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Details

Stereochemistry ACHIRAL
Molecular Formula C23H21N5O3S.C7H8O3S
Molecular Weight 619.711
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of DOMATINOSTAT TOSYLATE

SMILES

CC1=CC=C(C=C1)S(O)(=O)=O.CN2C=C(C=N2)C3=CC=C(C=C3)S(=O)(=O)N4C=CC(\C=C\C(=O)NC5=CC=CC=C5N)=C4

InChI

InChIKey=IAVXAZDVNICKFJ-ICSBZGNSSA-N
InChI=1S/C23H21N5O3S.C7H8O3S/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;1-6-2-4-7(5-3-6)11(8,9)10/h2-16H,24H2,1H3,(H,26,29);2-5H,1H3,(H,8,9,10)/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

Molecular Formula C7H8O3S
Molecular Weight 172.202
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
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.

Approval Year

T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
146 h
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
PubMed

PubMed

TitleDatePubMed
Pre-clinical characterization of 4SC-202, a novel class I HDAC inhibitor, against colorectal cancer cells.
2016 Aug
4SC-202 activates ASK1-dependent mitochondrial apoptosis pathway to inhibit hepatocellular carcinoma cells.
2016 Mar 4
Patents

Sample Use Guides

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 Sat Dec 16 14:35:57 GMT 2023
Edited
by admin
on Sat Dec 16 14:35:57 GMT 2023
Record UNII
9PW28FR8VD
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DOMATINOSTAT TOSYLATE
Common Name English
4SC-202 TOSYLATE
Code English
DOMATINOSTAT TOSILATE
Common Name English
2-PROPENAMIDE, N-(2-AMINOPHENYL)-3-(1-((4-(1-METHYL-1H-PYRAZOL-4-YL)PHENYL)SULFONYL)-1H-PYRROL-3-YL)-, (2E)-, 4-METHYLBENZENESULFONATE
Common Name English
Code System Code Type Description
FDA UNII
9PW28FR8VD
Created by admin on Sat Dec 16 14:35:57 GMT 2023 , Edited by admin on Sat Dec 16 14:35:57 GMT 2023
PRIMARY
PUBCHEM
44217246
Created by admin on Sat Dec 16 14:35:57 GMT 2023 , Edited by admin on Sat Dec 16 14:35:57 GMT 2023
PRIMARY
CAS
1186222-89-8
Created by admin on Sat Dec 16 14:35:57 GMT 2023 , Edited by admin on Sat Dec 16 14:35:57 GMT 2023
PRIMARY
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