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Home > Encyclopedia > 1-METHYL-D-TRYPTOPHAN

1-METHYL-D-TRYPTOPHAN

pharmaceutical raw materials
1-METHYL-D-TRYPTOPHAN structure

1-METHYL-D-TRYPTOPHAN 

structure
  • CAS No:

    110117-83-4

  • Formula:

    C12H14N2O2

  • Chemical Name:

    1-METHYL-D-TRYPTOPHAN

  • Synonyms:

    1-METHYL-D-TRYPTOPHAN;1-Methyl-D-tryptophane;1-METHYL-D-TRYPTOPHAN 95%;(R)-2-amino-3-(1-methyl-1H-indol-3-yl)propanoic acid;IndoxiMod;Indoximod (NLG-8189);NLG-8189;1-Me-D-Trp

  • Categories:

    Biochemical Engineering  >  Amino Acids and Derivatives

Description

Indoximod (D-1MT, NLG8189) is an indoleamine 2,3-dioxygenase (IDO) pathway inhibitor with a Ki of 19 μM.


Indoximod has been used in trials studying the treatment of Glioma, Melanoma, Ependymoma, Gliosarcoma, and Lung Cancer, among others.|Indoximod is a methylated tryptophan with immune checkpoint inhibitory activity. Indoximod inhibits the enzyme indoleamine 2,3-dioxygenase (IDO), which degrades the essential amino acid tryptophan, and may increase or maintain tryptophan levels important to T cell function. Tryptophan depletion is associated with immunosuppression involving T cell arrest and anergy.

1-METHYL-D-TRYPTOPHAN Basic Attributes

218.25

218.105530

TX5CYN1KMZ

721782

C71535

2933990090

Characteristics

68.2

-1.3

1.28

242-245 °C(lit.)

429.3±35.0 °C(Predicted)

213.4±25.9 °C

1.625

12.4o (C = 2 IN ACETIC ACID)

Safety Information

NONH for all modes of transport

3

Drug Information

1-methyl-DL-Trp

1-METHYL-D-TRYPTOPHAN Use and Manufacturing

Indoleamine 2,3-dioxygenase (IDO) metabolizes tryptophan to kynurenine, leading to the production of NAD+ via the kynurenine pathway. The overexpression of IDO in tumors and tumor-draining lymph nodes induces immune tolerance and enhances tumor growth in vivo. 1-methyl-D-Tryptophan is an inhibitor of IDO (IC50 = 7 μM) that is effective in vivo. In mice, 1-methyl-D-tryptophan prevents T-cell anergy triggered by dendritic cells overexpressing IDO. It augments the antitumor and antiviral immunoresponse of CD8+ T-cells and reduces tumor volume in mice with xenografts overexpressing IDO. 1-methyl-D-Tryptophan, in combination with chemotherapy, causes regression of tumors and prolongs survival. Surprisingly, 1-methyl-D-tryptophan induces the expression of IDO in human ovarian carcinoma SKOV3 cells in culture.

Computed Properties

Molecular Weight:218.25
XLogP3:-1.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:3
Exact Mass:218.105527694
Monoisotopic Mass:218.105527694
Topological Polar Surface Area:68.2
Heavy Atom Count:16
Complexity:270
Defined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

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