FRENTIZOLE

Possibly Marketed Outside US

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16781151 | https://www.ncbi.nlm.nih.gov/pubmed/7161058 |

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.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Aβ-ABAD/HSD17B10 interaction 1 Target ID: Aβ-ABAD/HSD17B10 interaction Sources: https://www.ncbi.nlm.nih.gov/pubmed/16781151 \| https://www.ncbi.nlm.nih.gov/pubmed/27287370	Inhibitor 8297		200.0 µM [IC50]
T cell mediated immunity 40 Target ID: GO:0002456 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7161058	Modulator 828

Conditions

Condition	Modality	Targets	Highest Phase	Product
Systemic lupus erythematosus 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7006613	Primary		Approved 8429	Unknown Approved Use Systemic Lupus Erythematosus
Rheumatoid arthritis 316 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7006613	Primary		Approved 8429	Unknown Approved Use Rheumatoid Arthritis

PubMed

Title	Date	PubMed
Effect of frentizole on mitogen-induced blastogenesis in human lymphocytes.	1979	401317
The immunomodulatory action of frentizole, a novel immunosuppressive agent.	1982 Dec	7161058
Determination of small molecule ABAD inhibitors crossing blood-brain barrier and pharmacokinetics.	2014	24858403

Patents

Sample Use Guides

In Vivo Use Guide

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

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