2-PHENYL-1,3-INDANDIONE Chemical Properties

Melting point:

144-148 °C(lit.)

Boiling point:

243.3 °C (0.3 mmHg)

Density 

1.1404 (rough estimate)

refractive index 

1.6600 (estimate)

Flash point:

208 °C

storage temp. 

Inert atmosphere,Room Temperature

solubility 

Very slightly soluble in water; slightly soluble in ethanol (96%) and in ether. Solutions are yellow to red.

form 

powder to crystal

pka

pKa 4.09(H2O,t =25,I=0.1) (Uncertain)

color 

White to Light yellow

Merck 

14,7234

CAS DataBase Reference

83-12-5(CAS DataBase Reference)

Safety Information

Hazard Codes 

T

Risk Statements 

25-43

Safety Statements 

36/37/39-45

RIDADR 

UN 2811 6.1/PG 3

WGK Germany 

3

RTECS 

NK6125000

HS Code 

2914.39.9000

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

83-12-5(Hazardous Substances Data)

MSDS

• Language:English Provider:ACROS
• Language:English Provider:SigmaAldrich

2-PHENYL-1,3-INDANDIONE Usage And Synthesis

Description

Phenindione is an anticoagulant and vitamin K antagonist. It inhibits the reduction of vitamin K₁ epoxide to vitamin K₁ by vitamin K₁ epoxide reductase in rat liver homogenates in a concentration-dependent manner. In vivo, phenindione (500 mg/kg) inhibits prothrombin synthesis and conversion of vitamin K₁ epoxide to vitamin K₁ in rats by 50 and 57%, respectively. Dietary administration of phenindione (4 mg/kg per day) inhibits aortic atherosclerosis or intracardial thrombosis in rat models of diet-induced atherosclerosis or intravascular thrombosis, respectively.

Chemical Properties

light yellow fluffy fine flakes

Uses

Oral anticoagulant (indanedione).

Uses

Like coumarin derivatives, phenindione, a compound of the indandione class, acts by altering biosynthesis of coagulant proteins in the liver. It is used for preventing and treating thrombosis, thrombophlebitis, and thromboembolism. However, because of a number of side effects such as polyurea, polydipsia, tachycardia, and others, it is rarely used in practical medicine.

Definition

ChEBI: Phenindione is a beta-diketone and an aromatic ketone. It has a role as an anticoagulant. It derives from a hydride of an indane.

brand name

Hedulin (Sanofi Aventis).

Clinical Use

Anticoagulant

Synthesis

Phenindione, 3-phenylindan-1,3-dion (24.1.16), is synthesized in two ways. The first consists of condensating benzaldehyde with phthalide in the presence of sodium ethoxide. Evidently, the resulting phenylmethylenphthalide (24.1.15) rearranges under the reaction conditions to give the desired phenindione (24.1.16). The second method consists of condensation of phenylacetic acid with phthalic anhydride, forming phenylmethylenphthalide (24.1.15), which rearranges further in the presence of sodium ethoxide to phenindione.

Drug interactions

Potentially hazardous interactions with other drugs There are many significant interactions with coumarins. Prescribe with care with regard to the following:
Anticoagulant effect enhanced by: alcohol, amiodarone, anabolic steroids, aspirin, aztreonam, bicalutamide, cephalosporins, chloramphenicol, cimetidine, ciprofloxacin, dronedarone, fibrates, clopidogrel, cranberry juice, danazol, dipyridamole, disulfiram, fibrates, grapefruit juice, levofloxacin, macrolides, metronidazole, nalidixic acid, neomycin, norfloxacin, NSAIDs, ofloxacin, paracetamol, penicillins, ritonavir, rosuvastatin, sulphonamides, thyroid hormones, testosterone, tetracyclines, tigecycline, tramadol, trimethoprim.
Anticoagulant effect decreased by: oral contraceptives, rifamycins, vitamin K.
Anticoagulant effects enhanced/reduced by: anion exchange resins, corticosteroids, dietary changes, enteral feeds.
Analgesics: increased risk of bleeding with IV diclofenac and ketorolac - avoid.
Anticoagulants: increased risk of haemorrhage with apixaban, dabigatran, edoxaban and rivaroxaban - avoid.
Ciclosporin: there have been a few reports of altered anticoagulant effect; decreased ciclosporin levels have been seen rarely

Metabolism

Hepatically metabolised. Metabolites of phenindione often colour the urine pink or orange.

Purification Methods

Crystallise the dione from EtOH (m 156o) or CHCl3 (m 148-150o). [Beilstein 7 H 808, 7 III 4100, 7 IV 2570.]

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