Givinostat Hydrochloride

Details

Stereochemistry	ACHIRAL
Molecular Formula	C24H27N3O4.ClH.H2O
Molecular Weight	475.965
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

O.Cl.CCN(CC)CC1=CC2=C(C=C1)C=C(COC(=O)NC3=CC=C(C=C3)C(=O)NO)C=C2

InChI

InChIKey=FKGKZBBDJSKCIS-UHFFFAOYSA-N

InChI=1S/C24H27N3O4.ClH.H2O/c1-3-27(4-2)15-17-5-7-21-14-18(6-8-20(21)13-17)16-31-24(29)25-22-11-9-19(10-12-22)23(28)26-30;;/h5-14,30H,3-4,15-16H2,1-2H3,(H,25,29)(H,26,28);1H;1H2

HIDE SMILES / InChI

Molecular Formula	H2O
Molecular Weight	18.0153
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	C24H27N3O4
Molecular Weight	421.4889
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug/?CdrID=560751
Curator's Comment: description was created based on several sources, including: http://adisinsight.springer.com/drugs/800023261 | https://newdrugapprovals.org/2015/03/05/givinostat/ | https://en.wikipedia.org/wiki/Givinostat

Gavinostat is an orally bioavailable hydroxymate inhibitor of histone deacetylase (HDAC) with potential anti-inflammatory, anti-angiogenic, and antineoplastic activities. Gavinostat inhibits class I and class II HDACs, resulting in an accumulation of highly acetylated histones, followed by the induction of chromatin remodeling and an altered pattern of gene expression. At low, nonapoptotic concentrations, this agent inhibits the production of pro-inflammatory cytokines such as tumor necrosis factor- (TNF-), interleukin-1 (IL-1), IL-6 and interferon-gamma. It is currently in phase 2 trials for Myeloproliferative disorders, Polycythaemia vera and Phase III for Duchenne muscular dystrophy announced. In clinical trials of givinostat as a salvage therapy for advanced Hodgkin's lymphoma, the most common adverse reactions were fatigue, mild diarrhea or abdominal pain, moderate thrombocytopenia, and mild leukopenia.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Histone deacetylase 1 51 Target ID: CHEMBL325 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17868033	Inhibitor 8504	28.0 nM [EC50]
Histone deacetylase 2 37 Target ID: CHEMBL1937 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17868033	Inhibitor 8504	56.0 nM [EC50]
Histone deacetylase 3 35 Target ID: CHEMBL1829 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17868033	Inhibitor 8504	21.0 nM [EC50]
Histone deacetylase 4 11 Target ID: CHEMBL3524 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17868033	Inhibitor 8504	52.0 nM [EC50]
Histone deacetylase 6 28 Target ID: CHEMBL1865 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17868033	Inhibitor 8504	27.0 nM [EC50]
Histone deacetylase 7 4 Target ID: CHEMBL2716 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17868033	Inhibitor 8504	163.0 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Polycythemia vera 18 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23573950	Primary	Phase II 1147	Unknown Approved Use Unknown
Systemic onset juvenile idiopathic arthritis 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/21538322	Primary	Phase II 1147	Unknown Approved Use Unknown
Duchenne muscular dystrophy 18 Sources: http://www.parentprojectmd.org/site/DocServer/16T_400_Italfarmaco_v03.pdf?docID=17035	Primary	Phase III 665	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
542 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21365126	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		GIVINOSTAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
3543 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21365126	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		GIVINOSTAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.3 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/21365126	600 mg single, oral dose: 600 mg route of administration: Oral experiment type: SINGLE co-administered:		GIVINOSTAT plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE food status: FASTED

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P00FFPV	https://www.1pchem.com/search?query=1P00FFPV
AbovChem LLC	HY-14842A	http://www.abovchem.com/pc/en/product_list.aspx?wd=HY-14842A
AChemBlock	L14962	http://www.achemblock.com/catalogsearch/result/?q=L14962
AK Scientific	X7525	https://aksci.com/item_detail.php?cat=X7525
AK Scientific	X7528	https://aksci.com/item_detail.php?cat=X7528
Ambeed	A113603	http://www.ambeed.com/search/Search.html?keyword=A113603
Angene	AGN-PC-0WHAMP	http://www.angenechemical.com/productshow/AGN-PC-0WHAMP.html
ApexBio Technology	A4093	https://www.apexbt.com/catalogsearch/result/?q=A4093
AstaTech	C76335	http://astatechinc.com/CPSResult.php?CRNO=C76335
AstaTech	P14959	http://astatechinc.com/CPSResult.php?CRNO=P14959
BLD Pharm	BD386438	http://www.bldpharm.com/search/Search.html?keyword=BD386438
BLD Pharm	BD630515	http://www.bldpharm.com/search/Search.html?keyword=BD630515
BLD Pharm	BD630733	http://www.bldpharm.com/search/Search.html?keyword=BD630733
Cayman Chemical	11045	http://www.caymanchem.com/app/template/Product.vm/catalog/11045
Chem Scene	CS-7576	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-7576
ChemShuttle	151598	https://www.chemshuttle.com/catalogsearch/result/?q=151598
eMolecules	300620222	https://orderbb.emolecules.com/search/#?query=300620222
eMolecules	43473175	https://orderbb.emolecules.com/search/#?query=43473175
eMolecules	56967806	https://orderbb.emolecules.com/search/#?query=56967806
eMolecules	72973401	https://orderbb.emolecules.com/search/#?query=72973401
Enamine	EN300-257964	https://www.enaminestore.com/catalog/EN300-257964
Enamine	EN300-260030	https://www.enaminestore.com/catalog/EN300-260030
eNovation Chemicals	D551929	https://www.enovationchem.com/Products.asp?SEARCHTEXT=D551929&searchbtn.x=0&searchbtn.y=0
Excenen	EX-A2286	http://www.excenen.com/searchresultlist.php?id=EX-A2286
Exclusive Chemistry	2471	http://www.exchemistry.com/chem-catalog/product-2471.html
KeyOrganics	AS-52365	http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-52365
mcule	MCULE-5339919477	https://mcule.com/MCULE-5339919477/
mcule	MCULE-9912891466	https://mcule.com/MCULE-9912891466/
MedChem Express	HY-14842B	https://www.medchemexpress.com/search.html?q=HY-14842B&ft=&fa=&fp=
Molnova	M15799	https://www.molnova.com/en/serch-list.html?keywords=M15799
MolPort	MolPort-016-633-293	https://www.molport.com/shop/molecule-link/MolPort-016-633-293
MolPort	MolPort-021-804-893	https://www.molport.com/shop/molecule-link/MolPort-021-804-893
MolPort	MolPort-039-139-328	https://www.molport.com/shop/molecule-link/MolPort-039-139-328
MuseChem	I006964	https://www.musechem.com/product/I006964.html
MuseChem	I013160	https://www.musechem.com/product/I013160.html
Selleck Chemicals	S2170	http://www.selleckchem.com/search.html?searchDTO.searchParam=S2170
ShangHai Biochempartner	BCP02886	http://www.biochempartner.com/search_BCP02886
Sigma Aldrich	SML1772	http://www.sigmaaldrich.com/catalog/search?term=SML1772&interface=All&N=0&mode=match%20partialmax&lang=en®ion=US&focus=product
TargetMol	T6279	https://www.targetmol.com/search?keyword=T6279

PubMed

Title	Date	PubMed
Optimization of the in vitro cardiac safety of hydroxamate-based histone deacetylase inhibitors.	2011-07-14	21650221
The histone deacetylase inhibitor ITF2357 decreases surface CXCR4 and CCR5 expression on CD4(+) T-cells and monocytes and is superior to valproic acid for latent HIV-1 expression in vitro.	2010-05-01	20300007
Chemical phylogenetics of histone deacetylases.	2010-03	20139990
Determination of the class and isoform selectivity of small-molecule histone deacetylase inhibitors.	2008-01-15	17868033

Patents

Sample Use Guides

In Vivo Use Guide

up to 12 weeks at a dosage of 1.5 mg/kg/day

Route of Administration: Oral

In Vitro Use Guide

ITF2357 at 100 nM reduced LPS-induced GM-CSF by 99% and 89%, respectively. However, when stimulated with anti-CD3, there was no reduction in GM-CSF by ITF2357 at 37 or 100 nM.

Substance Class	Chemical Created by `admin` on `Wed Apr 02 16:48:00 GMT 2025` Edited by `admin` on `Wed Apr 02 16:48:00 GMT 2025`
Record UNII	6R2GQ94CB5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Givinostat Hydrochloride

Official Name

English

DUVYZAT

Preferred Name

English

GIVINOSTAT HYDROCHLORIDE [USAN]

Common Name

English

Carbamic acid, [4-[(hydroxyamino)carbonyl]phenyl]-, [6-[(diethylamino)methyl]-2-naphthalenyl]methyl ester, monohydrochloride, monohydrate

Systematic Name

English

Carbamic acid, N-[4-[(hydroxyamino)carbonyl]phenyl]-, [6-[(diethylamino)methyl]-2-naphthalenyl]methyl ester, hydrochloride, hydrate (1:1:1)

Systematic Name

English

ITF2357 hydrochloride monohydrate

Code

English

ITF-2357 hydrochloride monohydrate

Code

English

Givinostat hydrochloride monohydrate

Common Name

English

Code System Code Type Description

PUBCHEM

9804991