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
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
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
PubMed
Title | Date | PubMed |
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Diphacinone and zinc phosphide toxicity in a flock of Peafowl. | 2001 Dec |
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[Study of diphacinone in biological samples by high performance liquid chromatography/diode array detector]. | 2001 May |
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Effect of diphacinone on blood coagulation in Spermophilus beecheyi as a basis for determining optimal timing of field bait applications. | 2002 Jul |
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Dermal absorption of a liquid diphacinone rodenticide causing coagulaopathy. | 2003 Dec |
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The genetic basis of resistance to anticoagulants in rodents. | 2005 Aug |
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Probabilistic risk assessment for snails, slugs, and endangered honeycreepers in diphacinone rodenticide baited areas on Hawaii, USA. | 2005 Jun |
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Multiresidue analysis of seven anticoagulant rodenticides by high-performance liquid chromatography/electrospray/mass spectrometry. | 2007 Feb 7 |
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Is there such a thing as psychological pain? And why it matters. | 2010 Dec |
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[Simultaneous determination of trace diphacinone and chlorophacinone in biological samples by high performance liquid chromatography coupled with ion trap mass spectrometry]. | 2010 Feb |
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Anatomy of life and well-being: A framework for the contributions of phenomenology and complexity theory. | 2010 Jul 2 |
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Acute toxicity of diphacinone in Northern bobwhite: effects on survival and blood clotting. | 2010 Sep |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/5068491
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.
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WHO-ATC |
B01AA10
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WHO-VATC |
QB01AA10
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EPA PESTICIDE CODE |
67701
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NCI_THESAURUS |
C263
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2788
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DIPHENADIONE
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C100262
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diphacinone
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m4605
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SUB07209MIG
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C75156
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DB13347
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ACTIVE MOIETY