ANISINDIONE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C16H12O3
Molecular Weight	252.2647
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=CC=C(C=C1)C2C(=O)C3=CC=CC=C3C2=O

InChI

InChIKey=XRCFXMGQEVUZFC-UHFFFAOYSA-N

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

HIDE SMILES / InChI

Molecular Formula	C16H12O3
Molecular Weight	252.2647
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.rxlist.com/miradon-drug.htm
Curator's Comment: description was created based on several sources, including: http://www.druglib.com/activeingredient/anisindione/ | http://en.pharmacodia.com/web/drug/1_7940.html

Anisindione (brand name Miradon) is a synthetic anticoagulant and an indanedione derivative with action similar to these of Warfarin. It is indicated 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. 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. Hemorrhage and/or necrosis are among the hazards of treatment with any anticoagulant and are the main serious complications of therapy. Drugs that have been reported to diminish oral anticoagulant response, ie, decreased prothrombin time response, in man significantly include: adrenocortical steroids; alcohol; antacids; antihistamines; barbiturates and others.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Vitamin K-dependent gamma-carboxylase 6 Target ID: CHEMBL2012 Sources: http://www.druglib.com/activeingredient/anisindione/	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Venous thrombosis 9 Sources: http://www.rxlist.com/miradon-drug/indications-dosage.htm	Preventing	Approved 8583	MIRADON Approved Use 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. Launch Date 1957
Atrial fibrillation with embolization 1 Sources: http://www.rxlist.com/miradon-drug/indications-dosage.htm	Primary	Approved 8583	MIRADON Approved Use 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. Launch Date 1957
Pulmonary embolism 19 Sources: http://www.rxlist.com/miradon-drug/indications-dosage.htm	Preventing	Approved 8583	MIRADON Approved Use 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. Launch Date 1957
Coronary occlusion 1 Sources: http://www.rxlist.com/miradon-drug/indications-dosage.htm	Primary	Approved 8583	MIRADON Approved Use 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. Launch Date 1957

T_1/2

Value	Dose	Co-administered	Analyte	Population
4 day OTHER https://www.pharmacompass.com/chemistry-chemical-name/anisindione	unknown, oral		ANISINDIONE plasma	Homo sapiens population: UNKNOWN age: UNKNOWN sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
600 mg multiple, oral Studied dose Dose: 600 mg Route: oral Route: multiple Dose: 600 mg Sources: https://pubmed.ncbi.nlm.nih.gov/13520554	unhealthy, 47 - 89 Health Status: unhealthy Age Group: 47 - 89 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/13520554	Sources: https://pubmed.ncbi.nlm.nih.gov/13520554

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:133809	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:133809
eMolecules	1985514	https://www.emolecules.com/cgi-bin/more?vid=1985514
MolPort	MolPort-002-318-562	https://www.molport.com/shop/molecule-link/MolPort-002-318-562
ZINC	ZINC000100015486	http://zinc15.docking.org/substances/ZINC000100015486

PubMed

Title	Date	PubMed
Prediction of pharmacological and xenobiotic responses to drugs based on time course gene expression profiles.	2009-12-02	19956587
Anticoagulation with anisindione in a patient with a warfarin-induced skin eruption.	2003-04	12680483
Anticoagulation with anisindione in patients who are intolerant of warfarin.	1994-06	8172181
Evaluation of anticoagulant therapy with anisindione (miradon).	1959-05-15	13652026

Patents

Sample Use Guides

In Vivo Use Guide

Initial dosage of anisindione is 300 mg the first day, 200 mg the second day, and 100 mg the third day. Maintenance dosage will vary between 25 to 250 mg a day.

Route of Administration: Oral

In Vitro Use Guide

Unknown

Substance Class	Chemical Created by `admin` on `Mon Mar 31 17:51:33 GMT 2025` Edited by `admin` on `Mon Mar 31 17:51:33 GMT 2025`
Record UNII	S747T1ERAJ
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MIRADON

Preferred Name

English

ANISINDIONE

Official Name

English

2-(P-METHOXYPHENYL)INDANE-1,3-DIONE

Common Name

English

Anisindione [WHO-DD]

Common Name

English

ANISINDIONE [HSDB]

Common Name

English

ANISINDIONE [MART.]

Common Name

English

NSC-759629

Code

English

ANISINDIONE [MI]

Common Name

English

ANISINDIONE [ORANGE BOOK]

Common Name

English

ANISINDIONE [VANDF]

Common Name

English

anisindione [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C263