Description In vitro In vivo
ChemicalBook > CAS DataBase List > indoleaMine-2,3-dioxygenase inhibitor INCB024360

indoleaMine-2,3-dioxygenase inhibitor INCB024360

Description In vitro In vivo
Product Name
indoleaMine-2,3-dioxygenase inhibitor INCB024360
CAS No.
914471-09-3
Chemical Name
indoleaMine-2,3-dioxygenase inhibitor INCB024360
Synonyms
IDO5L;CS-1034;IDO-IN-2;INCB14943;INCB024360;INCB-24360;INCB 024360;INCB-024360;IDO inhibitor;4-diaminobutane
CBNumber
CB22666639
Molecular Formula
C9H7ClFN5O2
Formula Weight
271.64
MOL File
914471-09-3.mol
More
Less

indoleaMine-2,3-dioxygenase inhibitor INCB024360 Property

Boiling point:
504.7±60.0 °C(Predicted)
Density 
1.78±0.1 g/cm3(Predicted)
storage temp. 
Store at -20°C
solubility 
≥13.55 mg/mL in DMSO
pka
7.54±0.69(Predicted)
form 
Solid
color 
Off-white to yellow
More
Less

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

More
Less

N-Bromosuccinimide Price

Sigma-Aldrich
Product number
5.38256
Product name
IDO Inhibitor
Packaging
10MG
Price
$195
Updated
2025/07/31
Cayman Chemical
Product number
18265
Product name
INCB024360 analog
Purity
≥98%
Packaging
5mg
Price
$66
Updated
2024/03/01
Cayman Chemical
Product number
18265
Product name
INCB024360 analog
Purity
≥98%
Packaging
1mg
Price
$25
Updated
2021/12/16
Cayman Chemical
Product number
18265
Product name
INCB024360 analog
Purity
≥98%
Packaging
10mg
Price
$117
Updated
2024/03/01
Cayman Chemical
Product number
18265
Product name
INCB024360 analog
Purity
≥98%
Packaging
25mg
Price
$259
Updated
2024/03/01
More
Less

indoleaMine-2,3-dioxygenase inhibitor INCB024360 Chemical Properties,Usage,Production

Description

Epacadostat (INCB024360) is a potent and selective indoleamine 2,3-dioxygenase (IDO1) inhibitor with IC50 of 10 nM and displays high selectivity over other related enzymes such as IDO2 or tryptophan 2,3-dioxygenase (TDO).

In vitro

In IFN-γ–treated human HeLa cells, INCB024360 potently inhibits kynurenine production. INCB024360 also promotes T and natural killer (NK)-cell growth, increases IFN-gamma production, and reduces conversion to regulatory T (T(reg))-like cells.

In vivo

INCB024360 (100 mg/kg, p.o.), via IDO1 inhibition, suppresses kyn generation and tumor growth in immunocompetent, but not immunodeficient, mice. In mice bearing CT26 colon carcinoma, INCB024360 (100 mg/kg, p.o.) also inhibits the growth of IDO-expressing tumors by reducing kynurenine.

Uses

INCB024360 acts as a competitive inhibitor of (IDO1) indoleamine 2,3-dioxygenase showing effect in mouse melanoma models. IC50 = 67 nM

Biological Activity

incb024360 analogue is a potent and selective inhibitor of ido1 with ic50 value of 67 nm. [1]ido (indoleamine-pyrrole 2, 3-dioxygenase) is an enzyme which is encoded by the ido1 gene. ido is the rate-limiting and first enzyme of tryptophan which is one amino acid of human catabolism through kynurenine pathway. the decrease of l-tryptophan can cause halted growth of t cells as well as microbes. ido belongs to immunomodulatory enzyme. it is produced by some activated macrophages and immunoregulatory cells. ido is overexpressed in a wide range of cancer cells such as lung, prostatic, pancreatic, colorectal cancer. it is indentified to help cancer cells to escape the immune system by reducing the level of l-tryptophan in the microenvironment of cells.[2]in hela cells, incb024360 analogue selectively inhibited the activity of human ido1 with ic50 value of 19 nm. on the other hand, incb024360 analogue demonstrated little inhibition activity against tdo (tryptophan 2, 3-dioxygenase). in murine b16 cells, incb024360 analogue inhibited ido with ic50 value of 46 nm [1].in naive c57bl/6 mice, 100 mg/kg incb024360 analogue injected subcutaneously reduced kynurenine levels by >50% via inhibition of ido activity. in c57bl/6 mice bearing gm-csf- secreting b16 tumors, incb024360 analogue (25, 50, and 75 mg/kg b.i.d.) injected subcutaneously for 14 days dose-dependently inhibited tumor growth [1].

Synthesis

367-21-5

147085-13-0

914471-09-3

The general procedure for the synthesis of 4-amino-N'-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide from 3-chloro-4-fluoroaniline and 4-amino-1,2,5-oxadiazole-3-carboxaldehyde oxime chloride is as follows: to 40 mL of ethanol was added 4-amino-N-hydroxy-1,2,5-oxadiazole-3-methanimidic acid chloride (3. 1.63 g, 10.020 mmol) and 3-chloro-4-fluoroaniline (1.60 g, 11.0 mmol). Subsequently, a solution formed by dissolving sodium bicarbonate (2.10 g, 25.0 mmol) in 20 mL of water was added. The reaction mixture was heated with stirring at 60°C for 1 hour. Upon completion of the reaction, the reaction mixture was concentrated using a rotary evaporator and the concentrate was dissolved in 100 mL of ethyl acetate, washed twice with 50 mL of brine and dried with anhydrous sodium sulfate. After evaporation of the solvent, the residue was recrystallized in a mixed ethyl acetate/hexane solvent to give the target product IDO5L (2.38 g, 88% yield) as a brown solid. Thin layer chromatography (TLC) analysis (unfolding agent: ethyl acetate/hexane = 1/1, v/v) showed an Rf value of 0.45. 1H-NMR (400 MHz, DMSO-d6) δ: 11.41 (s, br, 1H), 8.91 (s, br, 1H), 7.21 (dd, J = 9.2 and 9.2 Hz, 1H), 6.98 (dd, J = 6.4 and 2.8 Hz, 1H), 6.72-6.76 (m, 1H), 6.27 (s, 2H).13C-NMR (100 MHz, DMSO-d6) δ: 155.3, 152.2 (d, JCF = 239.3 Hz), 140.4, 139.3, 137.9 (d, J3CF = 2.9 Hz), 122.0 , 120.8 (d, J3CF = 6.8 Hz), 118.7 (d, J2CF = 18.5 Hz), 116.2 (d, J2CF = 21.7 Hz). High resolution mass spectrometry (HRMS) calculated value C9H8ClFN5O2 [M + H]+: m/z = 272.0345, measured value 272.0340.

in vivo

Testing of IDO5L in mice demonstrates pharmacodynamic inhibition of IDO, as measured by decreased kynurenine levels (>50%) in plasma and dose dependent efficacy in mice bearing GM-CSF-secreting B16 melanoma tumors. Initial oral pharmacokinetic studies show that IDO5L is rapidly cleared (t1/2<0.5 h) and that oral administration will not be a suitable dosing method for in vivo studies. The measured plasma exposure (2.5 μM) of IDO5L during this period exceeded our calculated mouse protein binding adjusted B16 cellular IC50 (PBadjIC50=1.0 μM, murine cellular B16 IC50=46 nM). Notably, kynurenine levels increase back to baseline after 4 h as IDO5L exposure levels decreased below the mouse PBadjIC50 from 1.0 to 0.1 μM[1].

IC 50

IDO: 67 nM (IC50); IDO: 19 nM (IC50, in HeLa cell)

storage

Store at -20°C

References

[1]. yue ew1, douty b, wayland b, et al. discovery of potent competitive inhibitors of indoleamine 2,3-dioxygenase with in vivo pharmacodynamic activity and efficacy in a mouse melanoma model. j med chem. 2009 dec 10;52(23):7364-7.
[2]. uyttenhove c, pilotte l, theate i, stroobant v, colau d, parmentier n, boon t, van den eynde bj: evidence for a tumoral immune resistance mechanism based on tryptophan degradation by indoleamine 2,3-dioxygenase. nat med 2003, 9(10):1269-1274.

indoleaMine-2,3-dioxygenase inhibitor INCB024360 Preparation Products And Raw materials

Raw materials

Preparation Products

More
Less

indoleaMine-2,3-dioxygenase inhibitor INCB024360 Suppliers

China 134 Germany 1 India 2 United Kingdom 1 United States 19 Global 157
Shanghai Boyle Chemical Co., Ltd.
Tel
Fax
86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2922
Advantage
55
J & K SCIENTIFIC LTD.
Tel
18210857532; 18210857532
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Chembest Research Laboratories Limited
Tel
+86-21-20908456
Fax
021-58180499
Email
sales@BioChemBest.com
Country
China
ProdList
6003
Advantage
61
Nanjing Chemlin Chemical Co., Ltd
Tel
025-83697070
Fax
+86-25-83453306
Email
info@chemlin.com.cn
Country
China
ProdList
15883
Advantage
64
Dalian Meilun Biotech Co., Ltd.
Tel
0411-62910999 13889544652
Email
sales@meilune.com
Country
China
ProdList
4747
Advantage
58
Shanghai Topbiochem Technology Co., Ltd
Tel
021-58170097
Email
info@topbiochem.com
Country
China
ProdList
9510
Advantage
58
Haoyuan Chemexpress Co., Ltd.
Tel
021-58950125
Fax
(86) 21-58955996
Email
info@chemexpress.com
Country
China
ProdList
7552
Advantage
61
Shanghai Aladdin Bio-Chem Technology Co.,LTD
Tel
400-6206333 13167063860
Fax
021-50323701
Email
anhua.mao@aladdin-e.com
Country
China
ProdList
25003
Advantage
65
Moltt Biocem Co., Ltd.
Tel
+86-21-38682181 15900741819
Fax
+86-21-38682181
Country
China
ProdList
282
Advantage
55
Shanghai Witofly Chemical Co.,Ltd
Tel
Email
sales@witofly.com
Country
China
ProdList
2864
Advantage
52
More
Less

View Lastest Price from indoleaMine-2,3-dioxygenase inhibitor INCB024360 manufacturers

Shaanxi Dideu Medichem Co. Ltd
Product
INCB024360 914471-09-3
Price
US $0.00-0.00/KG
Min. Order
5mg
Purity
99%
Supply Ability
2000tons
Release date
2019-12-31
Zhuozhou Wenxi import and Export Co., Ltd
Product
IDO5L 914471-09-3
Price
US $15.00-10.00/KG
Min. Order
1KG
Purity
99%+ HPLC
Supply Ability
Monthly supply of 1 ton
Release date
2021-06-26
Career Henan Chemical Co
Product
indoleaMine-2,3-dioxygenase inhibitor INCB024360 914471-09-3
Price
US $8.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
10tons
Release date
2018-12-24

914471-09-3, indoleaMine-2,3-dioxygenase inhibitor INCB024360Related Search:

AZD6738 SGC707 MS023 2-(2-Chlorophenyl)-4-(3-(diMethylaMino)phenyl)-5-Methyl-1H-pyrazolo[4,3-c]pyridine-3,6(2H,5H)-dione 3,4-dimethoxy-N-[4-(3-nitrophenyl)-1,3-thiazol-2-yl]benzenesulfonamide Enasidenib Epacadostat (INCB024360) LLY-507 4-BroMo-N-(4-broMophenyl)-3-[[(phenylMethyl)aMino]sulfonyl]benzaMide DBeQ Selumetinib Saracatinib 4-[6-[4-(1-Methylethoxy)phenyl]pyrazolo[1,5-a]pyrimidin-3-yl]-quinoline Pomalidomide NLG919 AZD-9291 1-METHYL-D-TRYPTOPHAN IDO-IN-3

  • CS-1034
  • Epacadostat-analog
  • INCB14943
  • INCB024360 analogue(IDO-IN-1)
  • 3-dioxygenase inhibitor INCB024360
  • INCB-024360; INCB 024360; INCB-24360; INDOLEAMINE-2;3-DIOXYGENASE INHIBITOR INCB024360
  • indoleaMine-2,3-dioxygenase inhibitor
  • INCB 024360-analog - IDO inhibitor 5l
  • (4E)-4-[(3-chloro-4-fluoroanilino)-nitrosomethylidene]-1,2,5-oxadiazol-3-amine
  • INCB 024360
  • INCB024360
  • INCB-024360
  • INCB-24360
  • indoleaMine-2,3-dioxygenase inhibitor INCB024360
  • INCB024360/INCB-024360
  • 4-Amino-N-(3-chloro-4-fluorophenyl)-N'-hydroxy-1,2,5-oxadiazole-3-carboximidamide
  • 4-Amino-N-(3-chloro-4-fluorophenyl)-N'-hydroxy-1,2,5-oxadiazole-3-carboximidamide INCB024360
  • IDO-IN-2
  • INCB024360 analogue
  • (E)-4-Amino-N'-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide
  • IDO5L
  • INCB024360 analog
  • IDO inhibitor
  • INCB024360 ANALOGUE;IDO5L
  • INCB024360 500MG
  • IDO-IN-2(1g 2000)
  • INCB024360-analog(IDO-IN-2)
  • 1,2,5-Oxadiazole-3-carboximidamide, 4-amino-N'-(3-chloro-4-fluorophenyl)-N-hydroxy-
  • indoleaMine-2,3-dioxygenase inhibitor INCB024360 USP/EP/BP
  • 4-diaminobutane
  • N-(3-Aminopropyl)-1
  • N-(4-Aminobutyl)-1
  • 4-Amino-N-(3-chloro-4-fluorophenyl)-N'-hydroxy-1,2,5-oxadiazole-3-carboxamidine
  • 4-Amino-N'-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazole-3-carboximidamide
  • IDO5L, 10 mM in DMSO
  • IDO5L (INCB024360 analog)
  • Epacadostat (INCB024360) analogue
  • Epacadostat (INCB024360) analogue ，S7587
  • 4-Amino-N'-(3-chloro-4-fluorophenyl)-N-hydroxy-1,2,5-oxadiazol-3-carboximidamide
  • 914471-09-3
  • C9H7ClFN5O2
  • Inhibitors