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=CC2=C(C=C1)N=C(NC(=O)NC3=CC=CC=C3)S2

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

Molecular Formula	C15H13N3O2S
Molecular Weight	299.348
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 8504		200.0 µM [IC50]
T cell mediated immunity 40 Target ID: GO:0002456 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7161058	Modulator 846

Conditions

Condition	Modality	Targets	Highest Phase	Product
Systemic lupus erythematosus 15 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7006613	Primary		Approved 8583	Unknown Approved Use Systemic Lupus Erythematosus
Rheumatoid arthritis 320 Sources: https://www.ncbi.nlm.nih.gov/pubmed/7006613	Primary		Approved 8583	Unknown Approved Use Rheumatoid Arthritis

Doses

Dose	Population	Adverse events
350 mg 1 times / day multiple, oral Studied dose Dose: 350 mg, 1 times / day Route: oral Route: multiple Dose: 350 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7006613/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7006613/	Disc. AE: Hepatotoxicity... AEs leading to discontinuation/dose reduction: Hepatotoxicity (9%) Sources: https://pubmed.ncbi.nlm.nih.gov/7006613/

AEs

AE	Significance	Dose	Population
Hepatotoxicity	9% Disc. AE	350 mg 1 times / day multiple, oral Studied dose Dose: 350 mg, 1 times / day Route: oral Route: multiple Dose: 350 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/7006613/	unhealthy, ADULT Health Status: unhealthy Age Group: ADULT Sex: M+F Food Status: UNKNOWN Sources: https://pubmed.ncbi.nlm.nih.gov/7006613/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
inhibitor 2252 inducer 1087	inhibitor 2438	inhibitor 2507	substrate 9

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP19A1 429 P-gp 1741 CYP1A2 2153 MRP1 116 CYP2C19 2057 BCRP 910	P-gp 2052

Drug as perpetrator

Target	Modality	Activity
CYP3A4 2633	inducer 1966 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/33334#section=Biological-Test-Results Page: 2.0	inconclusive [EC50 0.2239 uM]
BCRP 985	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/33334#section=Biological-Test-Results Page: 59.0	no
CYP19A1 430	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/33334#section=Biological-Test-Results Page: 12.0	no
CYP2D6 2546	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/33334#section=Biological-Test-Results Page: 263.0	no
MRP1 232	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/33334#section=Biological-Test-Results Page: 44.0	no
P-gp 1932	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/33334#section=Biological-Test-Results Page: 60.0	no
CYP1A2 2333	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/33334#section=Biological-Test-Results Page: 23.0	yes [IC50 12.3018 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/33334#section=Biological-Test-Results Page: 24.0	yes [IC50 13.8029 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/33334#section=Biological-Test-Results Page: 30.0	yes [IC50 21.8761 uM]
CYP3A4 2633	inhibitor 4027 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/33334#section=Biological-Test-Results Page: 20.0	yes [IC50 8.709 uM]

Drug as victim

Target	Modality	Activity	Metabolite	Clinical evidence
P-gp 2052	substrate 4014 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/33334#section=Biological-Test-Results Page: 26 \| 260	inconclusive

Tox targets

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 2263	substrate 9 Sources: https://pubchem.ncbi.nlm.nih.gov/compound/33334#section=Biological-Test-Results Page: 266.0

PubMed

Title	Date	PubMed
Determination of small molecule ABAD inhibitors crossing blood-brain barrier and pharmacokinetics.	2014	24858403
Identification of small-molecule inhibitors of the Abeta-ABAD interaction.	2006-09-01	16781151
The immunomodulatory action of frentizole, a novel immunosuppressive agent.	1982-12	7161058
Effect of frentizole on mitogen-induced blastogenesis in human lymphocytes.	1979	401317

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:46:11 GMT 2025` Edited by `admin` on `Mon Mar 31 18:46:11 GMT 2025`
Record UNII	7EY946394I
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

FRENTIZOLE

Official Name

English

COMPOUND-53616

Preferred 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

Code System Code Type Description

INN

3920