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Details

Stereochemistry ACHIRAL
Molecular Formula C15H13N3O2S
Molecular Weight 299.348
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FRENTIZOLE

SMILES

COC1=CC=C2N=C(NC(=O)NC3=CC=CC=C3)SC2=C1

InChI

InChIKey=JHBWYQRKOUBPCA-UHFFFAOYSA-N
InChI=1S/C15H13N3O2S/c1-20-11-7-8-12-13(9-11)21-15(17-12)18-14(19)16-10-5-3-2-4-6-10/h2-9H,1H3,(H2,16,17,18,19)

HIDE SMILES / InChI
Frentizole, a nontoxic antiviral and immunosuppressive agent, was used clinically in rheumatoid arthritis and systemic lupus erythematosus. Frentizole was more effective in suppressing human lymphocytes responding to Con A and PWM, than it was in cells activated by PHA, specific antigen, or alloantigen. Methylprednisolone, on the other hand, was more inhibitory for cells stimulated by PHA, specific antigen, or alloantigen. Frentizole, even at super immunosuppressive doses, does not predispose the hose (mice) to Pseudomonas aeruginosa, Candida albicans, herpes simplex virus, or Ann Arbor influenza virus. Frentizole is an inhibitor of the Aβ-ABAD interaction.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
200.0 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Systemic Lupus Erythematosus
Primary
Unknown

Approved Use

Rheumatoid Arthritis
PubMed

PubMed

TitleDatePubMed
The immunomodulatory action of frentizole, a novel immunosuppressive agent.
1982 Dec
Patents

Sample Use Guides

Eleven steroid-treated patients with active systemic lupus erythematosus received frentizole (150-350 mg/day) in combination with stable or decreasing doses of prednisone in an open label trial.
Route of Administration: Oral
In Vitro Use Guide
Frentizole (500 ng/ml) inhibited thymidine incorporation into DNA most effectively when added to human lymphocyte cultures at the same time as the addition of the mitogen. Frentizole (500 ng/ml) markedly inhibited the response to Con A (% inhibition, corporation was dose dependent with 125 ng/ml of Frentizole sufficient to inhibit significantly the response of all three mitogens. Frentizole (62.5 ng/ml) maximally inhibited uridine incorporation.
Name Type Language
FRENTIZOLE
INN   USAN   WHO-DD  
INN   USAN  
Official Name English
Frentizole [WHO-DD]
Common Name English
1-(6-Methoxy-2-benzothiazolyl)-3-phenylurea
Systematic Name English
COMPOUND 53616
Code English
frentizole [INN]
Common Name English
UREA, N-(6-METHOXY-2-BENZOTHIAZOLYL)-N'-PHENYL-
Systematic Name English
FRENTIZOLE [USAN]
Common Name English
COMPOUND-53616
Code English
Code System Code Type Description
INN
3920
Created by admin on Fri Dec 15 17:25:13 UTC 2023 , Edited by admin on Fri Dec 15 17:25:13 UTC 2023
PRIMARY
EVMPD
SUB07815MIG
Created by admin on Fri Dec 15 17:25:13 UTC 2023 , Edited by admin on Fri Dec 15 17:25:13 UTC 2023
PRIMARY
PUBCHEM
33334
Created by admin on Fri Dec 15 17:25:13 UTC 2023 , Edited by admin on Fri Dec 15 17:25:13 UTC 2023
PRIMARY
MESH
C013997
Created by admin on Fri Dec 15 17:25:13 UTC 2023 , Edited by admin on Fri Dec 15 17:25:13 UTC 2023
PRIMARY
NCI_THESAURUS
C167023
Created by admin on Fri Dec 15 17:25:13 UTC 2023 , Edited by admin on Fri Dec 15 17:25:13 UTC 2023
PRIMARY
EPA CompTox
DTXSID5046279
Created by admin on Fri Dec 15 17:25:13 UTC 2023 , Edited by admin on Fri Dec 15 17:25:13 UTC 2023
PRIMARY
ChEMBL
CHEMBL128988
Created by admin on Fri Dec 15 17:25:13 UTC 2023 , Edited by admin on Fri Dec 15 17:25:13 UTC 2023
PRIMARY
CAS
26130-02-9
Created by admin on Fri Dec 15 17:25:13 UTC 2023 , Edited by admin on Fri Dec 15 17:25:13 UTC 2023
PRIMARY
FDA UNII
7EY946394I
Created by admin on Fri Dec 15 17:25:13 UTC 2023 , Edited by admin on Fri Dec 15 17:25:13 UTC 2023
PRIMARY
SMS_ID
100000080447
Created by admin on Fri Dec 15 17:25:13 UTC 2023 , Edited by admin on Fri Dec 15 17:25:13 UTC 2023
PRIMARY