Vismodegib - DrugBank

ID Pharmacology Interactions References Trials Economics Properties Spectra Taxonomy

Targets (1)Enzymes (4)Carriers (2)Transporters (2)

Targets (1)Enzymes (4)Carriers (2)Transporters (2)Biointeractions (8)

Identification

Name

Vismodegib

Accession Number

DB08828

Type

Small Molecule

Groups

Approved

Description

Vismodegib inhibits the hedgehog signalling pathway and is indicated for treatment of adult basal cell carcinoma. FDA approved on Jan 30, 2012.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Erivedge

Hedgehog Antagonist GDC-0449

Vismodegibum

External IDs

GDC-0449 / RG-3616

Product Ingredients

Not Available

Approved Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
Erivedge	Capsule	150 mg/1	Oral	Genentech, Inc.	2012-01-30	Not applicable	US
Erivedge	Capsule	150 mg	Oral	Hoffmann La Roche	2013-08-09	Not applicable	Canada

Approved Generic Prescription Products

Not Available

Approved Over the Counter Products

Not Available

Unapproved/Other Products

Not Available

International Brands

Not Available

Brand mixtures

Not Available

Categories

UNII

25X868M3DS

CAS number

879085-55-9

Weight

Average: 421.297
Monoisotopic: 420.010218428

Chemical Formula

C₁₉H₁₄Cl₂N₂O₃S

InChI Key

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

Pharmacology

Indication

Vismodegib 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

Pharmacodynamics

Vismodegib selectively binds to and inhibits the transmembrane protein Smoothened homologue (SMO) to inhibit the Hedgehog signalling pathway.

Mechanism of action

Mutations 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.

Target	Kind	Pharmacological action	Actions	Organism	UniProt ID
Smoothened homolog	Protein	yes	antagonist	Human	Q99835	details

Absorption

The 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 binding

Vismodegib 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 elimination

Vismodegib is mostly excreted unchanged, and the main route of elimination is by the feces (82%) and the urine accounts for 4.4%.

Half life

The half-life after a single dose is 12 days, and after continuous daily dosing is 4 days.

Clearance

Not Available

Toxicity

Increased 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

Pathways

Not Available

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

Drug	Interaction	Drug group
Abiraterone	The metabolism of Vismodegib can be decreased when combined with Abiraterone.	Approved
Acetaminophen	The serum concentration of Vismodegib can be increased when it is combined with Acetaminophen.	Approved
Acetyldigitoxin	Acetyldigitoxin may decrease the cardiotoxic activities of Vismodegib.	Approved
Afatinib	The serum concentration of Vismodegib can be increased when it is combined with Afatinib.	Approved
Albendazole	The serum concentration of Vismodegib can be increased when it is combined with Albendazole.	Approved, Vet Approved
Aldosterone	The serum concentration of Vismodegib can be decreased when it is combined with Aldosterone.	Experimental
Alectinib	The serum concentration of Vismodegib can be increased when it is combined with Alectinib.	Approved
Alfentanil	The serum concentration of Vismodegib can be increased when it is combined with Alfentanil.	Approved, Illicit
Amantadine	The serum concentration of Vismodegib can be increased when it is combined with Amantadine.	Approved
Aminohippuric acid	The serum concentration of Vismodegib can be increased when it is combined with Aminohippuric acid.	Approved
Amiodarone	The metabolism of Vismodegib can be decreased when combined with Amiodarone.	Approved, Investigational
Amitriptyline	The serum concentration of Vismodegib can be increased when it is combined with Amitriptyline.	Approved
Amlodipine	The serum concentration of Vismodegib can be increased when it is combined with Amlodipine.	Approved
Amodiaquine	The serum concentration of Amodiaquine can be increased when it is combined with Vismodegib.	Approved
Amprenavir	The serum concentration of Vismodegib can be decreased when it is combined with Amprenavir.	Approved
Amsacrine	The serum concentration of Vismodegib can be increased when it is combined with Amsacrine.	Approved
Aprepitant	The serum concentration of Vismodegib can be increased when it is combined with Aprepitant.	Approved, Investigational
Astemizole	The serum concentration of Vismodegib can be increased when it is combined with Astemizole.	Approved, Withdrawn
Atazanavir	The metabolism of Vismodegib can be decreased when combined with Atazanavir.	Approved, Investigational
Atenolol	The serum concentration of Vismodegib can be increased when it is combined with Atenolol.	Approved
Atomoxetine	The metabolism of Vismodegib can be decreased when combined with Atomoxetine.	Approved
Atorvastatin	The serum concentration of Vismodegib can be increased when it is combined with Atorvastatin.	Approved
Azelastine	The serum concentration of Vismodegib can be increased when it is combined with Azelastine.	Approved
Azithromycin	The serum concentration of Vismodegib can be increased when it is combined with Azithromycin.	Approved
Benzocaine	The serum concentration of Vismodegib can be increased when it is combined with Benzocaine.	Approved
Bepridil	The serum concentration of Vismodegib can be increased when it is combined with Bepridil.	Approved, Withdrawn
Bevacizumab	Bevacizumab may increase the cardiotoxic activities of Vismodegib.	Approved, Investigational
Bexarotene	The serum concentration of Vismodegib can be decreased when it is combined with Bexarotene.	Approved, Investigational
Biperiden	The serum concentration of Vismodegib can be increased when it is combined with Biperiden.	Approved
Boceprevir	The metabolism of Vismodegib can be decreased when combined with Boceprevir.	Withdrawn
Bortezomib	The metabolism of Vismodegib can be decreased when combined with Bortezomib.	Approved, Investigational
Bosentan	The serum concentration of Vismodegib can be decreased when it is combined with Bosentan.	Approved, Investigational
Bosutinib	The serum concentration of Vismodegib can be increased when it is combined with Bosutinib.	Approved
Bromocriptine	The serum concentration of Vismodegib can be increased when it is combined with Bromocriptine.	Approved, Investigational
Buprenorphine	The serum concentration of Vismodegib can be increased when it is combined with Buprenorphine.	Approved, Illicit, Investigational, Vet Approved
Buspirone	The serum concentration of Vismodegib can be increased when it is combined with Buspirone.	Approved, Investigational
Cabazitaxel	The risk or severity of adverse effects can be increased when Cabazitaxel is combined with Vismodegib.	Approved
Caffeine	The serum concentration of Vismodegib can be increased when it is combined with Caffeine.	Approved
Canagliflozin	The serum concentration of Vismodegib can be increased when it is combined with Canagliflozin.	Approved
Candesartan	The serum concentration of Vismodegib can be increased when it is combined with Candesartan.	Approved
Capecitabine	The metabolism of Vismodegib can be decreased when combined with Capecitabine.	Approved, Investigational
Captopril	The serum concentration of Vismodegib can be increased when it is combined with Captopril.	Approved
Carbamazepine	The metabolism of Vismodegib can be increased when combined with Carbamazepine.	Approved, Investigational
Carvedilol	The serum concentration of Vismodegib can be increased when it is combined with Carvedilol.	Approved, Investigational
Caspofungin	The serum concentration of Vismodegib can be increased when it is combined with Caspofungin.	Approved
Ceritinib	The serum concentration of Vismodegib can be increased when it is combined with Ceritinib.	Approved
Chloroquine	The serum concentration of Vismodegib can be increased when it is combined with Chloroquine.	Approved, Vet Approved
Chlorpromazine	The serum concentration of Vismodegib can be increased when it is combined with Chlorpromazine.	Approved, Vet Approved
Chlorpropamide	The serum concentration of Vismodegib can be increased when it is combined with Chlorpropamide.	Approved
Chlorprothixene	The serum concentration of Vismodegib can be increased when it is combined with Chlorprothixene.	Approved, Withdrawn
Cholecalciferol	The metabolism of Vismodegib can be decreased when combined with Cholecalciferol.	Approved, Nutraceutical
Cholesterol	The serum concentration of Vismodegib can be increased when it is combined with Cholesterol.	Experimental
Cholic Acid	The serum concentration of Vismodegib can be decreased when it is combined with Cholic Acid.	Approved
Cilazapril	The serum concentration of Vismodegib can be increased when it is combined with Cilazapril.	Approved
Cilostazol	The serum concentration of Cilostazol can be increased when it is combined with Vismodegib.	Approved
Cimetidine	The serum concentration of Vismodegib can be decreased when it is combined with Cimetidine.	Approved
Ciprofloxacin	The serum concentration of Vismodegib can be increased when it is combined with Ciprofloxacin.	Approved, Investigational
Citalopram	The serum concentration of Vismodegib can be increased when it is combined with Citalopram.	Approved
Clarithromycin	The metabolism of Vismodegib can be decreased when combined with Clarithromycin.	Approved
Clemastine	The metabolism of Vismodegib can be decreased when combined with Clemastine.	Approved
Clofazimine	The serum concentration of Vismodegib can be increased when it is combined with Clofazimine.	Approved, Investigational
Clomipramine	The serum concentration of Vismodegib can be increased when it is combined with Clomipramine.	Approved, Vet Approved
Clotrimazole	The metabolism of Vismodegib can be decreased when combined with Clotrimazole.	Approved, Vet Approved
Cobicistat	The metabolism of Vismodegib can be decreased when combined with Cobicistat.	Approved
Colchicine	The serum concentration of Vismodegib can be increased when it is combined with Colchicine.	Approved
Colforsin	The serum concentration of Vismodegib can be increased when it is combined with Colforsin.	Experimental
Conivaptan	The serum concentration of Vismodegib can be increased when it is combined with Conivaptan.	Approved, Investigational
Crizotinib	The metabolism of Vismodegib can be decreased when combined with Crizotinib.	Approved
Cyclophosphamide	Cyclophosphamide may increase the cardiotoxic activities of Vismodegib.	Approved, Investigational
Cyclosporine	The metabolism of Vismodegib can be decreased when combined with Cyclosporine.	Approved, Investigational, Vet Approved
Dabrafenib	The serum concentration of Vismodegib can be decreased when it is combined with Dabrafenib.	Approved
Daclatasvir	The serum concentration of Vismodegib can be increased when it is combined with Daclatasvir.	Approved
Dactinomycin	The serum concentration of Vismodegib can be increased when it is combined with Dactinomycin.	Approved
Darunavir	The metabolism of Vismodegib can be decreased when combined with Darunavir.	Approved
Dasatinib	The serum concentration of Vismodegib can be increased when it is combined with Dasatinib.	Approved, Investigational
Daunorubicin	The serum concentration of Vismodegib can be decreased when it is combined with Daunorubicin.	Approved
Deferasirox	The serum concentration of Vismodegib can be decreased when it is combined with Deferasirox.	Approved, Investigational
Delavirdine	The metabolism of Vismodegib can be decreased when combined with Delavirdine.	Approved
Desipramine	The serum concentration of Vismodegib can be increased when it is combined with Desipramine.	Approved
Deslanoside	Deslanoside may decrease the cardiotoxic activities of Vismodegib.	Approved
Desloratadine	The serum concentration of Vismodegib can be increased when it is combined with Desloratadine.	Approved, Investigational
Dexamethasone	The serum concentration of Vismodegib can be decreased when it is combined with Dexamethasone.	Approved, Investigational, Vet Approved
Dextromethorphan	The serum concentration of Vismodegib can be increased when it is combined with Dextromethorphan.	Approved
Diclofenac	The serum concentration of Vismodegib can be increased when it is combined with Diclofenac.	Approved, Vet Approved
Digitoxin	Digitoxin may decrease the cardiotoxic activities of Vismodegib.	Approved
Digoxin	Digoxin may decrease the cardiotoxic activities of Vismodegib.	Approved
Dihydroergotamine	The metabolism of Vismodegib can be decreased when combined with Dihydroergotamine.	Approved
Diltiazem	The metabolism of Vismodegib can be decreased when combined with Diltiazem.	Approved
Dipyridamole	The serum concentration of Vismodegib can be increased when it is combined with Dipyridamole.	Approved
Docetaxel	The risk or severity of adverse effects can be increased when Docetaxel is combined with Vismodegib.	Approved, Investigational
Doxazosin	The serum concentration of Vismodegib can be increased when it is combined with Doxazosin.	Approved
Doxepin	The serum concentration of Vismodegib can be increased when it is combined with Doxepin.	Approved
Doxorubicin	The serum concentration of Vismodegib can be decreased when it is combined with Doxorubicin.	Approved, Investigational
Doxycycline	The metabolism of Vismodegib can be decreased when combined with Doxycycline.	Approved, Investigational, Vet Approved
Dronabinol	The serum concentration of Vismodegib can be increased when it is combined with Dronabinol.	Approved, Illicit
Dronedarone	The metabolism of Vismodegib can be decreased when combined with Dronedarone.	Approved
Efavirenz	The serum concentration of Vismodegib can be decreased when it is combined with Efavirenz.	Approved, Investigational
Elbasvir	The serum concentration of Vismodegib can be increased when it is combined with Elbasvir.	Approved
Enalapril	The serum concentration of Vismodegib can be increased when it is combined with Enalapril.	Approved, Vet Approved
Enzalutamide	The serum concentration of Vismodegib can be decreased when it is combined with Enzalutamide.	Approved
Ergonovine	The serum concentration of Vismodegib can be increased when it is combined with Ergonovine.	Approved
Ergotamine	The serum concentration of Vismodegib can be increased when it is combined with Ergotamine.	Approved
Erythromycin	The metabolism of Vismodegib can be decreased when combined with Erythromycin.	Approved, Vet Approved
Eslicarbazepine acetate	The serum concentration of Vismodegib can be decreased when it is combined with Eslicarbazepine acetate.	Approved
Estramustine	The serum concentration of Vismodegib can be increased when it is combined with Estramustine.	Approved
Estriol	The serum concentration of Vismodegib can be decreased when it is combined with Estriol.	Approved, Vet Approved
Estrone	The serum concentration of Vismodegib can be decreased when it is combined with Estrone.	Approved
Etoposide	The serum concentration of Vismodegib can be increased when it is combined with Etoposide.	Approved
Etravirine	The serum concentration of Vismodegib can be decreased when it is combined with Etravirine.	Approved
Felodipine	The serum concentration of Vismodegib can be increased when it is combined with Felodipine.	Approved, Investigational
Fentanyl	The serum concentration of Vismodegib can be increased when it is combined with Fentanyl.	Approved, Illicit, Investigational, Vet Approved
Fexofenadine	The serum concentration of Vismodegib can be increased when it is combined with Fexofenadine.	Approved
Fidaxomicin	The serum concentration of Vismodegib can be increased when it is combined with Fidaxomicin.	Approved
Floxuridine	The metabolism of Vismodegib can be decreased when combined with Floxuridine.	Approved
Fluconazole	The metabolism of Vismodegib can be decreased when combined with Fluconazole.	Approved
Fluorouracil	The metabolism of Vismodegib can be decreased when combined with Fluorouracil.	Approved
Fluoxetine	The serum concentration of Vismodegib can be increased when it is combined with Fluoxetine.	Approved, Vet Approved
Flupentixol	The serum concentration of Vismodegib can be increased when it is combined with Flupentixol.	Approved, Withdrawn
Fluphenazine	The serum concentration of Vismodegib can be increased when it is combined with Fluphenazine.	Approved
Flurazepam	The serum concentration of Vismodegib can be increased when it is combined with Flurazepam.	Approved, Illicit
Fluvastatin	The metabolism of Vismodegib can be decreased when combined with Fluvastatin.	Approved
Fluvoxamine	The metabolism of Vismodegib can be decreased when combined with Fluvoxamine.	Approved, Investigational
Fosamprenavir	The metabolism of Vismodegib can be decreased when combined with Fosamprenavir.	Approved
Fosaprepitant	The serum concentration of Vismodegib can be increased when it is combined with Fosaprepitant.	Approved
Fosphenytoin	The metabolism of Vismodegib can be increased when combined with Fosphenytoin.	Approved
Fusidic Acid	The serum concentration of Vismodegib can be increased when it is combined with Fusidic Acid.	Approved
Gefitinib	The serum concentration of Vismodegib can be increased when it is combined with Gefitinib.	Approved, Investigational
Gemfibrozil	The metabolism of Vismodegib can be decreased when combined with Gemfibrozil.	Approved
Genistein	The serum concentration of Vismodegib can be increased when it is combined with Genistein.	Investigational
Glyburide	The serum concentration of Vismodegib can be increased when it is combined with Glyburide.	Approved
Gramicidin D	The serum concentration of Vismodegib can be increased when it is combined with Gramicidin D.	Approved
Grepafloxacin	The serum concentration of Vismodegib can be increased when it is combined with Grepafloxacin.	Withdrawn
Haloperidol	The serum concentration of Vismodegib can be increased when it is combined with Haloperidol.	Approved
Hydrocortisone	The serum concentration of Vismodegib can be increased when it is combined with Hydrocortisone.	Approved, Vet Approved
Idelalisib	The serum concentration of Vismodegib can be increased when it is combined with Idelalisib.	Approved
Imatinib	The metabolism of Vismodegib can be decreased when combined with Imatinib.	Approved
Imipramine	The serum concentration of Vismodegib can be increased when it is combined with Imipramine.	Approved
Indinavir	The metabolism of Vismodegib can be decreased when combined with Indinavir.	Approved
Indomethacin	The serum concentration of Vismodegib can be increased when it is combined with Indomethacin.	Approved, Investigational
Irbesartan	The metabolism of Vismodegib can be decreased when combined with Irbesartan.	Approved, Investigational
Isavuconazonium	The metabolism of Vismodegib can be decreased when combined with Isavuconazonium.	Approved, Investigational
Isradipine	The metabolism of Vismodegib can be decreased when combined with Isradipine.	Approved
Itraconazole	The metabolism of Vismodegib can be decreased when combined with Itraconazole.	Approved, Investigational
Ivacaftor	The serum concentration of Vismodegib can be increased when it is combined with Ivacaftor.	Approved
Ivermectin	The serum concentration of Vismodegib can be increased when it is combined with Ivermectin.	Approved, Vet Approved
Ketamine	The serum concentration of Vismodegib can be increased when it is combined with Ketamine.	Approved, Vet Approved
Ketoconazole	The metabolism of Vismodegib can be decreased when combined with Ketoconazole.	Approved, Investigational
Lansoprazole	The serum concentration of Vismodegib can be increased when it is combined with Lansoprazole.	Approved, Investigational
Lapatinib	The serum concentration of Vismodegib can be increased when it is combined with Lapatinib.	Approved, Investigational
Leflunomide	The metabolism of Vismodegib can be decreased when combined with Leflunomide.	Approved, Investigational
Levofloxacin	The serum concentration of Vismodegib can be increased when it is combined with Levofloxacin.	Approved, Investigational
Levothyroxine	The serum concentration of Vismodegib can be decreased when it is combined with Levothyroxine.	Approved
Lidocaine	The serum concentration of Vismodegib can be increased when it is combined with Lidocaine.	Approved, Vet Approved
Liothyronine	The serum concentration of Vismodegib can be decreased when it is combined with Liothyronine.	Approved, Vet Approved
Liotrix	The serum concentration of Vismodegib can be decreased when it is combined with Liotrix.	Approved
Lisinopril	The serum concentration of Vismodegib can be increased when it is combined with Lisinopril.	Approved, Investigational
Lomitapide	The serum concentration of Vismodegib can be increased when it is combined with Lomitapide.	Approved
Loperamide	The serum concentration of Vismodegib can be increased when it is combined with Loperamide.	Approved
Lopinavir	The metabolism of Vismodegib can be decreased when combined with Lopinavir.	Approved
Loratadine	The serum concentration of Vismodegib can be increased when it is combined with Loratadine.	Approved
Losartan	The serum concentration of Vismodegib can be increased when it is combined with Losartan.	Approved
Lovastatin	The metabolism of Vismodegib can be decreased when combined with Lovastatin.	Approved, Investigational
Luliconazole	The serum concentration of Vismodegib can be increased when it is combined with Luliconazole.	Approved
Lumacaftor	The serum concentration of Vismodegib can be decreased when it is combined with Lumacaftor.	Approved
Maprotiline	The serum concentration of Vismodegib can be increased when it is combined with Maprotiline.	Approved
Mebendazole	The serum concentration of Vismodegib can be increased when it is combined with Mebendazole.	Approved, Vet Approved
Mefloquine	The serum concentration of Vismodegib can be increased when it is combined with Mefloquine.	Approved
Megestrol acetate	The serum concentration of Vismodegib can be increased when it is combined with Megestrol acetate.	Approved, Vet Approved
Meprobamate	The serum concentration of Vismodegib can be increased when it is combined with Meprobamate.	Approved, Illicit
Methadone	The serum concentration of Vismodegib can be increased when it is combined with Methadone.	Approved
Metoprolol	The serum concentration of Vismodegib can be increased when it is combined with Metoprolol.	Approved, Investigational
Mibefradil	The serum concentration of Vismodegib can be increased when it is combined with Mibefradil.	Withdrawn
Miconazole	The serum concentration of Vismodegib can be increased when it is combined with Miconazole.	Approved, Investigational, Vet Approved
Midazolam	The serum concentration of Vismodegib can be decreased when it is combined with Midazolam.	Approved, Illicit
Mifepristone	The serum concentration of Vismodegib can be increased when it is combined with Mifepristone.	Approved, Investigational
Mitomycin	The serum concentration of Vismodegib can be increased when it is combined with Mitomycin.	Approved
Mitotane	The serum concentration of Vismodegib can be decreased when it is combined with Mitotane.	Approved
Mitoxantrone	The serum concentration of Vismodegib can be decreased when it is combined with Mitoxantrone.	Approved, Investigational
Modafinil	The serum concentration of Vismodegib can be decreased when it is combined with Modafinil.	Approved, Investigational
Morphine	The serum concentration of Vismodegib can be increased when it is combined with Morphine.	Approved, Investigational
Nafcillin	The serum concentration of Vismodegib can be decreased when it is combined with Nafcillin.	Approved
Naltrexone	The serum concentration of Vismodegib can be increased when it is combined with Naltrexone.	Approved, Investigational, Vet Approved
Naringenin	The serum concentration of Vismodegib can be increased when it is combined with Naringenin.	Experimental
Nefazodone	The metabolism of Vismodegib can be decreased when combined with Nefazodone.	Approved, Withdrawn
Nelfinavir	The metabolism of Vismodegib can be decreased when combined with Nelfinavir.	Approved
Neostigmine	The serum concentration of Vismodegib can be increased when it is combined with Neostigmine.	Approved, Vet Approved
Netupitant	The serum concentration of Vismodegib can be increased when it is combined with Netupitant.	Approved
Nevirapine	The metabolism of Vismodegib can be increased when combined with Nevirapine.	Approved
Nicardipine	The metabolism of Vismodegib can be decreased when combined with Nicardipine.	Approved
Nifedipine	The serum concentration of Vismodegib can be decreased when it is combined with Nifedipine.	Approved
Nilotinib	The metabolism of Vismodegib can be decreased when combined with Nilotinib.	Approved, Investigational
Nisoldipine	The serum concentration of Vismodegib can be increased when it is combined with Nisoldipine.	Approved
Nitrazepam	The serum concentration of Vismodegib can be increased when it is combined with Nitrazepam.	Approved
Nitrendipine	The serum concentration of Vismodegib can be increased when it is combined with Nitrendipine.	Approved
Norethisterone	The serum concentration of Vismodegib can be decreased when it is combined with Norethisterone.	Approved
Olaparib	The metabolism of Vismodegib can be decreased when combined with Olaparib.	Approved
Oleandrin	Anvirzel may decrease the cardiotoxic activities of Vismodegib.	Experimental
Omeprazole	The serum concentration of Vismodegib can be increased when it is combined with Omeprazole.	Approved, Investigational, Vet Approved
Osimertinib	The serum concentration of Vismodegib can be increased when it is combined with Osimertinib.	Approved
Ouabain	Ouabain may decrease the cardiotoxic activities of Vismodegib.	Approved
P-Nitrophenol	The serum concentration of Vismodegib can be increased when it is combined with P-Nitrophenol.	Experimental
Paclitaxel	The risk or severity of adverse effects can be increased when Paclitaxel is combined with Vismodegib.	Approved, Vet Approved
Palbociclib	The serum concentration of Vismodegib can be increased when it is combined with Palbociclib.	Approved
Palmitic Acid	The serum concentration of Vismodegib can be increased when it is combined with Palmitic Acid.	Experimental
Pantoprazole	The serum concentration of Vismodegib can be increased when it is combined with Pantoprazole.	Approved
Paroxetine	The serum concentration of Vismodegib can be increased when it is combined with Paroxetine.	Approved, Investigational
Pazopanib	The serum concentration of Pazopanib can be increased when it is combined with Vismodegib.	Approved
Pentobarbital	The metabolism of Vismodegib can be increased when combined with Pentobarbital.	Approved, Vet Approved
Perindopril	The serum concentration of Vismodegib can be increased when it is combined with Perindopril.	Approved
Phenobarbital	The metabolism of Vismodegib can be increased when combined with Phenobarbital.	Approved
Phenytoin	The metabolism of Vismodegib can be increased when combined with Phenytoin.	Approved, Vet Approved
Pimozide	The serum concentration of Vismodegib can be increased when it is combined with Pimozide.	Approved
Platelet Activating Factor	The serum concentration of Vismodegib can be decreased when it is combined with Platelet Activating Factor.	Experimental
Ponatinib	The serum concentration of Vismodegib can be increased when it is combined with Ponatinib.	Approved
Posaconazole	The metabolism of Vismodegib can be decreased when combined with Posaconazole.	Approved, Investigational, Vet Approved
Pravastatin	The serum concentration of Vismodegib can be increased when it is combined with Pravastatin.	Approved
Prazosin	The serum concentration of Vismodegib can be increased when it is combined with Prazosin.	Approved
Prednisone	The serum concentration of Vismodegib can be increased when it is combined with Prednisone.	Approved, Vet Approved
Primidone	The metabolism of Vismodegib can be increased when combined with Primidone.	Approved, Vet Approved
Probenecid	The serum concentration of Vismodegib can be increased when it is combined with Probenecid.	Approved
Progesterone	The serum concentration of Vismodegib can be decreased when it is combined with Progesterone.	Approved, Vet Approved
Promethazine	The serum concentration of Vismodegib can be increased when it is combined with Promethazine.	Approved
Propafenone	The serum concentration of Vismodegib can be increased when it is combined with Propafenone.	Approved
Propranolol	The serum concentration of Vismodegib can be increased when it is combined with Propranolol.	Approved, Investigational
Protriptyline	The serum concentration of Vismodegib can be increased when it is combined with Protriptyline.	Approved
Pyrimethamine	The metabolism of Vismodegib can be decreased when combined with Pyrimethamine.	Approved, Vet Approved
Quercetin	The serum concentration of Vismodegib can be increased when it is combined with Quercetin.	Experimental
Quinacrine	The serum concentration of Vismodegib can be increased when it is combined with Quinacrine.	Approved
Quinidine	The serum concentration of Vismodegib can be increased when it is combined with Quinidine.	Approved
Quinine	The serum concentration of Vismodegib can be increased when it is combined with Quinine.	Approved
Ranitidine	The serum concentration of Vismodegib can be increased when it is combined with Ranitidine.	Approved
Ranolazine	The serum concentration of Vismodegib can be increased when it is combined with Ranolazine.	Approved, Investigational
Reboxetine	The serum concentration of Vismodegib can be increased when it is combined with Reboxetine.	Approved, Investigational
Regorafenib	The serum concentration of Vismodegib can be increased when it is combined with Regorafenib.	Approved
Reserpine	The serum concentration of Vismodegib can be decreased when it is combined with Reserpine.	Approved
Rifabutin	The metabolism of Vismodegib can be increased when combined with Rifabutin.	Approved
Rifampicin	The metabolism of Vismodegib can be increased when combined with Rifampicin.	Approved
Rifapentine	The metabolism of Vismodegib can be increased when combined with Rifapentine.	Approved
Rilpivirine	The serum concentration of Vismodegib can be increased when it is combined with Rilpivirine.	Approved
Ritonavir	The metabolism of Vismodegib can be decreased when combined with Ritonavir.	Approved, Investigational
Rolapitant	The serum concentration of Vismodegib can be increased when it is combined with Rolapitant.	Approved
Saquinavir	The metabolism of Vismodegib can be decreased when combined with Saquinavir.	Approved, Investigational
Scopolamine	The serum concentration of Vismodegib can be increased when it is combined with Scopolamine.	Approved
Secobarbital	The metabolism of Vismodegib can be increased when combined with Secobarbital.	Approved, Vet Approved
Selegiline	The serum concentration of Vismodegib can be increased when it is combined with Selegiline.	Approved, Investigational, Vet Approved
Sertraline	The serum concentration of Vismodegib can be increased when it is combined with Sertraline.	Approved
Sildenafil	The metabolism of Vismodegib can be decreased when combined with Sildenafil.	Approved, Investigational
Siltuximab	The serum concentration of Vismodegib can be decreased when it is combined with Siltuximab.	Approved
Simeprevir	The serum concentration of Vismodegib can be increased when it is combined with Simeprevir.	Approved
Simvastatin	The serum concentration of Vismodegib can be increased when it is combined with Simvastatin.	Approved
Sirolimus	The serum concentration of Vismodegib can be decreased when it is combined with Sirolimus.	Approved, Investigational
Sorafenib	The serum concentration of Vismodegib can be increased when it is combined with Sorafenib.	Approved, Investigational
Spironolactone	The serum concentration of Vismodegib can be increased when it is combined with Spironolactone.	Approved
St. John's Wort	The serum concentration of Vismodegib can be decreased when it is combined with St. John's Wort.	Nutraceutical
Staurosporine	The serum concentration of Vismodegib can be increased when it is combined with Staurosporine.	Experimental
Stiripentol	The serum concentration of Vismodegib can be increased when it is combined with Stiripentol.	Approved
Streptozocin	The serum concentration of Vismodegib can be decreased when it is combined with Streptozocin.	Approved
Sulfadiazine	The metabolism of Vismodegib can be decreased when combined with Sulfadiazine.	Approved, Vet Approved
Sulfamethoxazole	The metabolism of Vismodegib can be decreased when combined with Sulfamethoxazole.	Approved
Sulfinpyrazone	The serum concentration of Vismodegib can be increased when it is combined with Sulfinpyrazone.	Approved
Sulfisoxazole	The metabolism of Vismodegib can be decreased when combined with Sulfisoxazole.	Approved, Vet Approved
Sumatriptan	The serum concentration of Vismodegib can be increased when it is combined with Sumatriptan.	Approved, Investigational
Sunitinib	The serum concentration of Vismodegib can be increased when it is combined with Sunitinib.	Approved, Investigational
Tacrine	The serum concentration of Vismodegib can be increased when it is combined with Tacrine.	Withdrawn
Tacrolimus	The serum concentration of Vismodegib can be decreased when it is combined with Tacrolimus.	Approved, Investigational
Tamoxifen	The serum concentration of Vismodegib can be decreased when it is combined with Tamoxifen.	Approved
Taurocholic Acid	The serum concentration of Vismodegib can be increased when it is combined with Taurocholic Acid.	Experimental
Telaprevir	The metabolism of Vismodegib can be decreased when combined with Telaprevir.	Withdrawn
Telithromycin	The metabolism of Vismodegib can be decreased when combined with Telithromycin.	Approved
Telmisartan	The serum concentration of Vismodegib can be increased when it is combined with Telmisartan.	Approved, Investigational
Temsirolimus	The serum concentration of Vismodegib can be increased when it is combined with Temsirolimus.	Approved
Terazosin	The serum concentration of Vismodegib can be increased when it is combined with Terazosin.	Approved
Terfenadine	The serum concentration of Vismodegib can be increased when it is combined with Terfenadine.	Withdrawn
Tesmilifene	The serum concentration of Vismodegib can be decreased when it is combined with Tesmilifene.	Investigational
Testosterone	The serum concentration of Vismodegib can be increased when it is combined with Testosterone.	Approved, Investigational
Ticagrelor	The serum concentration of Vismodegib can be increased when it is combined with Ticagrelor.	Approved
Ticlopidine	The metabolism of Vismodegib can be decreased when combined with Ticlopidine.	Approved
Tocilizumab	The serum concentration of Vismodegib can be decreased when it is combined with Tocilizumab.	Approved
Tolbutamide	The metabolism of Vismodegib can be decreased when combined with Tolbutamide.	Approved
Tolvaptan	The serum concentration of Vismodegib can be increased when it is combined with Tolvaptan.	Approved
Topotecan	The serum concentration of Topotecan can be increased when it is combined with Vismodegib.	Approved, Investigational
Trastuzumab	Trastuzumab may increase the cardiotoxic activities of Vismodegib.	Approved, Investigational
Trazodone	The serum concentration of Vismodegib can be decreased when it is combined with Trazodone.	Approved, Investigational
Trifluoperazine	The serum concentration of Vismodegib can be increased when it is combined with Trifluoperazine.	Approved
Triflupromazine	The serum concentration of Vismodegib can be increased when it is combined with Triflupromazine.	Approved, Vet Approved
Trimethoprim	The serum concentration of Vismodegib can be decreased when it is combined with Trimethoprim.	Approved, Vet Approved
Trimipramine	The serum concentration of Vismodegib can be increased when it is combined with Trimipramine.	Approved
Valproic Acid	The metabolism of Vismodegib can be decreased when combined with Valproic Acid.	Approved, Investigational
Valsartan	The metabolism of Vismodegib can be decreased when combined with Valsartan.	Approved, Investigational
Venlafaxine	The metabolism of Vismodegib can be decreased when combined with Venlafaxine.	Approved
Verapamil	The metabolism of Vismodegib can be decreased when combined with Verapamil.	Approved
Vinblastine	The serum concentration of Vismodegib can be decreased when it is combined with Vinblastine.	Approved
Vincristine	The serum concentration of Vismodegib can be decreased when it is combined with Vincristine.	Approved, Investigational
Vinorelbine	The serum concentration of Vismodegib can be increased when it is combined with Vinorelbine.	Approved, Investigational
Voriconazole	The metabolism of Vismodegib can be decreased when combined with Voriconazole.	Approved, Investigational
Zafirlukast	The metabolism of Vismodegib can be decreased when combined with Zafirlukast.	Approved, Investigational
Zimelidine	The serum concentration of Vismodegib can be increased when it is combined with Zimelidine.	Withdrawn
Ziprasidone	The metabolism of Vismodegib can be decreased when combined with Ziprasidone.	Approved

Food Interactions

Food does not affect absorption.

References

Synthesis Reference

Not Available

General References

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 ]
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

Resource	Link
KEGG Drug	D09992
PubChem Compound	24776445
PubChem Substance	175427109
ChemSpider	23337846
BindingDB	50249522
ChEBI	66903
ChEMBL	CHEMBL473417
PharmGKB	PA166048558
HET	VIS
Drug Product Database	22125
RxList	http://www.rxlist.com/erivedge-drug.htm
Drugs.com	http://www.drugs.com/mtm/vismodegib.html
Wikipedia	Vismodegib

ATC Codes

L01XX43 — Vismodegib

AHFS Codes

10:00

PDB Entries

Not Available

FDA label

Download (211 KB)

MSDS

Not Available

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Active Not Recruiting	Treatment	Malignant Neoplasm of Prostate	1
0	Unknown Status	Treatment	Pancreatic Adenocarcinoma Resectable	1
1	Active Not Recruiting	Treatment	Adult Solid Neoplasm / Pancreatic Acinar Cell Carcinoma / Pancreatic Ductal Adenocarcinoma / Recurrent Pancreatic Carcinoma / Stage IV Pancreatic Cancer / Stage IV Pancreatic Cancer AJCC v6 and v7	1
1	Completed	Not Available	Healthy Volunteers	1
1	Completed	Treatment	Cancers / Solid Cancers	1
1	Completed	Treatment	DS Stage I Plasma Cell Myeloma / DS Stage II Plasma Cell Myeloma / DS Stage III Plasma Cell Myeloma / Refractory Plasma Cell Myeloma	1
1	Completed	Treatment	Healthy Volunteers	2
1	Completed	Treatment	Idiopathic Pulmonary Fibrosis (IPF)	1
1	Completed	Treatment	Recurrent Childhood Medulloblastoma	1
1	Completed	Treatment	Solid Cancers	2
1	Completed	Treatment	Unspecified Adult Solid Tumor, Protocol Specific	1
1	Recruiting	Treatment	Basal Cell Carcinoma (BCC)	1
1	Suspended	Treatment	Acinar Cell Adenocarcinoma of the Pancreas / Duct Cell Adenocarcinoma of the Pancreas / Recurrent Pancreatic Cancer / Stage IV Pancreatic Cancer / Unspecified Adult Solid Tumor, Protocol Specific	1
1	Terminated	Treatment	Estrogen Receptor Negative / HER2/Neu Negative / Progesterone Receptor Negative / Recurrent Breast Carcinoma / Stage IIIB Breast Cancer / Stage IIIC Breast Cancer / Stage IV Breast Cancer / Triple-Negative Breast Carcinoma	1
1, 2	Active Not Recruiting	Treatment	Adenocarcinoma, Prostate / Stage IIA Prostate Cancer / Stage IIB Prostate Cancer	1
1, 2	Active Not Recruiting	Treatment	Neoplasms, Malignant	1
1, 2	Completed	Treatment	Adenocarcinoma of the Pancreas / Recurrent Pancreatic Cancer / Stage IV Pancreatic Cancer	1
1, 2	Completed	Treatment	Adult Alveolar Soft Part Sarcoma / Adult Angiosarcoma / Adult Desmoplastic Small Round Cell Tumor / Adult Epithelioid Hemangioendothelioma / Adult Epithelioid Sarcoma / Adult Extraskeletal Myxoid Chondrosarcoma / Adult Extraskeletal Osteosarcoma / Adult Fibrosarcoma / Adult Leiomyosarcoma / Adult Liposarcoma / Adult Malignant Mesenchymoma / Adult Malignant Peripheral Nerve Sheath Tumor / Adult Rhabdomyosarcoma / Adult Synovial Sarcoma / Adult Unclassified Pleomorphic Sarcoma / Chondrosarcomas / Clear Cell Sarcoma of the Kidney / Conjunctival Kaposi Sarcoma / Dermatofibrosarcoma Protuberans / Gastrointestinal Stromal Tumors / Metastatic Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor / Metastatic Osteosarcoma / Ovarian Sarcoma / Recurrent Adult Soft Tissue Sarcoma / Recurrent Adult Unclassified Pleomorphic Sarcoma of Bone / Recurrent Ewing Sarcoma/Peripheral Primitive Neuroectodermal Tumor / Recurrent Kaposi's Sarcoma / Recurrent Osteosarcoma / Recurrent Uterine Corpus Sarcoma / Small Intestine Leiomyosarcoma / Stage III Adult Soft Tissue Sarcoma / Stage III Uterine Sarcoma / Stage IV Adult Soft Tissue Sarcoma / Stage IV Uterine Sarcoma / Unclassified Pleomorphic Sarcoma of Bone	1
1, 2	Not Yet Recruiting	Treatment	Glioblastoma, Adult	1
1, 2	Recruiting	Treatment	Activation of the Sonic Hedgehog (SHH) Pathway / Histologically Confirmed Medulloblastoma	1
1, 2	Recruiting	Treatment	Agnogenic Myeloid Metaplasia	1
2	Active Not Recruiting	Treatment	Basal Cell Carcinoma (BCC)	3
2	Active Not Recruiting	Treatment	Chondrosarcoma, Mesenchymal / Chondrosarcomas / Clear Cell Chondrosarcoma / Dedifferentiated Chondrosarcoma / Metastatic Chondrosarcoma / Primary Central Chondrosarcoma	1
2	Active Not Recruiting	Treatment	Extensive Stage Small Cell Lung Cancer / Extensive Stage Small Cell Lung Carcinoma / Recurrent Small Cell Lung Cancer / Recurrent Small Cell Lung Carcinoma	1
2	Active Not Recruiting	Treatment	Keratocystic Odontogenic Tumor	1
2	Active Not Recruiting	Treatment	Pancreatic Cancer Metastatic	1
2	Active Not Recruiting	Treatment	Recurrent Pancreatic Carcinoma / Stage IV Pancreatic Cancer	1
2	Completed	Prevention	Basal Cell Carcinoma (BCC)	1
2	Completed	Treatment	Adenocarcinoma of the Stomach / Adenocarcinomas of the Gastroesophageal Junction / Recurrent Gastric Cancer / Stage IIIA Gastric Cancer / Stage IIIB Gastric Cancer / Stage IIIC Gastric Cancer / Stage IV Gastric Cancer	1
2	Completed	Treatment	Adult Giant Cell Glioblastoma / Adult Glioblastoma / Adult Gliosarcoma / Recurrent Adult Brain Tumor	1
2	Completed	Treatment	Adult Medulloblastoma	1
2	Completed	Treatment	Basal Cell Carcinoma (BCC)	4
2	Completed	Treatment	Basal Cell Carcinoma (BCC) / Cancer, Ovarian / Metastatic Colorectal Cancers	1
2	Completed	Treatment	Basal Cell Nevus Syndrome / Gorlin's Syndrome	2
2	Completed	Treatment	Cancer, Ovarian	1
2	Completed	Treatment	Metastatic Colorectal Cancers	1
2	Completed	Treatment	Recurrent Childhood Medulloblastoma	1
2	Not Yet Recruiting	Treatment	Basal Cell Carcinoma (BCC)	1
2	Recruiting	Treatment	Acute Myeloid Leukaemias (AML)	1
2	Recruiting	Treatment	Advanced Malignant Neoplasm / Advanced Malignant Solid Neoplasm / Bladder Carcinoma / Carcinoma, Breast / Carcinoma, Colorectal / Carcinoma, Pancreatic / Cervical Carcinoma / Colon Carcinoma / Endometrial Carcinoma / Gastric Carcinoma / Gliomas / Head and Neck Carcinoma / Liver and Intrahepatic Bile Duct Carcinoma / Lung, Carcinoma / Malignant Lymphomas / Malignant Neoplasm of Prostate / Malignant Uterine Neoplasm / Melanoma / Oesophageal Carcinoma / Ovarian Carcinoma / Plasma Cell Myeloma / Rectal Carcinoma / Recurrent Bladder Carcinoma / Recurrent Breast Carcinoma / Recurrent Cervical Carcinoma / Recurrent Colon Carcinoma / Recurrent Colorectal Carcinoma / Recurrent Esophageal Carcinoma / Recurrent Gastric Carcinoma / Recurrent Gliomas / Recurrent Head and Neck Carcinoma / Recurrent Liver Carcinoma / Recurrent Lung Carcinoma / Recurrent Lymphoma / Recurrent Malignant Solid Neoplasm / Recurrent Melanoma / Recurrent Ovarian Carcinoma / Recurrent Pancreatic Carcinoma / Recurrent Plasma Cell Myeloma / Recurrent Prostate Carcinoma / Recurrent Rectal Carcinoma / Recurrent Skin Carcinoma / Recurrent Solid Neoplasm / Recurrent Thyroid Gland Carcinoma / Recurrent Uterine Corpus Carcinoma / Refractory Lymphomas / Refractory Malignant Neoplasm / Refractory Malignant Solid Neoplasm / Refractory Plasma Cell Myeloma / Renal Carcinoma / Skin Carcinoma / Solid Neoplasms / Thyroid Gland Carcinoma / Uterine Corpus Cancer	1
2	Recruiting	Treatment	Advanced Solid Tumors / Multiple Myeloma (MM) / Non-Hodgkin's Lymphoma (NHL)	1
2	Recruiting	Treatment	Basal Cell Carcinoma (BCC)	2
2	Recruiting	Treatment	Cancer, Breast	1
2	Recruiting	Treatment	Cancers / Neoplasia / Neoplasms / Tumors	1
2	Recruiting	Treatment	Cutaneous Malignancy / Locally Advanced Basal Cell Carcinoma / Skin Cancers	1
2	Recruiting	Treatment	Intracranial Meningioma / NF2 Gene Mutation / Recurrent Meningiomas	1
2	Recruiting	Treatment	Medulloblastomas	1
2	Recruiting	Treatment	Neoplasms	1
2	Recruiting	Treatment	Skin Basal Cell Carcinoma	1
2	Recruiting	Treatment	Stomach Neoplasms	1
2	Terminated	Treatment	"Indolent" Non-hodgkin Lymphoma / Chronic Lymphocytic Leukaemia (CLL) / Indolent Non-Hodgkin's Lymphomas / Lymphoma, Large B-Cell, Diffuse (DLBCL) / Primary Central Nervous System Lymphoma (PCNSL)	1
2	Terminated	Treatment	Myelodysplastic Syndromes, Myelogenous Leukemia, Acute	1
2	Terminated	Treatment	Pancreatic Ductal Adenocarcinoma	1
2	Terminated	Treatment	Pontine Glioma	1
2	Withdrawn	Treatment	Idiopathic Pulmonary Fibrosis (IPF)	1
4	Approved for Marketing	Not Available	Basal Cell Carcinoma (BCC)	1
4	Recruiting	Treatment	Basal Cell Carcinoma (BCC)	1
Not Available	Active Not Recruiting	Treatment	Basal Cell Carcinoma of the Skin / Recurrent Skin Cancer	1
Not Available	Recruiting	Not Available	Basal Cell Carcinoma (BCC)	1
Not Available	Recruiting	Not Available	Locally Advanced Basal Cell Carcinoma	1
Not Available	Suspended	Supportive Care	Chronic Graft Versus Host Disease / Progressive cGVHD	1

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Not Available

Dosage forms

Form	Route	Strength
Capsule	Oral	150 mg/1
Capsule	Oral	150 mg

Prices

Not Available

Patents

Patent Number	Pediatric Extension	Approved	Expires (estimated)
US7888364	No	2008-11-11	2028-11-11	US
US9278961	No	2008-12-15	2028-12-15	US

Properties

State

Solid

Experimental Properties

Property	Value	Source
water solubility	0.1 μg/mL and is pH dependent	FDA label
logP	2.7	FDA label
pKa	3.8	FDA label

Predicted Properties

Property	Value	Source
Water Solubility	0.00173 mg/mL	ALOGPS
logP	4.22	ALOGPS
logP	3.93	ChemAxon
logS	-5.4	ALOGPS
pKa (Strongest Acidic)	10.27	ChemAxon
pKa (Strongest Basic)	3.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	76.13 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	107.81 m³·mol^-1	ChemAxon
Polarizability	39.49 Å³	ChemAxon
Number of Rings	3	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	0.9547
Blood Brain Barrier	+	0.9387
Caco-2 permeable	+	0.6048
P-glycoprotein substrate	Non-substrate	0.8443
P-glycoprotein inhibitor I	Non-inhibitor	0.8663
P-glycoprotein inhibitor II	Non-inhibitor	0.9558
Renal organic cation transporter	Non-inhibitor	0.8925
CYP450 2C9 substrate	Non-substrate	0.6009
CYP450 2D6 substrate	Non-substrate	0.63
CYP450 3A4 substrate	Non-substrate	0.5083
CYP450 1A2 substrate	Non-inhibitor	0.6067
CYP450 2C9 inhibitor	Inhibitor	0.9078
CYP450 2D6 inhibitor	Non-inhibitor	0.6638
CYP450 2C19 inhibitor	Inhibitor	0.8515
CYP450 3A4 inhibitor	Inhibitor	0.8452
CYP450 inhibitory promiscuity	High CYP Inhibitory Promiscuity	0.9282
Ames test	Non AMES toxic	0.8271
Carcinogenicity	Non-carcinogens	0.6746
Biodegradation	Not ready biodegradable	0.9956
Rat acute toxicity	2.0840 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Weak inhibitor	0.9973
hERG inhibition (predictor II)	Non-inhibitor	0.8224

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

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum Type	Description	Splash Key
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	Not Available
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	Not Available

Taxonomy

Description

This compound belongs to the class of chemical entities known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.

Kingdom

Chemical entities

Super Class

Organic compounds

Class

Benzenoids

Sub Class

Benzene and substituted derivatives

Direct Parent

Benzanilides

Alternative Parents

Phenylpyridines / 2-halobenzoic acids and derivatives / Benzamides / Benzenesulfonyl compounds / Benzoyl derivatives / Chlorobenzenes / Aryl chlorides / Vinylogous halides / Sulfones / Heteroaromatic compounds

Substituents

Benzanilide / 2-phenylpyridine / 2-halobenzoic acid or derivatives / Halobenzoic acid or derivatives / Benzamide / Benzoic acid or derivatives / Benzenesulfonyl group / Benzoyl / Chlorobenzene / Halobenzene

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

sulfone, benzamides, pyridines, monochlorobenzenes (CHEBI:66903 )

Targets

Details

1. Smoothened homolog

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
Uniprot Name:: Smoothened homolog
Molecular Weight:: 86395.95 Da

References

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

Details

1. Cytochrome P450 2C9

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
Uniprot Name:: Cytochrome P450 2C9
Molecular Weight:: 55627.365 Da

References

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 ]

Details

2. Cytochrome P450 3A4

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
Uniprot Name:: Cytochrome P450 3A4
Molecular Weight:: 57342.67 Da

References

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 ]

Details

3. Cytochrome P450 2C8

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
Uniprot Name:: Cytochrome P450 2C8
Molecular Weight:: 55824.275 Da

Details

4. Cytochrome P450 2C19

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
Uniprot Name:: Cytochrome P450 2C19
Molecular Weight:: 55930.545 Da

Carriers

Details

1. Serum albumin

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
Uniprot Name:: Serum albumin
Molecular Weight:: 69365.94 Da

Details

2. Alpha-1-acid glycoprotein 1

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
Uniprot Name:: Alpha-1-acid glycoprotein 1
Molecular Weight:: 23511.38 Da

Transporters

Details

1. Multidrug resistance protein 1

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
Uniprot Name:: Multidrug resistance protein 1
Molecular Weight:: 141477.255 Da

References

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 ]

Details

2. ATP-binding cassette sub-family G member 2

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
Uniprot Name:: ATP-binding cassette sub-family G member 2
Molecular Weight:: 72313.47 Da

Drug created on January 04, 2013 14:48 / Updated on July 25, 2017 17:56

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Structure for DB08828 (Vismodegib)

Targets

References

Enzymes

References

References

Carriers

Transporters

References