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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Vismodegib
- Accession Number
- DB08828
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Description
Vismodegib inhibits the hedgehog signalling pathway and is indicated for treatment of adult basal cell carcinoma. FDA approved on Jan 30, 2012.
- Structure
Structure for DB08828 (Vismodegib)
- Synonyms
- Hedgehog Antagonist GDC-0449
- Vismodegibum
- External IDs
- GDC-0449 / RG-3616
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Erivedge Capsule 150 mg Oral Hoffmann La Roche 2013-08-09 Not applicable Canada 
Erivedge Capsule 150 mg/1 Oral Genentech, Inc. 2012-01-30 Not applicable US 
- International/Other Brands
- Erivedge
- Categories
- Amides
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- BCRP/ABCG2 Inhibitors
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 CYP3A4 Substrates (strength unknown)
- Cytochrome P-450 Enzyme Inhibitors
- Hedgehog Pathway Inhibitor
- P-glycoprotein/ABCB1 Substrates
- 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.
- Associated Conditions
- 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 Actions Organism ASmoothened homolog antagonistHuman - 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 Acetyl sulfisoxazole The metabolism of Vismodegib can be decreased when combined with Acetyl sulfisoxazole. Approved, Vet Approved Acetyldigitoxin Acetyldigitoxin may decrease the cardiotoxic activities of Vismodegib. Approved Acetyldigoxin Acetyldigoxin may decrease the cardiotoxic activities of Vismodegib. Experimental Amiodarone The serum concentration of Vismodegib can be increased when it is combined with Amiodarone. Approved, Investigational 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, Investigational Ancestim The risk or severity of cytotoxicity can be increased when Ancestim is combined with Vismodegib. Approved, Investigational, Withdrawn Apalutamide The serum concentration of Vismodegib can be decreased when it is combined with Apalutamide. Approved, Investigational Aprepitant The serum concentration of Vismodegib can be increased when it is combined with Aprepitant. Approved, Investigational Atazanavir The metabolism of Vismodegib can be decreased when combined with Atazanavir. Approved, Investigational Atomoxetine The metabolism of Vismodegib can be decreased when combined with Atomoxetine. 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 Boceprevir The metabolism of Vismodegib can be decreased when combined with Boceprevir. Approved, 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 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 Capecitabine The metabolism of Vismodegib can be decreased when combined with Capecitabine. Approved, Investigational 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 Ceritinib The serum concentration of Vismodegib can be increased when it is combined with Ceritinib. Approved Cholecalciferol The metabolism of Vismodegib can be decreased when combined with Cholecalciferol. Approved, Nutraceutical Cilostazol The serum concentration of Cilostazol can be increased when it is combined with Vismodegib. Approved, Investigational Clarithromycin The metabolism of Vismodegib can be decreased when combined with Clarithromycin. 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 Conivaptan The serum concentration of Conivaptan can be increased when it is combined with Vismodegib. Approved, Investigational Crisaborole The metabolism of Vismodegib can be decreased when combined with Crisaborole. Approved, Investigational Crizotinib The metabolism of Vismodegib can be decreased when combined with Crizotinib. Approved Curcumin The metabolism of Vismodegib can be decreased when combined with Curcumin. Approved, Investigational Cyclophosphamide Cyclophosphamide may increase the cardiotoxic activities of Vismodegib. Approved, Investigational Cyclosporine The serum concentration of Vismodegib can be increased when it is combined with Cyclosporine. Approved, Investigational, Vet Approved Cymarin Cymarin may decrease the cardiotoxic activities of Vismodegib. Experimental Dabrafenib The serum concentration of Vismodegib can be decreased when it is combined with Dabrafenib. Approved, Investigational 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 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 Deslanoside Deslanoside may decrease the cardiotoxic activities of Vismodegib. Approved Dexamethasone The serum concentration of Vismodegib can be decreased when it is combined with Dexamethasone. Approved, Investigational, Vet Approved Dexniguldipine The serum concentration of Vismodegib can be increased when it is combined with Dexniguldipine. Experimental Dexverapamil The serum concentration of Vismodegib can be increased when it is combined with Dexverapamil. Experimental Digitoxin Digitoxin may decrease the cardiotoxic activities of Vismodegib. Approved, Investigational Digoxin Digoxin may decrease the cardiotoxic activities of Vismodegib. Approved Digoxin Immune Fab (Ovine) Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Vismodegib. Approved Dihydroergotamine The metabolism of Vismodegib can be decreased when combined with Dihydroergotamine. Approved, Investigational Diltiazem The metabolism of Vismodegib can be decreased when combined with Diltiazem. Approved, Investigational Docetaxel The risk or severity of adverse effects can be increased when Docetaxel is combined with Vismodegib. Approved, Investigational Dosulepin The metabolism of Vismodegib can be decreased when combined with Dosulepin. Approved Doxazosin The serum concentration of Vismodegib can be increased when it is combined with Doxazosin. Approved Doxycycline The metabolism of Vismodegib can be decreased when combined with Doxycycline. Approved, Investigational, Vet Approved Dronedarone The metabolism of Vismodegib can be decreased when combined with Dronedarone. Approved Efavirenz The metabolism of Vismodegib can be decreased when combined with Efavirenz. Approved, Investigational Emopamil The serum concentration of Vismodegib can be increased when it is combined with Emopamil. Experimental Enzalutamide The serum concentration of Vismodegib can be decreased when it is combined with Enzalutamide. Approved Erythromycin The metabolism of Vismodegib can be decreased when combined with Erythromycin. Approved, Investigational, Vet Approved Etravirine The metabolism of Vismodegib can be decreased when combined with Etravirine. Approved Felodipine The serum concentration of Vismodegib can be increased when it is combined with Felodipine. Approved, Investigational 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, Investigational 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 Fluvoxamine The serum concentration of Vismodegib can be increased when it is 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, Investigational Fusidic Acid The serum concentration of Vismodegib can be increased when it is combined with Fusidic Acid. Approved, Investigational Gallopamil The serum concentration of Vismodegib can be increased when it is combined with Gallopamil. Investigational Gemfibrozil The metabolism of Vismodegib can be decreased when combined with Gemfibrozil. Approved Gitoformate Gitoformate may decrease the cardiotoxic activities of Vismodegib. Experimental Glycerin The serum concentration of Vismodegib can be increased when it is combined with Glycerin. Approved, Investigational Ibuprofen The serum concentration of Vismodegib can be increased when it is combined with Ibuprofen. Approved Idelalisib The metabolism of Vismodegib can be decreased when combined with Idelalisib. Approved Imatinib The metabolism of Vismodegib can be decreased when combined with Imatinib. Approved Indinavir The metabolism of Vismodegib can be decreased when combined with Indinavir. Approved Irbesartan The metabolism of Vismodegib can be decreased when combined with Irbesartan. Approved, Investigational Isavuconazole The serum concentration of Vismodegib can be increased when it is combined with Isavuconazole. Approved, Investigational Isavuconazonium The metabolism of Vismodegib can be decreased when combined with Isavuconazonium. Approved, Investigational Isradipine The serum concentration of Vismodegib can be increased when it is combined with Isradipine. Approved, Investigational 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 Ketoconazole The metabolism of Vismodegib can be decreased when combined with Ketoconazole. Approved, Investigational Lamivudine The serum concentration of Lamivudine can be increased when it is combined with Vismodegib. Approved, Investigational Lanatoside C Lanatoside C may decrease the cardiotoxic activities of Vismodegib. Experimental Leflunomide The metabolism of Vismodegib can be decreased when combined with Leflunomide. Approved, Investigational Lidocaine The serum concentration of Vismodegib can be increased when it is combined with Lidocaine. Approved, Vet Approved Lobeglitazone The metabolism of Vismodegib can be decreased when combined with Lobeglitazone. Approved, Investigational Lomerizine The serum concentration of Vismodegib can be increased when it is combined with Lomerizine. Experimental 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, Investigational Lorpiprazole The serum concentration of Vismodegib can be increased when it is combined with Lorpiprazole. 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 Metildigoxin Metildigoxin may decrease the cardiotoxic activities of Vismodegib. Experimental Mibefradil The metabolism of Vismodegib can be decreased when combined with Mibefradil. Investigational, Withdrawn Miconazole The serum concentration of Vismodegib can be increased when it is combined with Miconazole. Approved, Investigational, Vet Approved Midostaurin The metabolism of Vismodegib can be decreased when combined with Midostaurin. Approved, Investigational Mifepristone The serum concentration of Vismodegib can be increased when it is combined with Mifepristone. Approved, Investigational Mitotane The serum concentration of Vismodegib can be decreased when it is combined with Mitotane. Approved Nabilone The metabolism of Vismodegib can be decreased when combined with Nabilone. Approved, Investigational 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 Netupitant The serum concentration of Vismodegib can be increased when it is combined with Netupitant. Approved, Investigational Nevirapine The metabolism of Vismodegib can be increased when combined with Nevirapine. Approved Nicardipine The serum concentration of Vismodegib can be increased when it is combined with Nicardipine. Approved, Investigational Niguldipine The serum concentration of Vismodegib can be increased when it is combined with Niguldipine. Experimental Nilotinib The metabolism of Vismodegib can be decreased when combined with Nilotinib. Approved, Investigational Nimodipine The serum concentration of Vismodegib can be increased when it is combined with Nimodipine. Approved, Investigational Nisoldipine The serum concentration of Vismodegib can be increased when it is combined with Nisoldipine. Approved Nitrendipine The serum concentration of Vismodegib can be increased when it is combined with Nitrendipine. Approved, Investigational Olaparib The metabolism of Vismodegib can be decreased when combined with Olaparib. Approved Oleandrin Oleandrin may decrease the cardiotoxic activities of Vismodegib. Experimental, Investigational 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 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, Investigational 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, Investigational, Vet Approved Peruvoside Peruvoside may decrease the cardiotoxic activities of Vismodegib. Experimental Phenobarbital The metabolism of Vismodegib can be increased when combined with Phenobarbital. Approved, Investigational Phenytoin The metabolism of Vismodegib can be increased when combined with Phenytoin. Approved, Vet Approved Pitolisant The serum concentration of Vismodegib can be decreased when it is combined with Pitolisant. Approved, Investigational Posaconazole The metabolism of Vismodegib can be decreased when combined with Posaconazole. Approved, Investigational, Vet Approved Primidone The metabolism of Vismodegib can be increased when combined with Primidone. Approved, Vet Approved Promethazine The serum concentration of Vismodegib can be increased when it is combined with Promethazine. Approved, Investigational Propafenone The serum concentration of Vismodegib can be increased when it is combined with Propafenone. Approved Proscillaridin Proscillaridin may decrease the cardiotoxic activities of Vismodegib. Experimental Pyrimethamine The metabolism of Vismodegib can be decreased when combined with Pyrimethamine. Approved, Investigational, Vet Approved Quinine The metabolism of Vismodegib can be decreased when 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 Rifabutin The metabolism of Vismodegib can be increased when combined with Rifabutin. Approved, Investigational 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, Investigational Rosuvastatin The serum concentration of Rosuvastatin can be increased when it is combined with Vismodegib. Approved Rucaparib The metabolism of Vismodegib can be decreased when combined with Rucaparib. Approved, Investigational Saquinavir The metabolism of Vismodegib can be decreased when combined with Saquinavir. Approved, Investigational Sarilumab The therapeutic efficacy of Vismodegib can be decreased when used in combination with Sarilumab. Approved, Investigational Secobarbital The metabolism of Vismodegib can be increased when combined with Secobarbital. Approved, Vet 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, Investigational Simeprevir The serum concentration of Vismodegib can be increased when it is combined with Simeprevir. Approved Sorafenib The metabolism of Vismodegib can be decreased when combined with Sorafenib. Approved, Investigational St. John's Wort The serum concentration of Vismodegib can be decreased when it is combined with St. John's Wort. Approved, Investigational, Nutraceutical Stiripentol The serum concentration of Vismodegib can be increased when it is combined with Stiripentol. Approved Sulfadiazine The metabolism of Vismodegib can be decreased when combined with Sulfadiazine. Approved, Investigational, Vet Approved Sulfamethoxazole The metabolism of Vismodegib can be decreased when combined with Sulfamethoxazole. Approved Sulfasalazine The serum concentration of Sulfasalazine can be increased when it is combined with Vismodegib. Approved Sulfisoxazole The metabolism of Vismodegib can be decreased when combined with Sulfisoxazole. Approved, Vet Approved Telaprevir The metabolism of Vismodegib can be decreased when combined with Telaprevir. Approved, Withdrawn Telithromycin The metabolism of Vismodegib can be decreased when combined with Telithromycin. Approved Tetrandrine The serum concentration of Vismodegib can be increased when it is combined with Tetrandrine. Experimental Ticagrelor The metabolism of Vismodegib can be decreased when 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, Investigational Topiroxostat The metabolism of Vismodegib can be decreased when combined with Topiroxostat. Approved, Investigational 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 Trimethoprim The metabolism of Vismodegib can be decreased when combined with Trimethoprim. Approved, Vet Approved Valsartan The metabolism of Vismodegib can be decreased when combined with Valsartan. Approved, Investigational Vemurafenib The serum concentration of Vismodegib can be increased when it is combined with Vemurafenib. Approved Venlafaxine The serum concentration of Vismodegib can be increased when it is combined with Venlafaxine. Approved Verapamil The serum concentration of Vismodegib can be increased when it is combined with Verapamil. Approved 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 Ziprasidone The metabolism of Vismodegib can be decreased when combined with Ziprasidone. Approved - Food Interactions
- Food does not affect absorption.
References
- 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
- KEGG Drug
- D09992
- PubChem Compound
- 24776445
- PubChem Substance
- 175427109
- ChemSpider
- 23337846
- BindingDB
- 50249522
- ChEBI
- 66903
- ChEMBL
- CHEMBL473417
- PharmGKB
- PA166048558
- HET
- VIS
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Vismodegib
- ATC Codes
- L01XX43 — Vismodegib
- AHFS Codes
- 10:00.00 — Antineoplastic Agents
- PDB Entries
- 5l7i
- FDA label
- Download (211 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage forms
Form Route Strength Capsule Oral 150 mg Capsule Oral 150 mg/1 - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US9278961 No 2008-12-15 2028-12-15 US US7888364 No 2008-11-11 2028-11-11 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
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-00di-0212900000-190a5fdca2d781122e92
Taxonomy
- Description
- This compound belongs to the class of organic compounds 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
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Anilides
- Direct Parent
- Benzanilides
- Alternative Parents
- Phenylpyridines / 2-halobenzoic acids and derivatives / Benzamides / Benzenesulfonyl compounds / Benzoyl derivatives / Chlorobenzenes / Aryl chlorides / Vinylogous halides / Sulfones / Heteroaromatic compounds show 8 more
- Substituents
- Benzanilide / 2-phenylpyridine / 2-halobenzoic acid or derivatives / Halobenzoic acid or derivatives / Benzamide / Benzoic acid or derivatives / Benzenesulfonyl group / Benzoyl / Chlorobenzene / Halobenzene show 23 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- sulfone, benzamides, pyridines, monochlorobenzenes (CHEBI:66903)
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 t...
- 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
- 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 un...
- 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]
- 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 react...
- 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]
- 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 un...
- Gene Name
- CYP2C8
- Uniprot ID
- P10632
- Uniprot Name
- Cytochrome P450 2C8
- 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 im...
- Gene Name
- CYP2C19
- Uniprot ID
- P33261
- Uniprot Name
- Cytochrome P450 2C19
- 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 colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- 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...
- Gene Name
- ORM1
- Uniprot ID
- P02763
- Uniprot Name
- Alpha-1-acid glycoprotein 1
- 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
- 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]
- 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 fro...
- 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 August 14, 2018 04:31