Details
Stereochemistry | ACHIRAL |
Molecular Formula | C15H12O5 |
Molecular Weight | 272.2528 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)C1=CC=C(COC2=C(C=O)C(O)=CC=C2)C=C1
InChI
InChIKey=XEDONBRPTABQFB-UHFFFAOYSA-N
InChI=1S/C15H12O5/c16-8-12-13(17)2-1-3-14(12)20-9-10-4-6-11(7-5-10)15(18)19/h1-8,17H,9H2,(H,18,19)
Molecular Formula | C15H12O5 |
Molecular Weight | 272.2528 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
Tucaresol, a substituted benzaldehyde, was being developed by Glaxo Wellcome for the prevention of sickle cell disease. Tucaresol was designed to interact with haemoglobin to increase oxygen affinity and has been shown to inhibit sickling in vitro. Tucaresol is also a low-molecular-weight compound that enhances co-stimulatory signaling to CD4 cells. Immune induction is dependent on transient covalent bonding (Schiff base formation) between carbonyls and amines expressed on antigen presenting cell (APC) and T-cell surfaces. Tucaresol substitutes for the natural donor of carbonyl groups to mimic the transient bonding that is essential for T-cell activation. In preliminary studies, tucaresol has been shown to stimulate HIV-specific cytotoxic T lymphocyte responses and generation of naive T cells via thymopoiesis in patients receiving ART who have suppressed viremia. Tucaresol appears to specifically increase type 1 cytokine production. Tucaresol has been used in trials studying the treatment of HIV infections. However, the development of tucaresol for HIV, Hepatitis B and sickle cell diseas treatment has been discontinued.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2095168 |
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Target ID: Th1 cells Sources: https://adisinsight.springer.com/drugs/800003183 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8703810
Oral doses of tucaresol were given to nine stable sickle cell patients (aged 17-39 years) for 10 d. The first two patients on tucaresol were scheduled to receive a loading dose of 800 mg or 1200 mg (depending on body weight) for the first 4 d, followed by maintenance doses of 200 or 300 mg for the next 6 d.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/11112360
Curator's Comment: The immunomodulatory properties of tucaresol were tested on in vitro antigen- and mitogen-stimulated proliferation and cytokine production by peripheral blood mononuclear cells (PBMC) of HIV-infected individuals and healthy controls (HC).
The immunomodulatory effects of tucaresol on T cell functions are characterized by a bell-shaped dose response curve; the action of the compound is optimal in the 100 to 300 uM range.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 17:07:06 GMT 2023
by
admin
on
Sat Dec 16 17:07:06 GMT 2023
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Record UNII |
JH368G5B9M
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Record Status |
Validated (UNII)
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Record Version |
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C78275
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C152780
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SUB11363MIG
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6916
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C059629
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100000077470
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DTXSID70233247
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84290-27-7
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CHEMBL2104482
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JH368G5B9M
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Related Record | Type | Details | ||
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ACTIVE MOIETY |