EPACADOSTAT

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 Search

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
Sources: https://www.cancer.gov/publications/dictionaries/cancer-drug?cdrid=685310
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Indoleamine 2,3-dioxygenase 18 Target ID: CHEMBL4685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20197554	Inhibitor 7701	Melanoma Pancreatic cancer Advanced solid cancer	71.7999999999999972 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase
Melanoma 81 Sources: http://adisinsight.springer.com/drugs/800025047 https://newdrugapprovals.org/2016/04/page/4/	Primary	Indoleamine 2,3-dioxygenase	Phase III 650
Pancreatic cancer 91 Sources: http://adisinsight.springer.com/drugs/800025047	Primary	Indoleamine 2,3-dioxygenase	Phase II
Advanced solid cancer 28 Sources: http://adisinsight.springer.com/drugs/800025047 https://newdrugapprovals.org/2016/04/page/4/	Primary	Indoleamine 2,3-dioxygenase	Phase II

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

50, 100, or 300 mg taken by mouth twice a day

Route of Administration: Oral

In Vitro Use Guide

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

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