DIAMTHAZOLE

US Previously Marketed

First approved in 1951

Details

Stereochemistry	ACHIRAL
Molecular Formula	C15H23N3OS
Molecular Weight	293.428
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCN(CC)CCOC1=CC=C2N=C(SC2=C1)N(C)C

InChI

InChIKey=WGMYEOIMVYADRJ-UHFFFAOYSA-N

InChI=1S/C15H23N3OS/c1-5-18(6-2)9-10-19-12-7-8-13-14(11-12)20-15(16-13)17(3)4/h7-8,11H,5-6,9-10H2,1-4H3

HIDE SMILES / InChI

Molecular Formula	C15H23N3OS
Molecular Weight	293.428
Charge	0
Count

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

Description
Sources: http://www.fda.gov/ohrms/dockets/ac/98/briefingbook/1998-3454B1_03_WL16.pdf

Diamthazole is an antifungal drug that was used for the treatment of tinea pedis. The drug was withdrawn from the market, because it was associated with neuropsychiatric adverse reactions.

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Athlete’s foot 7 Sources: http://www.fda.gov/ohrms/dockets/ac/98/briefingbook/1998-3454B1_03_WL16.pdf	Curative		Withdrawn	Unknown Approved Use Unknown

Doses

Dose	Population	Adverse events
5 % 3 times / day steady, topical Dose: 5 %, 3 times / day Route: topical Route: steady Dose: 5 %, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14424470/	unhealthy, 4 weeks n = 1 Health Status: unhealthy Condition: ringworm Age Group: 4 weeks Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14424470/	Disc. AE: Convulsions... AEs leading to discontinuation/dose reduction: Convulsions (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/14424470/

AEs

AE	Significance	Dose	Population
Convulsions	1 patient Disc. AE	5 % 3 times / day steady, topical Dose: 5 %, 3 times / day Route: topical Route: steady Dose: 5 %, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/14424470/	unhealthy, 4 weeks n = 1 Health Status: unhealthy Condition: ringworm Age Group: 4 weeks Sex: F Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/14424470/

Sourcing

Vendor/Aggregator	ID	URL
AAA Chemistry	AR-1I5366
ABI Chem	AC1L1RJS
ABI Chem	AC1Q3AOM
Alfa Chemistry	136-96-9	https://www.alfa-chemistry.com/cas_136-96-9.htm
ChemTik	CTK8G8774
MuseChem	M070795	https://www.musechem.com/product/M070795.html
NovoSeek	8707
PubChem	8707	https://pubchem.ncbi.nlm.nih.gov/compound/8707
Smolecule	S576139	https://www.smolecule.com/products/s576139

PubMed

Title	Date	PubMed
Treatment of superficial dermatomycoses with asterol dihydrochloride.	1952 Mar 22	14897701
Asterol dihydrochloride in the treatment of dermatophytosis caused by Trichophyton rubrum (purpureum).	1952 Nov	13000196
Experimental studies on drug resistance of dermatophytes. I. The development of drug resistance of Trichophyton mentagrophytes and Microsporum lanosum to undecylenic acid and 2-dimethyl amino-6-(beta-di-ethylaminoethoxy) benzothiazole dihydrochloride (asterol).	1955 Aug	13263683
The effects of sugar deprivation on the anti-fungal properties of asterol; an in vitro study.	1959 Jul	13673207
Extrapyramidal reaction in a patient on combined drug therapy: report of a case.	1971 Jul-Aug	5284823
A survey of reported synthesis of methaqualone and some positional and structural isomers.	2001 Nov 1	11672968
Molecular epidemiology of multidrug-resistant tuberculosis, New York City, 1995-1997.	2002 Nov	12453347
Chinese red yeast rice (Monascus purpureus) for primary hyperlipidemia: a meta-analysis of randomized controlled trials.	2006 Nov 23	17302963
A case of acute myeloid leukemia-M2 with trisomy 4 in addition to t(8;21).	2008 Jan	20300287
The Summary Index of Malaria Surveillance (SIMS): a stable index of malaria within India.	2010 Feb 11	20181218
Semiautomatic quantification of angiogenesis.	2010 Jul	19345375
Retrospective cohort study of a new infant formula during the first 6 months of life: reflections on growth curves, human milk and formula feeding.	2010 Nov	21243867

Patents

Sample Use Guides

In Vivo Use Guide

Unknown

Route of Administration: Unknown

In Vitro Use Guide

Tnichophyton purpureum was treated by various concentrations of Diamthazole (Asterol) in both sugar-free and sugar-containing media. The drug concentration varied from 0.39-6.24 ug/ml. 50% of growth inhibition was achieved at 1 ug/ml in sugar-containing media and at 0.25 ug/ml in sugar-free media.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:18:20 GMT 2023` Edited by `admin` on `Fri Dec 15 15:18:20 GMT 2023`
Record UNII	2KL01R8ZV1
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DIAMTHAZOLE

Common Name

English

dimazole [INN]

Common Name

English

Dimazole [WHO-DD]

Common Name

English

2-BENZOTHIAZOLAMINE, 6-(2-(DIETHYLAMINO)ETHOXY)-N,N-DIMETHYL-

Systematic Name

English

DIMAZOLE

Official Name

English

Classification Tree Code System Code

WHO-VATC

QD01AE17