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2-PHENYL-1,3-INDANDIONE

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2-PHENYL-1,3-INDANDIONE Basic information

Product Name:
2-PHENYL-1,3-INDANDIONE
Synonyms:
  • AURORA KA-4422
  • 2-PHENYL-1,3-INDANDIONE
  • 2-PHENYL-1,3-INDANEDIONE
  • 2-PHENYL-1,3-DIKETOHYDRINDENE
  • 2-PHENYL-1H-INDEN-1,3(2H)-DIONE
  • PHENYLINDIONE
  • PHENINDIONE
  • PHENINDONE
CAS:
83-12-5
MF:
C15H10O2
MW:
222.24
EINECS:
201-454-4
Product Categories:
  • HEDULIN
  • Indane/Indanone and Derivatives
Mol File:
83-12-5.mol
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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)
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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

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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.]

2-PHENYL-1,3-INDANDIONESupplier

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