vismodegib   

GtoPdb Ligand ID: 6975

Synonyms: Erivedge® | GDC-0449 | HhAntag691
vismodegib is an approved drug (FDA (2012), EMA (2013))
Compound class: Synthetic organic
Comment: Vismodegib inhibits smoothened homolog (SMO), a constituent of the Hedgehog signalling pathway which is essential for proper embryonic development. This pathway is also involved in the maintenance and regeneration of adult tissues by regulating adult stem cells and has been implicated in the development of some cancers.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 5
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 84.51
Molecular weight 420.01
XLogP 4.54
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C(c1ccc(cc1Cl)S(=O)(=O)C)Nc1ccc(c(c1)c1ccccn1)Cl
Isomeric SMILES O=C(c1ccc(cc1Cl)S(=O)(=O)C)Nc1ccc(c(c1)c1ccccn1)Cl
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)
InChI Key BPQMGSKTAYIVFO-UHFFFAOYSA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2012), EMA (2013))
IUPAC Name
2-chloro-N-(4-chloro-3-pyridin-2-ylphenyl)-4-methylsulfonylbenzamide
International Nonproprietary Names
INN number INN
9311 vismodegib
Synonyms
Erivedge® | GDC-0449 | HhAntag691
Database Links
CAS Registry No. 879085-55-9
ChEMBL Ligand CHEMBL473417
DrugBank Ligand DB08828
DrugCentral Ligand 4227
GtoPdb PubChem SID 178103554
PubChem CID 24776445
RCSB PDB Ligand VIS
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Wikipedia Vismodegib