Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C12H14N2O2.ClH |
| Molecular Weight | 254.713 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN1C=C(C[C@@H](N)C(O)=O)C2=C1C=CC=C2
InChI
InChIKey=XHHFEVHSOOFMGW-HNCPQSOCSA-N
InChI=1S/C12H14N2O2.ClH/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);1H/t10-;/m1./s1
| Molecular Formula | C12H14N2O2 |
| Molecular Weight | 218.2518 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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.
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4685 |
75.0 nM [IC50] | ||
Target ID: CHEMBL1865 |
|||
Target ID: Q6ZQW0 Gene ID: 169355.0 Gene Symbol: IDO2 Target Organism: Homo sapiens (Human) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
12 μM EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27008709 |
2000 mg 2 times / day steady-state, oral dose: 2000 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDOXIMOD plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
30000 ng × h/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25327557 |
1200 mg 2 times / day steady-state, oral dose: 1200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDOXIMOD plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
120 μM × h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27008709 |
2000 mg 2 times / day steady-state, oral dose: 2000 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDOXIMOD plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
11.3 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/25327557 |
1200 mg 2 times / day steady-state, oral dose: 1200 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDOXIMOD plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
10.5 h EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/27008709 |
2000 mg 2 times / day steady-state, oral dose: 2000 mg route of administration: Oral experiment type: STEADY-STATE co-administered: |
INDOXIMOD plasma | Homo sapiens population: UNHEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
PubMed
| Title | Date | PubMed |
|---|---|---|
| IDO2 is critical for IDO1-mediated T-cell regulation and exerts a non-redundant function in inflammation. | 2014-07 |
|
| Indoleamine 2,3-dioxygenase 2 (IDO2) and the kynurenine pathway: characteristics and potential roles in health and disease. | 2013-12 |
|
| Purification and kinetic characterization of human indoleamine 2,3-dioxygenases 1 and 2 (IDO1 and IDO2) and discovery of selective IDO1 inhibitors. | 2011-12 |
|
| Mesenchymal stem cells inhibit complement activation by secreting factor H. | 2010-11 |
|
| Ability of IDO to attenuate liver injury in alpha-galactosylceramide-induced hepatitis model. | 2010-10-15 |
|
| Inhibitor of indoleamine-2,3-dioxygenase 1-methyl-D-tryptophan can stimulate the growth of immunogenic tumors. | 2010-10 |
|
| Biochemical characteristics and inhibitor selectivity of mouse indoleamine 2,3-dioxygenase-2. | 2010-07 |
|
| Melanoma: a model for testing new agents in combination therapies. | 2010-04-20 |
|
| Expression of indoleamine 2,3-dioxygenase in nasopharyngeal carcinoma impairs the cytolytic function of peripheral blood lymphocytes. | 2009-11-30 |
|
| Combined effect of antiretroviral therapy and blockade of IDO in SIV-infected rhesus macaques. | 2009-04-01 |
|
| Indoleamine 2,3-dioxygenase-2; a new enzyme in the kynurenine pathway. | 2009-03 |
|
| Overexpression of indoleamine 2,3-dioxygenase in human endometrial carcinoma cells induces rapid tumor growth in a mouse xenograft model. | 2008-11-15 |
|
| The indoleamine 2,3-dioxygenase pathway is essential for human plasmacytoid dendritic cell-induced adaptive T regulatory cell generation. | 2008-10-15 |
|
| HIV-induced type I interferon and tryptophan catabolism drive T cell dysfunction despite phenotypic activation. | 2008-08-13 |
|
| Indoleamine 2,3-dioxygenase expression promotes renal ischemia-reperfusion injury. | 2008-07 |
|
| Abatacept modulates human dendritic cell-stimulated T-cell proliferation and effector function independent of IDO induction. | 2008-01 |
|
| Toxicology and pharmacokinetics of 1-methyl-d-tryptophan: absence of toxicity due to saturating absorption. | 2008-01 |
|
| Proapoptotic activity of indoleamine 2,3-dioxygenase expressed in renal tubular epithelial cells. | 2007-09 |
|
| Novel tryptophan catabolic enzyme IDO2 is the preferred biochemical target of the antitumor indoleamine 2,3-dioxygenase inhibitory compound D-1-methyl-tryptophan. | 2007-08-01 |
|
| Synovial autoreactive T cells in rheumatoid arthritis resist IDO-mediated inhibition. | 2006-12-01 |
|
| Indoleamine 2,3-dioxygenase participates in the interferon-gamma-induced cell death process in cultured bovine luteal cells. | 2006-03 |
|
| Inhibition of indoleamine 2,3-dioxygenase (IDO) enhances elimination of virus-infected macrophages in an animal model of HIV-1 encephalitis. | 2005-10-01 |
|
| Temperature-sensitive polymer-conjugated IFN-gamma induces the expression of IDO mRNA and activity by fibroblasts populated in collagen gel (FPCG). | 2004-10 |
|
| Expression of indoleamine 2,3-dioxygenase by plasmacytoid dendritic cells in tumor-draining lymph nodes. | 2004-07 |
| Substance Class |
Chemical
Created
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| Record UNII |
R695HAR9OQ
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| Record Status |
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| Record Version |
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