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Vismodegib

From Wikipedia, the free encyclopedia

Vismodegib
Clinical data
Pronunciation/ˌvɪsmoʊˈdɛɡɪb/
VIS-moh-DEG-ib
Trade namesErivedge
Other namesGDC-0449, RG-3616
AHFS/Drugs.comMonograph
License data
Pregnancy
category
  • AU: X (High risk)[1]
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability31.8%
Protein binding>99%
Metabolism<2% metabolised by CYP2C9, CYP3A4, CYP3A5
Elimination half-life4 days (continuous use),
12 days (single dose)
ExcretionFecal (82%), Urinary (4.4%)
Identifiers
  • 2-Chloro-N-(4-chloro-3-pyridin-2-ylphenyl)-4-methylsulfonylbenzamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.234.019 Edit this at Wikidata
Chemical and physical data
FormulaC19H14Cl2N2O3S
Molar mass421.29 g·mol−1
3D model (JSmol)
  • CS(=O)(=O)C1=CC(=C(C=C1)C(=O)NC2=CC(=C(C=C2)Cl)C3=CC=CC=N3)Cl
  • 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)
  • Key:BPQMGSKTAYIVFO-UHFFFAOYSA-N

Vismodegib, sold under the brand name Erivedge, is a medication used for the treatment of basal-cell carcinoma (BCC).[3] 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.[4] The drug is also undergoing clinical trials for metastatic colorectal cancer, small-cell lung cancer, advanced stomach cancer, pancreatic cancer, medulloblastoma and chondrosarcoma as of June 2011.[5] The drug was developed by the biotechnology/pharmaceutical company Genentech.[4]

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Transcription

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.[4][6]

Mechanism of action

The substance acts as a cyclopamine-competitive antagonist of the smoothened receptor (SMO) which is part of the Hedgehog signaling pathway.[5] SMO inhibition causes the transcription factors GLI1 and GLI2 to remain inactive, which prevents the expression of tumor mediating genes within the hedgehog pathway.[7] This pathway is pathogenetically relevant in more than 90% of basal-cell carcinomas.[8]

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).[3]

Development

Vismodegib has undergone several promising phase I and phase II clinical trials for its use in treating medulloblastoma.[9]

References

  1. ^ a b "Erivedge® (vismodegib)". Australian Prescribing Information, Australian Register of Therapeutic Goods (ARTG). Roche Products Pty Limited. 17 November 2022.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 Oct 2023.
  3. ^ a b c "Erivedge- vismodegib capsule". DailyMed. U.S. National Library of Medicine. 9 April 2019. Retrieved 8 January 2023.
  4. ^ a b c "FDA approves Erivedge (vismodegib) capsule, the first medicine for adults with advanced basal cell carcinoma". Roche. 30 January 2012. Retrieved 9 August 2020.
  5. ^ a b "Vismodegib". Molecule of the Month. Prous Science. June 2011. Archived from the original on 27 September 2011.
  6. ^ Lacroix M (2014). Targeted Therapies in Cancer. Hauppauge, NY: Nova Sciences Publishers. ISBN 978-1-63321-687-7. Archived from the original on 2015-06-26. Retrieved 2014-07-13.
  7. ^ "Vismodegib (GDC-0449) Smoothened Inhibitor". BioOncology. Genentech. Archived from the original on 4 June 2011.
  8. ^ Spreitzer H (4 July 2011). "Neue Wirkstoffe – Vismodegib". Österreichische Apothekerzeitung (in German) (14/2011): 10.
  9. ^ Li Y, Song Q, Day BW (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 (1): 123. doi:10.1186/s40478-019-0773-8. PMC 6668073. PMID 31362788.

Further reading

External links

  • "Vismodegib". Drug Information Portal. U.S. National Library of Medicine.
This page was last edited on 20 December 2023, at 19:42
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