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
Thumb
Weight
Average: 396.454
Monoisotopic: 396.169859288
Chemical Formula
C23H20N6O
Synonyms
  • Mocetinostat
External IDs
  • MGCD-0103
  • MGCD0103

Pharmacology

Indication

Not Available

Pharmacology
Reduce drug development failure rates
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Contraindications & Blackbox Warnings
Contraindications
Avoid life-threatening adverse drug events
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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
Adverseeffects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
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
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.
AmantadineThe risk or severity of QTc prolongation can be increased when Amantadine is combined with Mocetinostat.
AmifampridineThe risk or severity of QTc prolongation can be increased when Amifampridine is combined with Mocetinostat.
AmiodaroneThe risk or severity of QTc prolongation can be increased when Mocetinostat is combined with Amiodarone.
AmisulprideThe risk or severity of QTc prolongation can be increased when Mocetinostat is combined with Amisulpride.
AmitriptylineThe risk or severity of QTc prolongation can be increased when Amitriptyline is combined with Mocetinostat.
Interactions
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Food Interactions
Not Available

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]
PubChem Compound
9865515
PubChem Substance
347828176
ChemSpider
8041206
BindingDB
24624
ChEBI
94525
ChEMBL
CHEMBL272980
ZINC
ZINC000013986811
Wikipedia
Mocetinostat

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2Active Not RecruitingTreatmentNon-Small Cell Lung Carcinoma (NSCLC)1
2CompletedTreatmentChronic Lymphocytic Leukemia (CLL)1
2CompletedTreatmentMalignant Lymphomas1
2CompletedTreatmentMetastatic Leiomyosarcoma1
2CompletedTreatmentTransitional Cell, Carcinoma1
2TerminatedTreatmentAcute Myeloid Leukemia (AML) / Myelodysplastic Syndromes (MDS)2
2TerminatedTreatmentLymphoma, Hodgkins1
2TerminatedTreatmentLymphoma, Hodgkins / Non-Hodgkin Lymphoma (Follicular or Large Diffuse B-cell Lymphoma or Mantle Cell Lymphoma)1
1Active Not RecruitingTreatmentLung Cancers1
1CompletedTreatmentLeukemias / Myelodysplastic Syndromes (MDS)2

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/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Drugtargets2
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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]
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]
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 on October 20, 2016 20:51 / Updated on February 21, 2021 18:53