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Identification
NameVismodegib
Accession NumberDB08828
TypeSmall Molecule
GroupsApproved
DescriptionVismodegib inhibits the hedgehog signalling pathway and is indicated for treatment of adult basal cell carcinoma. FDA approved on Jan 30, 2012.
Structure
Thumb
Synonyms
Erivedge
GDC-0449
Hedgehog Antagonist GDC-0449
Vismodegibum
External Identifiers
  • RG-3616
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Erivedgecapsule150 mg/1oralGenentech, Inc.2012-01-30Not applicableUs
Erivedgecapsule150 mgoralHoffmann La Roche Limited2013-08-09Not applicableCanada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNII25X868M3DS
CAS number879085-55-9
WeightAverage: 421.297
Monoisotopic: 420.010218428
Chemical FormulaC19H14Cl2N2O3S
InChI KeyInChIKey=BPQMGSKTAYIVFO-UHFFFAOYSA-N
InChI
InChI=1S/C19H14Cl2N2O3S/c1-27(25,26)13-6-7-14(17(21)11-13)19(24)23-12-5-8-16(20)15(10-12)18-4-2-3-9-22-18/h2-11H,1H3,(H,23,24)
IUPAC Name
2-chloro-N-[4-chloro-3-(pyridin-2-yl)phenyl]-4-methanesulfonylbenzamide
SMILES
CS(=O)(=O)C1=CC(Cl)=C(C=C1)C(=O)NC1=CC=C(Cl)C(=C1)C1=CC=CC=N1
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as n-phenylbenzamides. These are benzamides that are N-linked to a phenyl group via the carboxamide group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzamides
Direct ParentN-phenylbenzamides
Alternative Parents
Substituents
  • N-phenylbenzamide
  • 2-phenylpyridine
  • N-arylamide
  • Halobenzoic acid or derivatives
  • 2-halobenzoic acid or derivatives
  • Benzoic acid or derivatives
  • Benzoyl
  • Halobenzene
  • Chlorobenzene
  • Pyridine
  • Aryl halide
  • Aryl chloride
  • Heteroaromatic compound
  • Vinylogous halide
  • Sulfonyl
  • Sulfone
  • Secondary carboxylic acid amide
  • Carboxamide group
  • Azacycle
  • Organoheterocyclic compound
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organosulfur compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organochloride
  • Organohalogen compound
  • Carbonyl group
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationVismodegib is used for treating locally advanced or metastatic basal cell carcinoma in patients whose carcinoma has recurred after surgery, and in patients who are not candidates for surgery or radiation.
PharmacodynamicsVismodegib selectively binds to and inhibits the transmembrane protein Smoothened homologue (SMO) to inhibit the Hedgehog signalling pathway.
Mechanism of actionMutations of the Hedgehog pathway may results in uncontrolled proliferation of skin basal cells. Vismodegib binds to and inhibits the transmembrane protein Smoothened homologue (SMO) to inhibit the Hedgehog signalling pathway.
Related Articles
AbsorptionThe absolute bioavailability of a single dose is 31.8%. Absorption is saturable and is not affected by food.
Volume of distribution

Vismodegib has a volume of distribution of 16.4 to 26.6 L.

Protein bindingVismodegib is highly protein bound with plasma protein binding at about 99%. Vismodegib binds to the plasma proteins, albumin and alpha-1-acid glycoprotein (saturable bnding).
Metabolism

The main metabolic enzymes are CYP2C9 and CYP3A4, however more than 98% of total systemic vismodegib is not metabolized. Metabolic pathways of vismodegib in humans include oxidation, glucuronidation, and pyridine ring cleavage. The two most abundant oxidative metabolites recovered in feces are produced in vitro by recombinant CYP2C9 and CYP3A4/5.

Route of eliminationVismodegib is mostly excreted unchanged, and the main route of elimination is by the feces (82%) and the urine accounts for 4.4%.
Half lifeThe half-life after a single dose is 12 days, and after continuous daily dosing is 4 days.
ClearanceNot Available
ToxicityIncreased risk of embryo-fetal death and significant birth defects. Common adverse event include muscle spasms, alopecia, dysgeusia, weight loss, fatigue, nausea, diarrhea, decreased appetite, constipation, arthralgias, vomiting, and ageusia.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9547
Blood Brain Barrier+0.9387
Caco-2 permeable+0.6048
P-glycoprotein substrateNon-substrate0.8443
P-glycoprotein inhibitor INon-inhibitor0.8663
P-glycoprotein inhibitor IINon-inhibitor0.9558
Renal organic cation transporterNon-inhibitor0.8925
CYP450 2C9 substrateNon-substrate0.6009
CYP450 2D6 substrateNon-substrate0.63
CYP450 3A4 substrateNon-substrate0.5083
CYP450 1A2 substrateNon-inhibitor0.6067
CYP450 2C9 inhibitorInhibitor0.9078
CYP450 2D6 inhibitorNon-inhibitor0.6638
CYP450 2C19 inhibitorInhibitor0.8515
CYP450 3A4 inhibitorInhibitor0.8452
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.9282
Ames testNon AMES toxic0.8271
CarcinogenicityNon-carcinogens0.6746
BiodegradationNot ready biodegradable0.9956
Rat acute toxicity2.0840 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9973
hERG inhibition (predictor II)Non-inhibitor0.8224
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Capsuleoral150 mg/1
Capsuleoral150 mg
PricesNot Available
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US7888364 No2008-11-112028-11-11Us
US9278961 No2008-12-152028-12-15Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubility0.1 μg/mL and is pH dependent FDA label
logP2.7 FDA label
pKa3.8FDA label
Predicted Properties
PropertyValueSource
Water Solubility0.00173 mg/mLALOGPS
logP4.22ALOGPS
logP3.93ChemAxon
logS-5.4ALOGPS
pKa (Strongest Acidic)10.27ChemAxon
pKa (Strongest Basic)3.7ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count4ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area76.13 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity107.81 m3·mol-1ChemAxon
Polarizability39.49 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis ReferenceNot Available
General References
  1. Von Hoff DD, LoRusso PM, Rudin CM, Reddy JC, Yauch RL, Tibes R, Weiss GJ, Borad MJ, Hann CL, Brahmer JR, Mackey HM, Lum BL, Darbonne WC, Marsters JC Jr, de Sauvage FJ, Low JA: Inhibition of the hedgehog pathway in advanced basal-cell carcinoma. N Engl J Med. 2009 Sep 17;361(12):1164-72. doi: 10.1056/NEJMoa0905360. Epub 2009 Sep 2. [PubMed:19726763 ]
  2. Sandhiya S, Melvin G, Kumar SS, Dkhar SA: The dawn of hedgehog inhibitors: Vismodegib. J Pharmacol Pharmacother. 2013 Jan;4(1):4-7. doi: 10.4103/0976-500X.107628. [PubMed:23662017 ]
External Links
ATC CodesL01XX43
AHFS Codes
  • 10:00
PDB EntriesNot Available
FDA labelDownload (211 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbirateroneThe metabolism of Vismodegib can be decreased when combined with Abiraterone.
AcetaminophenThe serum concentration of Vismodegib can be increased when it is combined with Acetaminophen.
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Vismodegib.
AfatinibThe serum concentration of Vismodegib can be increased when it is combined with Afatinib.
AlbendazoleThe serum concentration of Vismodegib can be increased when it is combined with Albendazole.
AldosteroneThe serum concentration of Vismodegib can be decreased when it is combined with Aldosterone.
AlectinibThe serum concentration of Vismodegib can be increased when it is combined with Alectinib.
AlfentanilThe serum concentration of Vismodegib can be increased when it is combined with Alfentanil.
AmantadineThe serum concentration of Vismodegib can be increased when it is combined with Amantadine.
Aminohippuric acidThe serum concentration of Vismodegib can be increased when it is combined with Aminohippuric acid.
AmiodaroneThe serum concentration of Vismodegib can be decreased when it is combined with Amiodarone.
AmitriptylineThe serum concentration of Vismodegib can be increased when it is combined with Amitriptyline.
AmlodipineThe serum concentration of Vismodegib can be increased when it is combined with Amlodipine.
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Vismodegib.
AmprenavirThe serum concentration of Vismodegib can be decreased when it is combined with Amprenavir.
AmsacrineThe serum concentration of Vismodegib can be increased when it is combined with Amsacrine.
AprepitantThe serum concentration of Vismodegib can be increased when it is combined with Aprepitant.
AstemizoleThe serum concentration of Vismodegib can be increased when it is combined with Astemizole.
AtazanavirThe serum concentration of Vismodegib can be increased when it is combined with Atazanavir.
AtenololThe serum concentration of Vismodegib can be increased when it is combined with Atenolol.
AtomoxetineThe metabolism of Vismodegib can be decreased when combined with Atomoxetine.
AtorvastatinThe serum concentration of Vismodegib can be increased when it is combined with Atorvastatin.
AzelastineThe serum concentration of Vismodegib can be increased when it is combined with Azelastine.
AzithromycinThe serum concentration of Vismodegib can be increased when it is combined with Azithromycin.
BenzocaineThe serum concentration of Vismodegib can be increased when it is combined with Benzocaine.
BepridilThe serum concentration of Vismodegib can be increased when it is combined with Bepridil.
BevacizumabBevacizumab may increase the cardiotoxic activities of Vismodegib.
BexaroteneThe serum concentration of Vismodegib can be decreased when it is combined with Bexarotene.
BiperidenThe serum concentration of Vismodegib can be increased when it is combined with Biperiden.
BoceprevirThe metabolism of Vismodegib can be decreased when combined with Boceprevir.
BortezomibThe metabolism of Vismodegib can be decreased when combined with Bortezomib.
BosentanThe serum concentration of Vismodegib can be decreased when it is combined with Bosentan.
BosutinibThe serum concentration of Vismodegib can be increased when it is combined with Bosutinib.
BromocriptineThe serum concentration of Vismodegib can be increased when it is combined with Bromocriptine.
BuprenorphineThe serum concentration of Vismodegib can be increased when it is combined with Buprenorphine.
BuspironeThe serum concentration of Vismodegib can be increased when it is combined with Buspirone.
CabazitaxelThe serum concentration of Vismodegib can be increased when it is combined with Cabazitaxel.
CaffeineThe serum concentration of Vismodegib can be increased when it is combined with Caffeine.
CanagliflozinThe serum concentration of Vismodegib can be increased when it is combined with Canagliflozin.
CandesartanThe serum concentration of Vismodegib can be increased when it is combined with Candesartan.
CapecitabineThe metabolism of Vismodegib can be decreased when combined with Capecitabine.
CaptoprilThe serum concentration of Vismodegib can be increased when it is combined with Captopril.
CarbamazepineThe serum concentration of Vismodegib can be decreased when it is combined with Carbamazepine.
CarvedilolThe serum concentration of Vismodegib can be increased when it is combined with Carvedilol.
CaspofunginThe serum concentration of Vismodegib can be increased when it is combined with Caspofungin.
CeritinibThe serum concentration of Vismodegib can be increased when it is combined with Ceritinib.
ChloroquineThe serum concentration of Vismodegib can be increased when it is combined with Chloroquine.
ChlorpromazineThe serum concentration of Vismodegib can be increased when it is combined with Chlorpromazine.
ChlorpropamideThe serum concentration of Vismodegib can be increased when it is combined with Chlorpropamide.
ChlorprothixeneThe serum concentration of Vismodegib can be increased when it is combined with Chlorprothixene.
CholecalciferolThe metabolism of Vismodegib can be decreased when combined with Cholecalciferol.
CholesterolThe serum concentration of Vismodegib can be increased when it is combined with Cholesterol.
Cholic AcidThe serum concentration of Vismodegib can be decreased when it is combined with Cholic Acid.
CilazaprilThe serum concentration of Vismodegib can be increased when it is combined with Cilazapril.
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Vismodegib.
CimetidineThe serum concentration of Vismodegib can be decreased when it is combined with Cimetidine.
CiprofloxacinThe serum concentration of Vismodegib can be increased when it is combined with Ciprofloxacin.
CitalopramThe serum concentration of Vismodegib can be increased when it is combined with Citalopram.
ClarithromycinThe serum concentration of Vismodegib can be increased when it is combined with Clarithromycin.
ClemastineThe metabolism of Vismodegib can be decreased when combined with Clemastine.
ClofazimineThe serum concentration of Vismodegib can be increased when it is combined with Clofazimine.
ClomipramineThe serum concentration of Vismodegib can be increased when it is combined with Clomipramine.
ClotrimazoleThe metabolism of Vismodegib can be decreased when combined with Clotrimazole.
CobicistatThe serum concentration of Vismodegib can be increased when it is combined with Cobicistat.
ColchicineThe serum concentration of Vismodegib can be increased when it is combined with Colchicine.
ColforsinThe serum concentration of Vismodegib can be increased when it is combined with Colforsin.
ConivaptanThe serum concentration of Vismodegib can be increased when it is combined with Conivaptan.
CrizotinibThe metabolism of Vismodegib can be decreased when combined with Crizotinib.
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Vismodegib.
CyclosporineThe metabolism of Vismodegib can be decreased when combined with Cyclosporine.
DabrafenibThe serum concentration of Vismodegib can be decreased when it is combined with Dabrafenib.
DaclatasvirThe serum concentration of Vismodegib can be increased when it is combined with Daclatasvir.
DactinomycinThe serum concentration of Vismodegib can be increased when it is combined with Dactinomycin.
DarunavirThe metabolism of Vismodegib can be decreased when combined with Darunavir.
DasatinibThe serum concentration of Vismodegib can be increased when it is combined with Dasatinib.
DaunorubicinThe serum concentration of Vismodegib can be decreased when it is combined with Daunorubicin.
DeferasiroxThe serum concentration of Vismodegib can be decreased when it is combined with Deferasirox.
DelavirdineThe metabolism of Vismodegib can be decreased when combined with Delavirdine.
DesipramineThe serum concentration of Vismodegib can be increased when it is combined with Desipramine.
DeslanosideDeslanoside may decrease the cardiotoxic activities of Vismodegib.
DesloratadineThe serum concentration of Vismodegib can be increased when it is combined with Desloratadine.
DexamethasoneThe serum concentration of Vismodegib can be decreased when it is combined with Dexamethasone.
DextromethorphanThe serum concentration of Vismodegib can be increased when it is combined with Dextromethorphan.
DiclofenacThe serum concentration of Vismodegib can be increased when it is combined with Diclofenac.
DigitoxinDigitoxin may decrease the cardiotoxic activities of Vismodegib.
DigoxinDigoxin may decrease the cardiotoxic activities of Vismodegib.
DihydroergotamineThe metabolism of Vismodegib can be decreased when combined with Dihydroergotamine.
DiltiazemThe metabolism of Vismodegib can be decreased when combined with Diltiazem.
DipyridamoleThe serum concentration of Vismodegib can be increased when it is combined with Dipyridamole.
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Vismodegib.
DoxazosinThe serum concentration of Vismodegib can be increased when it is combined with Doxazosin.
DoxepinThe serum concentration of Vismodegib can be increased when it is combined with Doxepin.
DoxorubicinThe serum concentration of Vismodegib can be decreased when it is combined with Doxorubicin.
DoxycyclineThe metabolism of Vismodegib can be decreased when combined with Doxycycline.
DronabinolThe serum concentration of Vismodegib can be increased when it is combined with Dronabinol.
DronedaroneThe metabolism of Vismodegib can be decreased when combined with Dronedarone.
EfavirenzThe serum concentration of Vismodegib can be decreased when it is combined with Efavirenz.
ElbasvirThe serum concentration of Vismodegib can be increased when it is combined with Elbasvir.
EnalaprilThe serum concentration of Vismodegib can be increased when it is combined with Enalapril.
EnzalutamideThe serum concentration of Vismodegib can be increased when it is combined with Enzalutamide.
ErgonovineThe serum concentration of Vismodegib can be increased when it is combined with Ergonovine.
ErgotamineThe serum concentration of Vismodegib can be increased when it is combined with Ergotamine.
ErythromycinThe metabolism of Vismodegib can be decreased when combined with Erythromycin.
Eslicarbazepine acetateThe serum concentration of Vismodegib can be decreased when it is combined with Eslicarbazepine acetate.
EstramustineThe serum concentration of Vismodegib can be increased when it is combined with Estramustine.
EstriolThe serum concentration of Vismodegib can be decreased when it is combined with Estriol.
EstroneThe serum concentration of Vismodegib can be decreased when it is combined with Estrone.
EtoposideThe serum concentration of Vismodegib can be increased when it is combined with Etoposide.
EtravirineThe serum concentration of Vismodegib can be decreased when it is combined with Etravirine.
FelodipineThe serum concentration of Vismodegib can be increased when it is combined with Felodipine.
FentanylThe serum concentration of Vismodegib can be increased when it is combined with Fentanyl.
FexofenadineThe serum concentration of Vismodegib can be increased when it is combined with Fexofenadine.
FidaxomicinThe serum concentration of Vismodegib can be increased when it is combined with Fidaxomicin.
FloxuridineThe metabolism of Vismodegib can be decreased when combined with Floxuridine.
FluconazoleThe metabolism of Vismodegib can be decreased when combined with Fluconazole.
FluorouracilThe metabolism of Vismodegib can be decreased when combined with Fluorouracil.
FluoxetineThe serum concentration of Vismodegib can be increased when it is combined with Fluoxetine.
FlupentixolThe serum concentration of Vismodegib can be increased when it is combined with Flupentixol.
FluphenazineThe serum concentration of Vismodegib can be increased when it is combined with Fluphenazine.
FlurazepamThe serum concentration of Vismodegib can be increased when it is combined with Flurazepam.
FluvastatinThe metabolism of Vismodegib can be decreased when combined with Fluvastatin.
FluvoxamineThe metabolism of Vismodegib can be decreased when combined with Fluvoxamine.
FosamprenavirThe metabolism of Vismodegib can be decreased when combined with Fosamprenavir.
FosaprepitantThe serum concentration of Vismodegib can be increased when it is combined with Fosaprepitant.
FosphenytoinThe metabolism of Vismodegib can be increased when combined with Fosphenytoin.
Fusidic AcidThe serum concentration of Vismodegib can be increased when it is combined with Fusidic Acid.
GefitinibThe serum concentration of Vismodegib can be increased when it is combined with Gefitinib.
GemfibrozilThe metabolism of Vismodegib can be decreased when combined with Gemfibrozil.
GenisteinThe serum concentration of Vismodegib can be increased when it is combined with Genistein.
GlyburideThe serum concentration of Vismodegib can be increased when it is combined with Glyburide.
GlycerolThe serum concentration of Vismodegib can be increased when it is combined with Glycerol.
Gramicidin DThe serum concentration of Vismodegib can be increased when it is combined with Gramicidin D.
GrepafloxacinThe serum concentration of Vismodegib can be increased when it is combined with Grepafloxacin.
HaloperidolThe serum concentration of Vismodegib can be increased when it is combined with Haloperidol.
HydrocortisoneThe serum concentration of Vismodegib can be increased when it is combined with Hydrocortisone.
IdelalisibThe serum concentration of Vismodegib can be increased when it is combined with Idelalisib.
ImatinibThe metabolism of Vismodegib can be decreased when combined with Imatinib.
ImipramineThe serum concentration of Vismodegib can be increased when it is combined with Imipramine.
IndinavirThe serum concentration of Vismodegib can be decreased when it is combined with Indinavir.
IndomethacinThe serum concentration of Vismodegib can be increased when it is combined with Indomethacin.
IrbesartanThe metabolism of Vismodegib can be decreased when combined with Irbesartan.
IsavuconazoniumThe metabolism of Vismodegib can be decreased when combined with Isavuconazonium.
IsradipineThe metabolism of Vismodegib can be decreased when combined with Isradipine.
ItraconazoleThe serum concentration of Vismodegib can be increased when it is combined with Itraconazole.
IvacaftorThe serum concentration of Vismodegib can be increased when it is combined with Ivacaftor.
IvermectinThe serum concentration of Vismodegib can be increased when it is combined with Ivermectin.
KetamineThe serum concentration of Vismodegib can be increased when it is combined with Ketamine.
KetoconazoleThe serum concentration of Vismodegib can be increased when it is combined with Ketoconazole.
LansoprazoleThe serum concentration of Vismodegib can be increased when it is combined with Lansoprazole.
LapatinibThe serum concentration of Vismodegib can be increased when it is combined with Lapatinib.
LeflunomideThe metabolism of Vismodegib can be decreased when combined with Leflunomide.
LevofloxacinThe serum concentration of Vismodegib can be increased when it is combined with Levofloxacin.
LevothyroxineThe serum concentration of Vismodegib can be decreased when it is combined with Levothyroxine.
LidocaineThe serum concentration of Vismodegib can be increased when it is combined with Lidocaine.
LiothyronineThe serum concentration of Vismodegib can be decreased when it is combined with Liothyronine.
LiotrixThe serum concentration of Vismodegib can be decreased when it is combined with Liotrix.
LisinoprilThe serum concentration of Vismodegib can be increased when it is combined with Lisinopril.
LomitapideThe serum concentration of Vismodegib can be increased when it is combined with Lomitapide.
LoperamideThe serum concentration of Vismodegib can be increased when it is combined with Loperamide.
LopinavirThe serum concentration of Vismodegib can be increased when it is combined with Lopinavir.
LoratadineThe serum concentration of Vismodegib can be increased when it is combined with Loratadine.
LosartanThe serum concentration of Vismodegib can be increased when it is combined with Losartan.
LovastatinThe metabolism of Vismodegib can be decreased when combined with Lovastatin.
LuliconazoleThe serum concentration of Vismodegib can be increased when it is combined with Luliconazole.
LumacaftorThe serum concentration of Vismodegib can be decreased when it is combined with Lumacaftor.
MaprotilineThe serum concentration of Vismodegib can be increased when it is combined with Maprotiline.
MebendazoleThe serum concentration of Vismodegib can be increased when it is combined with Mebendazole.
MefloquineThe serum concentration of Vismodegib can be increased when it is combined with Mefloquine.
Megestrol acetateThe serum concentration of Vismodegib can be increased when it is combined with Megestrol acetate.
MeprobamateThe serum concentration of Vismodegib can be increased when it is combined with Meprobamate.
MethadoneThe serum concentration of Vismodegib can be increased when it is combined with Methadone.
MetoprololThe serum concentration of Vismodegib can be increased when it is combined with Metoprolol.
MibefradilThe serum concentration of Vismodegib can be increased when it is combined with Mibefradil.
MiconazoleThe serum concentration of Vismodegib can be increased when it is combined with Miconazole.
MidazolamThe serum concentration of Vismodegib can be decreased when it is combined with Midazolam.
MifepristoneThe metabolism of Vismodegib can be decreased when combined with Mifepristone.
MitomycinThe serum concentration of Vismodegib can be increased when it is combined with Mitomycin.
MitotaneThe serum concentration of Vismodegib can be decreased when it is combined with Mitotane.
MitoxantroneThe serum concentration of Vismodegib can be decreased when it is combined with Mitoxantrone.
ModafinilThe serum concentration of Vismodegib can be decreased when it is combined with Modafinil.
MorphineThe serum concentration of Vismodegib can be increased when it is combined with Morphine.
NafcillinThe serum concentration of Vismodegib can be decreased when it is combined with Nafcillin.
NaltrexoneThe serum concentration of Vismodegib can be increased when it is combined with Naltrexone.
NaringeninThe serum concentration of Vismodegib can be increased when it is combined with Naringenin.
NefazodoneThe serum concentration of Vismodegib can be decreased when it is combined with Nefazodone.
NelfinavirThe serum concentration of Vismodegib can be decreased when it is combined with Nelfinavir.
NeostigmineThe serum concentration of Vismodegib can be increased when it is combined with Neostigmine.
NetupitantThe serum concentration of Vismodegib can be increased when it is combined with Netupitant.
NevirapineThe metabolism of Vismodegib can be decreased when combined with Nevirapine.
NicardipineThe serum concentration of Vismodegib can be increased when it is combined with Nicardipine.
NifedipineThe serum concentration of Vismodegib can be decreased when it is combined with Nifedipine.
NilotinibThe metabolism of Vismodegib can be decreased when combined with Nilotinib.
NisoldipineThe serum concentration of Vismodegib can be increased when it is combined with Nisoldipine.
NitrazepamThe serum concentration of Vismodegib can be increased when it is combined with Nitrazepam.
NitrendipineThe serum concentration of Vismodegib can be increased when it is combined with Nitrendipine.
NorethisteroneThe serum concentration of Vismodegib can be decreased when it is combined with Norethisterone.
OlaparibThe metabolism of Vismodegib can be decreased when combined with Olaparib.
OmeprazoleThe serum concentration of Vismodegib can be increased when it is combined with Omeprazole.
OsimertinibThe serum concentration of Vismodegib can be increased when it is combined with Osimertinib.
OuabainOuabain may decrease the cardiotoxic activities of Vismodegib.
P-NitrophenolThe serum concentration of Vismodegib can be increased when it is combined with P-Nitrophenol.
PaclitaxelThe serum concentration of Vismodegib can be increased when it is combined with Paclitaxel.
PalbociclibThe serum concentration of Vismodegib can be increased when it is combined with Palbociclib.
Palmitic AcidThe serum concentration of Vismodegib can be increased when it is combined with Palmitic Acid.
PantoprazoleThe serum concentration of Vismodegib can be increased when it is combined with Pantoprazole.
ParoxetineThe serum concentration of Vismodegib can be increased when it is combined with Paroxetine.
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Vismodegib.
PentobarbitalThe metabolism of Vismodegib can be increased when combined with Pentobarbital.
PerindoprilThe serum concentration of Vismodegib can be increased when it is combined with Perindopril.
PhenobarbitalThe serum concentration of Vismodegib can be decreased when it is combined with Phenobarbital.
PhenytoinThe metabolism of Vismodegib can be increased when combined with Phenytoin.
PimozideThe serum concentration of Vismodegib can be increased when it is combined with Pimozide.
Platelet Activating FactorThe serum concentration of Vismodegib can be decreased when it is combined with Platelet Activating Factor.
PonatinibThe serum concentration of Vismodegib can be increased when it is combined with Ponatinib.
PosaconazoleThe serum concentration of Vismodegib can be increased when it is combined with Posaconazole.
PravastatinThe serum concentration of Vismodegib can be increased when it is combined with Pravastatin.
PrazosinThe serum concentration of Vismodegib can be increased when it is combined with Prazosin.
PrednisoneThe serum concentration of Vismodegib can be increased when it is combined with Prednisone.
PrimidoneThe metabolism of Vismodegib can be increased when combined with Primidone.
ProbenecidThe serum concentration of Vismodegib can be increased when it is combined with Probenecid.
ProgesteroneThe serum concentration of Vismodegib can be decreased when it is combined with Progesterone.
PromethazineThe serum concentration of Vismodegib can be increased when it is combined with Promethazine.
PropafenoneThe serum concentration of Vismodegib can be increased when it is combined with Propafenone.
PropranololThe serum concentration of Vismodegib can be increased when it is combined with Propranolol.
ProtriptylineThe serum concentration of Vismodegib can be increased when it is combined with Protriptyline.
PyrimethamineThe metabolism of Vismodegib can be decreased when combined with Pyrimethamine.
QuercetinThe serum concentration of Vismodegib can be increased when it is combined with Quercetin.
QuinacrineThe serum concentration of Vismodegib can be increased when it is combined with Quinacrine.
QuinidineThe serum concentration of Vismodegib can be increased when it is combined with Quinidine.
QuinineThe serum concentration of Vismodegib can be increased when it is combined with Quinine.
RanitidineThe serum concentration of Vismodegib can be increased when it is combined with Ranitidine.
RanolazineThe serum concentration of Vismodegib can be increased when it is combined with Ranolazine.
ReboxetineThe serum concentration of Vismodegib can be increased when it is combined with Reboxetine.
RegorafenibThe serum concentration of Vismodegib can be increased when it is combined with Regorafenib.
ReserpineThe serum concentration of Vismodegib can be decreased when it is combined with Reserpine.
RifabutinThe metabolism of Vismodegib can be increased when combined with Rifabutin.
RifampicinThe serum concentration of Vismodegib can be decreased when it is combined with Rifampicin.
RifapentineThe metabolism of Vismodegib can be increased when combined with Rifapentine.
RilpivirineThe serum concentration of Vismodegib can be increased when it is combined with Rilpivirine.
RitonavirThe serum concentration of Vismodegib can be decreased when it is combined with Ritonavir.
RolapitantThe serum concentration of Vismodegib can be increased when it is combined with Rolapitant.
SaquinavirThe serum concentration of Vismodegib can be decreased when it is combined with Saquinavir.
ScopolamineThe serum concentration of Vismodegib can be increased when it is combined with Scopolamine.
SecobarbitalThe metabolism of Vismodegib can be increased when combined with Secobarbital.
SelegilineThe serum concentration of Vismodegib can be increased when it is combined with Selegiline.
SertralineThe serum concentration of Vismodegib can be increased when it is combined with Sertraline.
SildenafilThe metabolism of Vismodegib can be decreased when combined with Sildenafil.
SiltuximabThe serum concentration of Vismodegib can be decreased when it is combined with Siltuximab.
SimeprevirThe serum concentration of Vismodegib can be increased when it is combined with Simeprevir.
SimvastatinThe serum concentration of Vismodegib can be increased when it is combined with Simvastatin.
SirolimusThe serum concentration of Vismodegib can be decreased when it is combined with Sirolimus.
SorafenibThe serum concentration of Vismodegib can be increased when it is combined with Sorafenib.
SpironolactoneThe serum concentration of Vismodegib can be increased when it is combined with Spironolactone.
St. John's WortThe serum concentration of Vismodegib can be decreased when it is combined with St. John's Wort.
StaurosporineThe serum concentration of Vismodegib can be increased when it is combined with Staurosporine.
StiripentolThe serum concentration of Vismodegib can be increased when it is combined with Stiripentol.
StreptozocinThe serum concentration of Vismodegib can be decreased when it is combined with Streptozocin.
SulfadiazineThe metabolism of Vismodegib can be decreased when combined with Sulfadiazine.
SulfamethoxazoleThe metabolism of Vismodegib can be decreased when combined with Sulfamethoxazole.
SulfinpyrazoneThe serum concentration of Vismodegib can be increased when it is combined with Sulfinpyrazone.
SulfisoxazoleThe metabolism of Vismodegib can be decreased when combined with Sulfisoxazole.
SumatriptanThe serum concentration of Vismodegib can be increased when it is combined with Sumatriptan.
SunitinibThe serum concentration of Vismodegib can be increased when it is combined with Sunitinib.
TacrineThe serum concentration of Vismodegib can be increased when it is combined with Tacrine.
TacrolimusThe serum concentration of Vismodegib can be decreased when it is combined with Tacrolimus.
TamoxifenThe serum concentration of Vismodegib can be decreased when it is combined with Tamoxifen.
Taurocholic AcidThe serum concentration of Vismodegib can be increased when it is combined with Taurocholic Acid.
TelaprevirThe metabolism of Vismodegib can be decreased when combined with Telaprevir.
TelithromycinThe metabolism of Vismodegib can be decreased when combined with Telithromycin.
TelmisartanThe serum concentration of Vismodegib can be increased when it is combined with Telmisartan.
TemsirolimusThe serum concentration of Vismodegib can be increased when it is combined with Temsirolimus.
TerazosinThe serum concentration of Vismodegib can be increased when it is combined with Terazosin.
TerfenadineThe serum concentration of Vismodegib can be increased when it is combined with Terfenadine.
TesmilifeneThe serum concentration of Vismodegib can be decreased when it is combined with Tesmilifene.
TestosteroneThe serum concentration of Vismodegib can be increased when it is combined with Testosterone.
TicagrelorThe serum concentration of Vismodegib can be increased when it is combined with Ticagrelor.
TiclopidineThe metabolism of Vismodegib can be decreased when combined with Ticlopidine.
TocilizumabThe serum concentration of Vismodegib can be decreased when it is combined with Tocilizumab.
TolbutamideThe metabolism of Vismodegib can be decreased when combined with Tolbutamide.
TolvaptanThe serum concentration of Vismodegib can be increased when it is combined with Tolvaptan.
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Vismodegib.
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Vismodegib.
TrazodoneThe serum concentration of Vismodegib can be decreased when it is combined with Trazodone.
TrifluoperazineThe serum concentration of Vismodegib can be increased when it is combined with Trifluoperazine.
TriflupromazineThe serum concentration of Vismodegib can be increased when it is combined with Triflupromazine.
TrimethoprimThe serum concentration of Vismodegib can be decreased when it is combined with Trimethoprim.
TrimipramineThe serum concentration of Vismodegib can be increased when it is combined with Trimipramine.
TroleandomycinThe serum concentration of Vismodegib can be increased when it is combined with Troleandomycin.
Valproic AcidThe metabolism of Vismodegib can be decreased when combined with Valproic Acid.
ValsartanThe metabolism of Vismodegib can be decreased when combined with Valsartan.
VenlafaxineThe metabolism of Vismodegib can be decreased when combined with Venlafaxine.
VerapamilThe metabolism of Vismodegib can be decreased when combined with Verapamil.
VinblastineThe serum concentration of Vismodegib can be decreased when it is combined with Vinblastine.
VincristineThe serum concentration of Vismodegib can be decreased when it is combined with Vincristine.
VinorelbineThe serum concentration of Vismodegib can be increased when it is combined with Vinorelbine.
VoriconazoleThe metabolism of Vismodegib can be decreased when combined with Voriconazole.
ZafirlukastThe metabolism of Vismodegib can be decreased when combined with Zafirlukast.
ZimelidineThe serum concentration of Vismodegib can be increased when it is combined with Zimelidine.
ZiprasidoneThe metabolism of Vismodegib can be decreased when combined with Ziprasidone.
Food Interactions
  • Food does not affect absorption.

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
antagonist
General Function:
Wnt-protein binding
Specific Function:
G protein-coupled receptor that probably associates with the patched protein (PTCH) to transduce the hedgehog's proteins signal. Binding of sonic hedgehog (SHH) to its receptor patched is thought to prevent normal inhibition by patched of smoothened (SMO). Required for the accumulation of KIF7 and GLI3 in the cilia.
Gene Name:
SMO
Uniprot ID:
Q99835
Molecular Weight:
86395.95 Da
References
  1. Sandhiya S, Melvin G, Kumar SS, Dkhar SA: The dawn of hedgehog inhibitors: Vismodegib. J Pharmacol Pharmacother. 2013 Jan;4(1):4-7. doi: 10.4103/0976-500X.107628. [PubMed:23662017 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
no
Actions
substrateinhibitor
General Function:
Steroid 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Sandhiya S, Melvin G, Kumar SS, Dkhar SA: The dawn of hedgehog inhibitors: Vismodegib. J Pharmacol Pharmacother. 2013 Jan;4(1):4-7. doi: 10.4103/0976-500X.107628. [PubMed:23662017 ]
Kind
Protein
Organism
Human
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 reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Sandhiya S, Melvin G, Kumar SS, Dkhar SA: The dawn of hedgehog inhibitors: Vismodegib. J Pharmacol Pharmacother. 2013 Jan;4(1):4-7. doi: 10.4103/0976-500X.107628. [PubMed:23662017 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid 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 oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. In the epoxidation of arachidonic acid it generates only 14,15- and 11,12-cis-epoxyeicosatrienoic acids. It is the principal enzyme...
Gene Name:
CYP2C8
Uniprot ID:
P10632
Molecular Weight:
55824.275 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
inhibitor
General Function:
Steroid hydroxylase activity
Specific Function:
Responsible for the metabolism of a number of therapeutic agents such as the anticonvulsant drug S-mephenytoin, omeprazole, proguanil, certain barbiturates, diazepam, propranolol, citalopram and imipramine.
Gene Name:
CYP2C19
Uniprot ID:
P33261
Molecular Weight:
55930.545 Da

Carriers

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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 colloidal osmotic pressure of blood. Major zinc transporter in plasma, typically binds about 80% of all plasma zinc.
Gene Name:
ALB
Uniprot ID:
P02768
Molecular Weight:
69365.94 Da
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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 the body. Appears to function in modulating the activity of the immune system during the acute-phase reaction.
Gene Name:
ORM1
Uniprot ID:
P02763
Molecular Weight:
23511.38 Da

Transporters

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
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
Molecular Weight:
141477.255 Da
References
  1. Sandhiya S, Melvin G, Kumar SS, Dkhar SA: The dawn of hedgehog inhibitors: Vismodegib. J Pharmacol Pharmacother. 2013 Jan;4(1):4-7. doi: 10.4103/0976-500X.107628. [PubMed:23662017 ]
Kind
Protein
Organism
Human
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 from mitochondria to cytosol and from cytosol to extracellular space, and cellular export of hemin, and heme. Xenobiotic transporter that may play an important role in the exclusion of xenobiotics from t...
Gene Name:
ABCG2
Uniprot ID:
Q9UNQ0
Molecular Weight:
72313.47 Da
Comments
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Drug created on January 04, 2013 14:48 / Updated on September 29, 2016 03:00