Vismodegib

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Chemical compound

title: "Vismodegib" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["benzanilides", "chloroarenes", "2-pyridyl-compounds", "benzosulfones", "teratogens", "antineoplastic-drugs", "drugs-developed-by-hoffmann-la-roche", "drugs-developed-by-genentech"] description: "Chemical compound" topic_path: "general/benzanilides" source: "https://en.wikipedia.org/wiki/Vismodegib" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

| image = Vismodegib2DACS.svg | image_class = skin-invert-image

| pronounce =

| tradename = Erivedge | Drugs.com = | licence_EU = yes | licence_US = Vismodegib | pregnancy_AU = X | pregnancy_AU_comment= | pregnancy_category = | routes_of_administration = By mouth

| legal_AU = S4 | legal_AU_comment = | legal_CA = Rx-only | legal_UK = POM | legal_US = Rx-only | legal_US_comment = | legal_EU = Rx-only | legal_status =

| bioavailability = 31.8% | protein_bound = 99% | metabolism = | elimination_half-life = 4 days (continuous use), 12 days (single dose) | excretion = Fecal (82%), Urinary (4.4%)

| IUPHAR_ligand = 6975 | CAS_number = 879085-55-9 | ATC_prefix = L01 | ATC_suffix = XJ01 | PubChem = 24776445 | ChEBI_Ref = | ChEBI = 66903 | ChEMBL = 473417 | UNII = 25X868M3DS | DrugBank = DB08828 | ChemSpiderID = 23337846 | KEGG = D09992 | synonyms = GDC-0449, RG-3616

| IUPAC_name = 2-Chloro-N-(4-chloro-3-pyridin-2-ylphenyl)-4-methylsulfonylbenzamide | C=19 | H=14 | Cl=2 | N=2 | O=3 | S=1 | smiles = CS(=O)(=O)C1=CC(=C(C=C1)C(=O)NC2=CC(=C(C=C2)Cl)C3=CC=CC=N3)Cl | StdInChI = 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) | StdInChIKey = BPQMGSKTAYIVFO-UHFFFAOYSA-N

Vismodegib, sold under the brand name Erivedge, is a medication used for the treatment of basal-cell carcinoma (BCC). The approval of vismodegib on January 30, 2012, represents the first Hedgehog signaling pathway targeting agent to gain U.S. Food and Drug Administration (FDA) approval. The drug is also undergoing clinical trials for metastatic colorectal cancer, small-cell lung cancer, advanced stomach cancer, pancreatic cancer, medulloblastoma and chondrosarcoma . The drug was developed by the biotechnology/pharmaceutical company Genentech.

Indication

Vismodegib is indicated for people with basal-cell carcinoma (BCC) which has metastasized to other parts of the body, relapsed after surgery, or cannot be treated with surgery or radiation.

Mechanism of action

The substance acts as a cyclopamine-competitive antagonist of the smoothened receptor (SMO) which is part of the Hedgehog signaling pathway. SMO inhibition causes the transcription factors GLI1 and GLI2 to remain inactive, which prevents the expression of tumor mediating genes within the hedgehog pathway. This pathway is pathogenetically relevant in more than 90% of basal-cell carcinomas.

Side effects

In clinical trials, common side effects included gastrointestinal disorders (nausea, vomiting, diarrhoea, constipation), muscle spasms, fatigue, hair loss, and dysgeusia (distortion of the sense of taste).

Development

Vismodegib has undergone several promising phase I and phase II clinical trials for its use in treating medulloblastoma.

References

References

  1. (17 November 2022). "Erivedge® (vismodegib)". Roche Products Pty Limited.
  2. (9 April 2019). "Erivedge- vismodegib capsule". U.S. National Library of Medicine.
  3. (30 January 2012). "FDA approves Erivedge (vismodegib) capsule, the first medicine for adults with advanced basal cell carcinoma".
  4. (2014). "Targeted Therapies in Cancer". Nova Sciences Publishers.
  5. "Vismodegib (GDC-0449) Smoothened Inhibitor". Genentech.
  6. (July 2019). "Phase I and phase II sonidegib and vismodegib clinical trials for the treatment of paediatric and adult MB patients: a systemic review and meta-analysis". Acta Neuropathologica Communications.
  7. (4 July 2011). "Neue Wirkstoffe – Vismodegib". Österreichische Apothekerzeitung.
  8. (June 2011). "Vismodegib". Prous Science.

::callout[type=info title="Wikipedia Source"] This article was imported from Wikipedia and is available under the Creative Commons Attribution-ShareAlike 4.0 License. Content has been adapted to SurfDoc format. Original contributors can be found on the article history page. ::

benzanilideschloroarenes2-pyridyl-compoundsbenzosulfonesteratogensantineoplastic-drugsdrugs-developed-by-hoffmann-la-rochedrugs-developed-by-genentech