U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C12H14N2O2
Molecular Weight 218.2518
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of INDOXIMOD

SMILES

CN1C=C(C[C@@H](N)C(O)=O)C2=CC=CC=C12

InChI

InChIKey=ZADWXFSZEAPBJS-SNVBAGLBSA-N
InChI=1S/C12H14N2O2/c1-14-7-8(6-10(13)12(15)16)9-4-2-3-5-11(9)14/h2-5,7,10H,6,13H2,1H3,(H,15,16)/t10-/m1/s1

HIDE SMILES / InChI
Indoximod is an orally available Indoleamine 2,3-dioxigenase inhibitor. It shows higher potency in reversing IDO-mediated T cell suppression. Indoximod improves the efficacy of multiple chemotherapeutics agents and some immunological checkpoints mediators in Phase I/II clinical studies for metastatic breast cancer, metastatic melanoma, non-small cell lung cancer, primary malignant brain tumors, metastatic pancreatic cancer, as well as metastatic prostate cancer.

Originator

Curator's Comment: 1-Methyltryptophan synthesis https://www.ncbi.nlm.nih.gov/pubmed/18102966 N-Methyltryptophan synthesis DOI: 10.1002/jlac.19345130102

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
75.0 nM [IC50]
Target ID: Q6ZQW0
Gene ID: 169355.0
Gene Symbol: IDO2
Target Organism: Homo sapiens (Human)
Conditions
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Temperature-sensitive polymer-conjugated IFN-gamma induces the expression of IDO mRNA and activity by fibroblasts populated in collagen gel (FPCG).
2004 Oct
Inhibition of indoleamine 2,3-dioxygenase (IDO) enhances elimination of virus-infected macrophages in an animal model of HIV-1 encephalitis.
2005 Oct 1
Indoleamine 2,3-dioxygenase participates in the interferon-gamma-induced cell death process in cultured bovine luteal cells.
2006 Mar
Novel tryptophan catabolic enzyme IDO2 is the preferred biochemical target of the antitumor indoleamine 2,3-dioxygenase inhibitory compound D-1-methyl-tryptophan.
2007 Aug 1
Abatacept modulates human dendritic cell-stimulated T-cell proliferation and effector function independent of IDO induction.
2008 Jan
The indoleamine 2,3-dioxygenase pathway is essential for human plasmacytoid dendritic cell-induced adaptive T regulatory cell generation.
2008 Oct 15
Melanoma: a model for testing new agents in combination therapies.
2010 Apr 20
Biochemical characteristics and inhibitor selectivity of mouse indoleamine 2,3-dioxygenase-2.
2010 Jul
Mesenchymal stem cells inhibit complement activation by secreting factor H.
2010 Nov
Inhibitor of indoleamine-2,3-dioxygenase 1-methyl-D-tryptophan can stimulate the growth of immunogenic tumors.
2010 Oct
Ability of IDO to attenuate liver injury in alpha-galactosylceramide-induced hepatitis model.
2010 Oct 15
Purification and kinetic characterization of human indoleamine 2,3-dioxygenases 1 and 2 (IDO1 and IDO2) and discovery of selective IDO1 inhibitors.
2011 Dec
Indoleamine 2,3-dioxygenase 2 (IDO2) and the kynurenine pathway: characteristics and potential roles in health and disease.
2013 Dec
IDO2 is critical for IDO1-mediated T-cell regulation and exerts a non-redundant function in inflammation.
2014 Jul
Patents

Sample Use Guides

Twice daily (1200 mg total) for 6 months
Route of Administration: Oral
In Vitro Use Guide
Unknown
Name Type Language
INDOXIMOD
INN   USAN   WHO-DD  
USAN   INN  
Official Name English
1-METHYL-D-TRYPTOPHAN
Systematic Name English
INDOXIMOD [USAN]
Common Name English
N-1-Methyl-D-tryptophan
Common Name English
D-TRYPTOPHAN, 1-METHYL-
Systematic Name English
indoximod [INN]
Common Name English
NSC-721782
Code English
(2R)-2-Amino-3-(1-methyl-1H-indol-3-yl)propanoic acid
Systematic Name English
D-1MT
Code English
Indoximod [WHO-DD]
Common Name English
1-METHYLTRYPTOPHAN, D-
Common Name English
NLG-8189
Code English
D-1-METHYLTRYPTOPHAN
Common Name English
D-(+)-1-METHYLTRYPTOPHAN
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 608917
Created by admin on Sat Dec 16 16:33:13 GMT 2023 , Edited by admin on Sat Dec 16 16:33:13 GMT 2023
NCI_THESAURUS C141137
Created by admin on Sat Dec 16 16:33:13 GMT 2023 , Edited by admin on Sat Dec 16 16:33:13 GMT 2023
NCI_THESAURUS C129820
Created by admin on Sat Dec 16 16:33:13 GMT 2023 , Edited by admin on Sat Dec 16 16:33:13 GMT 2023
Code System Code Type Description
ChEMBL
CHEMBL571209
Created by admin on Sat Dec 16 16:33:12 GMT 2023 , Edited by admin on Sat Dec 16 16:33:12 GMT 2023
PRIMARY
EPA CompTox
DTXSID40911500
Created by admin on Sat Dec 16 16:33:13 GMT 2023 , Edited by admin on Sat Dec 16 16:33:13 GMT 2023
PRIMARY
PUBCHEM
405012
Created by admin on Sat Dec 16 16:33:13 GMT 2023 , Edited by admin on Sat Dec 16 16:33:13 GMT 2023
PRIMARY
DRUG BANK
DB12827
Created by admin on Sat Dec 16 16:33:13 GMT 2023 , Edited by admin on Sat Dec 16 16:33:13 GMT 2023
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INN
9896
Created by admin on Sat Dec 16 16:33:13 GMT 2023 , Edited by admin on Sat Dec 16 16:33:13 GMT 2023
PRIMARY
CAS
110117-83-4
Created by admin on Sat Dec 16 16:33:12 GMT 2023 , Edited by admin on Sat Dec 16 16:33:12 GMT 2023
PRIMARY
USAN
ZZ-80
Created by admin on Sat Dec 16 16:33:13 GMT 2023 , Edited by admin on Sat Dec 16 16:33:13 GMT 2023
PRIMARY
NSC
721782
Created by admin on Sat Dec 16 16:33:13 GMT 2023 , Edited by admin on Sat Dec 16 16:33:13 GMT 2023
PRIMARY
FDA UNII
TX5CYN1KMZ
Created by admin on Sat Dec 16 16:33:13 GMT 2023 , Edited by admin on Sat Dec 16 16:33:13 GMT 2023
PRIMARY
NCI_THESAURUS
C71535
Created by admin on Sat Dec 16 16:33:13 GMT 2023 , Edited by admin on Sat Dec 16 16:33:13 GMT 2023
PRIMARY
SMS_ID
100000173012
Created by admin on Sat Dec 16 16:33:13 GMT 2023 , Edited by admin on Sat Dec 16 16:33:13 GMT 2023
PRIMARY