[CAS NO. 110117-83-4] Indoximod
PRODUCTS SPECIFICATIONS [110117-83-4]
DESCRIPTION [110117-83-4]
Overview
| MDL | MFCD00274271 |
|---|---|
| Molecular Weight | 218.25 |
| Molecular Formula | C12H14N2O2 |
| SMILES | N[C@H](CC1=CN(C)C2=CC=CC=C12)C(O)=O |
5 Publications Citing Use of MCE
Summary
IC50 & Target
|
IDO 19 μM (Ki) |
In Vitro
The IDO inhibitor 1-methyl-tryptophan exists in two stereoisomers with potentially different biological properties. The L isomer is the more potent inhibitor of IDO activity using the purified enzyme and in HeLa cell–based assays. However, the D isomer is significantly more effective in reversing the suppression of T cells created by IDO-expressing dendritic cells. The L isomer of 1-methyl-tryptophan functioned as a competitive inhibitor (K i =19 μM), whereas the d isomer is much less effective. The DL mixture is intermediate, with a K i of 35 μM [1] .
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
In Vivo
The D isomer is more efficacious as an anticancer agent in chemo-immunotherapy regimens using NSC-26271, NSC 125973, or LY 188011, when tested in mouse models of transplantable melanoma and transplantable and autochthonous breast cancer. The D isomer of 1-methyl-tryptophan specifically targets the IDO gene because the antitumor effect of d-1-methyl-tryptophan is completely lost in mice with a disruption of the IDO gene (IDO-knockout mice). Oral administration of dl-1-methyl-tryptophan in combination with NSC 125973 can elicit regression of autochthonous breast tumors [1] .
MCE has not independently confirmed the accuracy of these methods. They are for reference only.
Clinical Trial
| NCT Number | Sponsor | Condition | Start Date | Phase |
|---|---|---|---|---|
| NCT03852446 | NewLink Genetics Corporation|Lumos Pharma |
Healthy
|
March 5, 2018 | Early Phase 1 |
| NCT03301636 | NewLink Genetics Corporation|Lumos Pharma |
Melanoma
|
December 8, 2017 | Phase 2 |
| NCT04049669 | Theodore S. Johnson|National Cancer Institute (NCI)|Augusta University|Emory University |
Glioblastoma|Medulloblastoma|Ependymoma|Diffuse Intrinsic Pontine Glioma
|
October 2, 2019 | Phase 2 |
| NCT01191216 | National Cancer Institute (NCI) |
Unspecified Adult Solid Tumor, Protocol Specific
|
September 2010 | Phase 1 |
| NCT02502708 | NewLink Genetics Corporation|Lumos Pharma |
Glioblastoma Multiforme|Glioma|Gliosarcoma|Malignant Brain Tumor|Ependymoma|Medulloblastoma|Diffuse Intrinsic Pontine Glioma|Primary CNS Tumor
|
October 2015 | Phase 1 |
| NCT02835729 | NewLink Genetics Corporation|Lumos Pharma |
Acute Myeloid Leukemia
|
July 2016 | Phase 1 |
| NCT02460367 | NewLink Genetics Corporation|Lumos Pharma |
Non-small Cell Lung Cancer|Progression of Non-small Cell Lung Cancer|Non-small Cell Lung Cancer Recurrent
|
January 2016 | Phase 1 |
| NCT02073123 | NewLink Genetics Corporation|Lumos Pharma |
Metastatic Melanoma|Stage III Melanoma|Stage IV Melanoma
|
July 2014 | Phase 1|Phase 2 |
| NCT05106296 | Theodore S. Johnson|Augusta University |
Ependymoma|Medulloblastoma|Glioblastoma|Primitive Neuroectodermal Tumor (PNET)
|
February 8, 2022 | Phase 1 |
| NCT01042535 | H. Lee Moffitt Cancer Center and Research Institute|National Cancer Institute (NCI) |
Male Breast Cancer|Recurrent Breast Cancer|Stage IV Breast Cancer|Unspecified Adult Solid Tumor, Protocol Specific
|
December 28, 2009 | Phase 1|Phase 2 |
| NCT01560923 | Masonic Cancer Center, University of Minnesota |
Metastatic Prostate Cancer
|
October 1, 2012 | Phase 2 |
| NCT03372239 | NewLink Genetics Corporation|Lumos Pharma |
Healthy
|
November 21, 2017 | Phase 1 |
| NCT01792050 | NewLink Genetics Corporation|Lumos Pharma |
Metastatic Breast Cancer
|
February 2013 | Phase 2 |
| NCT00739609 | NewLink Genetics Corporation|Lumos Pharma |
Breast Cancer|Lung Cancer|Melanoma|Pancreatic Cancer|Solid Tumors
|
August 2008 | Phase 1 |
| NCT02052648 | NewLink Genetics Corporation|Lumos Pharma |
Glioblastoma Multiforme|Glioma|Gliosarcoma|Malignant Brain Tumor
|
March 2014 | Phase 1|Phase 2 |
| NCT02077881 | NewLink Genetics Corporation|Lumos Pharma |
Metastatic Pancreatic Adenocarcinoma|Metastatic Pancreatic Cancer
|
August 2014 | Phase 1|Phase 2 |
| NCT01302821 | H. Lee Moffitt Cancer Center and Research Institute|National Cancer Institute (NCI) |
Breast Cancer
|
January 2013 | Not Applicable |
| NCT00567931 | National Cancer Institute (NCI) |
Unspecified Adult Solid Tumor, Protocol Specific
|
October 2007 | Phase 1 |
Appearance
Solid
Shipping
Room temperature in continental US; may vary elsewhere.
Storage
| Powder | -20°C | 3 years |
|---|---|---|
| 4°C | 2 years | |
| In solvent | -80°C | 6 months |
| -20°C | 1 month |
Solvent & Solubility
H 2 O : 5 mg/mL ( 22.91 mM ; ultrasonic and adjust pH to 2 with HCl)
DMSO : 0.55 mg/mL ( 2.52 mM ; Need ultrasonic and warming)
Stock Solutions
| Concentration Solvent Mass | 1 mg | 5 mg | 10 mg |
|---|
| 1 mM | 4.5819 mL | 22.9095 mL | 45.8190 mL |
| 5 mM | 0.9164 mL | 4.5819 mL | 9.1638 mL |
| 10 mM | 0.4582 mL | 2.2910 mL | 4.5819 mL |
-
1.
Add each solvent one by one: PBS
Solubility: 1 mg/mL (4.58 mM); Clear solution; Need ultrasonic and warming and heat to 60°C
References
- [1] Hou DY, et al. Inhibition of indoleamine 2,3-dioxygenase in dendritic cells by stereoisomers of 1-methyl-tryptophancorrelates with antitumor responses. Cancer Res. 2007 Jan 15;67(2):792-801.
- [2] Metz R, et al. IDO inhibits a tryptophan sufficiency signal that stimulates mTOR: A novel IDO effector pathway targeted by D-1-methyl-tryptophan. Oncoimmunology. 2012;1(9):1460-1468.