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Details

Stereochemistry ACHIRAL
Molecular Formula C19H14Cl2N2O3S
Molecular Weight 421.297
Optical Activity UNSPECIFIED
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
Stereochemistry ACHIRAL
Additional Stereochemistry
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

Targets

Primary TargetPharmacologyConditionPotency
3.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
ERIVEDGE
PubMed

PubMed

TitleDatePubMed
Preclinical assessment of the absorption, distribution, metabolism and excretion of GDC-0449 (2-chloro-N-(4-chloro-3-(pyridin-2-yl)phenyl)-4-(methylsulfonyl)benzamide), an orally bioavailable systemic Hedgehog signalling pathway inhibitor.
2009 Nov
Inhibition of the hedgehog pathway in advanced basal-cell carcinoma.
2009 Sep 17
Up-regulation of sonic hedgehog contributes to TGF-β1-induced epithelial to mesenchymal transition in NSCLC cells.
2011 Jan 13
Effects of the Hedgehog pathway inhibitor GDC-0449 on lung cancer cell lines are mediated by side populations.
2012 Mar
The dawn of hedgehog inhibitors: Vismodegib.
2013 Jan
The Hedgehog pathway: role in cell differentiation, polarity and proliferation.
2015 Feb
Patents

Sample Use Guides

In Vivo Use Guide
150 mg orally once daily
Route of Administration: Oral
Substance Class Chemical
Created
by admin
on Mon Oct 21 22:29:00 UTC 2019
Edited
by admin
on Mon Oct 21 22:29:00 UTC 2019
Record UNII
25X868M3DS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VISMODEGIB
DASH   INN   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
INN   USAN  
Official Name English
GDC-0449
Code English
ERIVEDGE
Brand Name English
VISMODEGIB [WHO-DD]
Common Name English
VISMODEGIB [INN]
Common Name English
VISMODEGIB [VANDF]
Common Name English
2-CHLORO-N-(4-CHLORO-3-PYRIDIN-2-YL)PHENYL)-4-(METHYLSULFONYL)BENZAMIDE
Common Name English
BENZAMIDE, 2-CHLORO-N-(4-CHLORO-3-(2-PYRIDINYL)PHENYL)-4-(METHYLSULFONYL)-
Systematic Name English
VISMODEGIB [USAN]
Common Name English
NSC-747691
Code English
VISMODEGIB [MI]
Common Name English
VISMODEGIB [ORANGE BOOK]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C2189
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
LIVERTOX 1032
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
EMA ASSESSMENT REPORTS ERIVEDGE (AUTHORIZED: CARCINOMA, BASAL CELL)
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
NDF-RT N0000184149
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
WHO-ATC L01XX43
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
WHO-VATC QL01XX43
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
Code System Code Type Description
CAS
879085-55-9
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY
DRUG BANK
DB08828
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY
HSDB
879085-55-9
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY
EVMPD
SUB32354
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY
INN
9311
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY
MERCK INDEX
M11477
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY Merck Index
NDF-RT
N0000184148
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY Smoothened Receptor Antagonists [MoA]
PUBCHEM
24776445
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY
EPA CompTox
879085-55-9
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY
WIKIPEDIA
Vismodegib
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY
LactMed
879085-55-9
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY
ChEMBL
CHEMBL473417
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY
RXCUI
1242987
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY RxNorm
IUPHAR
6975
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY
NCI_THESAURUS
C74038
Created by admin on Mon Oct 21 22:29:01 UTC 2019 , Edited by admin on Mon Oct 21 22:29:01 UTC 2019
PRIMARY
Related Record Type Details
METABOLIC ENZYME -> SUBSTRATE
MINOR
METABOLIC ENZYME -> SUBSTRATE
MINOR
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
IC50
METABOLIC ENZYME -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC SINGLE DOSE

Volume of Distribution PHARMACOKINETIC