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Details

Stereochemistry ACHIRAL
Molecular Formula C19H14Cl2N2O3S
Molecular Weight 421.297
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Vismodegib

SMILES

CS(=O)(=O)C1=CC(Cl)=C(C=C1)C(=O)NC2=CC(=C(Cl)C=C2)C3=NC=CC=C3

InChI

InChIKey=BPQMGSKTAYIVFO-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Molecular Formula C19H14Cl2N2O3S
Molecular Weight 421.297
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Vismodegib (trade name Erivedge) is a drug for the treatment of basal-cell carcinoma (BCC). It was approved by FDA on January 30, 2012 and by the European Commission on 12 July 2013, for the treatment of adult patients with symptomatic metastatic BCC, or locally advanced BCC inappropriate for surgery or radiotherapy. 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. The substance acts as a cyclopamine-competitive antagonist of the smoothened receptor (SMO) which is part of the hedgehog signaling pathway. 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. SMO inhibition causes the transcription factors GLI1 and GLI2 to remain inactive, which prevents the expression of tumor mediating genes within the hedgehog pathway. This pathway is pathogenetically relevant in more than 90% of basal-cell carcinomas.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
3.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ERIVEDGE

Cmax

ValueDoseCo-administeredAnalytePopulation
5.95 μM
150 mg 1 times / day multiple, oral
VISMODEGIB plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
2850 μM × h
150 mg 1 times / day multiple, oral
VISMODEGIB plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
11.3 day
150 mg 1 times / day multiple, oral
VISMODEGIB plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
0.45%
VISMODEGIB plasma
Homo sapiens

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
150 mg orally once daily
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Record UNII
25X868M3DS
Record Status Validated (UNII)
Record Version