2-PHENYL-1,3-INDANDIONE

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
2-PHENYL-1,3-INDANDIONE Structure
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)
Fp 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.
pkapKa 4.09(H2O,t =25,I=0.1) (Uncertain)
form powder to crystal
color White to Light yellow
Merck 14,7234
CAS DataBase Reference83-12-5(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 Data83-12-5(Hazardous Substances Data)
MSDS Information
ProviderLanguage
ACROS English
SigmaAldrich English
2-PHENYL-1,3-INDANDIONE Usage And Synthesis
DescriptionPhenindione 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 Propertieslight yellow fluffy fine flakes
UsesOral anticoagulant (indanedione).
UsesLike 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.
DefinitionChEBI: 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 nameHedulin (Sanofi Aventis).
Clinical UseAnticoagulant
SynthesisPhenindione, 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.

Synthesis_83-12-5

Drug interactionsPotentially 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





MetabolismHepatically metabolised. Metabolites of phenindione often colour the urine pink or orange.
Purification MethodsCrystallise 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-INDANDIONE Preparation Products And Raw materials
1H-Indene-1,3(2H)-dione, 2-hydroxy-2-(2-hydroxy-4,5-dimethoxyphenyl)- 2-(2-BROMOPHENYL)INDANE-1,3-DIONE (Dihydroxy-3,4 phenyl)-2 hydroxy-2 indanedione-1,3 [French] CHEMBRDG-BB 5303536 2-P-ANISYL-1,3-INDANDIONE Bromindione 1H-Indene-1,3(2H)-dione, 2-hydroxy-2-(4-hydroxy-3-methoxyphenyl)- 2-PHENYL-1,3-INDANDIONE 2-Hydroxy-2-(2-hydroxy-p-tolyl)-1,3-indandione 2-(4-METHYLPHENYL)-1H-INDENE-1,3(2H)-DIONE [2-(1-NAPHTHYL)-1,3-DIOXO-2,3-DIHYDRO-1H-INDEN-2-YL]ACETIC ACID FLUINDAROL oxazidione 2-naphthalen-1-ylindene-1,3-dione fluindione 1H-Indene-1,3(2H)-dione, 2-(4-ethyl-2-hydroxyphenyl)-2-hydroxy- 2-BENZYL-2-(4-METHOXYPHENYL)-1H-INDENE-1,3(2H)-DIONE TIMTEC-BB SBB001033

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