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

Details

Stereochemistry ACHIRAL
Molecular Formula C23H15O3.Na
Molecular Weight 362.3532
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DIPHACINONE-SODIUM

SMILES

[Na+].O=C(C(C1=CC=CC=C1)C2=CC=CC=C2)[C-]3C(=O)C4=C(C=CC=C4)C3=O

InChI

InChIKey=TURJLPVZRPWSJO-UHFFFAOYSA-N
InChI=1S/C23H15O3.Na/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;/h1-14,19H;/q-1;+1

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

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
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
Effect of diphacinone on blood coagulation in Spermophilus beecheyi as a basis for determining optimal timing of field bait applications.
2002 Jul
Determination of diphacinone residues in Hawaiian invertebrates.
2006 Jan
Multiresidue analysis of seven anticoagulant rodenticides by high-performance liquid chromatography/electrospray/mass spectrometry.
2007 Feb 7
Evaluating the potential effectiveness of compensatory mitigation strategies for marine bycatch.
2008 Jun 18
Chemical substructures that enrich for biological activity.
2008 Nov 1
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 Sat Dec 16 07:53:37 GMT 2023
Edited
by admin
on Sat Dec 16 07:53:37 GMT 2023
Record UNII
3P3GDA5QJC
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DIPHACINONE-SODIUM
ISO  
Common Name English
SODIUM DIPHACINONE
Common Name English
DIPHACINONE-SODIUM [ISO]
Common Name English
1H-INDENE-1,3(2H)-DIONE, 2-(2,2-DIPHENYLACETYL)-, ION(1-), SODIUM SALT (1:1)
Systematic Name English
SODIUM DIPHACIN
Common Name English
Classification Tree Code System Code
EPA PESTICIDE CODE 67705
Created by admin on Sat Dec 16 07:53:37 GMT 2023 , Edited by admin on Sat Dec 16 07:53:37 GMT 2023
Code System Code Type Description
CAS
42721-99-3
Created by admin on Sat Dec 16 07:53:37 GMT 2023 , Edited by admin on Sat Dec 16 07:53:37 GMT 2023
PRIMARY
FDA UNII
3P3GDA5QJC
Created by admin on Sat Dec 16 07:53:37 GMT 2023 , Edited by admin on Sat Dec 16 07:53:37 GMT 2023
PRIMARY
EPA CompTox
DTXSID1034551
Created by admin on Sat Dec 16 07:53:37 GMT 2023 , Edited by admin on Sat Dec 16 07:53:37 GMT 2023
PRIMARY
ECHA (EC/EINECS)
255-918-6
Created by admin on Sat Dec 16 07:53:37 GMT 2023 , Edited by admin on Sat Dec 16 07:53:37 GMT 2023
PRIMARY
PUBCHEM
23707509
Created by admin on Sat Dec 16 07:53:37 GMT 2023 , Edited by admin on Sat Dec 16 07:53:37 GMT 2023
PRIMARY
ALANWOOD
diphacinone-sodium
Created by admin on Sat Dec 16 07:53:37 GMT 2023 , Edited by admin on Sat Dec 16 07:53:37 GMT 2023
PRIMARY