Details of the Drug

General Information of Drug (ID: DM2PYNR)

Drug Name

Phenindione

Synonyms

Athrombon; Bindan; Cronodione; Danedion; Danilon; Danilone; Diadilan; Dindevan; Dineval; Diophindane; Emandion; Emandione; Eridione; Fenhydren; Fenilin; Fenindion; Fenindiona; Hedulin; Hemolidione; Indema; Indion; Indon; Phenhydren; Phenillin; Phenindionum; Phenylen; Phenylin; Phenylindanedione; Phenylindione; Phenyline; Phenyllin; Pindione; Rectadione; Theradione; Thrombasal; Tromazal; Trombol; Boots Brand of Phenindione; Goldshield Brand of Phenindione; Merck Lipha Sante Brand of Phenindione; P1029; P26406_ALDRICH; Fenindiona [INN-Spanish]; Hedulin (TN); Phenindione (INN); Phenindione [INN:BAN]; Phenindionum [INN-Latin]; 2 Phenyl 1,3 indandione; 2-Fenyloindandion-1,3; 2-Fenyloindandion-1,3 [Polish]; 2-Phenyl-1,3-diketohydrindene; 2-Phenyl-1,3-indandione; 2-Phenyl-1,3-indanedione; 2-Phenyl-1H-indene-1,3(2H)-dione; 2-Phenylindan-1,3-dione; 2-Phenylindandione; 2-phenyl-1,3(2H)-Indenedione; 2-phenyl-2,3-dihydro-1H-indene-1,3-dione; 2-phenylindene-1,3-dione

Indication

Disease Entry	ICD 11	Status	REF
Coagulation defect	3B10.0	Approved	[1]
Pulmonary embolism	BB00	Approved	[1]
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Therapeutic Class

Anticoagulants

Drug Type

Small molecular drug

Structure

3D MOL

2D MOL

#Ro5 Violations (Lipinski): 0

Molecular Weight (mw)

222.24

Logarithm of the Partition Coefficient (xlogp)

2.9

Rotatable Bond Count (rotbonds)

Hydrogen Bond Donor Count (hbonddonor)

Hydrogen Bond Acceptor Count (hbondacc)

ADMET Property

Absorption: The drug is absorbed slowly from the gastrointestinal tract []
Bioavailability: 97% of drug becomes completely available to its intended biological destination(s) [2]
Half-life: The concentration or amount of drug in body reduced by one-half in 5 - 10 hours [3]
Metabolism: The drug is metabolized via the hepatic []
MRTD: The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 14.98341 micromolar/kg/day [4]

Chemical Identifiers

Formula: C15H10O2
IUPAC Name: 2-phenylindene-1,3-dione
Canonical SMILES: C1=CC=C(C=C1)C2C(=O)C3=CC=CC=C3C2=O
InChI: InChI=1S/C15H10O2/c16-14-11-8-4-5-9-12(11)15(17)13(14)10-6-2-1-3-7-10/h1-9,13H
InChIKey: NFBAXHOPROOJAW-UHFFFAOYSA-N

Cross-matching ID

PubChem CID: 4760
ChEBI ID: CHEBI:8066
CAS Number: 83-12-5
DrugBank ID: DB00498
TTD ID: D08FTG

Combinatorial Drugs (CBD)

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Repurposed Drugs (RPD)

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Molecular Interaction Atlas of This Drug

Drug Therapeutic Target (DTT)

DTT Name	DTT ID	UniProt ID	MOA	REF
Vitamin K epoxide reductase complex 1 (VKORC1)	TTEUC8H	VKOR1_HUMAN	Inhibitor	[5]

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Drug Off-Target (DOT)

DOT Name	DOT ID	UniProt ID	Interaction	REF
Cellular tumor antigen p53 (TP53)	OTIE1VH3	P53_HUMAN	Protein Interaction/Cellular Processes	[6]
Vitamin K epoxide reductase complex subunit 1	OTOJNJRD	VKOR1_HUMAN	Gene/Protein Processing	[7]
Vitamin K epoxide reductase complex subunit 1-like protein 1	OT7QSEWT	VKORL_HUMAN	Gene/Protein Processing	[7]

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Molecular Interaction Atlas (MIA)

MIA Detail

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References

1	URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 6838).
2	Critical Evaluation of Human Oral Bioavailability for Pharmaceutical Drugs by Using Various Cheminformatics Approaches
3	Trend Analysis of a Database of Intravenous Pharmacokinetic Parameters in Humans for 1352 Drug Compounds
4	Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
5	[Oral anticoagulation and pharmacogenetics: importance in the clinical setting]. Rev Med Suisse. 2007 Sep 12;3(124):2030, 2033-4, 2036.
6	P53 hot-spot mutants are resistant to ubiquitin-independent degradation by increased binding to NAD(P)H:quinone oxidoreductase 1. Proc Natl Acad Sci U S A. 2003 Dec 9;100(25):15065-70. doi: 10.1073/pnas.2436329100. Epub 2003 Nov 21.
7	VKORC1 and VKORC1L1 have distinctly different oral anticoagulant dose-response characteristics and binding sites. Blood Adv. 2018 Mar 27;2(6):691-702.