vismodegib   Click here for help

GtoPdb Ligand ID: 6975

Synonyms: Erivedge® | GDC-0449 | HhAntag691
Approved drug PDB Ligand
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.
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2D Structure
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Physico-chemical Properties
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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
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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)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2012), EMA (2013))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
9311 vismodegib
Synonyms Click here for help
Erivedge® | GDC-0449 | HhAntag691
Database Links Click here for help
Specialist databases
GPCRdb Ligand vismodegib
Other databases
CAS Registry No. 879085-55-9
ChEMBL Ligand CHEMBL473417
DrugBank Ligand DB08828
DrugCentral Ligand 4227
GtoPdb PubChem SID 178103554
PubChem CID 24776445
Search Google for chemical match using the InChIKey BPQMGSKTAYIVFO-UHFFFAOYSA-N
Search Google for chemicals with the same backbone BPQMGSKTAYIVFO
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UniChem Compound Search for chemical match using the InChIKey BPQMGSKTAYIVFO-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey BPQMGSKTAYIVFO-UHFFFAOYSA-N
Wikipedia Vismodegib