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
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
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
Sources: http://adisinsight.springer.com/drugs/800027736
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
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL4685 |
75.0 nM [IC50] | ||
Target ID: CHEMBL1865 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28365507 |
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Target ID: Q6ZQW0 Gene ID: 169355.0 Gene Symbol: IDO2 Target Organism: Homo sapiens (Human) |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Inhibition of indoleamine 2,3-dioxygenase (IDO) enhances elimination of virus-infected macrophages in an animal model of HIV-1 encephalitis. | 2005 Oct 1 |
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Synovial autoreactive T cells in rheumatoid arthritis resist IDO-mediated inhibition. | 2006 Dec 1 |
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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 |
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Proapoptotic activity of indoleamine 2,3-dioxygenase expressed in renal tubular epithelial cells. | 2007 Sep |
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Toxicology and pharmacokinetics of 1-methyl-d-tryptophan: absence of toxicity due to saturating absorption. | 2008 Jan |
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Indoleamine 2,3-dioxygenase expression promotes renal ischemia-reperfusion injury. | 2008 Jul |
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Combined effect of antiretroviral therapy and blockade of IDO in SIV-infected rhesus macaques. | 2009 Apr 1 |
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Expression of indoleamine 2,3-dioxygenase in nasopharyngeal carcinoma impairs the cytolytic function of peripheral blood lymphocytes. | 2009 Nov 30 |
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Inhibitor of indoleamine-2,3-dioxygenase 1-methyl-D-tryptophan can stimulate the growth of immunogenic tumors. | 2010 Oct |
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Purification and kinetic characterization of human indoleamine 2,3-dioxygenases 1 and 2 (IDO1 and IDO2) and discovery of selective IDO1 inhibitors. | 2011 Dec |
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Indoleamine 2,3-dioxygenase 2 (IDO2) and the kynurenine pathway: characteristics and potential roles in health and disease. | 2013 Dec |
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IDO2 is critical for IDO1-mediated T-cell regulation and exerts a non-redundant function in inflammation. | 2014 Jul |
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT01560923
Twice daily (1200 mg total) for 6 months
Route of Administration:
Oral
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Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
608917
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NCI_THESAURUS |
C141137
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NCI_THESAURUS |
C129820
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CHEMBL571209
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DB12827
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C71535
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100000173012
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ACTIVE MOIETY
PRODRUG (METABOLITE ACTIVE)
SALT/SOLVATE (PARENT)