link]
Details
3. Protein-tyrosine kinase 6
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Receptor binding
Specific Function
Non-receptor tyrosine-protein kinase implicated in the regulation of a variety of signaling pathways that control the differentiation and maintenance of normal epithelia, as well as tumor growth. F...
Gene Name
PTK6
Uniprot ID
Q13882
Uniprot Name
Protein-tyrosine kinase 6
Molecular Weight
51833.72 Da
References
  1. Link [Link]
Details
4. Angiopoietin-1 receptor
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transmembrane receptor protein tyrosine kinase activity
Specific Function
Tyrosine-protein kinase that acts as cell-surface receptor for ANGPT1, ANGPT2 and ANGPT4 and regulates angiogenesis, endothelial cell survival, proliferation, migration, adhesion and cell spreading...
Gene Name
TEK
Uniprot ID
Q02763
Uniprot Name
Angiopoietin-1 receptor
Molecular Weight
125829.005 Da
References
  1. Link [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transmembrane receptor protein tyrosine kinase activity
Specific Function
Receptor tyrosine-protein kinase involved in numerous cellular mechanisms including cell proliferation, neuronal navigation, cell migration, and cell differentiation upon binding with glial cell de...
Gene Name
RET
Uniprot ID
P07949
Uniprot Name
Proto-oncogene tyrosine-protein kinase receptor Ret
Molecular Weight
124317.465 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Nadp binding
Specific Function
This protein is involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. Form I catalyzes the N-oxygenation of secondary and tertiary amines.
Gene Name
FMO1
Uniprot ID
Q01740
Uniprot Name
Dimethylaniline monooxygenase [N-oxide-forming] 1
Molecular Weight
60310.285 Da
References
  1. Link [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Trimethylamine monooxygenase activity
Specific Function
Involved in the oxidative metabolism of a variety of xenobiotics such as drugs and pesticides. It N-oxygenates primary aliphatic alkylamines as well as secondary and tertiary amines. Plays an impor...
Gene Name
FMO3
Uniprot ID
P31513
Uniprot Name
Dimethylaniline monooxygenase [N-oxide-forming] 3
Molecular Weight
60032.975 Da
References
  1. Link [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
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
  1. Link [Link]

Carriers

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Not Available
Specific Function
Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
Gene Name
ORM1
Uniprot ID
P02763
Uniprot Name
Alpha-1-acid glycoprotein 1
Molecular Weight
23511.38 Da
References
  1. Link [Link]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Binder
General Function
Toxic substance binding
Specific Function
Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
Gene Name
ALB
Uniprot ID
P02768
Uniprot Name
Serum albumin
Molecular Weight
69365.94 Da
References
  1. Link [Link]

Transporters

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Transporter activity
Specific Function
Mediates export of organic anions and drugs from the cytoplasm. Mediates ATP-dependent transport of glutathione and glutathione conjugates, leukotriene C4, estradiol-17-beta-o-glucuronide, methotre...
Gene Name
ABCC1
Uniprot ID
P33527
Uniprot Name
Multidrug resistance-associated protein 1
Molecular Weight
171589.5 Da
References
  1. Zheng LS, Wang F, Li YH, Zhang X, Chen LM, Liang YJ, Dai CL, Yan YY, Tao LY, Mi YJ, Yang AK, To KK, Fu LW: Vandetanib (Zactima, ZD6474) antagonizes ABCC1- and ABCG2-mediated multidrug resistance by inhibition of their transport function. PLoS One. 2009;4(4):e5172. doi: 10.1371/journal.pone.0005172. Epub 2009 Apr 23. [PubMed:19390592]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
Gene Name
ABCG2
Uniprot ID
Q9UNQ0
Uniprot Name
ATP-binding cassette sub-family G member 2
Molecular Weight
72313.47 Da
References
  1. Zheng LS, Wang F, Li YH, Zhang X, Chen LM, Liang YJ, Dai CL, Yan YY, Tao LY, Mi YJ, Yang AK, To KK, Fu LW: Vandetanib (Zactima, ZD6474) antagonizes ABCC1- and ABCG2-mediated multidrug resistance by inhibition of their transport function. PLoS One. 2009;4(4):e5172. doi: 10.1371/journal.pone.0005172. Epub 2009 Apr 23. [PubMed:19390592]
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Inhibitor
General Function
Quaternary ammonium group transmembrane transporter activity
Specific Function
Mediates tubular uptake of organic compounds from circulation. Mediates the influx of agmatine, dopamine, noradrenaline (norepinephrine), serotonin, choline, famotidine, ranitidine, histamin, creat...
Gene Name
SLC22A2
Uniprot ID
O15244
Uniprot Name
Solute carrier family 22 member 2
Molecular Weight
62579.99 Da
References
  1. Shen H, Yang Z, Zhao W, Zhang Y, Rodrigues AD: Assessment of vandetanib as an inhibitor of various human renal transporters: inhibition of multidrug and toxin extrusion as a possible mechanism leading to decreased cisplatin and creatinine clearance. Drug Metab Dispos. 2013 Dec;41(12):2095-103. doi: 10.1124/dmd.113.053215. Epub 2013 Sep 11. [PubMed:24026623]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Jovelet C, Benard J, Forestier F, Farinotti R, Bidart JM, Gil S: Inhibition of P-glycoprotein functionality by vandetanib may reverse cancer cell resistance to doxorubicin. Eur J Pharm Sci. 2012 Aug 15;46(5):484-91. doi: 10.1016/j.ejps.2012.03.012. Epub 2012 Mar 30. [PubMed:22484209]
  2. CAPRELSA® (vandetanib) FDA Label [Link]

Drug created on November 18, 2007 11:23 / Updated on October 23, 2020 21:53

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