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Identification
NameAnisindione
Accession NumberDB01125  (APRD00799)
TypeSmall Molecule
GroupsApproved
Description

Anisindione is a synthetic anticoagulant and an indanedione derivative. It prevents the formation of active procoagulation factors II, VII, IX, and X, as well as the anticoagulant proteins C and S, in the liver by inhibiting the vitamin K-mediated gamma-carboxylation of precursor proteins.

Structure
Thumb
Synonyms
SynonymLanguageCode
2-(4-Methoxyphenyl)-1H-indene-1,3(2H)-dioneNot AvailableNot Available
2-(4-Methoxyphenyl)indan-1,3-dioneNot AvailableNot Available
2-(P-Methoxyphenyl)-1,3-indandioneNot AvailableNot Available
2-(P-Methoxyphenyl)indane-1,3-dioneNot AvailableNot Available
2-P-Anisyl-1,3-indandioneNot AvailableNot Available
2-Para-anisyl-1,3-indandioneNot AvailableNot Available
Anisin indandioneNot AvailableNot Available
AnisindionaNot AvailableNot Available
AnisindionumNot AvailableNot Available
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
MiradonNot Available
UnidoneNot Available
Brand mixturesNot Available
SaltsNot Available
CategoriesNot Available
CAS number117-37-3
WeightAverage: 252.2647
Monoisotopic: 252.07864425
Chemical FormulaC16H12O3
InChI KeyXRCFXMGQEVUZFC-UHFFFAOYSA-N
InChI
InChI=1S/C16H12O3/c1-19-11-8-6-10(7-9-11)14-15(17)12-4-2-3-5-13(12)16(14)18/h2-9,14H,1H3
IUPAC Name
2-(4-methoxyphenyl)-2,3-dihydro-1H-indene-1,3-dione
SMILES
COC1=CC=C(C=C1)C1C(=O)C2=CC=CC=C2C1=O
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as indanones. These are compounds containing an indane ring bearing a ketone group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassIndanes
Sub ClassIndanones
Direct ParentIndanones
Alternative Parents
Substituents
  • Indanone
  • Indanedione
  • Methoxybenzene
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • Anisole
  • 1,3-diketone
  • Alkyl aryl ether
  • 1,3-dicarbonyl compound
  • Monocyclic benzene moiety
  • Ketone
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the prophylaxis and treatment of venous thrombosis and its extension, the treatment of atrial fibrillation with embolization, the prophylaxis and treatment of pulmonary embolism, and as an adjunct in the treatment of coronary occlusion.
PharmacodynamicsAnisindione is a synthetic anticoagulant and an indanedione derivative. It is prescribed only if you cannot take coumarin-type anticoagulants such as coumadin as anisindione is a powerful drug with serious potential side effects. Anticoagulants decrease the clotting ability of the blood and therefore help to prevent harmful clots from forming in the blood vessels. These medicines are sometimes called blood thinners, although they do not actually thin the blood. They also will not dissolve clots that already have formed, but they may prevent the clots from becoming larger and causing more serious problems.
Mechanism of actionLike phenindione, to which it is related chemically, anisindione exercises its therapeutic action by reducing the prothrombin activity of the blood. Anisindione prevents the formation of active procoagulation factors II, VII, IX, and X, as well as the anticoagulant proteins C and S, in the liver by inhibiting the vitamin K–mediated gamma-carboxylation of precursor proteins. Anisindione has no direct thrombolytic effect and does not reverse ischemic tissue damage, although it may limit extension of existing thrombi and prevent secondary thromboembolic complications.
AbsorptionAccumulation does not occur with repeated dosing.
Volume of distributionNot Available
Protein bindingNot Known
MetabolismNot Available
Route of eliminationNot Available
Half lifeNot Known
ClearanceNot Available
ToxicityAn overdose is likely to cause abnormal bleeding, for which the symptoms include: bleeding from gums or nose, blood in urine or stools, excessive bleeding from minor cuts, patches of discoloration or bruises on the skin.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9051
Caco-2 permeable+0.8206
P-glycoprotein substrateNon-substrate0.6289
P-glycoprotein inhibitor IInhibitor0.5099
P-glycoprotein inhibitor IINon-inhibitor0.534
Renal organic cation transporterNon-inhibitor0.8467
CYP450 2C9 substrateNon-substrate0.7584
CYP450 2D6 substrateNon-substrate0.8872
CYP450 3A4 substrateNon-substrate0.5965
CYP450 1A2 substrateInhibitor0.9594
CYP450 2C9 substrateInhibitor0.8996
CYP450 2D6 substrateNon-inhibitor0.9457
CYP450 2C19 substrateInhibitor0.6234
CYP450 3A4 substrateNon-inhibitor0.8639
CYP450 inhibitory promiscuityHigh CYP Inhibitory Promiscuity0.6618
Ames testAMES toxic0.6006
CarcinogenicityNon-carcinogens0.8733
BiodegradationNot ready biodegradable0.8575
Rat acute toxicity2.4052 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.944
hERG inhibition (predictor II)Non-inhibitor0.8898
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point155-156Sperber, N.; US. Patent 2,899,358; August 11, 1959; assigned to Schering Corporation
water solubility79.8 mg/LNot Available
logP2.88SANGSTER (1993)
Predicted Properties
PropertyValueSource
Water Solubility0.0128 mg/mLALOGPS
logP2.99ALOGPS
logP2.72ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)4.5ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area43.37 Å2ChemAxon
Rotatable Bond Count2ChemAxon
Refractivity71.7 m3·mol-1ChemAxon
Polarizability26.3 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Sperber, N.; US. Patent 2,899,358; August 11, 1959; assigned to Schering Corporation

General Reference
  1. CONNELL WF, MAYER GA: Evaluation of anticoagulant therapy with anisindione (miradon). Can Med Assoc J. 1959 May 15;80(10):785-90. Pubmed
External Links
ATC CodesNot Available
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNot Available
Food InteractionsNot Available

Targets

1. Vitamin K-dependent gamma-carboxylase

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Vitamin K-dependent gamma-carboxylase P38435 Details

References:

  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Anisindione – Basic Profile / Key Facts. Source
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on March 28, 2014 10:09