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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 of PYRITHYLDIONE

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

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 Pyrithyldione was withdrawn from the marked due to several cases of agranulocytosis.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

1948
93
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
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Withdrawn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.
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Withdrawn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.
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
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

Doses

DosePopulationAdverse events​
600 mg single, oral
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/1354982/
unhealthy, 23 years
Health Status: unhealthy
Age Group: 23 years
Sex: M
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
Health Status: healthy
Age Group: adult
Sex: unknown
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

AEs

AESignificanceDosePopulation
Death grade 5, 1 patient
Disc. AE
600 mg single, oral
Dose: 600 mg
Route: oral
Route: single
Dose: 600 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/1354982/
unhealthy, 23 years
Health Status: unhealthy
Age Group: 23 years
Sex: M
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
Health Status: healthy
Age Group: adult
Sex: unknown
Sources:
https://pubmed.ncbi.nlm.nih.gov/18147853/
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG
inducer
109

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
CYP2D6
2546
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
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
abcr GmbH
AB384763
http://www.abcr.com/shop/en/AB384763
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
eNovation Chemicals
D949225
https://www.enovationchem.com/ProductDetails.asp?ProductID=D949225
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
mcule
MCULE-7842760182
https://mcule.com/MCULE-7842760182/
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
PubMed

PubMed

TitleDatePubMed
Occurrence and distribution of psychoactive compounds and their metabolites in the urban water cycle of Berlin (Germany).
2012-11-15
Occurrence of psychoactive compounds and their metabolites in groundwater downgradient of a decommissioned sewage farm in Berlin (Germany).
2012-07
A tale of two polymorphic pharmaceuticals: pyrithyldione and propyphenazone and their 1937 co-crystal patent.
2011-11-25
Population-based drug-induced agranulocytosis.
2005-04-25
Agranulocytosis induced by pyrithyldione, a sedative hypnotic drug.
2000-01
Livedo reticularis and thrombotic purpura related to the use of diphenhydramine associated with pyrithyldione.
1996
Fatal intoxication due to the combined use of heroin and pyrithyldione.
1992-07
[In vitro studies of the adsorption behavior of Wofatit Y 88 in relation to various drugs].
1990-11
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.
1990-09-14
Spectrophotometric characterization of some analgesics and antipyretics.
1989-09
Patents

Patents

EP0129285B1
1
WO2014036528A2
1

Sample Use Guides

In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 17:45:41 GMT 2025
Edited
by admin
on Mon Mar 31 17:45:41 GMT 2025
Record UNII
8AB20823CK
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PYRITHYLDIONE
INN   MART.   MI   WHO-DD  
INN  
Official Name English
NSC-89733
Preferred 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
Classification Tree Code System Code
WHO-ATC N05CE03
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
NCI_THESAURUS C29756
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
WHO-VATC QN05CE03
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
Code System Code Type Description
PUBCHEM
4994
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
MERCK INDEX
m9378
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY Merck Index
EVMPD
SUB10173MIG
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
SMS_ID
100000080850
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
NSC
89733
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
NCI_THESAURUS
C80677
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-000-5
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
ChEMBL
CHEMBL1722501
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
CAS
77-04-3
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
EPA CompTox
DTXSID4045262
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
DRUG BANK
DB13331
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
WIKIPEDIA
PYRITHYLDIONE
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
DRUG CENTRAL
3509
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
MESH
C005589
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
INN
5022
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
FDA UNII
8AB20823CK
Created by admin on Mon Mar 31 17:45:41 GMT 2025 , Edited by admin on Mon Mar 31 17:45:41 GMT 2025
PRIMARY
Related Record Type Details
Structure of PYRITHYLDIONE
ACTIVE MOIETY
NIH
NCATS
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