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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
Structure of TUCARESOL

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)

HIDE SMILES / InChI

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
In vitro immunomodulatory properties of tucaresol in HIV infection.
2000 Dec
Tucaresol down-modulation of MUC1-stimulated human mononuclear cells.
2014
Lipid tucaresol as an adjuvant for methamphetamine vaccine development.
2014 Apr 21
Patents

Sample Use Guides

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
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 Sat Dec 16 17:07:06 GMT 2023
Edited
by admin
on Sat Dec 16 17:07:06 GMT 2023
Record UNII
JH368G5B9M
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
TUCARESOL
INN   MART.  
INN  
Official Name English
.ALPHA.-(2-FORMYL-3-HYDROXYPHENOXY)-P-TOLUIC ACID
Common Name English
TUCARESOL [MART.]
Common Name English
589C
Code English
589-C
Code English
tucaresol [INN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C78275
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C152780
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
PRIMARY
EVMPD
SUB11363MIG
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
PRIMARY
INN
6916
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
PRIMARY
MESH
C059629
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
PRIMARY
SMS_ID
100000077470
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
PRIMARY
EPA CompTox
DTXSID70233247
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
PRIMARY
DRUG BANK
DB13027
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
PRIMARY
CAS
84290-27-7
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
PRIMARY
ChEMBL
CHEMBL2104482
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
PRIMARY
PUBCHEM
55223
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
PRIMARY
FDA UNII
JH368G5B9M
Created by admin on Sat Dec 16 17:07:06 GMT 2023 , Edited by admin on Sat Dec 16 17:07:06 GMT 2023
PRIMARY
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