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Details

Stereochemistry ACHIRAL
Molecular Formula C23H21N5O3S
Molecular Weight 447.51
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DOMATINOSTAT

SMILES

CN1C=C(C=N1)C2=CC=C(C=C2)S(=O)(=O)N3C=CC(\C=C\C(=O)NC4=CC=CC=C4N)=C3

InChI

InChIKey=PRXXYMVLYKJITB-IZZDOVSWSA-N
InChI=1S/C23H21N5O3S/c1-27-16-19(14-25-27)18-7-9-20(10-8-18)32(30,31)28-13-12-17(15-28)6-11-23(29)26-22-5-3-2-4-21(22)24/h2-16H,24H2,1H3,(H,26,29)/b11-6+

HIDE SMILES / InChI
Molecular Formula C23H21N5O3S
Molecular Weight 447.51
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including http://www.4sc.de/wp-content/uploads/160621__4SC_CompanyPres_Citi.pdf

4SC-202 is an epigenetic oncology compound with a unique therapeutic profile, which was developed by biotechnology company: 4SC. 4SC-202 works as a selective inhibitor of LSD1 (lysine-specific demethylase 1) and HDAC (histone deacetylase) 1, 2 and 3. 4SC-202 also strengthens the endogenous immune response to cancer tissue. This compound demonstrated successfully completed Phase I of the clinical study, where it was proved safe and well tolerated in patients with advanced hematologic cancer. In addition, 4SC-202 shows substantial anti-tumor activity in a broad range of cancer cell lines including hepatocellular carcinoma, Urothelial Carcinoma Cell Lines and colorectal cancer.

Originator

Approval Year

Unknown
134361
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8228
Inhibitor
8228
Inhibitor
8228
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Phase I
424
Unknown

Approved Use

Unknown
Primary
Preclinical
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
Primary
Basic research
Unknown

Approved Use

Unknown
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
146 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/26357940/
200 mg 2 times / day multiple, oral
dose: 200 mg
route of administration: Oral
experiment type: MULTIPLE
co-administered:
4SC-202 plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY442973
https://www.001chemical.com/chem/search?q=DY442973
1PlusChem LLC
1P008TTB
https://www.1pchem.com/search?query=1P008TTB
AOBIOUS INC
AOB87342
http://aobious.com/aobious/search?search_query=AOB87342
Aceschem
ACS019816
https://www.aceschem.com/catalog/search.do?q=ACS019816
ApexBio Technology
B4106
https://www.apexbt.com/catalogsearch/result/?q=B4106
AstaTech
40587
http://astatechinc.com/CPSResult.php?CRNO=40587
AstaTech
C14281
http://astatechinc.com/CPSResult.php?CRNO=C14281
BLD Pharm
BD629963
http://www.bldpharm.com/search/Search.html?keyword=BD629963
BLD Pharm
BD630987
http://www.bldpharm.com/search/Search.html?keyword=BD630987
Capot Chemical
33944
https://www.capotchem.com/search.do?q=33944
Chem Scene
CS-3102
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3102
Chem Scene
CS-3275
http://www.chemscene.com/goproductList/searchProductList?productObj=CS-3275
ChemShuttle
152026
https://www.chemshuttle.com/catalogsearch/result/?q=152026
Excenen
EX-A3012
http://www.excenen.com/searchresultlist.php?id=EX-A3012
Excenen
EX-A761
http://www.excenen.com/searchresultlist.php?id=EX-A761
Hairui
HR32969
http://www.hairuichem.com/en/product/search.do?q=HR32969
MedChem Express
HY-16012
https://www.medchemexpress.com/search.html?q=HY-16012A&ft=&fa=&fp=
MedChem Express
HY-16012A
https://www.medchemexpress.com/search.html?q=HY-16012A&ft=&fa=&fp=
Molcore
MC442973
http://www.molcore.com/CatMC442973.html
Molnova
M16538
https://www.molnova.com/en/serch-list.html?keywords=M16538
Molnova
M17177
https://www.molnova.com/en/serch-list.html?keywords=M17177
MuseChem
I000667
https://www.musechem.com/product/I000667.html
MuseChem
I005425
https://www.musechem.com/product/I005425.html
Selleck Chemicals
S7555
http://www.selleckchem.com/search.html?searchDTO.searchParam=S7555
ShangHai Biochempartner
BCP18522
http://www.biochempartner.com/search_BCP18522
ShangHai Biochempartner
BCP25159
http://www.biochempartner.com/search_BCP25159
TargetMol
T4477
https://www.targetmol.com/search?keyword=T4477
TargetMol
T6362
https://www.targetmol.com/search?keyword=T6362
W&J PharmaChem
50C2062986
http://wjpharmachem.com/new/searcht.php?keyword=50C2062986
eMolecules
275064675
https://orderbb.emolecules.com/search/#?query=275064675
eMolecules
275079257
https://orderbb.emolecules.com/search/#?query=275079257
eMolecules
301183964
https://orderbb.emolecules.com/search/#?query=301183964
eMolecules
50282176
https://orderbb.emolecules.com/search/#?query=50282176
eMolecules
50282860
https://orderbb.emolecules.com/search/#?query=50282860
mcule
MCULE-6153178017
https://mcule.com/MCULE-6153178017/
mcule
MCULE-6359547612
https://mcule.com/MCULE-6359547612/
mcule
MCULE-8746431540
https://mcule.com/MCULE-8746431540/
mcule
MCULE-9133550588
https://mcule.com/MCULE-9133550588/
PubMed

PubMed

TitleDatePubMed
Pre-clinical characterization of 4SC-202, a novel class I HDAC inhibitor, against colorectal cancer cells.
2016 Aug
Evaluation of the Therapeutic Potential of the Novel Isotype Specific HDAC Inhibitor 4SC-202 in Urothelial Carcinoma Cell Lines.
2016 Dec
4SC-202 activates ASK1-dependent mitochondrial apoptosis pathway to inhibit hepatocellular carcinoma cells.
2016 Mar 4
Patents

Patents

20110086897
2
8557858
2
WO2009112522A1
2

Sample Use Guides

In Vivo Use Guide
oral administration dose escalation twice daily (bid) or three times a day (tid) continuous dosing for 21 days per cycle
Route of Administration: Oral
In Vitro Use Guide
Curator's Comment: 4SC-202 treatment induced potent cytotoxic and proliferation-inhibitory activities against established hepatocellular carcinoma (HCC) cell lines (HepG2, HepB3, SMMC-7721) and patient-derived primary HCC cells. Further, adding 4SC-202 in HCC cells activated mitochondrial apoptosis pathway, which was evidenced by mitochondrial permeability transition pore (mPTP) opening, cytochrome C cytosol release and caspase-3/-9 activation. 4SC-202 induced apoptosis signal-regulating kinase 1 (ASK1) activation, causing it translocation to mitochondria and physical association with Cyp-D. This mitochondrial ASK1-Cyp-D complexation appeared required for mediating 4SC-202-induced apoptosis activation. ASK1 stable knockdown by targeted-shRNAs largely inhibited 4SC-202-induced mPTP opening, cytochrome C release, and following HCC cell apoptotic death.
Unknown
Substance Class Chemical
Created
by admin
on Thu Jul 06 16:37:16 UTC 2023
Edited
by admin
on Thu Jul 06 16:37:16 UTC 2023
Record UNII
264ARM7UXX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOMATINOSTAT
INN  
Official Name English
2-PROPENAMIDE, N-(2-AMINOPHENYL)-3-(1-((4-(1-METHYL-1H-PYRAZOL-4-YL)PHENYL)SULFONYL)-1H-PYRROL-3-YL)-, (2E)-
Systematic Name English
domatinostat [INN]
Common Name English
(E)-N-(2-AMINOPHENYL)-3-(1-((4-(1-METHYL-1H-PYRAZOL-4-YL)PHENYL)SULFONYL)-1H-PYRROL-3-YL)ACRYLAMIDE
Systematic Name English
4SC-202
Common Name English
HDAC INHIBITOR 4SC-202
Common Name English
Domatinostat [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C129825
Created by admin on Thu Jul 06 16:37:16 UTC 2023 , Edited by admin on Thu Jul 06 16:37:16 UTC 2023
NCI_THESAURUS C1946
Created by admin on Thu Jul 06 16:37:16 UTC 2023 , Edited by admin on Thu Jul 06 16:37:16 UTC 2023
Code System Code Type Description
NCI_THESAURUS
C96797
Created by admin on Thu Jul 06 16:37:16 UTC 2023 , Edited by admin on Thu Jul 06 16:37:16 UTC 2023
PRIMARY
DRUG BANK
DB13101
Created by admin on Thu Jul 06 16:37:16 UTC 2023 , Edited by admin on Thu Jul 06 16:37:16 UTC 2023
PRIMARY
PUBCHEM
15985904
Created by admin on Thu Jul 06 16:37:16 UTC 2023 , Edited by admin on Thu Jul 06 16:37:16 UTC 2023
PRIMARY
SMS_ID
100000181106
Created by admin on Thu Jul 06 16:37:16 UTC 2023 , Edited by admin on Thu Jul 06 16:37:16 UTC 2023
PRIMARY
FDA UNII
264ARM7UXX
Created by admin on Thu Jul 06 16:37:16 UTC 2023 , Edited by admin on Thu Jul 06 16:37:16 UTC 2023
PRIMARY
INN
10700
Created by admin on Thu Jul 06 16:37:16 UTC 2023 , Edited by admin on Thu Jul 06 16:37:16 UTC 2023
PRIMARY
CAS
910462-43-0
Created by admin on Thu Jul 06 16:37:16 UTC 2023 , Edited by admin on Thu Jul 06 16:37:16 UTC 2023
PRIMARY
Related Record Type Details
HISTONE DEACETYLASE 2
TARGET -> INHIBITOR
4SC-202 is a selective class I HDAC inhibitor and also displays inhibitory activity against Lysine specific demethylase 1 (LSD1). Phase 1.
INHIBITOR
IC50
Structure of DOMATINOSTAT TOSYLATE
SALT/SOLVATE -> PARENT
HISTONE DEACETYLASE 3
TARGET -> INHIBITOR
4SC-202 is a selective class I HDAC inhibitor and also displays inhibitory activity against Lysine specific demethylase 1 (LSD1). Phase 1.
INHIBITOR
IC50
HISTONE DEACETYLASE 1
TARGET -> INHIBITOR
4SC-202 is a selective class I HDAC inhibitor and also displays inhibitory activity against Lysine specific demethylase 1 (LSD1). Phase 1.
INHIBITOR
IC50
Related Record Type Details
Structure of DOMATINOSTAT
ACTIVE MOIETY
NIH
NCATS
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