EPACADOSTAT

Details

Stereochemistry	ACHIRAL
Molecular Formula	C11H13BrFN7O4S
Molecular Weight	438.233
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NS(=O)(=O)NCCNC1=NON=C1\C(NC2=CC(Br)=C(F)C=C2)=N\O

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	438.233
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: description was created based on several sources, including: 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 20 Target ID: CHEMBL4685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/20197554	Inhibitor 8504		71.8 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Melanoma 88 Sources: http://adisinsight.springer.com/drugs/800025047 https://newdrugapprovals.org/2016/04/page/4/	Primary	Phase III 665	Unknown Approved Use Unknown
Pancreatic cancer 98 Sources: http://adisinsight.springer.com/drugs/800025047	Primary	Phase II 1147	Unknown Approved Use Unknown
Advanced solid cancer 30 Sources: http://adisinsight.springer.com/drugs/800025047 https://newdrugapprovals.org/2016/04/page/4/	Primary	Phase II 1147	Unknown Approved Use Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
0.5 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30894212/	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: IPILIMUMAB	IPILIMUMAB	EPACADOSTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
2.6 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30894212/	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: IPILIMUMAB	IPILIMUMAB	EPACADOSTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
1.23 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28053021/	100 mg 2 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		EPACADOSTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
1.9 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30894212/	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: IPILIMUMAB	IPILIMUMAB	EPACADOSTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
9.5 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30894212/	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: IPILIMUMAB	IPILIMUMAB	EPACADOSTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
5.77 μM × h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28053021/	100 mg 2 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		EPACADOSTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
7.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30894212/	50 mg 2 times / day multiple, oral dose: 50 mg route of administration: Oral experiment type: MULTIPLE co-administered: IPILIMUMAB	IPILIMUMAB	EPACADOSTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
6.2 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30894212/	300 mg 2 times / day multiple, oral dose: 300 mg route of administration: Oral experiment type: MULTIPLE co-administered: IPILIMUMAB	IPILIMUMAB	EPACADOSTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN
3.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/28053021/	100 mg 2 times / day steady-state, oral dose: 100 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		EPACADOSTAT plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

PubMed

Title	Date	PubMed
Selective inhibition of IDO1 effectively regulates mediators of antitumor immunity.	2010-04-29	20197554
Hydroxyamidine inhibitors of indoleamine-2,3-dioxygenase potently suppress systemic tryptophan catabolism and the growth of IDO-expressing tumors.	2010-02	20124451

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 `Mon Mar 31 22:31:50 GMT 2025` Edited by `admin` on `Mon Mar 31 22:31:50 GMT 2025`
Record UNII	71596A9R13
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

epacadostat [INN]

Preferred Name

English

EPACADOSTAT

Official Name

English

INCB-024360

Code

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 [JAN]

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

Epacadostat [WHO-DD]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C129820