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Details

Stereochemistry ACHIRAL
Molecular Formula C20H30N4O2
Molecular Weight 358.4778
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of PRACINOSTAT

SMILES

CCCCC1=NC2=CC(\C=C\C(=O)NO)=CC=C2N1CCN(CC)CC

InChI

InChIKey=JHDKZFFAIZKUCU-ZRDIBKRKSA-N
InChI=1S/C20H30N4O2/c1-4-7-8-19-21-17-15-16(10-12-20(25)22-26)9-11-18(17)24(19)14-13-23(5-2)6-3/h9-12,15,26H,4-8,13-14H2,1-3H3,(H,22,25)/b12-10+

HIDE SMILES / InChI
Molecular Formula C20H30N4O2
Molecular Weight 358.4778
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description

Pracinostat is a pan-histone deacetylase inhibitor being tested in phase II of clinical trials for the treatment of sarcoma, prostate cancer, acute myeloid leukemia, myelofibrosis, myelodysplastic syndrome. The drug was shown to be active in vitro on HCT116 and HL-60 cells.

Originator

Approval Year

Unknown
139594
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Primary
Phase II
1132
Unknown

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
120 mg 3 times / week multiple, oral
MTD
Dose: 120 mg, 3 times / week
Route: oral
Route: multiple
Dose: 120 mg, 3 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/28841236
Page: p.5
unhealthy, ADULT
n = 6
Health Status: unhealthy
Condition: Hematological tumors
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/28841236
Page: p.5
DLT: febrile neutropeni...
Dose limiting toxicities:
febrile neutropeni (16.7%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/28841236
Page: p.5
80 mg 3 times / week multiple, oral
MTD
Dose: 80 mg, 3 times / week
Route: oral
Route: multiple
Dose: 80 mg, 3 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21385886
Page: p.2518
unhealthy, ADULT
n = 6
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/21385886
Page: p.2518
DLT: Fatigue, Troponin T increased...
Dose limiting toxicities:
Fatigue (grade 3, 16.7%)
Troponin T increased (grade 3, 16.7%)
QTc interval prolongation (grade 3, 16.7%)
Sources:
https://pubmed.ncbi.nlm.nih.gov/21385886
Page: p.2518
AEs

AEs

AESignificanceDosePopulation
febrile neutropeni 16.7%
DLT
120 mg 3 times / week multiple, oral
MTD
Dose: 120 mg, 3 times / week
Route: oral
Route: multiple
Dose: 120 mg, 3 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/28841236
Page: p.5
unhealthy, ADULT
n = 6
Health Status: unhealthy
Condition: Hematological tumors
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/28841236
Page: p.5
Fatigue grade 3, 16.7%
DLT
80 mg 3 times / week multiple, oral
MTD
Dose: 80 mg, 3 times / week
Route: oral
Route: multiple
Dose: 80 mg, 3 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21385886
Page: p.2518
unhealthy, ADULT
n = 6
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/21385886
Page: p.2518
Troponin T increased grade 3, 16.7%
DLT
80 mg 3 times / week multiple, oral
MTD
Dose: 80 mg, 3 times / week
Route: oral
Route: multiple
Dose: 80 mg, 3 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21385886
Page: p.2518
unhealthy, ADULT
n = 6
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/21385886
Page: p.2518
QTc interval prolongation grade 3, 16.7%
DLT, Disc. AE
80 mg 3 times / week multiple, oral
MTD
Dose: 80 mg, 3 times / week
Route: oral
Route: multiple
Dose: 80 mg, 3 times / week
Sources:
https://pubmed.ncbi.nlm.nih.gov/21385886
Page: p.2518
unhealthy, ADULT
n = 6
Health Status: unhealthy
Condition: cancer
Age Group: ADULT
Sex: M+F
Food Status: FASTED
Population Size: 6
Sources:
https://pubmed.ncbi.nlm.nih.gov/21385886
Page: p.2518
Sourcing

Sourcing

Vendor/AggregatorIDURL
1PlusChem LLC
1P00GTSD
https://www.1pchem.com/search?query=1P00GTSD
A2B Chem
AH84301
http://a2bchem.com/prod/AH84301
AChemBlock
O33905
http://www.achemblock.com/catalogsearch/result/?q=O33905
AK Scientific
X7533
https://aksci.com/item_detail.php?cat=X7533
Ambeed
A477591
http://www.ambeed.com/search/Search.html?keyword=A477591
Angene
AGN-PC-0WH9M6
http://www.angenechemical.com/productshow/AGN-PC-0WH9M6.html
ApexBio Technology
A4095
https://www.apexbt.com/catalogsearch/result/?q=A4095
AstaTech
41302
http://astatechinc.com/CPSResult.php?CRNO=41302
Axon MedChem
1777
https://www.axonmedchem.com/product/1777
BLD Pharm
BD306059
http://www.bldpharm.com/search/Search.html?keyword=BD306059
BOC Sciences
929016-96-6
http://www.bocsci.com/description.asp?cas=929016-96-6
Cayman Chemical
10443
http://www.caymanchem.com/app/template/Product.vm/catalog/10443
Chem Scene
CS-0567
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0567
ChemShuttle
109807
https://www.chemshuttle.com/catalogsearch/result/?q=109807
Excenen
EX-A351
http://www.excenen.com/searchresultlist.php?id=EX-A351
Exclusive Chemistry
2481
http://www.exchemistry.com/chem-catalog/product-2481.html
Fluorochem
468349
http://www.fluorochem.co.uk/Products/Product?code=468349
KeyOrganics
AS-19395
http://www.keyorganicsinc.com/bionet/catalogsearch/result?q=AS-19395
Lab Network
LN01309076
https://labnetwork.com/frontend-app/p/#!/moleculedetails/LN01309076
Lab Seeker
SC-86253
http://www.labseeker.com/search.php?keywords=SC-86253&category=0
LabSeeker
SC-86253
http://www.labseeker.com/search.php?keywords=SC-86253&category=0
Matrix Scientific
146692
http://www.matrixscientific.com/146692.html
MedChem Express
HY-13322
https://www.medchemexpress.com/search.html?q=HY-13322&ft=&fa=&fp=
Molnova
M16653
https://www.molnova.com/en/serch-list.html?keywords=M16653
MuseChem
R056762
https://www.musechem.com/product/R056762.html
PI Chemicals
PI-38231
http://www.pipharm.com/catalog_products/PI-38231.html
Ryan Scientific
Enasidenib
https://ryansci.com/products?q=Enasidenib&list_q=&search_type=exact
ShangHai Biochempartner
BCP02073
http://www.biochempartner.com/search_BCP02073
TargetMol
T1890
https://www.targetmol.com/search?keyword=T1890
Toronto Research Chemicals
P699100
https://www.trc-canada.com/product-detail/?CatNum=P699100
eMolecules
260589092
https://orderbb.emolecules.com/search/#?query=260589092
eMolecules
32278042
https://orderbb.emolecules.com/search/#?query=32278042
eMolecules
44842455
https://orderbb.emolecules.com/search/#?query=44842455
eNovation Chemicals
D372406
https://www.enovationchem.com/Products.asp?SEARCHTEXT=D372406&searchbtn.x=0&searchbtn.y=0
mcule
MCULE-2504252505
https://mcule.com/MCULE-2504252505/
mcule
MCULE-2775283324
https://mcule.com/MCULE-2775283324/
PubMed

PubMed

TitleDatePubMed
Deactylase inhibition in myeloproliferative neoplasms.
2010 Dec
A novel histone deacetylase inhibitor Chidamide induces apoptosis of human colon cancer cells.
2010 Feb 5
SB939, a novel potent and orally active histone deacetylase inhibitor with high tumor exposure and efficacy in mouse models of colorectal cancer.
2010 Mar
Vorinostat in acute myeloid leukemia and myelodysplastic syndromes.
2011 Feb
Optimization of the in vitro cardiac safety of hydroxamate-based histone deacetylase inhibitors.
2011 Jul 14
Discovery of (2E)-3-{2-butyl-1-[2-(diethylamino)ethyl]-1H-benzimidazol-5-yl}-N-hydroxyacrylamide (SB939), an orally active histone deacetylase inhibitor with a superior preclinical profile.
2011 Jul 14
Antimalarial activity of the anticancer histone deacetylase inhibitor SB939.
2012 Jul
Synthesis, antimalarial properties, and SAR studies of alkoxyurea-based HDAC inhibitors.
2014 Mar
Patents

Patents

20090048300
1

Sample Use Guides

In Vivo Use Guide
The recommended dose is 60 mg given by mouth every other day, three times weekly for 3 weeks
Route of Administration: Oral
In Vitro Use Guide
Three micrograms of protein lysate from either HCT116 or HL-60 cells were treated for 24 hours with 2 uM pracinostat to obtain a strong acetylation of K9 and K14 of histone H3. The lowest concentration of the drug leading to acH3 was 22 ng/mL (0.06 uM) for both HCT-116 and HL-60 cells treated for 24 hours with pracinostat. In HL-60 cells, maximal acH3 levels were reached at 1 uM not increasing further after treatment with 2 uM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:21:20 UTC 2023
Edited
by admin
on Fri Dec 15 17:21:20 UTC 2023
Record UNII
GPO2JN4UON
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PRACINOSTAT
INN   WHO-DD  
INN  
Official Name English
SB-939
Code English
Pracinostat [WHO-DD]
Common Name English
SB939
Common Name English
SB 939
Code English
KAEMPFEROL 3-O-.BETA.-D-(6-E-P-COUMAROYLGLUCOSIDE)
Common Name English
(2E)-3-(2-BUTYL-1-(2-(DIMETHYLAMINO)ETHYL)-1H-BENZIMIDAZOL-5-YL)-N-HYDROXYPROP-2-ENAMIDE
Systematic Name English
pracinostat [INN]
Common Name English
(E)-3-(2-BUTYL-1-(2-DIETHYLAMINOETHYL)-1H-BENZIMIDAZOL-5-YL)-N-HYDROXY-2-PROPENAMIDE
Systematic Name English
2-PROPENAMIDE, 3-(2-BUTYL-1-(2-(DIETHYLAMINO)ETHYL)-1H-BENZIMIDAZOL-5-YL)-N-HYDROXY-, (2E)-
Systematic Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 421313
Created by admin on Fri Dec 15 17:21:20 UTC 2023 , Edited by admin on Fri Dec 15 17:21:20 UTC 2023
NCI_THESAURUS C1946
Created by admin on Fri Dec 15 17:21:20 UTC 2023 , Edited by admin on Fri Dec 15 17:21:20 UTC 2023
EU-Orphan Drug EU/3/17/1927
Created by admin on Fri Dec 15 17:21:20 UTC 2023 , Edited by admin on Fri Dec 15 17:21:20 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C71708
Created by admin on Fri Dec 15 17:21:20 UTC 2023 , Edited by admin on Fri Dec 15 17:21:20 UTC 2023
PRIMARY
PUBCHEM
49855250
Created by admin on Fri Dec 15 17:21:20 UTC 2023 , Edited by admin on Fri Dec 15 17:21:20 UTC 2023
PRIMARY
CHEBI
95071
Created by admin on Fri Dec 15 17:21:20 UTC 2023 , Edited by admin on Fri Dec 15 17:21:20 UTC 2023
PRIMARY
CAS
929016-96-6
Created by admin on Fri Dec 15 17:21:20 UTC 2023 , Edited by admin on Fri Dec 15 17:21:20 UTC 2023
PRIMARY
FDA UNII
GPO2JN4UON
Created by admin on Fri Dec 15 17:21:20 UTC 2023 , Edited by admin on Fri Dec 15 17:21:20 UTC 2023
PRIMARY
DRUG BANK
DB05223
Created by admin on Fri Dec 15 17:21:20 UTC 2023 , Edited by admin on Fri Dec 15 17:21:20 UTC 2023
PRIMARY
INN
9386
Created by admin on Fri Dec 15 17:21:20 UTC 2023 , Edited by admin on Fri Dec 15 17:21:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID00239196
Created by admin on Fri Dec 15 17:21:20 UTC 2023 , Edited by admin on Fri Dec 15 17:21:20 UTC 2023
PRIMARY
WIKIPEDIA
Pracinostat
Created by admin on Fri Dec 15 17:21:20 UTC 2023 , Edited by admin on Fri Dec 15 17:21:20 UTC 2023
PRIMARY
SMS_ID
100000174901
Created by admin on Fri Dec 15 17:21:20 UTC 2023 , Edited by admin on Fri Dec 15 17:21:20 UTC 2023
PRIMARY
Related Record Type Details
HISTONE DEACETYLASE 1
TARGET -> INHIBITOR
CYTOCHROME P450 1A2
METABOLIC ENZYME -> SUBSTRATE
MAJOR
CYTOCHROME P450 3A4
METABOLIC ENZYME -> SUBSTRATE
MAJOR
Related Record Type Details
Structure of 2-PROPENOIC ACID, 3-(2-BUTYL-1-(2-(DIETHYLAMINO)ETHYL)-1H-BENZIMIDAZOL-5-YL)-, (2E)-
METABOLITE -> PARENT
Structure of 2-PROPENAMIDE, 3-(1-(2-AMINOETHYL)-2-BUTYL-1H-BENZIMIDAZOL-5-YL)-N-HYDROXY-, (2E)-
METABOLITE -> PARENT
Structure of (2E)-3-(2-BUTYL-1-(2-(ETHYLAMINO)ETHYL)-1H-BENZIMIDAZOL-5-YL)-N-HYDROXY-2-PROPENAMIDE
METABOLITE -> PARENT
Related Record Type Details
Structure of PRACINOSTAT
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Biological Half-life PHARMACOKINETIC ORAL SINGLE DOSE ADMINISTRATION

Tmax PHARMACOKINETIC ORAL SINGLE DOSE ADMINISTRATION

blood-toplasma ratio PHARMACOKINETIC
NIH
NCATS
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