U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C23H16O3
Molecular Weight 340.3713
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPHENADIONE

SMILES

O=C(C(C1=CC=CC=C1)C2=CC=CC=C2)C3C(=O)C4=C(C=CC=C4)C3=O

InChI

InChIKey=JYGLAHSAISAEAL-UHFFFAOYSA-N
InChI=1S/C23H16O3/c24-21-17-13-7-8-14-18(17)22(25)20(21)23(26)19(15-9-3-1-4-10-15)16-11-5-2-6-12-16/h1-14,19-20H

HIDE SMILES / InChI

Molecular Formula C23H16O3
Molecular Weight 340.3713
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Diphenadione is a vitamin K antagonist that exhibits anticoagulant effects and is used as a rodenticide against rats, mice, voles, ground squirrels and others. When orally ingested it is toxic to mammals causing irregular heartbeat and major maladies associated with its impact on blood clotting. It is also used in South America to control vampire bat populations.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q6TEK4
Gene ID: 309004.0
Gene Symbol: Vkorc1
Target Organism: Rattus norvegicus (Rat)
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
Dipaxin

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
3 mg single, oral
Dose: 3 mg
Route: oral
Route: single
Dose: 3 mg
Sources:
healthy, 5 years
Health Status: healthy
Age Group: 5 years
Sex: M
Sources:
Other AEs: Hemorrhage...
Other AEs:
Hemorrhage
Sources:
AEs

AEs

AESignificanceDosePopulation
Hemorrhage
3 mg single, oral
Dose: 3 mg
Route: oral
Route: single
Dose: 3 mg
Sources:
healthy, 5 years
Health Status: healthy
Age Group: 5 years
Sex: M
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
Is there such a thing as psychological pain? And why it matters.
2010-12
Warfarin toxicity and individual variability-clinical case.
2010-11
Acute toxicity of diphacinone in Northern bobwhite: effects on survival and blood clotting.
2010-09
Anatomy of life and well-being: A framework for the contributions of phenomenology and complexity theory.
2010-07-02
Analysis of multiple anticoagulant rodenticides in animal blood and liver tissue using principles of QuEChERS method.
2010-06
The 23rd International Mammalian Genome Conference meeting report.
2010-06
[Simultaneous determination of trace diphacinone and chlorophacinone in biological samples by high performance liquid chromatography coupled with ion trap mass spectrometry].
2010-02
Anticoagulant rodenticides in three owl species from Western Canada, 1988-2003.
2010-02
Potentiometric determination of ionisation constants for diphacinone and chlorophacinone in a dioxane-water cosolvent system.
2009-08-15
Simultaneous measurement of indandione-type rodenticides in human serum by liquid chromatography-electrospray ionization- tandem mass spectrometry.
2009-08-06
Analysis of indandione anticoagulant rodenticides in animal liver by eluent generator reagent free ion chromatography coupled with electrospray mass spectrometry.
2008-12-05
Chemical substructures that enrich for biological activity.
2008-11-01
Evaluating the potential effectiveness of compensatory mitigation strategies for marine bycatch.
2008-06-18
Multiresidue analysis of seven anticoagulant rodenticides by high-performance liquid chromatography/electrospray/mass spectrometry.
2007-02-07
Determination of diphacinone residues in Hawaiian invertebrates.
2006-01
The genetic basis of resistance to anticoagulants in rodents.
2005-08
Probabilistic risk assessment for snails, slugs, and endangered honeycreepers in diphacinone rodenticide baited areas on Hawaii, USA.
2005-06
Anticoagulant rodenticides.
2005
Dermal absorption of a liquid diphacinone rodenticide causing coagulaopathy.
2003-12
Effect of diphacinone on blood coagulation in Spermophilus beecheyi as a basis for determining optimal timing of field bait applications.
2002-07
Diphacinone and zinc phosphide toxicity in a flock of Peafowl.
2001-12
[Study of diphacinone in biological samples by high performance liquid chromatography/diode array detector].
2001-05
Patents

Sample Use Guides

Beef cattle were given a single dose (1 mg/kg bw) of diphenadione. Blood extracted from these cows proved toxic to vampire bats (Desmodus rotundus) and remained toxic for 3 days without harming the cattle. Cattle treated this way experienced a 93 % reduction in vampire bat bites. Bioassays of the milk and liver from these cattle indicated that there was no residual diphenadione.
Route of Administration: Oral
Rat livers were homogenized in 0.25 M sucrose, 0.05 M potassium phosphate buffer, pH 7.5. Dithiothreitol was added to a final concentration of 0.5 mM. Nitrogen gas was bubbled through the homogenate for 3 minutes in order to inhibit the epoxidation of [3H]vitamin-K1. The epoxidation reaction was initiated by addition of 3 micro-g of [3H]epoxide and incubated for 30 min at 37 deg-C. The reaction was terminated by adding 7 mL of isopropanol-hexane (3:2). After centrifugation, the hexane layer was chromatographed by thin-layer chromatography. Diphenandione demonstrated a 90% inhibition of vitamin K1 epoxide reductase at a concentration of 50 microM.
Substance Class Chemical
Created
by admin
on Wed Apr 02 06:52:07 GMT 2025
Edited
by admin
on Wed Apr 02 06:52:07 GMT 2025
Record UNII
54CA01C6JX
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIPHACINONE
ISO   MI  
Preferred Name English
DIPHENADIONE
HSDB   INN   MART.   WHO-DD  
INN  
Official Name English
U-1363
Code English
DIFENADIONE
Common Name English
2-(DIPHENYLACETYL)INDAN-1,3-DIONE
Systematic Name English
diphenadione [INN]
Common Name English
1,3-INDANDIONE, 2-(DIPHENYLACETYL)-
Systematic Name English
2-(Diphenylacetyl)-1,3-indandione
Systematic Name English
1H-INDENE-1,3-(2H)-DIONE, 2-(DIPHENYLACETYL)-
Common Name English
DIPHACINONE [MI]
Common Name English
DIPHACINONE [ISO]
Common Name English
DIPHENYLACETYLINDANDIONE
Systematic Name English
DIPHENADIONE [MART.]
Common Name English
2-(DIPHENYLACETYL)-1H-INDENE-1,3(2H)-DIONE
Systematic Name English
Diphenadione [WHO-DD]
Common Name English
NCI-9138
Code English
DIDANDIN
Brand Name English
DIPHENADIONE [HSDB]
Common Name English
NSC-9138
Code English
Classification Tree Code System Code
WHO-ATC B01AA10
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
WHO-VATC QB01AA10
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
EPA PESTICIDE CODE 67701
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
NCI_THESAURUS C263
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
Code System Code Type Description
HSDB
2788
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
FDA UNII
54CA01C6JX
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
PUBCHEM
6719
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
SMS_ID
100000082897
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
WIKIPEDIA
DIPHENADIONE
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
CAS
82-66-6
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
MESH
C100262
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
ALANWOOD
diphacinone
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
DRUG CENTRAL
4450
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
INN
557
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
EPA CompTox
DTXSID4032378
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-434-5
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
ChEMBL
CHEMBL1413199
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
NSC
9138
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
MERCK INDEX
m4605
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY Merck Index
EVMPD
SUB07209MIG
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
NCI_THESAURUS
C75156
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
DRUG BANK
DB13347
Created by admin on Wed Apr 02 06:52:07 GMT 2025 , Edited by admin on Wed Apr 02 06:52:07 GMT 2025
PRIMARY
Related Record Type Details
ACTIVE MOIETY