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Details

Stereochemistry ACHIRAL
Molecular Formula C11H13BrFN7O4S
Molecular Weight 438.2339
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of EPACADOSTAT

SMILES

c1cc(c(cc1N=C(c2c(NCCNS(=O)(=O)N)non2)NO)Br)F

InChI

InChIKey=FBKMWOJEPMPVTQ-UHFFFAOYSA-N
InChI=1S/C11H13BrFN7O4S/c12-7-5-6(1-2-8(7)13)17-11(18-21)9-10(20-24-19-9)15-3-4-16-25(14,22)23/h1-2,5,16,21H,3-4H2,(H,15,20)(H,17,18)(H2,14,22,23)

HIDE SMILES / InChI

Molecular Formula C11H13BrFN7O4S
Molecular Weight 438.2339
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Description
Curator's Comment:: http://adisinsight.springer.com/drugs/800025047 | https://newdrugapprovals.org/2016/04/page/4/ | https://www.ncbi.nlm.nih.gov/pubmed/28053021

Epacadostat (INCB024360) is an orally available hydroxyamidine and inhibitor of indoleamine 2,3- dioxygenase (IDO1). It shows little activity against other related enzymes such as IDO2 or tryptophan 2,3-dioxygenase (TDO). Epacadostat displays potential immune modulating and antineoplastic activities. Epacadostat has been tested in phase II and III studies for the treatment of malignant melanoma, fallopian tube cancer, non-small cell lung cancer, ovarian cancer, peritoneal cancer, solid tumors, pancreatic cancer. The most common detected adverse events were fatigue, nausea, decreased appetite, vomiting, constipation, abdominal pain, diarrhea, dyspnea, back pain, and cough.

Approval Year

PubMed

PubMed

TitleDatePubMed
Patents

Sample Use Guides

50, 100, or 300 mg taken by mouth twice a day
Route of Administration: Oral
Epacadostat demonstrated little inhibition of TDO or IDO2 activity at 10 or 5uM, respectively, and no effect on trp uptake at 30 uM.
Substance Class Chemical
Created
by admin
on Sat Jun 26 13:44:35 UTC 2021
Edited
by admin
on Sat Jun 26 13:44:35 UTC 2021
Record UNII
71596A9R13
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
EPACADOSTAT
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
INCB-024360
Code English
EPACADOSTAT [WHO-DD]
Common Name English
1,2,5-OXADIAZOLE-3-CARBOXIMIDAMIDE, 4-((2-((AMINOSULFONYL)AMINO)ETHYL)AMINO)-N'-(3-BROMO-4-FLUOROPHENYL)-N-HYDROXY-
Systematic Name English
EPACADOSTAT [USAN]
Common Name English
EPACADOSTAT [INN]
Common Name English
1,2,5-OXADIAZOLE-3-CARBOXIMIDAMIDE, 4-((2-((AMINOSULFONYL)AMINO)ETHYL)AMINO)-N-(3-BROMO-4-FLUOROPHENYL)-N'-HYDROXY-
Systematic Name English
INCB024360
Code English
1,2,5-OXADIAZOLE-3-CARBOXIMIDAMIDE, 4-((2-((AMINOSULFONYL)AMINO)ETHYL)AMINO)-N-(3-BROMO-4-FLUOROPHENYL)-N'-HYDROXY-, (C(Z))-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C129820
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
NCI_THESAURUS C141137
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
FDA ORPHAN DRUG 493015
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
WHO-ATC L01XX58
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
Code System Code Type Description
CAS
1204669-37-3
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
NON-SPECIFIC STEREOCHEMISTRY
INN
10180
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
PRIMARY
FDA UNII
71596A9R13
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
PRIMARY
DRUG BANK
DB11717
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
PRIMARY
NCI_THESAURUS
C92582
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
PRIMARY
EVMPD
SUB182018
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
PRIMARY
PUBCHEM
135564890
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
PRIMARY
CAS
1204669-58-8
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
PRIMARY
CAS
1220975-17-6
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
NO STRUCTURE GIVEN
ChEMBL
CHEMBL3545369
Created by admin on Sat Jun 26 13:44:36 UTC 2021 , Edited by admin on Sat Jun 26 13:44:36 UTC 2021
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TRANSPORTER -> SUBSTRATE
TRANSPORTER -> SUBSTRATE
Related Record Type Details
ACTIVE MOIETY