VIS

2-chloranyl-~{N}-(4-chloranyl-3-pyridin-2-yl-phenyl)-4-methylsulfonyl-benzamide

Created: 2016-06-03
Last modified:  2016-07-20

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Chemical Details

Formal Charge0
Atom Count41
Chiral Atom Count0
Bond Count43
Aromatic Bond Count18
2D diagram of VIS
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Chemical Component Summary

Name2-chloranyl-~{N}-(4-chloranyl-3-pyridin-2-yl-phenyl)-4-methylsulfonyl-benzamide
Systematic Name (OpenEye OEToolkits)2-chloranyl-~{N}-(4-chloranyl-3-pyridin-2-yl-phenyl)-4-methylsulfonyl-benzamide
FormulaC19 H14 Cl2 N2 O3 S
Molecular Weight421.297
TypeNON-POLYMER

Chemical Descriptors

TypeProgram Version Descriptor
SMILESCACTVS3.385C[S](=O)(=O)c1ccc(c(Cl)c1)C(=O)Nc2ccc(Cl)c(c2)c3ccccn3
SMILESOpenEye OEToolkits2.0.5CS(=O)(=O)c1ccc(c(c1)Cl)C(=O)Nc2ccc(c(c2)c3ccccn3)Cl
Canonical SMILESCACTVS3.385 C[S](=O)(=O)c1ccc(c(Cl)c1)C(=O)Nc2ccc(Cl)c(c2)c3ccccn3
Canonical SMILESOpenEye OEToolkits2.0.5 CS(=O)(=O)c1ccc(c(c1)Cl)C(=O)Nc2ccc(c(c2)c3ccccn3)Cl
InChIInChI1.03 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)
InChIKeyInChI1.03 BPQMGSKTAYIVFO-UHFFFAOYSA-N

Drug Info: DrugBank

DrugBank IDDB08828 
NameVismodegib
Groups
  • investigational
  • approved
DescriptionVismodegib is an orally active small molecule that inhibits the hedgehog signaling pathway by binding to and inhibiting the transmembrane protein smoothened homologue (SMO).[A258613,A258618,L45803] It was discovered by high-throughput screening of a library of small-molecule compounds and subsequent optimization through medicinal chemistry.[A7369] 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.[A258608,L45803] 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.[A7370,A258618,L45803]
Synonyms
  • Vismodegibum
  • Vismodégib
  • Benzamide, 2-chloro-N-(4-chloro-3-(2-pyridinyl)phenyl)-4-(methylsulfonyl)-
  • Vismodegib
  • 2-chloro-N-(4-chloro-3-pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide
Brand NamesErivedge
IndicationVismodegib 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.[L45803]
Categories
  • Amides
  • Amines
  • Aniline Compounds
  • Antineoplastic Agents
  • Antineoplastic and Immunomodulating Agents
ATC-CodeL01XJ01
CAS number879085-55-9

Drug Targets

NameTarget SequencePharmacological ActionActions
Smoothened homologMAAARPARGPELPLLGLLLLLLLGDPGRGAASSGNATGPGPRSAGGSARR...unknownantagonist,inhibitor
Cytochrome P450 2C9MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...unknownsubstrate,inhibitor
Cytochrome P450 3A4MALIPDLAMETWLLLAVSLVLLYLYGTHSHGLFKKLGIPGPTPLPFLGNI...unknownsubstrate
Cytochrome P450 2C8MEPFVVLVLCLSFMLLFSLWRQSCRRRKLPPGPTPLPIIGNMLQIDVKDI...unknowninhibitor
Cytochrome P450 2C19MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...unknowninhibitor
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Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682

Related Resource References

Resource NameReference
Pharos CHEMBL473417
PubChem 24776445
ChEMBL CHEMBL473417
ChEBI CHEBI:66903