NAV

Mocetinostat

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Mocetinostat
DrugBank Accession Number
DB11830
Background

Mocetinostat has been used in trials studying the treatment of Lymphoma, Urothelial Carcinoma, Relapsed and Refractory, Myelodysplastic Syndrome, and Metastatic Leiomyosarcoma, among others.

Type
Small Molecule
Groups
Investigational
Structure
3D
Similar Structures
Weight
Average: 396.454
Monoisotopic: 396.169859288
Chemical Formula
C23H20N6O
Synonyms
  • Mocetinostat
External IDs
  • MGCD-0103
  • MGCD0103
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

All HDAC inhibitors induce histone H3 hyperacetylation, correlating with inhibition of proliferation, induction of cell differentiation and apoptosis.

Mechanism of action

Mocetinostat is a novel isotypic-selective inhibitor of the enzyme histone deacetylase (HDAC). HDAC inhibitors act by turning on tumour suppressor genes that have been inappropriately turned off. Tumour suppressor genes are a natural defense against cancer. It is therefore hypothesized that specifically inhibiting those HDACs involved in cancer with Mocetinostat may restore normal cell function and reduce or inhibit tumour growth.

TargetActionsOrganism
UHistone deacetylase 1Not AvailableHumans
UHistone deacetylase 3Not AvailableHumans
UHistone deacetylase 2Not AvailableHumans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
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AcrivastineThe risk or severity of QTc prolongation can be increased when Acrivastine is combined with Mocetinostat.
AdenosineThe risk or severity of QTc prolongation can be increased when Adenosine is combined with Mocetinostat.
AjmalineThe risk or severity of QTc prolongation can be increased when Ajmaline is combined with Mocetinostat.
AlfuzosinThe risk or severity of QTc prolongation can be increased when Alfuzosin is combined with Mocetinostat.
AlimemazineThe risk or severity of QTc prolongation can be increased when Alimemazine is combined with Mocetinostat.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Mocetinostat Dihydrobromide4V9P667Y2G944537-89-7ACPWZKZFDFBALX-UHFFFAOYSA-N

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as benzanilides. These are aromatic compounds containing an anilide group in which the carboxamide group is substituted with a benzene ring. They have the general structure RNC(=O)R', where R,R'= benzene.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Anilides
Direct Parent
Benzanilides
Alternative Parents
Pyridinylpyrimidines / Benzamides / Aniline and substituted anilines / Benzylamines / Benzoyl derivatives / Secondary alkylarylamines / Aminopyrimidines and derivatives / Pyridines and derivatives / Heteroaromatic compounds / Secondary carboxylic acid amides
show 7 more
Substituents
Amine / Amino acid or derivatives / Aminopyrimidine / Aniline or substituted anilines / Aromatic heteromonocyclic compound / Azacycle / Benzamide / Benzanilide / Benzoic acid or derivatives / Benzoyl
show 19 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
A6GWB8T96J
CAS number
726169-73-9
InChI Key
HRNLUBSXIHFDHP-UHFFFAOYSA-N
InChI
InChI=1S/C23H20N6O/c24-19-5-1-2-6-21(19)28-22(30)17-9-7-16(8-10-17)14-27-23-26-13-11-20(29-23)18-4-3-12-25-15-18/h1-13,15H,14,24H2,(H,28,30)(H,26,27,29)
IUPAC Name
N-(2-aminophenyl)-4-({[4-(pyridin-3-yl)pyrimidin-2-yl]amino}methyl)benzamide
SMILES
NC1=CC=CC=C1NC(=O)C1=CC=C(CNC2=NC=CC(=N2)C2=CC=CN=C2)C=C1

References

General References
  1. Kell J: Drug evaluation: MGCD-0103, a histone deacetylase inhibitor for the treatment of cancer. Curr Opin Investig Drugs. 2007 Jun;8(6):485-92. [Article]
  2. Beckers T, Burkhardt C, Wieland H, Gimmnich P, Ciossek T, Maier T, Sanders K: Distinct pharmacological properties of second generation HDAC inhibitors with the benzamide or hydroxamate head group. Int J Cancer. 2007 Sep 1;121(5):1138-48. [Article]
  3. Khan N, Jeffers M, Kumar S, Hackett C, Boldog F, Khramtsov N, Qian X, Mills E, Berghs SC, Carey N, Finn PW, Collins LS, Tumber A, Ritchie JW, Jensen PB, Lichenstein HS, Sehested M: Determination of the class and isoform selectivity of small-molecule histone deacetylase inhibitors. Biochem J. 2008 Jan 15;409(2):581-9. [Article]
Human Metabolome Database
HMDB0254820
PubChem Compound
9865515
PubChem Substance
347828176
ChemSpider
8041206
BindingDB
24624
ChEBI
94525
ChEMBL
CHEMBL272980
ZINC
ZINC000013986811
Wikipedia
Mocetinostat

Clinical Trials

Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
2CompletedTreatmentChronic Lymphocytic Leukemia1
2CompletedTreatmentLymphoma1
2CompletedTreatmentMetastatic Leiomyosarcoma1
2CompletedTreatmentNon-Small Cell Lung Carcinoma1
2CompletedTreatmentUrothelial Carcinoma1

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00854 mg/mLALOGPS
logP3.01ALOGPS
logP3Chemaxon
logS-4.7ALOGPS
pKa (Strongest Acidic)13.98Chemaxon
pKa (Strongest Basic)4.37Chemaxon
Physiological Charge0Chemaxon
Hydrogen Acceptor Count6Chemaxon
Hydrogen Donor Count3Chemaxon
Polar Surface Area105.82 Å2Chemaxon
Rotatable Bond Count6Chemaxon
Refractivity120.32 m3·mol-1Chemaxon
Polarizability42.56 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleNoChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-000i-0090000000-34e33042be662b2724b8
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-002s-0194000000-6091887a003acc247441
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0002-0029000000-2cbd491a9efafd08e339
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-00si-2922000000-6df2cd12b4d744a3472d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0a4i-0904000000-3beca7d69f8e1882f5a5
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-00yl-1922000000-bcec5e3ee75b1bf7fa99
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-228.1871682
predicted
DarkChem Lite v0.1.0
[M-H]-190.65244
predicted
DeepCCS 1.0 (2019)
[M+H]+228.3697682
predicted
DarkChem Lite v0.1.0
[M+H]+193.01044
predicted
DeepCCS 1.0 (2019)
[M+Na]+228.4480682
predicted
DarkChem Lite v0.1.0
[M+Na]+199.65434
predicted
DeepCCS 1.0 (2019)

Targets

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Details1. Histone deacetylase 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription regulatory region sequence-specific dna binding
Specific Function
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
Gene Name
HDAC1
Uniprot ID
Q13547
Uniprot Name
Histone deacetylase 1
Molecular Weight
55102.615 Da
References
  1. Beckers T, Burkhardt C, Wieland H, Gimmnich P, Ciossek T, Maier T, Sanders K: Distinct pharmacological properties of second generation HDAC inhibitors with the benzamide or hydroxamate head group. Int J Cancer. 2007 Sep 1;121(5):1138-48. [Article]
  2. Khan N, Jeffers M, Kumar S, Hackett C, Boldog F, Khramtsov N, Qian X, Mills E, Berghs SC, Carey N, Finn PW, Collins LS, Tumber A, Ritchie JW, Jensen PB, Lichenstein HS, Sehested M: Determination of the class and isoform selectivity of small-molecule histone deacetylase inhibitors. Biochem J. 2008 Jan 15;409(2):581-9. [Article]
Details2. Histone deacetylase 3
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription factor binding
Specific Function
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4), and some other non-histone substrates. Histone deacetylation gives a tag for ...
Gene Name
HDAC3
Uniprot ID
O15379
Uniprot Name
Histone deacetylase 3
Molecular Weight
48847.385 Da
References
  1. Beckers T, Burkhardt C, Wieland H, Gimmnich P, Ciossek T, Maier T, Sanders K: Distinct pharmacological properties of second generation HDAC inhibitors with the benzamide or hydroxamate head group. Int J Cancer. 2007 Sep 1;121(5):1138-48. [Article]
Details3. Histone deacetylase 2
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
General Function
Transcription factor binding
Specific Function
Responsible for the deacetylation of lysine residues on the N-terminal part of the core histones (H2A, H2B, H3 and H4). Histone deacetylation gives a tag for epigenetic repression and plays an impo...
Gene Name
HDAC2
Uniprot ID
Q92769
Uniprot Name
Histone deacetylase 2
Molecular Weight
55363.855 Da
References
  1. Khan N, Jeffers M, Kumar S, Hackett C, Boldog F, Khramtsov N, Qian X, Mills E, Berghs SC, Carey N, Finn PW, Collins LS, Tumber A, Ritchie JW, Jensen PB, Lichenstein HS, Sehested M: Determination of the class and isoform selectivity of small-molecule histone deacetylase inhibitors. Biochem J. 2008 Jan 15;409(2):581-9. [Article]

Drug created at October 20, 2016 20:51 / Updated at September 28, 2023 05:47