You are using an unsupported browser. Please upgrade your browser to a newer version to get the best experience on DrugBank.
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 KeyBPQMGSKTAYIVFO-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
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.
Structured Indications
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.
TargetKindPharmacological actionActionsOrganismUniProt ID
Smoothened homologProteinyes
antagonist
HumanQ99835 details
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
Interactions
Drug Interactions
DrugInteractionDrug group
AbirateroneThe metabolism of Vismodegib can be decreased when combined with Abiraterone.Approved
AcetaminophenThe serum concentration of Vismodegib can be increased when it is combined with Acetaminophen.Approved
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Vismodegib.Approved
AfatinibThe serum concentration of Vismodegib can be increased when it is combined with Afatinib.Approved
AlbendazoleThe serum concentration of Vismodegib can be increased when it is combined with Albendazole.Approved, Vet Approved
AldosteroneThe serum concentration of Vismodegib can be decreased when it is combined with Aldosterone.Experimental
AlectinibThe serum concentration of Vismodegib can be increased when it is combined with Alectinib.Approved
AlfentanilThe serum concentration of Vismodegib can be increased when it is combined with Alfentanil.Approved, Illicit
AmantadineThe serum concentration of Vismodegib can be increased when it is combined with Amantadine.Approved
Aminohippuric acidThe serum concentration of Vismodegib can be increased when it is combined with Aminohippuric acid.Approved
AmiodaroneThe metabolism of Vismodegib can be decreased when combined with Amiodarone.Approved, Investigational
AmitriptylineThe serum concentration of Vismodegib can be increased when it is combined with Amitriptyline.Approved
AmlodipineThe serum concentration of Vismodegib can be increased when it is combined with Amlodipine.Approved
AmodiaquineThe serum concentration of Amodiaquine can be increased when it is combined with Vismodegib.Approved
AmprenavirThe serum concentration of Vismodegib can be decreased when it is combined with Amprenavir.Approved
AmsacrineThe serum concentration of Vismodegib can be increased when it is combined with Amsacrine.Approved
AnvirzelAnvirzel may decrease the cardiotoxic activities of Vismodegib.Investigational
AprepitantThe serum concentration of Vismodegib can be increased when it is combined with Aprepitant.Approved, Investigational
AstemizoleThe serum concentration of Vismodegib can be increased when it is combined with Astemizole.Approved, Withdrawn
AtazanavirThe metabolism of Vismodegib can be decreased when combined with Atazanavir.Approved, Investigational
AtenololThe serum concentration of Vismodegib can be increased when it is combined with Atenolol.Approved
AtomoxetineThe metabolism of Vismodegib can be decreased when combined with Atomoxetine.Approved
AtorvastatinThe serum concentration of Vismodegib can be increased when it is combined with Atorvastatin.Approved
AzelastineThe serum concentration of Vismodegib can be increased when it is combined with Azelastine.Approved
AzithromycinThe serum concentration of Vismodegib can be increased when it is combined with Azithromycin.Approved
BenzocaineThe serum concentration of Vismodegib can be increased when it is combined with Benzocaine.Approved
BepridilThe serum concentration of Vismodegib can be increased when it is combined with Bepridil.Approved, Withdrawn
BevacizumabBevacizumab may increase the cardiotoxic activities of Vismodegib.Approved, Investigational
BexaroteneThe serum concentration of Vismodegib can be decreased when it is combined with Bexarotene.Approved, Investigational
BiperidenThe serum concentration of Vismodegib can be increased when it is combined with Biperiden.Approved
BoceprevirThe metabolism of Vismodegib can be decreased when combined with Boceprevir.Approved
BortezomibThe metabolism of Vismodegib can be decreased when combined with Bortezomib.Approved, Investigational
BosentanThe serum concentration of Vismodegib can be decreased when it is combined with Bosentan.Approved, Investigational
BosutinibThe serum concentration of Vismodegib can be increased when it is combined with Bosutinib.Approved
BromocriptineThe serum concentration of Vismodegib can be increased when it is combined with Bromocriptine.Approved, Investigational
BuprenorphineThe serum concentration of Vismodegib can be increased when it is combined with Buprenorphine.Approved, Illicit, Investigational, Vet Approved
BuspironeThe serum concentration of Vismodegib can be increased when it is combined with Buspirone.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Vismodegib.Approved
CaffeineThe serum concentration of Vismodegib can be increased when it is combined with Caffeine.Approved
CanagliflozinThe serum concentration of Vismodegib can be increased when it is combined with Canagliflozin.Approved
CandesartanThe serum concentration of Vismodegib can be increased when it is combined with Candesartan.Approved
CapecitabineThe metabolism of Vismodegib can be decreased when combined with Capecitabine.Approved, Investigational
CaptoprilThe serum concentration of Vismodegib can be increased when it is combined with Captopril.Approved
CarbamazepineThe metabolism of Vismodegib can be increased when combined with Carbamazepine.Approved, Investigational
CarvedilolThe serum concentration of Vismodegib can be increased when it is combined with Carvedilol.Approved, Investigational
CaspofunginThe serum concentration of Vismodegib can be increased when it is combined with Caspofungin.Approved
CeritinibThe serum concentration of Vismodegib can be increased when it is combined with Ceritinib.Approved
ChloroquineThe serum concentration of Vismodegib can be increased when it is combined with Chloroquine.Approved, Vet Approved
ChlorpromazineThe serum concentration of Vismodegib can be increased when it is combined with Chlorpromazine.Approved, Vet Approved
ChlorpropamideThe serum concentration of Vismodegib can be increased when it is combined with Chlorpropamide.Approved
ChlorprothixeneThe serum concentration of Vismodegib can be increased when it is combined with Chlorprothixene.Approved, Withdrawn
CholecalciferolThe metabolism of Vismodegib can be decreased when combined with Cholecalciferol.Approved, Nutraceutical
CholesterolThe serum concentration of Vismodegib can be increased when it is combined with Cholesterol.Experimental
Cholic AcidThe serum concentration of Vismodegib can be decreased when it is combined with Cholic Acid.Approved
CilazaprilThe serum concentration of Vismodegib can be increased when it is combined with Cilazapril.Approved
CilostazolThe serum concentration of Cilostazol can be increased when it is combined with Vismodegib.Approved
CimetidineThe serum concentration of Vismodegib can be decreased when it is combined with Cimetidine.Approved
CiprofloxacinThe serum concentration of Vismodegib can be increased when it is combined with Ciprofloxacin.Approved, Investigational
CitalopramThe serum concentration of Vismodegib can be increased when it is combined with Citalopram.Approved
ClarithromycinThe metabolism of Vismodegib can be decreased when combined with Clarithromycin.Approved
ClemastineThe metabolism of Vismodegib can be decreased when combined with Clemastine.Approved
ClofazimineThe serum concentration of Vismodegib can be increased when it is combined with Clofazimine.Approved, Investigational
ClomipramineThe serum concentration of Vismodegib can be increased when it is combined with Clomipramine.Approved, Vet Approved
ClotrimazoleThe metabolism of Vismodegib can be decreased when combined with Clotrimazole.Approved, Vet Approved
CobicistatThe metabolism of Vismodegib can be decreased when combined with Cobicistat.Approved
ColchicineThe serum concentration of Vismodegib can be increased when it is combined with Colchicine.Approved
ColforsinThe serum concentration of Vismodegib can be increased when it is combined with Colforsin.Experimental
ConivaptanThe serum concentration of Vismodegib can be increased when it is combined with Conivaptan.Approved, Investigational
CrizotinibThe metabolism of Vismodegib can be decreased when combined with Crizotinib.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Vismodegib.Approved, Investigational
CyclosporineThe metabolism of Vismodegib can be decreased when combined with Cyclosporine.Approved, Investigational, Vet Approved
DabrafenibThe serum concentration of Vismodegib can be decreased when it is combined with Dabrafenib.Approved
DaclatasvirThe serum concentration of Vismodegib can be increased when it is combined with Daclatasvir.Approved
DactinomycinThe serum concentration of Vismodegib can be increased when it is combined with Dactinomycin.Approved
DarunavirThe metabolism of Vismodegib can be decreased when combined with Darunavir.Approved
DasatinibThe serum concentration of Vismodegib can be increased when it is combined with Dasatinib.Approved, Investigational
DaunorubicinThe serum concentration of Vismodegib can be decreased when it is combined with Daunorubicin.Approved
DeferasiroxThe serum concentration of Vismodegib can be decreased when it is combined with Deferasirox.Approved, Investigational
DelavirdineThe metabolism of Vismodegib can be decreased when combined with Delavirdine.Approved
DesipramineThe serum concentration of Vismodegib can be increased when it is combined with Desipramine.Approved
DeslanosideDeslanoside may decrease the cardiotoxic activities of Vismodegib.Approved
DesloratadineThe serum concentration of Vismodegib can be increased when it is combined with Desloratadine.Approved, Investigational
DexamethasoneThe serum concentration of Vismodegib can be decreased when it is combined with Dexamethasone.Approved, Investigational, Vet Approved
DextromethorphanThe serum concentration of Vismodegib can be increased when it is combined with Dextromethorphan.Approved
DiclofenacThe serum concentration of Vismodegib can be increased when it is combined with Diclofenac.Approved, Vet Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Vismodegib.Approved
DigoxinDigoxin may decrease the cardiotoxic activities of Vismodegib.Approved
DihydroergotamineThe metabolism of Vismodegib can be decreased when combined with Dihydroergotamine.Approved
DiltiazemThe metabolism of Vismodegib can be decreased when combined with Diltiazem.Approved
DipyridamoleThe serum concentration of Vismodegib can be increased when it is combined with Dipyridamole.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Vismodegib.Approved, Investigational
DoxazosinThe serum concentration of Vismodegib can be increased when it is combined with Doxazosin.Approved
DoxepinThe serum concentration of Vismodegib can be increased when it is combined with Doxepin.Approved
DoxorubicinThe serum concentration of Vismodegib can be decreased when it is combined with Doxorubicin.Approved, Investigational
DoxycyclineThe metabolism of Vismodegib can be decreased when combined with Doxycycline.Approved, Investigational, Vet Approved
DronabinolThe serum concentration of Vismodegib can be increased when it is combined with Dronabinol.Approved, Illicit
DronedaroneThe metabolism of Vismodegib can be decreased when combined with Dronedarone.Approved
EfavirenzThe serum concentration of Vismodegib can be decreased when it is combined with Efavirenz.Approved, Investigational
ElbasvirThe serum concentration of Vismodegib can be increased when it is combined with Elbasvir.Approved
EnalaprilThe serum concentration of Vismodegib can be increased when it is combined with Enalapril.Approved, Vet Approved
EnzalutamideThe serum concentration of Vismodegib can be decreased when it is combined with Enzalutamide.Approved
ErgonovineThe serum concentration of Vismodegib can be increased when it is combined with Ergonovine.Approved
ErgotamineThe serum concentration of Vismodegib can be increased when it is combined with Ergotamine.Approved
ErythromycinThe metabolism of Vismodegib can be decreased when combined with Erythromycin.Approved, Vet Approved
Eslicarbazepine acetateThe serum concentration of Vismodegib can be decreased when it is combined with Eslicarbazepine acetate.Approved
EstramustineThe serum concentration of Vismodegib can be increased when it is combined with Estramustine.Approved
EstriolThe serum concentration of Vismodegib can be decreased when it is combined with Estriol.Approved, Vet Approved
EstroneThe serum concentration of Vismodegib can be decreased when it is combined with Estrone.Approved
EtoposideThe serum concentration of Vismodegib can be increased when it is combined with Etoposide.Approved
EtravirineThe serum concentration of Vismodegib can be decreased when it is combined with Etravirine.Approved
FelodipineThe serum concentration of Vismodegib can be increased when it is combined with Felodipine.Approved, Investigational
FentanylThe serum concentration of Vismodegib can be increased when it is combined with Fentanyl.Approved, Illicit, Investigational, Vet Approved
FexofenadineThe serum concentration of Vismodegib can be increased when it is combined with Fexofenadine.Approved
FidaxomicinThe serum concentration of Vismodegib can be increased when it is combined with Fidaxomicin.Approved
FloxuridineThe metabolism of Vismodegib can be decreased when combined with Floxuridine.Approved
FluconazoleThe metabolism of Vismodegib can be decreased when combined with Fluconazole.Approved
FluorouracilThe metabolism of Vismodegib can be decreased when combined with Fluorouracil.Approved
FluoxetineThe serum concentration of Vismodegib can be increased when it is combined with Fluoxetine.Approved, Vet Approved
FlupentixolThe serum concentration of Vismodegib can be increased when it is combined with Flupentixol.Approved, Withdrawn
FluphenazineThe serum concentration of Vismodegib can be increased when it is combined with Fluphenazine.Approved
FlurazepamThe serum concentration of Vismodegib can be increased when it is combined with Flurazepam.Approved, Illicit
FluvastatinThe metabolism of Vismodegib can be decreased when combined with Fluvastatin.Approved
FluvoxamineThe metabolism of Vismodegib can be decreased when combined with Fluvoxamine.Approved, Investigational
FosamprenavirThe metabolism of Vismodegib can be decreased when combined with Fosamprenavir.Approved
FosaprepitantThe serum concentration of Vismodegib can be increased when it is combined with Fosaprepitant.Approved
FosphenytoinThe metabolism of Vismodegib can be increased when combined with Fosphenytoin.Approved
Fusidic AcidThe serum concentration of Vismodegib can be increased when it is combined with Fusidic Acid.Approved
GefitinibThe serum concentration of Vismodegib can be increased when it is combined with Gefitinib.Approved, Investigational
GemfibrozilThe metabolism of Vismodegib can be decreased when combined with Gemfibrozil.Approved
GenisteinThe serum concentration of Vismodegib can be increased when it is combined with Genistein.Investigational
GlyburideThe serum concentration of Vismodegib can be increased when it is combined with Glyburide.Approved
GlycerolThe serum concentration of Vismodegib can be increased when it is combined with Glycerol.Experimental
Gramicidin DThe serum concentration of Vismodegib can be increased when it is combined with Gramicidin D.Approved
GrepafloxacinThe serum concentration of Vismodegib can be increased when it is combined with Grepafloxacin.Withdrawn
HaloperidolThe serum concentration of Vismodegib can be increased when it is combined with Haloperidol.Approved
HydrocortisoneThe serum concentration of Vismodegib can be increased when it is combined with Hydrocortisone.Approved, Vet Approved
IdelalisibThe serum concentration of Vismodegib can be increased when it is combined with Idelalisib.Approved
ImatinibThe metabolism of Vismodegib can be decreased when combined with Imatinib.Approved
ImipramineThe serum concentration of Vismodegib can be increased when it is combined with Imipramine.Approved
IndinavirThe metabolism of Vismodegib can be decreased when combined with Indinavir.Approved
IndomethacinThe serum concentration of Vismodegib can be increased when it is combined with Indomethacin.Approved, Investigational
IrbesartanThe metabolism of Vismodegib can be decreased when combined with Irbesartan.Approved, Investigational
IsavuconazoniumThe metabolism of Vismodegib can be decreased when combined with Isavuconazonium.Approved, Investigational
IsradipineThe metabolism of Vismodegib can be decreased when combined with Isradipine.Approved
ItraconazoleThe metabolism of Vismodegib can be decreased when combined with Itraconazole.Approved, Investigational
IvacaftorThe serum concentration of Vismodegib can be increased when it is combined with Ivacaftor.Approved
IvermectinThe serum concentration of Vismodegib can be increased when it is combined with Ivermectin.Approved, Vet Approved
KetamineThe serum concentration of Vismodegib can be increased when it is combined with Ketamine.Approved, Vet Approved
KetoconazoleThe metabolism of Vismodegib can be decreased when combined with Ketoconazole.Approved, Investigational
LansoprazoleThe serum concentration of Vismodegib can be increased when it is combined with Lansoprazole.Approved, Investigational
LapatinibThe serum concentration of Vismodegib can be increased when it is combined with Lapatinib.Approved, Investigational
LeflunomideThe metabolism of Vismodegib can be decreased when combined with Leflunomide.Approved, Investigational
LevofloxacinThe serum concentration of Vismodegib can be increased when it is combined with Levofloxacin.Approved, Investigational
LevothyroxineThe serum concentration of Vismodegib can be decreased when it is combined with Levothyroxine.Approved
LidocaineThe serum concentration of Vismodegib can be increased when it is combined with Lidocaine.Approved, Vet Approved
LiothyronineThe serum concentration of Vismodegib can be decreased when it is combined with Liothyronine.Approved, Vet Approved
LiotrixThe serum concentration of Vismodegib can be decreased when it is combined with Liotrix.Approved
LisinoprilThe serum concentration of Vismodegib can be increased when it is combined with Lisinopril.Approved, Investigational
LomitapideThe serum concentration of Vismodegib can be increased when it is combined with Lomitapide.Approved
LoperamideThe serum concentration of Vismodegib can be increased when it is combined with Loperamide.Approved
LopinavirThe metabolism of Vismodegib can be decreased when combined with Lopinavir.Approved
LoratadineThe serum concentration of Vismodegib can be increased when it is combined with Loratadine.Approved
LosartanThe serum concentration of Vismodegib can be increased when it is combined with Losartan.Approved
LovastatinThe metabolism of Vismodegib can be decreased when combined with Lovastatin.Approved, Investigational
LuliconazoleThe serum concentration of Vismodegib can be increased when it is combined with Luliconazole.Approved
LumacaftorThe serum concentration of Vismodegib can be decreased when it is combined with Lumacaftor.Approved
MaprotilineThe serum concentration of Vismodegib can be increased when it is combined with Maprotiline.Approved
MebendazoleThe serum concentration of Vismodegib can be increased when it is combined with Mebendazole.Approved, Vet Approved
MefloquineThe serum concentration of Vismodegib can be increased when it is combined with Mefloquine.Approved
Megestrol acetateThe serum concentration of Vismodegib can be increased when it is combined with Megestrol acetate.Approved, Vet Approved
MeprobamateThe serum concentration of Vismodegib can be increased when it is combined with Meprobamate.Approved, Illicit
MethadoneThe serum concentration of Vismodegib can be increased when it is combined with Methadone.Approved
MetoprololThe serum concentration of Vismodegib can be increased when it is combined with Metoprolol.Approved, Investigational
MibefradilThe serum concentration of Vismodegib can be increased when it is combined with Mibefradil.Withdrawn
MiconazoleThe serum concentration of Vismodegib can be increased when it is combined with Miconazole.Approved, Investigational, Vet Approved
MidazolamThe serum concentration of Vismodegib can be decreased when it is combined with Midazolam.Approved, Illicit
MifepristoneThe serum concentration of Vismodegib can be increased when it is combined with Mifepristone.Approved, Investigational
MitomycinThe serum concentration of Vismodegib can be increased when it is combined with Mitomycin.Approved
MitotaneThe serum concentration of Vismodegib can be decreased when it is combined with Mitotane.Approved
MitoxantroneThe serum concentration of Vismodegib can be decreased when it is combined with Mitoxantrone.Approved, Investigational
ModafinilThe serum concentration of Vismodegib can be decreased when it is combined with Modafinil.Approved, Investigational
MorphineThe serum concentration of Vismodegib can be increased when it is combined with Morphine.Approved, Investigational
NafcillinThe serum concentration of Vismodegib can be decreased when it is combined with Nafcillin.Approved
NaltrexoneThe serum concentration of Vismodegib can be increased when it is combined with Naltrexone.Approved, Investigational, Vet Approved
NaringeninThe serum concentration of Vismodegib can be increased when it is combined with Naringenin.Experimental
NefazodoneThe metabolism of Vismodegib can be decreased when combined with Nefazodone.Approved, Withdrawn
NelfinavirThe metabolism of Vismodegib can be decreased when combined with Nelfinavir.Approved
NeostigmineThe serum concentration of Vismodegib can be increased when it is combined with Neostigmine.Approved, Vet Approved
NetupitantThe serum concentration of Vismodegib can be increased when it is combined with Netupitant.Approved
NevirapineThe metabolism of Vismodegib can be increased when combined with Nevirapine.Approved
NicardipineThe metabolism of Vismodegib can be decreased when combined with Nicardipine.Approved
NifedipineThe serum concentration of Vismodegib can be decreased when it is combined with Nifedipine.Approved
NilotinibThe metabolism of Vismodegib can be decreased when combined with Nilotinib.Approved, Investigational
NisoldipineThe serum concentration of Vismodegib can be increased when it is combined with Nisoldipine.Approved
NitrazepamThe serum concentration of Vismodegib can be increased when it is combined with Nitrazepam.Approved
NitrendipineThe serum concentration of Vismodegib can be increased when it is combined with Nitrendipine.Approved
NorethisteroneThe serum concentration of Vismodegib can be decreased when it is combined with Norethisterone.Approved
OlaparibThe metabolism of Vismodegib can be decreased when combined with Olaparib.Approved
OmeprazoleThe serum concentration of Vismodegib can be increased when it is combined with Omeprazole.Approved, Investigational, Vet Approved
OsimertinibThe serum concentration of Vismodegib can be increased when it is combined with Osimertinib.Approved
OuabainOuabain may decrease the cardiotoxic activities of Vismodegib.Approved
P-NitrophenolThe serum concentration of Vismodegib can be increased when it is combined with P-Nitrophenol.Experimental
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Vismodegib.Approved, Vet Approved
PalbociclibThe serum concentration of Vismodegib can be increased when it is combined with Palbociclib.Approved
Palmitic AcidThe serum concentration of Vismodegib can be increased when it is combined with Palmitic Acid.Experimental
PantoprazoleThe serum concentration of Vismodegib can be increased when it is combined with Pantoprazole.Approved
ParoxetineThe serum concentration of Vismodegib can be increased when it is combined with Paroxetine.Approved, Investigational
PazopanibThe serum concentration of Pazopanib can be increased when it is combined with Vismodegib.Approved
PentobarbitalThe metabolism of Vismodegib can be increased when combined with Pentobarbital.Approved, Vet Approved
PerindoprilThe serum concentration of Vismodegib can be increased when it is combined with Perindopril.Approved
PhenobarbitalThe metabolism of Vismodegib can be increased when combined with Phenobarbital.Approved
PhenytoinThe metabolism of Vismodegib can be increased when combined with Phenytoin.Approved, Vet Approved
PimozideThe serum concentration of Vismodegib can be increased when it is combined with Pimozide.Approved
Platelet Activating FactorThe serum concentration of Vismodegib can be decreased when it is combined with Platelet Activating Factor.Experimental
PonatinibThe serum concentration of Vismodegib can be increased when it is combined with Ponatinib.Approved
PosaconazoleThe metabolism of Vismodegib can be decreased when combined with Posaconazole.Approved, Investigational, Vet Approved
PravastatinThe serum concentration of Vismodegib can be increased when it is combined with Pravastatin.Approved
PrazosinThe serum concentration of Vismodegib can be increased when it is combined with Prazosin.Approved
PrednisoneThe serum concentration of Vismodegib can be increased when it is combined with Prednisone.Approved, Vet Approved
PrimidoneThe metabolism of Vismodegib can be increased when combined with Primidone.Approved, Vet Approved
ProbenecidThe serum concentration of Vismodegib can be increased when it is combined with Probenecid.Approved
ProgesteroneThe serum concentration of Vismodegib can be decreased when it is combined with Progesterone.Approved, Vet Approved
PromethazineThe serum concentration of Vismodegib can be increased when it is combined with Promethazine.Approved
PropafenoneThe serum concentration of Vismodegib can be increased when it is combined with Propafenone.Approved
PropranololThe serum concentration of Vismodegib can be increased when it is combined with Propranolol.Approved, Investigational
ProtriptylineThe serum concentration of Vismodegib can be increased when it is combined with Protriptyline.Approved
PyrimethamineThe metabolism of Vismodegib can be decreased when combined with Pyrimethamine.Approved, Vet Approved
QuercetinThe serum concentration of Vismodegib can be increased when it is combined with Quercetin.Experimental
QuinacrineThe serum concentration of Vismodegib can be increased when it is combined with Quinacrine.Approved
QuinidineThe serum concentration of Vismodegib can be increased when it is combined with Quinidine.Approved
QuinineThe serum concentration of Vismodegib can be increased when it is combined with Quinine.Approved
RanitidineThe serum concentration of Vismodegib can be increased when it is combined with Ranitidine.Approved
RanolazineThe serum concentration of Vismodegib can be increased when it is combined with Ranolazine.Approved, Investigational
ReboxetineThe serum concentration of Vismodegib can be increased when it is combined with Reboxetine.Approved, Investigational
RegorafenibThe serum concentration of Vismodegib can be increased when it is combined with Regorafenib.Approved
ReserpineThe serum concentration of Vismodegib can be decreased when it is combined with Reserpine.Approved
RifabutinThe metabolism of Vismodegib can be increased when combined with Rifabutin.Approved
RifampicinThe metabolism of Vismodegib can be increased when combined with Rifampicin.Approved
RifapentineThe metabolism of Vismodegib can be increased when combined with Rifapentine.Approved
RilpivirineThe serum concentration of Vismodegib can be increased when it is combined with Rilpivirine.Approved
RitonavirThe metabolism of Vismodegib can be decreased when combined with Ritonavir.Approved, Investigational
RolapitantThe serum concentration of Vismodegib can be increased when it is combined with Rolapitant.Approved
SaquinavirThe metabolism of Vismodegib can be decreased when combined with Saquinavir.Approved, Investigational
ScopolamineThe serum concentration of Vismodegib can be increased when it is combined with Scopolamine.Approved
SecobarbitalThe metabolism of Vismodegib can be increased when combined with Secobarbital.Approved, Vet Approved
SelegilineThe serum concentration of Vismodegib can be increased when it is combined with Selegiline.Approved, Investigational, Vet Approved
SertralineThe serum concentration of Vismodegib can be increased when it is combined with Sertraline.Approved
SildenafilThe metabolism of Vismodegib can be decreased when combined with Sildenafil.Approved, Investigational
SiltuximabThe serum concentration of Vismodegib can be decreased when it is combined with Siltuximab.Approved
SimeprevirThe serum concentration of Vismodegib can be increased when it is combined with Simeprevir.Approved
SimvastatinThe serum concentration of Vismodegib can be increased when it is combined with Simvastatin.Approved
SirolimusThe serum concentration of Vismodegib can be decreased when it is combined with Sirolimus.Approved, Investigational
SorafenibThe serum concentration of Vismodegib can be increased when it is combined with Sorafenib.Approved, Investigational
SpironolactoneThe serum concentration of Vismodegib can be increased when it is combined with Spironolactone.Approved
St. John's WortThe serum concentration of Vismodegib can be decreased when it is combined with St. John's Wort.Nutraceutical
StaurosporineThe serum concentration of Vismodegib can be increased when it is combined with Staurosporine.Experimental
StiripentolThe serum concentration of Vismodegib can be increased when it is combined with Stiripentol.Approved
StreptozocinThe serum concentration of Vismodegib can be decreased when it is combined with Streptozocin.Approved
SulfadiazineThe metabolism of Vismodegib can be decreased when combined with Sulfadiazine.Approved, Vet Approved
SulfamethoxazoleThe metabolism of Vismodegib can be decreased when combined with Sulfamethoxazole.Approved
SulfinpyrazoneThe serum concentration of Vismodegib can be increased when it is combined with Sulfinpyrazone.Approved
SulfisoxazoleThe metabolism of Vismodegib can be decreased when combined with Sulfisoxazole.Approved, Vet Approved
SumatriptanThe serum concentration of Vismodegib can be increased when it is combined with Sumatriptan.Approved, Investigational
SunitinibThe serum concentration of Vismodegib can be increased when it is combined with Sunitinib.Approved, Investigational
TacrineThe serum concentration of Vismodegib can be increased when it is combined with Tacrine.Withdrawn
TacrolimusThe serum concentration of Vismodegib can be decreased when it is combined with Tacrolimus.Approved, Investigational
TamoxifenThe serum concentration of Vismodegib can be decreased when it is combined with Tamoxifen.Approved
Taurocholic AcidThe serum concentration of Vismodegib can be increased when it is combined with Taurocholic Acid.Experimental
TelaprevirThe metabolism of Vismodegib can be decreased when combined with Telaprevir.Approved
TelithromycinThe metabolism of Vismodegib can be decreased when combined with Telithromycin.Approved
TelmisartanThe serum concentration of Vismodegib can be increased when it is combined with Telmisartan.Approved, Investigational
TemsirolimusThe serum concentration of Vismodegib can be increased when it is combined with Temsirolimus.Approved
TerazosinThe serum concentration of Vismodegib can be increased when it is combined with Terazosin.Approved
TerfenadineThe serum concentration of Vismodegib can be increased when it is combined with Terfenadine.Withdrawn
TesmilifeneThe serum concentration of Vismodegib can be decreased when it is combined with Tesmilifene.Investigational
TestosteroneThe serum concentration of Vismodegib can be increased when it is combined with Testosterone.Approved, Investigational
TicagrelorThe serum concentration of Vismodegib can be increased when it is combined with Ticagrelor.Approved
TiclopidineThe metabolism of Vismodegib can be decreased when combined with Ticlopidine.Approved
TocilizumabThe serum concentration of Vismodegib can be decreased when it is combined with Tocilizumab.Approved
TolbutamideThe metabolism of Vismodegib can be decreased when combined with Tolbutamide.Approved
TolvaptanThe serum concentration of Vismodegib can be increased when it is combined with Tolvaptan.Approved
TopotecanThe serum concentration of Topotecan can be increased when it is combined with Vismodegib.Approved, Investigational
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Vismodegib.Approved, Investigational
TrazodoneThe serum concentration of Vismodegib can be decreased when it is combined with Trazodone.Approved, Investigational
TrifluoperazineThe serum concentration of Vismodegib can be increased when it is combined with Trifluoperazine.Approved
TriflupromazineThe serum concentration of Vismodegib can be increased when it is combined with Triflupromazine.Approved, Vet Approved
TrimethoprimThe serum concentration of Vismodegib can be decreased when it is combined with Trimethoprim.Approved, Vet Approved
TrimipramineThe serum concentration of Vismodegib can be increased when it is combined with Trimipramine.Approved
TroleandomycinThe serum concentration of Vismodegib can be increased when it is combined with Troleandomycin.Approved
Valproic AcidThe metabolism of Vismodegib can be decreased when combined with Valproic Acid.Approved, Investigational
ValsartanThe metabolism of Vismodegib can be decreased when combined with Valsartan.Approved, Investigational
VenlafaxineThe metabolism of Vismodegib can be decreased when combined with Venlafaxine.Approved
VerapamilThe metabolism of Vismodegib can be decreased when combined with Verapamil.Approved
VinblastineThe serum concentration of Vismodegib can be decreased when it is combined with Vinblastine.Approved
VincristineThe serum concentration of Vismodegib can be decreased when it is combined with Vincristine.Approved, Investigational
VinorelbineThe serum concentration of Vismodegib can be increased when it is combined with Vinorelbine.Approved, Investigational
VoriconazoleThe metabolism of Vismodegib can be decreased when combined with Voriconazole.Approved, Investigational
ZafirlukastThe metabolism of Vismodegib can be decreased when combined with Zafirlukast.Approved, Investigational
ZimelidineThe serum concentration of Vismodegib can be increased when it is combined with Zimelidine.Withdrawn
ZiprasidoneThe metabolism of Vismodegib can be decreased when combined with Ziprasidone.Approved
Food Interactions
  • Food does not affect absorption.
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
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
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

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
comments powered by Disqus
Drug created on January 04, 2013 14:48 / Updated on December 04, 2016 03:20