VORINOSTAT

Search structure
Trade Names:
Synonyms:
Status: Approved (2006)
Entry Type: Small molecule
Molecule Category: UNKNOWN
ATC: L01XH01
UNII: 58IFB293JI

Structure
InChI Key WAEXFXRVDQXREF-UHFFFAOYSA-N
Smile O=C(CCCCCCC(=O)Nc1ccccc1)NO
InChI
InChI=1S/C14H20N2O3/c17-13(15-12-8-4-3-5-9-12)10-6-1-2-7-11-14(18)16-19/h3-5,8-9,19H,1-2,6-7,10-11H2,(H,15,17)(H,16,18)

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H20N2O3
Molecular Weight 264.32
AlogP 2.47
Hydrogen Bond Acceptor 3.0
Hydrogen Bond Donor 3.0
Number of Rotational Bond 8.0
Polar Surface Area 78.43
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 19.0

Pharmacology

Action Mechanism of Action Reference
INHIBITOR Histone deacetylase 1 inhibitor DailyMed
Primary Target
histone deacetylase 1
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Cytochrome P450 Cytochrome P450 family 1 Cytochrome P450 family 1A Cytochrome P450 1A2
- - - - 14-25
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C19
- - - - 14-69
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2C Cytochrome P450 2C9
- - - - 28
Enzyme Cytochrome P450 Cytochrome P450 family 2 Cytochrome P450 family 2D Cytochrome P450 2D6
- - - - 8-25
Enzyme Cytochrome P450 Cytochrome P450 family 3 Cytochrome P450 family 3A Cytochrome P450 3A4
- 12000 - - 35
Enzyme Hydrolase
- 1000 300 1000-1300 -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase EGFR family
- 900 - - -
Enzyme Kinase Protein Kinase TK protein kinase group Tyrosine protein kinase Met family
- - - - 3
Enzyme Protease Metallo protease Metallo protease MAE clan Metallo protease M1 family
- 1670-7650 - - -
Enzyme
- 50-1000 300 1000-1300 85-85
Epigenetic regulator Eraser Histone deacetylase HDAC class I
180-6700 4-2200 580-2900 173-15700 47-100
Epigenetic regulator Eraser Histone deacetylase HDAC class IIa
180-6700 10-98350 36000 16-30100 47-100
Epigenetic regulator Eraser Histone deacetylase HDAC class IIb
180-6700 1-5600 300 1-126 47-100
Epigenetic regulator Eraser Histone deacetylase HDAC class IV
180-6700 10-98350 - 13-60 47-100
Epigenetic regulator Eraser Lysine demethylase Jumonji domain-containing
- 14000 - - -
Epigenetic regulator Reader Bromodomain
- 10-740 - - 2-88
Epigenetic regulator Writer Histone acetyltransferase SRC family
- 10-54 - 10-12 -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 322 - - 18
Membrane receptor
- - - - 0
Transcription factor Nuclear receptor Nuclear hormone receptor subfamily 1 Nuclear hormone receptor subfamily 1 group I Nuclear hormone receptor subfamily 1 group I member 2
25100-35500 - - - -
Transcription factor
25100-35500 - - - -
Unclassified protein
- 10-350 - 2-22 99

Indications

Mesh Heading Maximum Phase Mesh ID Reference
Neoplasms 4 D009369 ClinicalTrials
Neoplasms 4 D009369 ClinicalTrials
Lung Neoplasms 3 D008175 ClinicalTrials
Multiple Myeloma 3 D009101 ClinicalTrials
Leukemia, Myeloid, Acute 3 D015470 ClinicalTrials
Lymphoma 3 D008223 ClinicalTrials
Mesothelioma 3 D008654 ClinicalTrials
Mesothelioma 3 D008654 ClinicalTrials
Mycosis Fungoides 2 D009182 ClinicalTrials
Gliosarcoma 2 D018316 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Leukemia, Lymphocytic, Chronic, B-Cell 2 D015451 ClinicalTrials
Lymphoma, Follicular 2 D008224 ClinicalTrials
Lymphoma, B-Cell, Marginal Zone 2 D018442 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Prostatic Neoplasms, Castration-Resistant 2 D064129 ClinicalTrials
Carcinoma, Non-Small-Cell Lung 2 D002289 ClinicalTrials
Neuroblastoma 2 D009447 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Brain Diseases 2 D001927 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Myelodysplastic Syndromes 2 D009190 ClinicalTrials
Breast Neoplasms, Male 2 D018567 ClinicalTrials
Carcinoma, Renal Cell 2 D002292 ClinicalTrials
Anemia, Sickle Cell 2 D000755 ClinicalTrials
Carcinoma, Renal Cell 2 D002292 ClinicalTrials
Glioblastoma 2 D005909 ClinicalTrials
Leukemia 2 D007938 ClinicalTrials
Prostatic Neoplasms 2 D011471 ClinicalTrials
Astrocytoma 2 D001254 ClinicalTrials
Spinal Cord Neoplasms 2 D013120 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Lymphoma, Non-Hodgkin 2 D008228 ClinicalTrials
Sezary Syndrome 2 D012751 ClinicalTrials
Lymphoma, Mantle-Cell 2 D020522 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Sarcoma 2 D012509 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
Colorectal Neoplasms 2 D015179 ClinicalTrials
Thrombocythemia, Essential 2 D013920 ClinicalTrials
Thyroid Neoplasms 2 D013964 ClinicalTrials
Polycythemia Vera 2 D011087 ClinicalTrials
Rectal Neoplasms 2 D012004 ClinicalTrials
Pituitary ACTH Hypersecretion 2 D047748 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Precursor Cell Lymphoblastic Leukemia-Lymphoma 2 D054198 ClinicalTrials
Brain Neoplasms 2 D001932 ClinicalTrials
Breast Neoplasms 2 D001943 ClinicalTrials
Ovarian Neoplasms 2 D010051 ClinicalTrials
HIV Infections 2 D015658 ClinicalTrials
Carcinoma, Medullary 2 D018276 ClinicalTrials
Lymphoma, Follicular 2 D008224 ClinicalTrials
Leukemia, Biphenotypic, Acute 2 D015456 ClinicalTrials
Colonic Neoplasms 2 D003110 ClinicalTrials
Brain Neoplasms 2 D001932 ClinicalTrials
Urinary Bladder Neoplasms 2 D001749 ClinicalTrials
Liver Neoplasms 1 D008113 ClinicalTrials
Alzheimer Disease 1 D000544 ClinicalTrials
Glioma 1 D005910 ClinicalTrials
Burkitt Lymphoma 1 D002051 ClinicalTrials
Leukemia, Myelogenous, Chronic, BCR-ABL Positive 1 D015464 ClinicalTrials
Skin Neoplasms 1 D012878 ClinicalTrials
Crohn Disease 1 D003424 ClinicalTrials
Lymphoma, Large B-Cell, Diffuse 1 D016403 ClinicalTrials
Esophageal Neoplasms 1 D004938 ClinicalTrials
Hypopharyngeal Neoplasms 1 D007012 ClinicalTrials
Diffuse Intrinsic Pontine Glioma 1 D000080443 ClinicalTrials
Leukemia, Promyelocytic, Acute 1 D015473 ClinicalTrials
Small Cell Lung Carcinoma 1 D055752 ClinicalTrials
Lymphoma, T-Cell, Peripheral 1 D016411 ClinicalTrials
Oropharyngeal Neoplasms 1 D009959 ClinicalTrials
Oligodendroglioma 1 D009837 ClinicalTrials
Medulloblastoma 1 D008527 ClinicalTrials
Hodgkin Disease 1 D006689 ClinicalTrials
Squamous Cell Carcinoma of Head and Neck 1 D000077195 ClinicalTrials
Melanoma 1 D008545 ClinicalTrials
Carcinoma, Verrucous 1 D018289 ClinicalTrials
Leukemia, Myelomonocytic, Juvenile 1 D054429 ClinicalTrials
Stomach Neoplasms 1 D013274 ClinicalTrials
Niemann-Pick Diseases 1 D009542 ClinicalTrials
Pancreatic Neoplasms 1 D010190 ClinicalTrials
Precursor T-Cell Lymphoblastic Leukemia-Lymphoma 1 D054218 ClinicalTrials
Anus Neoplasms 1 D001005 ClinicalTrials
Peritoneal Neoplasms 1 D010534 ClinicalTrials
Fallopian Tube Neoplasms 1 D005185 ClinicalTrials
Schizophrenia 0 D012559 ClinicalTrials

Related Entries

MCS

Adverse Reactions

SOC By Demographic Distribution
System Organ Classification (SOC)
Relative Frequency (%)
Investigations
13.97
General disorders and administration site conditions
11.54
Gastrointestinal disorders
10.51
Blood and lymphatic system disorders
8.52
Infections and infestations
8.49
Metabolism and nutrition disorders
7.69
Respiratory, thoracic and mediastinal disorders
6.78
Vascular disorders
5.87
Nervous system disorders
5.26
Renal and urinary disorders
3.63
Injury, poisoning and procedural complications
3.02
Cardiac disorders
3.0
Hepatobiliary disorders
2.74
Skin and subcutaneous tissue disorders
2.32

Cross References

Resources Reference
CAS NUMBER 149647-78-9
ChEBI 45716
ChEMBL CHEMBL98
DrugBank DB02546
DrugCentral 4124
EPA CompTox DTXSID6041133
FDA SRS 58IFB293JI
Human Metabolome Database HMDB0015568
Guide to Pharmacology 6852
KEGG D06320
PDB SHH
PharmGKB PA164748224
PubChem 5311
SureChEMBL SCHEMBL9018
ZINC ZINC000001543873
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