Identification
- Summary
Vismodegib is a hedgehog pathway inhibitor used to treat patients with locally advanced or metastatic basal cell carcinoma.
- Brand Names
- Erivedge
- Generic Name
- Vismodegib
- DrugBank Accession Number
- DB08828
- Background
Vismodegib is an orally active small molecule that inhibits the hedgehog signaling pathway by binding to and inhibiting the transmembrane protein smoothened homologue (SMO).4,5,6 It was discovered by high-throughput screening of a library of small-molecule compounds and subsequent optimization through medicinal chemistry.1 Since it targets the hedgehog signaling pathway, vismodegib has anti-tumor activity in basal-cell carcinoma. The Hedgehog signaling pathway plays an important role in the development of organs and tissues during embryogenesis. Afterwards, it is silenced in all cells and tissues, except for hair, skin and stem cells. However, dysregulated or aberrant Hedgehog signaling has been associated with basal cell carcinoma pathogenesis.3,6 In January 2012, vismodegib was approved by the FDA for the treatment of adult basal cell carcinoma. In July 2013, it was approved by the EMA, and since then, it has been approved by several other countries.2,5,6
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Vismodegib (DB08828)
- Weight
- Average: 421.297
Monoisotopic: 420.010218428 - Chemical Formula
- C19H14Cl2N2O3S
- Synonyms
- 2-chloro-N-(4-chloro-3-pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide
- Benzamide, 2-chloro-N-(4-chloro-3-(2-pyridinyl)phenyl)-4-(methylsulfonyl)-
- Vismodegib
- Vismodégib
- Vismodegibum
- External IDs
- GDC-0449
- NSC-747691
- NSC-755986
- RG-3616
Pharmacology
- Indication
Vismodegib is indicated for the treatment of adults with metastatic basal cell carcinoma, or with locally advanced basal cell carcinoma that has recurred following surgery or who are not candidates for surgery and who are not candidates for radiation.6
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- Contraindications & Blackbox Warnings
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Vismodegib selectively binds to and inhibits the transmembrane protein smoothened homologue (SMO) to inhibit the Hedgehog signalling pathway. Following 7 days of 150 mg once-daily dosing, the use of vismodegib was not associated with a clinically significant QT interval prolongation.6 Vismodegib can cause embryo-fetal death or severe birth defects, as well as severe cutaneous adverse reactions and musculoskeletal adverse reactions. In pediatric patients given vismodegib, premature fusion of the epiphyses has been reported.6
- Mechanism of action
During embryogenesis, the Hedgehog signaling pathway plays an important role in cell growth, differentiation apoptosis and self-renewal. After this developmental stage, the Hedgehog signaling pathway is silenced in all cells and tissues, except for hair, skin and stem cells. Mutations on elements of the Hedgehog signaling pathway may result in uncontrolled proliferation of basal skin cells, and dysregulated or aberrant Hedgehog signaling has been associated with the pathogenesis of basal cell carcinoma. Therefore, drugs that target and block this pathway, such as vismodegib, may be used to treat this condition. Vismodegib binds to and inhibits the transmembrane protein smoothened homologue (SMO), a protein that leads to the activation and nuclear translocation of several factors involved in the Hedgehog signaling pathway, inhibiting the activation of downstream Hedgehog target genes.3,6
Target Actions Organism ASmoothened homolog antagonistinhibitorHumans - Absorption
Vismodegib appears to have a nonlinear pharmacokinetic profile following daily oral dosing, and steady state is achieved within 7 days. A dose increase from 150 mg to 540 mg (1 to 3.6 times the recommended dose) does not lead to an increase in steady-state plasma concentrations. With a once-daily dose of 150 mg, the average plasma concentration of vismodegib at steady state is approximately 23 µM. The absolute bioavailability of a single dose of vismodegib is 31.8%. Absorption is saturable and is not affected by food.6
- Volume of distribution
The volume of distribution of vismodegib ranges between 16.4 and 26.6 L.6
- Protein binding
Vismodegib has high plasma protein binding (>99%). Vismodegib binds to plasma albumin and alpha-1-acid glycoprotein (saturable binding).6
- Metabolism
Vismodegib is mainly metabolized by CYP2C9 and CYP3A4 in the liver; 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 CYP3A4/5.6
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- Route of elimination
Vismodegib is excreted mostly unchanged. Vismodegib and its metabolites are mainly eliminated through feces. Approximately 82% and 4.4% of the administered dose are recovered in feces and urine, respectively.6
- Half-life
The half-life of vismodegib after a single dose is 12 days, and after continuous daily dosing is 4 days.6
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Toxicity information regarding vismodegib is not readily available. Patients experiencing an overdose are at an increased risk of severe adverse effects such as severe cutaneous adverse reactions and musculoskeletal adverse reactions. Symptomatic and supportive measures are recommended. Patients treated with vismodegib have an 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.6
Based on the results of in vitro and in vivo studies, vismodegib is not mutagenic. No evidence of carcinogenicity was found in mice and rats given vismodegib. A 26-week rat fertility study found that at doses of 100 mg/kg/day, vismodegib has no effects on male reproductive organs or fertility. In female rats, the administration of vismodegib was associated with decreased implantations, increased percent preimplantation loss, and decreased numbers of dams with viable embryos.6
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbemaciclib Vismodegib may decrease the excretion rate of Abemaciclib which could result in a higher serum level. Afatinib Vismodegib may decrease the excretion rate of Afatinib which could result in a higher serum level. Allopurinol Vismodegib may decrease the excretion rate of Allopurinol which could result in a higher serum level. Alpelisib The serum concentration of Alpelisib can be increased when it is combined with Vismodegib. Ambroxol The risk or severity of methemoglobinemia can be increased when Vismodegib is combined with Ambroxol. Apixaban Vismodegib may decrease the excretion rate of Apixaban which could result in a higher serum level. Articaine The risk or severity of methemoglobinemia can be increased when Vismodegib is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Vismodegib is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Vismodegib is combined with Benzyl alcohol. Berotralstat The serum concentration of Berotralstat can be increased when it is combined with Vismodegib. 
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- Take with or without food. Food does not affect absorption. The Cmax and AUC of vismodegib at steady state are not affected by food.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- International/Other Brands
- Erivedge (Genentech)
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Erivedge Capsule 150 mg Oral Roche Registration Gmb H 2020-12-22 Not applicable EU 
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 
Categories
- ATC Codes
- L01XJ01 — Vismodegib
- Drug Categories
- Amides
- Amines
- Aniline Compounds
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- BCRP/ABCG2 Inhibitors
- Cytochrome P-450 CYP2C19 Inhibitors
- Cytochrome P-450 CYP2C19 inhibitors (strength unknown)
- Cytochrome P-450 CYP2C8 Inhibitors
- Cytochrome P-450 CYP2C8 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Inhibitors
- Cytochrome P-450 CYP2C9 Inhibitors (strength unknown)
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Substrates
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inhibitors
- Cytochrome P-450 Substrates
- Hedgehog Pathway Inhibitor
- Hedgehog pathway inhibitors
- P-glycoprotein substrates
- Smoothened Receptor Antagonists
- Chemical TaxonomyProvided by Classyfire
- 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
- 2-halobenzoic acid or derivatives / 2-phenylpyridine / Aromatic heteromonocyclic compound / Aryl chloride / Aryl halide / Azacycle / Benzamide / Benzanilide / Benzenesulfonyl group / Benzoic acid or derivatives show 23 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- sulfone, benzamides, pyridines, monochlorobenzenes (CHEBI:66903)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- 25X868M3DS
- CAS number
- 879085-55-9
- 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
References
- Synthesis Reference
Gunzner-Toste, JL., et al. (2020). Pyridyl inhibitors of hedgehog signalling (U.S. Patent No. 2020/0010420 A1 ). U.S. Patent and Trademark Office. https://patentimages.storage.googleapis.com/72/c1/79/c08582c18507d5/US20200010420A1.pdf
- 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. [Article]
- 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. [Article]
- Aditya S, Rattan A: Vismodegib: A smoothened inhibitor for the treatment of advanced basal cell carcinoma. Indian Dermatol Online J. 2013 Oct;4(4):365-8. doi: 10.4103/2229-5178.120685. [Article]
- Abou-Alfa GK, Lewis LD, LoRusso P, Maitland M, Chandra P, Cheeti S, Colburn D, Williams S, Simmons B, Graham RA: Pharmacokinetics and safety of vismodegib in patients with advanced solid malignancies and hepatic impairment. Cancer Chemother Pharmacol. 2017 Jul;80(1):29-36. doi: 10.1007/s00280-017-3315-8. Epub 2017 May 18. [Article]
- Dessinioti C, Plaka M, Stratigos AJ: Vismodegib for the treatment of basal cell carcinoma: results and implications of the ERIVANCE BCC trial. Future Oncol. 2014 May;10(6):927-36. doi: 10.2217/fon.14.50. [Article]
- FDA Approved Drug Products: ERIVEDGE (vismodegib) capsules for oral use (March 2023) [Link]
- MedChemExpress: Vismodegib SDS [Link]
- External Links
- Human Metabolome Database
- HMDB0259838
- KEGG Drug
- D09992
- PubChem Compound
- 24776445
- PubChem Substance
- 175427109
- ChemSpider
- 23337846
- BindingDB
- 50249522
- 1242987
- ChEBI
- 66903
- ChEMBL
- CHEMBL473417
- ZINC
- ZINC000040899447
- PharmGKB
- PA166048558
- PDBe Ligand
- VIS
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Vismodegib
- PDB Entries
- 5l7i / 8hje
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule Oral 150 mg/1 Capsule Oral 150.000 mg Capsule, coated Oral 150 mg Capsule Oral 150 mg - Prices
- Not Available
- Patents
Patent Number Pediatric Extension Approved Expires (estimated) Region US9278961 No 2016-03-08 2028-12-15 US US7888364 No 2011-02-15 2028-11-11 US US9790183 No 2017-10-17 2025-09-02 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source boiling point (°C) 561.6°C SDS water solubility 0.1 μg/mL at pH 7 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) 13.5 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
Targets
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- AntagonistInhibitor
- 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. [Article]
- Aditya S, Rattan A: Vismodegib: A smoothened inhibitor for the treatment of advanced basal cell carcinoma. Indian Dermatol Online J. 2013 Oct;4(4):365-8. doi: 10.4103/2229-5178.120685. [Article]
- FDA Approved Drug Products: ERIVEDGE (vismodegib) capsules for oral use (March 2023) [Link]
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- SubstrateInhibitor
- Curator comments
- Shown to be an inhibitor in vitro.
- 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. [Article]
- Fellner C: Vismodegib (erivedge) for advanced Basal cell carcinoma. P T. 2012 Dec;37(12):670-82. [Article]
- FDA Approved Drug Products: ERIVEDGE (vismodegib) capsules for oral use (March 2023) [Link]
- Kind
- Protein
- Organism
- Humans
- 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
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Shown to be an inhibitor in vitro.
- 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
References
- Fellner C: Vismodegib (erivedge) for advanced Basal cell carcinoma. P T. 2012 Dec;37(12):670-82. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- Curator comments
- Shown to be an inhibitor in vitro.
- 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
References
- Fellner C: Vismodegib (erivedge) for advanced Basal cell carcinoma. P T. 2012 Dec;37(12):670-82. [Article]
Carriers
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Toxic substance binding
- Specific Function
- Serum albumin, the main protein of plasma, has a good binding capacity for water, Ca(2+), Na(+), K(+), fatty acids, hormones, bilirubin and drugs. Its main function is the regulation of the colloid...
- Gene Name
- ALB
- Uniprot ID
- P02768
- Uniprot Name
- Serum albumin
- Molecular Weight
- 69365.94 Da
References
- FDA Approved Drug Products: ERIVEDGE (vismodegib) capsules for oral use (March 2023) [Link]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Binder
- General Function
- Not Available
- Specific Function
- Functions as transport protein in the blood stream. Binds various ligands in the interior of its beta-barrel domain. Also binds synthetic drugs and influences their distribution and availability in...
- Gene Name
- ORM1
- Uniprot ID
- P02763
- Uniprot Name
- Alpha-1-acid glycoprotein 1
- Molecular Weight
- 23511.38 Da
References
- FDA Approved Drug Products: ERIVEDGE (vismodegib) capsules for oral use (March 2023) [Link]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Xenobiotic-transporting atpase activity
- Specific Function
- High-capacity urate exporter functioning in both renal and extrarenal urate excretion. Plays a role in porphyrin homeostasis as it is able to mediates the export of protoporhyrin IX (PPIX) both fro...
- Gene Name
- ABCG2
- Uniprot ID
- Q9UNQ0
- Uniprot Name
- ATP-binding cassette sub-family G member 2
- Molecular Weight
- 72313.47 Da
References
- Kind
- Protein
- Organism
- Humans
- 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. [Article]
Drug created at January 04, 2013 21:48 / Updated at September 26, 2023 18:23