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Compound Report Card

Compound Name and Classification

Compound ID CHEMBL98
CHEMBL98
Compound Name VORINOSTAT
ChEMBL Synonyms VORINOSTAT | ZOLINZA
Max Phase 4 (Approved)
Trade Names ZOLINZA
Molecular Formula C14H20N2O3

Additional synonyms for CHEMBL98 found using NCI Chemical Identifier Resolver

Compound Representations

Molfile Download MolFile
Canonical SMILES ONC(=O)CCCCCCC(=O)Nc1ccccc1
Standard InChI InChI=1S/C14H20N2O3/c17-13(15-12-8-4-3-5-9-12)10-6-1-2-7-11- ...
Download InChI
Standard InChI Key WAEXFXRVDQXREF-UHFFFAOYSA-N

Sources

  • AstraZeneca Deposited Data
  • BindingDB Database
  • Gene Expression Atlas Compounds
  • Orange Book
  • Patent Bioactivity Data
  • PubChem BioAssays
  • Sanger Institute Genomics of Drug Sensitivity in Cancer
  • Scientific Literature
  • USP Dictionary of USAN and International Drug Names
  • WHO Anatomical Therapeutic Chemical Classification

Alternate Forms of Compound in ChEMBL


CHEMBL98

Molecule Features

CHEMBL98 compound icon
Drug Type:Synthetic Small Molecule Rule of Five:Y First In Class:N Chirality:Achiral Molecule Prodrug:N Oral:Y Parenteral:N Topical:N Black Box:N Availability Type:Prescription-only

Mechanism of Action

Mechanism of Action ChEMBL Target References
Histone deacetylase 1 inhibitor Histone deacetylase 1 DailyMed
Histone deacetylase 2 inhibitor Histone deacetylase 2 DailyMed
Histone deacetylase 3 inhibitor Histone deacetylase 3 DailyMed
Histone deacetylase 6 inhibitor Histone deacetylase 6 DailyMed

Indications

MESH Heading MESH ID EFO ID EFO Term Max phase for indication References
Breast NeoplasmsD001943EFO:0003869breast neoplasm2ClinicalTrials
Carcinoma, Non-Small-Cell LungD002289EFO:0003060non-small cell lung carcinoma2ClinicalTrials
Leukemia, Myeloid, AcuteD015470EFO:0000222acute myeloid leukemia3ClinicalTrials
Leukemia, Myelomonocytic, JuvenileD054429EFO:1000309Juvenile Myelomonocytic Leukemia1ClinicalTrials
LymphomaD008223EFO:0000574lymphoma3ClinicalTrials
Lymphoma, FollicularD008224EFO:0000096neoplasm of mature B-cells2ClinicalTrials
MedulloblastomaD008527EFO:0002939medulloblastoma1ClinicalTrials
NeuroblastomaD009447EFO:0000621neuroblastoma2ClinicalTrials
SarcomaD012509EFO:0000691sarcoma2ClinicalTrials
Breast NeoplasmsD001943EFO:0000305breast carcinoma2ClinicalTrials
LeukemiaD007938EFO:0000565leukemia2ClinicalTrials
Lymphoma, Large B-Cell, DiffuseD016403EFO:0000403diffuse large B-cell lymphoma1ClinicalTrials
Mycosis FungoidesD009182EFO:1001051mycosis fungoides2ClinicalTrials
GlioblastomaD005909EFO:0000519glioblastoma multiforme2ClinicalTrials
Leukemia, Promyelocytic, AcuteD015473EFO:0000224acute promyelocytic leukemia1ClinicalTrials
Lymphoma, B-Cell, Marginal ZoneD018442EFO:1000630marginal zone B-cell lymphoma2ClinicalTrials
Lymphoma, Mantle-CellD020522EFO:1001469Mantle cell lymphoma2ClinicalTrials
NeoplasmsD009369EFO:0000311cancer4ClinicalTrials
Prostatic NeoplasmsD011471EFO:0000673prostate adenocarcinoma2ClinicalTrials
Prostatic NeoplasmsD011471EFO:0001663prostate carcinoma2ClinicalTrials
SchizophreniaD012559EFO:0000692schizophrenia0ClinicalTrials
Small Cell Lung CarcinomaD055752EFO:0000702small cell lung carcinoma1ClinicalTrials
Urinary Bladder NeoplasmsD001749EFO:0000292bladder carcinoma2ClinicalTrials
Brain DiseasesD001927EFO:0005774brain disease2ClinicalTrials
Breast Neoplasms, MaleD018567EFO:0006861male breast carcinoma2ClinicalTrials
Burkitt LymphomaD002051EFO:0000309Burkitts lymphoma1ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000681renal cell carcinoma2ClinicalTrials
Carcinoma, VerrucousD018289EFO:0007535verrucous carcinoma1ClinicalTrials
Esophageal NeoplasmsD004938EFO:0002916esophageal carcinoma1ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL PositiveD015464EFO:0000339chronic myelogenous leukemia1ClinicalTrials
MesotheliomaD008654EFO:0000770malignant pleural mesothelioma1ClinicalTrials
Multiple MyelomaD009101EFO:0001378multiple myeloma3ClinicalTrials
NeoplasmsD009369EFO:0000616neoplasm4ATC
ClinicalTrials
Pancreatic NeoplasmsD010190EFO:0002618pancreatic carcinoma1ClinicalTrials
Spinal Cord NeoplasmsD013120EFO:0003828spinal cord neoplasm2ClinicalTrials
Ureteral NeoplasmsD014516EFO:0003844ureteral neoplasm2ClinicalTrials
Carcinoma, Squamous CellD002294EFO:0000181head and neck squamous cell carcinoma1ClinicalTrials
Crohn DiseaseD003424EFO:0000384Crohn's disease1ClinicalTrials
GliosarcomaD018316EFO:1001465gliosarcoma2ClinicalTrials
Myelodysplastic SyndromesD009190EFO:0000198myelodysplastic syndrome2ClinicalTrials
Neuroectodermal Tumors, PrimitiveD018242EFO:0005235primitive neuroectodermal tumor1ClinicalTrials
Colorectal NeoplasmsD015179EFO:1001951colorectal carcinoma2ClinicalTrials
GliomaD005910EFO:0000326central nervous system cancer1ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-CellD015451EFO:0000095chronic lymphocytic leukemia1ClinicalTrials
Lymphoma, B-Cell, Marginal ZoneD018442EFO:0000191MALT lymphoma2ClinicalTrials
Ovarian NeoplasmsD010051Orphanet:398934Malignant epithelial tumor of ovary2ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-LymphomaD054198EFO:0000220acute lymphoblastic leukemia2ClinicalTrials
SarcomaD012509EFO:1001968soft tissue sarcoma2ClinicalTrials
Sezary SyndromeD012751EFO:1000785Sezary's disease2ClinicalTrials
Anemia, Sickle CellD000755Orphanet:232Sickle cell anemia2ClinicalTrials
AstrocytomaD001254EFO:0002499anaplastic astrocytoma2ClinicalTrials
Carcinoma, HepatocellularD006528EFO:0000182hepatocellular carcinoma1ClinicalTrials
Carcinoma, Renal CellD002292EFO:0000349clear cell renal carcinoma2ClinicalTrials
Lymphoma, T-Cell, CutaneousD016410EFO:0002913Cutaneous T-cell lymphoma4ClinicalTrials
DailyMed
MelanomaD008545EFO:0000756melanoma1ClinicalTrials
Niemann-Pick DiseasesD009542EFO:1001380Niemann-Pick disease1ClinicalTrials
OligodendrogliomaD009837EFO:0002501anaplastic oligodendroglioma1ClinicalTrials
Precursor T-Cell Lymphoblastic Leukemia-LymphomaD054218EFO:1001830precursor T-cell lymphoblastic leukemia-lymphoma1ClinicalTrials
Stomach NeoplasmsD013274EFO:0000178gastric carcinoma1ClinicalTrials
Alzheimer DiseaseD000544EFO:0000249Alzheimers disease1ClinicalTrials
Anus NeoplasmsD001005EFO:0003835anal neoplasm1ClinicalTrials
HIV InfectionsD015658EFO:0000180HIV-1 infection2ClinicalTrials
HIV InfectionsD015658EFO:0000764HIV infection2ClinicalTrials
Hodgkin DiseaseD006689EFO:0000183Hodgkins lymphoma1ClinicalTrials
Leukemia, LymphoidD007945EFO:0004289lymphoid leukemia1ClinicalTrials
Lymphoma, Non-HodgkinD008228EFO:0005952non-Hodgkins lymphoma2ClinicalTrials
Lymphoma, T-Cell, PeripheralD016411EFO:0000211unspecified peripheral T-cell lymphoma1ClinicalTrials
OligodendrogliomaD009837EFO:0000630oligoastrocytoma1ClinicalTrials
Ovarian NeoplasmsD010051EFO:0001075ovarian carcinoma2ClinicalTrials
Ovarian NeoplasmsD010051EFO:0003893ovarian neoplasm2ClinicalTrials

Clinical Data

ClinicalTrials.gov VORINOSTAT
The Cochrane Collaboration VORINOSTAT

Compound Bioactivity Summary

Compound Assay Summary

Compound Target Summary

Target Predictions

The two tables below display ChEMBL single-protein targets which are predicted to interact with CHEMBL98. A 1uM and 10 uM cut-off have been applied to ChEMBL bioactivity data used to generate the respective models and the yellow coloured rows correspond to genuine predictions, i.e. targets not included in the original training set for this compound.


1uM


ChEMBL_ID Target Name Organism Score
CHEMBL5103 Histone deacetylase 10 Homo sapiens 1.000
CHEMBL1865 Histone deacetylase 6 Homo sapiens 1.000
CHEMBL1829 Histone deacetylase 3 Homo sapiens 1.000
CHEMBL3192 Histone deacetylase 8 Homo sapiens 1.000
CHEMBL325 Histone deacetylase 1 Homo sapiens 1.000
CHEMBL1937 Histone deacetylase 2 Homo sapiens 1.000
CHEMBL3310 Histone deacetylase 11 Homo sapiens 1.000
CHEMBL4145 Histone deacetylase 9 Homo sapiens 1.000
CHEMBL4919 Histone deacetylase HD2 Zea mays 1.000
CHEMBL2563 Histone deacetylase 5 Homo sapiens 1.000
CHEMBL2716 Histone deacetylase 7 Homo sapiens 1.000
CHEMBL3524 Histone deacetylase 4 Homo sapiens 1.000
CHEMBL4588 Matrix metalloproteinase 8 Homo sapiens 1.000
CHEMBL333 Matrix metalloproteinase-2 Homo sapiens 1.000
CHEMBL4001 Histone deacetylase 1 Mus musculus 0.999
CHEMBL3541 Histone deacetylase HD1B Zea mays 0.999
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 0.999
CHEMBL321 Matrix metalloproteinase 9 Homo sapiens 0.978
CHEMBL335 Protein-tyrosine phosphatase 1B Homo sapiens 0.914
CHEMBL332 Matrix metalloproteinase-1 Homo sapiens 0.865



10uM


ChEMBL_ID Target Name Organism Score
CHEMBL5103 Histone deacetylase 10 Homo sapiens 1.000
CHEMBL3192 Histone deacetylase 8 Homo sapiens 1.000
CHEMBL1865 Histone deacetylase 6 Homo sapiens 1.000
CHEMBL1829 Histone deacetylase 3 Homo sapiens 1.000
CHEMBL325 Histone deacetylase 1 Homo sapiens 1.000
CHEMBL1937 Histone deacetylase 2 Homo sapiens 1.000
CHEMBL3310 Histone deacetylase 11 Homo sapiens 1.000
CHEMBL4145 Histone deacetylase 9 Homo sapiens 1.000
CHEMBL2716 Histone deacetylase 7 Homo sapiens 1.000
CHEMBL2563 Histone deacetylase 5 Homo sapiens 1.000
CHEMBL4919 Histone deacetylase HD2 Zea mays 1.000
CHEMBL3524 Histone deacetylase 4 Homo sapiens 1.000
CHEMBL4588 Matrix metalloproteinase 8 Homo sapiens 0.999
CHEMBL333 Matrix metalloproteinase-2 Homo sapiens 0.999
CHEMBL283 Matrix metalloproteinase 3 Homo sapiens 0.997
CHEMBL4001 Histone deacetylase 1 Mus musculus 0.995
CHEMBL3541 Histone deacetylase HD1B Zea mays 0.993
CHEMBL321 Matrix metalloproteinase 9 Homo sapiens 0.962
CHEMBL4140 Epoxide hydratase Mus musculus 0.896
CHEMBL3807 T-cell protein-tyrosine phosphatase Homo sapiens 0.836

Calculated Compound Parent Properties

Mol. Weight Mol. Weight Monoisotopic ALogP #Rotatable Bonds Polar Surface Area Molecular Species
264.3 264.1474 2.47 8 78.43 NEUTRAL


HBA HBD #Ro5 Violations HBA (Lipinski) HBD (Lipinski) #Ro5 Violations (Lipinski)
3 3 0 5 3 0


ACD Acidic pKa ACD Basic pKa ACD LogP ACD LogD pH7.4 Aromatic Rings Heavy Atoms QED Weighted
9.48 .5 2.34 2.34 1 19 0.38

Structural Alerts

There are 10 structural alerts for CHEMBL98. To view alerts please click here.

Compound Cross References

ATC L - ANTINEOPLASTIC AND IMMUNOMODULATING AGENTS
L01 - ANTINEOPLASTIC AGENTS
L01X - OTHER ANTINEOPLASTIC AGENTS
L01XX - Other antineoplastic agents
L01XX38 - vorinostat

ChemSpider ChemSpider:WAEXFXRVDQXREF-UHFFFAOYSA-N
DailyMed vorinostat
PubChem SID: 104171411 SID: 124893442 SID: 144206158 SID: 144207172 SID: 170465180 SID: 49645508 SID: 50113029
Wikipedia Vorinostat

UniChem Cross References

View the UniChem Connectivity matches for CHEMBL98



ACToR 149647-78-9
Atlas vorinostat SAHA
BindingDB 19149
Brenda 41261 1547 217024 151869 7817 206568
ChEBI 45716
ChemicalBook CB3506806
DrugBank DB02546
DrugCentral 4124
eMolecules 1989084
EPA CompTox Dashboard DTXSID6041133
FDA SRS 58IFB293JI
Guide to Pharmacology 6852
Human Metabolome Database HMDB0015568
IBM Patent System 2E55AB1669C6BAC97E5E7399B258C23F
LINCS LSM-3828
Mcule MCULE-4234367506
MolPort MolPort-003-850-293
Nikkaji J653.349C
PDBe SHH
PharmGKB PA164748224
PubChem 5311
PubChem: Drugs of the Future 12015019
PubChem: Thomson Pharma 14823867
Selleck Vorinostat-(SAHA)
SureChEMBL SCHEMBL9018
ZINC ZINC000001543873

UniChem REST Service Call:
https://www.ebi.ac.uk/unichem/rest/verbose_inchikey/WAEXFXRVDQXREF-UHFFFAOYSA-N spacer
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