MedKoo Cat#: 203500 Name: Vismodegib CAS#: 879085-55-9 Chemical Formula: C19H14Cl2N2O3S Exact Mass: 420.01022 Molecular Weight: 421.3 Elemental Analysis: C, 54.17; H, 3.35; Cl, 16.83; N, 6.65; O, 11.39; S, 7.61

Synonym: GDC0449, GDC 0449, GDC-0449, RG3616, RG 3616, RG-3616, Vismodegib, Erivedge

IUPAC/Chemical Name: 2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide

InChi Key: BPQMGSKTAYIVFO-UHFFFAOYSA-N

InChi Code: 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)

SMILES Code: O=C(NC1=CC=C(Cl)C(C2=NC=CC=C2)=C1)C3=CC=C(S(=O)(C)=O)C=C3Cl

Technical Data

Appearance: White solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Certificate of Analysis: View CoA: current batch, Lot#TZC50806

QC Data: View QC data: current batch, Lot#TZC50806

Safety Data Sheet (MSDS): View Material Safety Data Sheet (MSDS)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO, not in water

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

Harmonized System Code: 293490

Additional Information

The Hedgehog signaling pathway plays an important role in tissue growth and repair; aberrant constitutive activation of Hedgehog pathway signaling and uncontrolled cellular proliferation may be associated with mutations in the Hedgehog-ligand cell surface receptors PTCH and SMO.

References

1: Poggi L, Kolesar JM. Vismodegib for the treatment of basal cell skin cancer. Am J Health Syst Pharm. 2013 Jun 15;70(12):1033-8. doi: 10.2146/ajhp120311. Review. PubMed PMID: 23719880.

2: Dubey AK, Dubey S, Handu SS, Qazi MA. Vismodegib: the first drug approved for advanced and metastatic basal cell carcinoma. J Postgrad Med. 2013 Jan-Mar;59(1):48-50. Review. PubMed PMID: 23525058.

3: Cirrone F, Harris CS. Vismodegib and the hedgehog pathway: a new treatment for basal cell carcinoma. Clin Ther. 2012 Oct;34(10):2039-50. doi: 10.1016/j.clinthera.2012.08.011. Epub 2012 Oct 1. Review. PubMed PMID: 23036338.

4: Amaria RN, Bowles DW, Lewis KD, Jimeno A. Vismodegib in basal cell carcinoma. Drugs Today (Barc). 2012 Jul;48(7):459-67. doi: 10.1358/dot.2012.48.7.1808490. Review. PubMed PMID: 22844657.

5: Keating GM. Vismodegib: in locally advanced or metastatic basal cell carcinoma. Drugs. 2012 Jul 30;72(11):1535-41. doi: 10.2165/11209590-000000000-00000. Review. PubMed PMID: 22788238.

6: De Smaele E, Ferretti E, Gulino A. Vismodegib, a small-molecule inhibitor of the hedgehog pathway for the treatment of advanced cancers. Curr Opin Investig Drugs. 2010 Jun;11(6):707-18. Review. PubMed PMID: 20496266.