2-P-ANISYL-1,3-INDANDIONE

Absorption

Accumulation does not occur with repeated dosing.

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.

Chemical properties

Slightly beige or yellow powder

Originator

Miradon,Schering,US,1960

The Uses of 2-P-ANISYL-1,3-INDANDIONE

radiopaque agent

The Uses of 2-P-ANISYL-1,3-INDANDIONE

Anisindione is a synthetic anticoagulant that prevents the formation of active procoagulation factors and proteins in the liver.

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.

Indications

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.

Definition

ChEBI: A cyclic beta-diketone consisting of indane-1,3-dione having a 4-methoxyphenyl substituent at the 4-position.

Manufacturing Process

To a hot solution of 20.6 g of sodium in 400 ml of absolute ethanol, there is added a solution of 110 g of phthalide and 110 g of p-methoxybenzaldehyde. A vigorous reaction ensues and one-half of the alcohol is distilled off over a two hour period. Ice and water are added to the red solution and the diluted solution is acidified with hydrochloric acid. The resulting gum solidifies and the aqueous phase is removed by decantation. The crude solid is recrystallized twice from two liters of ethanol yielding 2-(p-methoxyphenyl)-1,3-indandione as pale yellow crystals, MP 155-156°C.

brand name

Miradon (Schering).

Therapeutic Function

Anticoagulant

General Description

Anisindione, 2-(p-methoxyphenyl)-1,3-indandione, 2-(p-anisyl)-1,3-indandione (Miradon), is ap-methoxy congener of phenindione. It is a white, crystallinepowder, slightly soluble in water, tasteless, and absorbedwell after oral administration.
In instances when the urine may be alkaline, an orangecolor may be detected. This is caused by metabolic productsof anisindione and is not hematuria.

Pharmacokinetics

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.

Metabolism

Not Available

Purification Methods

Crystallise anisidinone from acetic acid or EtOH. [Horeau & Jacqius Bull Soc Chim Fr 53 1948, Koelsch J Am Chem. Soc 58 1331 1936, Beilstein 8 III 2931.]