PYRITHYLDIONE

US Previously Marketed

First approved in 1948

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H13NO2
Molecular Weight	167.205
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCC1(CC)C(=O)NC=CC1=O

InChI

InChIKey=NZASCBIBXNPDMH-UHFFFAOYSA-N

InChI=1S/C9H13NO2/c1-3-9(4-2)7(11)5-6-10-8(9)12/h5-6H,3-4H2,1-2H3,(H,10,12)

HIDE SMILES / InChI

Molecular Formula	C9H13NO2
Molecular Weight	167.205
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/14802156 | https://www.ncbi.nlm.nih.gov/pubmed/10663456 | https://www.ncbi.nlm.nih.gov/pubmed/18144514

Pyrithyldione is a sedative and hypnotic drug. It was demonstrated that drug has certain advantages over the barbiturates. It was indicated in mild cases of insomnia and in small doses as a sedative agent during the day. Pyrithyldione was withdrawn from the marked due to several cases of agranulocytosis.

CNS Activity

Originator

Approval Year

Conditions

Condition	Modality	Targets	Highest Phase	Product
Insomnia 108 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15398402 https://www.ncbi.nlm.nih.gov/pubmed/18144514	Primary		Withdrawn	Persedon Approved Use Pyrithyldione is very useful in mild cases of insomnia. It may also be used in small doses as a sedative agent during the day.
Psychotic disorder 26 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14773306	Primary		Withdrawn	Persedon Approved Use Pyrithyldione is very useful in mild cases of insomnia. It may also be used in small doses as a sedative agent during the day.

T_1/2

Value	Dose	Co-administered	Analyte	Population
14.5 h REVIEW https://pubmed.ncbi.nlm.nih.gov/10663456/	single, oral		PYRITHYLDIONE plasma	Homo sapiens population: HEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
600 mg single, oral Dose: 600 mg Route: oral Route: single Dose: 600 mg Co-administed with:: heroin Sources: https://pubmed.ncbi.nlm.nih.gov/1354982/	unhealthy, 23 years n = 1 Health Status: unhealthy Condition: heroin addict Age Group: 23 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/1354982/	Disc. AE: Death... AEs leading to discontinuation/dose reduction: Death (grade 5, 1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/1354982/
600 mg 1 times / day steady, oral Recommended Dose: 600 mg, 1 times / day Route: oral Route: steady Dose: 600 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18147853/	healthy, adult n = 10 Health Status: healthy Age Group: adult Sex: unknown Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/18147853/	Disc. AE: Agranulocytosis... AEs leading to discontinuation/dose reduction: Agranulocytosis (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/18147853/

AEs

AE	Significance	Dose	Population
Death	grade 5, 1 patient Disc. AE	600 mg single, oral Dose: 600 mg Route: oral Route: single Dose: 600 mg Co-administed with:: heroin Sources: https://pubmed.ncbi.nlm.nih.gov/1354982/	unhealthy, 23 years n = 1 Health Status: unhealthy Condition: heroin addict Age Group: 23 years Sex: M Population Size: 1 Sources: https://pubmed.ncbi.nlm.nih.gov/1354982/
Agranulocytosis	1 patient Disc. AE	600 mg 1 times / day steady, oral Recommended Dose: 600 mg, 1 times / day Route: oral Route: steady Dose: 600 mg, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/18147853/	healthy, adult n = 10 Health Status: healthy Age Group: adult Sex: unknown Population Size: 10 Sources: https://pubmed.ncbi.nlm.nih.gov/18147853/

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
		inducer 97

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
CYP2D6 1891	inducer 1573 Sources: https://pubmed.ncbi.nlm.nih.gov/7071114/ (from https://en.wikipedia.org/wiki/Pyrithyldione)	yes

Sourcing

Vendor/Aggregator	ID	URL
001 Chemical	DY571127	https://www.001chemical.com/chem/77-04-3
3B Scientific (Wuhan) Corp	3B3-029581	http://www.3bsc.com/index/pro_info.php?id=50838
AHH Chemical co.,ltd	MR-1000342	http://www.ahhchemical.com/product/MR-1000342.html
Aronis	ARONIS24414	http://www.aronis.ru/store/index.php?main_page=product_info&cPath=1&products_id=1554
Aurora Fine Chemicals LLC	K02.043.953	http://online.aurorafinechemicals.com/info?ID=K02.043.953
Aurum Pharmatech LLC	T8171	http://www.Aurumpharmatech.com/Product/ProductDetails/T8171
BOC Sciences	77-04-3	https://www.bocsci.com/pyrithyldione-cas-77-04-3-item-76884.html
ChemMol	99147270	http://www.chemmol.com/chemmol/99147270.html
Chemspace	CSSB00000034618	https://chem-space.com/CSSB00000034618
Hairui	HR143235	http://www.hairuichem.com/en/product/77-04-3.html
LGC Standards	LGCFOR3217.00	https://www.lgcstandards.com/US/en/p/LGCFOR3217.00
Matrix Scientific	207260	https://www.matrixscientific.com/207260.html
Molcore	MC571127	https://www.molcore.com/product/77-04-3
Parchem	42141	https://www.parchem.com/chemical-supplier-distributor/Pyrithyldione-042141.aspx
Sigma-Aldrich	R279072_ALDRICH	https://www.sigmaaldrich.com/catalog/product/aldrich/r279072
Smolecule	S576277	https://www.smolecule.com/products/s576277
THE BioTek	bt-403988	https://www.thebiotek.com/product/others/bt-403988
abcr GmbH	AB384763	http://www.abcr.com/shop/en/AB384763
eNovation Chemicals	D949225	https://www.enovationchem.com/ProductDetails.asp?ProductID=D949225
mcule	MCULE-7842760182	https://mcule.com/MCULE-7842760182/

PubMed

Title	Date	PubMed
Spectrophotometric characterization of some analgesics and antipyretics.	1989 Sep	18964835
[In vitro studies of the adsorption behavior of Wofatit Y 88 in relation to various drugs].	1990 Nov	1983102
Identification and differentiation of barbiturates, other sedative-hypnotics and their metabolites in urine integrated in a general screening procedure using computerized gas chromatography-mass spectrometry.	1990 Sep 14	2079506
Fatal intoxication due to the combined use of heroin and pyrithyldione.	1992 Jul	1354982
Livedo reticularis and thrombotic purpura related to the use of diphenhydramine associated with pyrithyldione.	1996	8864620
Agranulocytosis induced by pyrithyldione, a sedative hypnotic drug.	2000 Jan	10663456
Population-based drug-induced agranulocytosis.	2005 Apr 25	15851637
A tale of two polymorphic pharmaceuticals: pyrithyldione and propyphenazone and their 1937 co-crystal patent.	2011 Nov 25	22076942
Occurrence of psychoactive compounds and their metabolites in groundwater downgradient of a decommissioned sewage farm in Berlin (Germany).	2012 Jul	22227832
Occurrence and distribution of psychoactive compounds and their metabolites in the urban water cycle of Berlin (Germany).	2012 Nov 15	22967903

Patents

Sample Use Guides

In Vivo Use Guide

0.2-0.4 g (1-2 tablets) 15-20 minutes before going to bed

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:04:47 GMT 2023` Edited by `admin` on `Fri Dec 15 15:04:47 GMT 2023`
Record UNII	8AB20823CK
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

PYRITHYLDIONE

Official Name

English

PYRITHYLDIONE [MI]

Common Name

English

3,3-DIETHYL-2,4(1H,3H)-PYRIDINEDIONE

Systematic Name

English

Pyrithyldione [WHO-DD]

Common Name

English

PYRITHYLDIONE [MART.]

Common Name

English

pyrithyldione [INN]

Common Name

English

NSC-89733

Code

English

Classification Tree Code System Code

WHO-ATC

N05CE03