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
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
Diphacinone and zinc phosphide toxicity in a flock of Peafowl.
2001 Dec
[Study of diphacinone in biological samples by high performance liquid chromatography/diode array detector].
2001 May
Effect of diphacinone on blood coagulation in Spermophilus beecheyi as a basis for determining optimal timing of field bait applications.
2002 Jul
Dermal absorption of a liquid diphacinone rodenticide causing coagulaopathy.
2003 Dec
The genetic basis of resistance to anticoagulants in rodents.
2005 Aug
Probabilistic risk assessment for snails, slugs, and endangered honeycreepers in diphacinone rodenticide baited areas on Hawaii, USA.
2005 Jun
Multiresidue analysis of seven anticoagulant rodenticides by high-performance liquid chromatography/electrospray/mass spectrometry.
2007 Feb 7
Is there such a thing as psychological pain? And why it matters.
2010 Dec
[Simultaneous determination of trace diphacinone and chlorophacinone in biological samples by high performance liquid chromatography coupled with ion trap mass spectrometry].
2010 Feb
Anatomy of life and well-being: A framework for the contributions of phenomenology and complexity theory.
2010 Jul 2
Acute toxicity of diphacinone in Northern bobwhite: effects on survival and blood clotting.
2010 Sep
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.
Name Type Language
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
DIPHACINONE
ISO   MI  
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 Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
WHO-VATC QB01AA10
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
EPA PESTICIDE CODE 67701
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
NCI_THESAURUS C263
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
Code System Code Type Description
HSDB
2788
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
FDA UNII
54CA01C6JX
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
PUBCHEM
6719
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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SMS_ID
100000082897
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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WIKIPEDIA
DIPHENADIONE
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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CAS
82-66-6
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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MESH
C100262
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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ALANWOOD
diphacinone
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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DRUG CENTRAL
4450
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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INN
557
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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EPA CompTox
DTXSID4032378
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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ECHA (EC/EINECS)
201-434-5
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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ChEMBL
CHEMBL1413199
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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NSC
9138
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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MERCK INDEX
m4605
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY Merck Index
EVMPD
SUB07209MIG
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
PRIMARY
NCI_THESAURUS
C75156
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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DRUG BANK
DB13347
Created by admin on Sat Dec 16 15:50:11 GMT 2023 , Edited by admin on Sat Dec 16 15:50:11 GMT 2023
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