VISMODEGIB

Search structure
Trade Names:
Synonyms:
Status: Approved (2012)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: L01XJ01
UNII: 25X868M3DS

Structure
InChI Key BPQMGSKTAYIVFO-UHFFFAOYSA-N
Smile CS(=O)(=O)c1ccc(C(=O)Nc2ccc(Cl)c(-c3ccccn3)c2)c(Cl)c1
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)

Physicochemical Descriptors

Property Name Value
Molecular Formula C19H14Cl2N2O3S
Molecular Weight 421.31
AlogP 4.71
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 4.0
Polar Surface Area 76.13
Molecular species NEUTRAL
Aromatic Rings 3.0
Heavy Atoms 27.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Smoothened homolog inhibitor FDA
Primary Target
SMO
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Membrane receptor Frizzled family G protein-coupled receptor Smoothened receptor (frizzled family GPCR)
0-5 0-74 98 12-16 97-100
Secreted protein
- - 5500-6000 - -
Unclassified protein
- 3-17 - - -

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Neoplasms 4 D009369 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Carcinoma, Basal Cell 4 D002280 ClinicalTrials
Carcinoma, Basal Cell 4 D002280 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Meningioma 2 D008579 ClinicalTrials
Gliosarcoma 2 D018316 ClinicalTrials
Leukemia, Myeloid, Acute 2 D015470 ClinicalTrials
Graft vs Host Disease 2 D006086 ClinicalTrials
Medulloblastoma 2 D008527 ClinicalTrials
Idiopathic Pulmonary Fibrosis 2 D054990 ClinicalTrials
Glioma 2 D005910 ClinicalTrials
Pancreatic Neoplasms 2 D010190 ClinicalTrials
Stomach Neoplasms 2 D013274 ClinicalTrials
Basal Cell Nevus Syndrome 2 D001478 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Small Cell Lung Carcinoma 2 D055752 ClinicalTrials
Carcinoma, Pancreatic Ductal 2 D021441 ClinicalTrials
Prostatic Neoplasms 1 D011471 ClinicalTrials
Primary Myelofibrosis 1 D055728 ClinicalTrials
Glioblastoma 1 D005909 ClinicalTrials
Multiple Myeloma 1 D009101 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 0 D064129 ClinicalTrials

Related Entries

Scaffolds

Side Effects from Label

Side effects Relative Frequency (%) Labels
Musculoskeletal and connective tissue disorders Muscle spasms 74.6
Musculoskeletal and connective tissue disorders Muscle spasms 71.7
Skin and subcutaneous tissue disorders Alopecia 65.2
Skin and subcutaneous tissue disorders Alopecia 63.8
Gastrointestinal disorders Dysgeusia 57.2
Gastrointestinal disorders Dysgeusia 55.1
Investigations Weight decreased 48.6
General disorders and administration site conditions Asthenia 44.9
General disorders and administration site conditions Fatigue 44.9
Investigations Weight decreased 44.9
General disorders and administration site conditions Asthenia 39.9
General disorders and administration site conditions Fatigue 39.9
Gastrointestinal disorders Nausea 34.8
Gastrointestinal disorders Nausea 30.4
Gastrointestinal disorders Diarrhoea 29.0
General disorders and administration site conditions Decreased appetite 25.4
Gastrointestinal disorders Constipation 21.0
Musculoskeletal and connective tissue disorders Arthralgia 15.9
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 15.9
Gastrointestinal disorders Vomiting 13.8
Gastrointestinal disorders Ageusia 10.9
Investigations Weight decreased 7.2
General disorders and administration site conditions Asthenia 5.1
General disorders and administration site conditions Fatigue 5.1
Musculoskeletal and connective tissue disorders Muscle spasms 3.6
General disorders and administration site conditions Decreased appetite 2.2
Musculoskeletal and connective tissue disorders Arthralgia 0.7
General disorders and administration site conditions Asthenia 0.7
Gastrointestinal disorders Diarrhoea 0.7
General disorders and administration site conditions Fatigue 0.7
Musculoskeletal and connective tissue disorders Musculoskeletal discomfort 0.7
Gastrointestinal disorders Nausea 0.7

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Gastrointestinal disorders
17.52
General disorders and administration site conditions
13.67
Nervous system disorders
11.75
Musculoskeletal and connective tissue disorders
11.36
Skin and subcutaneous tissue disorders
9.92
Investigations
6.77
Metabolism and nutrition disorders
5.11
Respiratory, thoracic and mediastinal disorders
3.08
Psychiatric disorders
2.94
Vascular disorders
2.89
Neoplasms benign, malignant and unspecified (incl cysts and polyps)
2.47
Infections and infestations
2.34
Injury, poisoning and procedural complications
2.16

Cross References

Resources Reference
CAS NUMBER 879085-55-9
ChEBI 66903
ChEMBL CHEMBL473417
DrugBank DB08828
DrugCentral 4227
EPA CompTox DTXSID40236689
FDA SRS 25X868M3DS
Guide to Pharmacology 6975
KEGG D09992
PDB VIS
PubChem 24776445
SureChEMBL SCHEMBL302587
ZINC ZINC000040899447
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