NAV

Anisindione

Identification

Generic Name
Anisindione
DrugBank Accession Number
DB01125
Background

Anisindione is a synthetic anticoagulant and an indanedione derivative. Its anticoagulant action is mediated through the inhibition of the vitamin K-mediated gamma-carboxylation of precursor proteins that are critical in forming the formation of active procoagulation factors II, VII, IX, and X, as well as the anticoagulant proteins C and S, in the liver.

Type
Small Molecule
Groups
Approved
Structure
 3D
Similar Structures
Weight
Average: 252.2647
Monoisotopic: 252.07864425
Chemical Formula
C16H12O3
Synonyms
  • 2-(4-Methoxyphenyl)-1H-indene-1,3(2H)-dione
  • 2-(4-Methoxyphenyl)indan-1,3-dione
  • 2-(p-Methoxyphenyl)-1,3-indandione
  • 2-(p-Methoxyphenyl)indane-1,3-dione
  • 2-p-Anisyl-1,3-indandione
  • 2-para-Anisyl-1,3-indandione
  • Anisin indandione
  • Anisindiona
  • Anisindione
  • Anisindionum

Pharmacology

Indication

For 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.

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Anisindione 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 action

Like phenindione, to which it is related chemically, anisindione exercises its therapeutic action by reducing the prothrombin activity of the blood. By inhibiting the vitamin K–mediated gamma-carboxylation of precursor proteins, the formation of active procoagulation factors II, VII, IX, and X, as well as the anticoagulant proteins C and S is prevented. 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.

Target Actions Organism
AVitamin K-dependent gamma-carboxylase
inhibitor
 Humans
Absorption

积累不出现重复给药。

Volume of distribution

Not Available

Protein binding

Not Known

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Known

Clearance

Not Available

Adverse Effects
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Toxicity

An 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.

Pathways
Not Available
Pharmacogenomic Effects/ADRsBrowse all" title="" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug InteractionsLearn More" title="" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
这些信息不应该interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
Not Available

Products

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International/Other Brands
Miradon/Unidone

Categories

Drug Categories
Chemical TaxonomyProvided byClassyfire
Description
This compound belongs to the class of organic compounds known as indanediones. These are compounds containing an indane ring bearing two ketone groups.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Indanes
Sub Class
Indanones
Direct Parent
Indanediones
Alternative Parents
Phenoxy compounds/Methoxybenzenes/Aryl alkyl ketones/Anisoles/Beta-diketones/Alkyl aryl ethers/Organic oxides/Hydrocarbon derivatives
Substituents
1,3-dicarbonyl compound/1,3-diketone/Alkyl aryl ether/Anisole/Aromatic homopolycyclic compound/Aryl alkyl ketone/Aryl ketone/Ether/Hydrocarbon derivative/Indanedione
Molecular Framework
Aromatic homopolycyclic compounds
External Descriptors
aromatic ketone, beta-diketone (CHEBI:133809)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
S747T1ERAJ
CAS number
117-37-3
InChI Key
XRCFXMGQEVUZFC-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

References

Synthesis Reference

Sperber, N.; US. Patent 2,899,358; August 11, 1959; assigned to Schering Corporation
一般引用
  1. CONNELL WF, MAYER GA: Evaluation of anticoagulant therapy with anisindione (miradon). Can Med Assoc J. 1959 May 15;80(10):785-90. [Article]
Human Metabolome Database
HMDB0015257
KEGG Drug
D07457
PubChem Compound
2197
PubChem Substance
46504660
ChemSpider
2112
BindingDB
50280155
RxNav
17941
ChEBI
133809
ChEMBL
CHEMBL712
ZINC
ZINC000100015486
Therapeutic Targets Database
DAP001274
PharmGKB
PA164746467
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
PDRhealth
PDRhealth Drug Page
Wikipedia
Anisindione

Clinical Trials

Clinical TrialsLearn More" title="" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Property Value Source
melting point (°C) 155-156 Sperber, N.; US. Patent 2,899,358; August 11, 1959; assigned to Schering Corporation
water solubility 79.8 mg/L Not Available
logP 2.88 SANGSTER (1993)
Predicted Properties
Property Value Source
Water Solubility 0.0128 mg/mL ALOGPS
logP 2.99 ALOGPS
logP 2.72 Chemaxon
logS -4.3 ALOGPS
pKa (Strongest Acidic) 4.55 Chemaxon
pKa (Strongest Basic) -4.8 Chemaxon
Physiological Charge -1 Chemaxon
Hydrogen Acceptor Count 3 Chemaxon
Hydrogen Donor Count 0 Chemaxon
Polar Surface Area 43.37 Å2 Chemaxon
Rotatable Bond Count 2 Chemaxon
Refractivity 71.7 m3·mol-1 Chemaxon
Polarizability 26.3 Å3 Chemaxon
Number of Rings 3 Chemaxon
Bioavailability 1 Chemaxon
Rule of Five Yes Chemaxon
Ghose Filter Yes Chemaxon
Veber's Rule No Chemaxon
MDDR-like规则 No Chemaxon
Predicted ADMET Features
Property Value Probability
Human Intestinal Absorption + 1.0
Blood Brain Barrier + 0.9051
Caco-2 permeable + 0.8206
P-glycoprotein substrate Non-substrate 0.6289
P-glycoprotein inhibitor I Inhibitor 0.5099
P-glycoprotein inhibitor II Non-inhibitor 0.534
Renal organic cation transporter Non-inhibitor 0.8467
CYP450 2C9 substrate Non-substrate 0.7584
CYP450 2D6 substrate Non-substrate 0.8872
CYP450 3A4 substrate Non-substrate 0.5965
CYP450 1A2 substrate Inhibitor 0.9594
CYP450 2C9 inhibitor Inhibitor 0.8996
CYP450 2D6 inhibitor Non-inhibitor 0.9457
CYP450 2C19 inhibitor Inhibitor 0.6234
CYP450 3A4 inhibitor Non-inhibitor 0.8639
CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.6618
Ames test AMES toxic 0.6006
Carcinogenicity Non-carcinogens 0.8733
Biodegradation Not ready biodegradable 0.8575
Rat acute toxicity 2.4052 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.944
hERG inhibition (predictor II) Non-inhibitor 0.8898
ADMET data is predicted usingadmetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
Spectrum Spectrum Type Splash Key
Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available

Targets

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Details 1.Vitamin K-dependent gamma-carboxylase
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Gamma-glutamyl carboxylase activity
Specific Function
Mediates the vitamin K-dependent carboxylation of glutamate residues to calcium-binding gamma-carboxyglutamate (Gla) residues with the concomitant conversion of the reduced hydroquinone form of vit...
Gene Name
GGCX
Uniprot ID
P38435
Uniprot Name
Vitamin K-dependent gamma-carboxylase
分子量
87560.065 Da
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. [Article]
  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. [Article]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
  4. Source [Link]

Drug created at June 13, 2005 13:24 / Updated at May 07, 2021 21:23