2-Phenyl-1H-inden-1,3(2H)-dion

Bezeichnung:2-Phenyl-1H-inden-1,3(2H)-dion

CAS-Nr83-12-5

Englisch Name:2-PHENYL-1,3-INDANDIONE

CBNumberCB3429480

SummenformelC15H10O2

Molgewicht222.24

MOL-Datei83-12-5.mol

Synonyma

Phenindion

2-Phenyl-1H-inden-1,3(2H)-dion

2-Phenyl-1H-inden-1,3(2H)-dion physikalisch-chemischer Eigenschaften

Schmelzpunkt	144-148 °C(lit.)
Siedepunkt	243.3 °C (0.3 mmHg)
Dichte	1.1404 (rough estimate)
Brechungsindex	1.6600 (estimate)
Flammpunkt	208 °C
storage temp.	Inert atmosphere,Room Temperature
Löslichkeit	Very slightly soluble in water; slightly soluble in ethanol (96%) and in ether. Solutions are yellow to red.
Aggregatzustand	powder to crystal
pka	pKa 4.09(H2O,t =25,I=0.1) (Uncertain)
Farbe	White to Light yellow
Merck	14,7234
CAS Datenbank	83-12-5(CAS DataBase Reference)

Sicherheit

Kennzeichnung gefährlicher	T
R-Sätze:	25-43
S-Sätze:	36/37/39-45
RIDADR	UN 2811 6.1/PG 3
WGK Germany	3
RTECS-Nr.	NK6125000
HS Code	2914.39.9000
HazardClass	6.1(b)
PackingGroup	III
Giftige Stoffe Daten	83-12-5(Hazardous Substances Data)

Gefahreninformationscode (GHS)

2-PHENYL-1,3-INDANDIONE Chemische Eigenschaften,Einsatz,Produktion Methoden

R-Sätze Betriebsanweisung:
R25:Giftig beim Verschlucken.
S-Sätze Betriebsanweisung:
S36/37/39:Bei der Arbeit geeignete Schutzkleidung,Schutzhandschuhe und Schutzbrille/Gesichtsschutz tragen.
S45:Bei Unfall oder Unwohlsein sofort Arzt zuziehen (wenn möglich, dieses Etikett vorzeigen).
Beschreibung
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.
Chemische Eigenschaften
light yellow fluffy fine flakes
Verwenden
Oral anticoagulant (indanedione).
Verwenden
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.
Trademarks
Hedulin (Sanofi Aventis).
Clinical Use
Anticoagulant
Synthese
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.
Arzneimittelwechselwirkung
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
Stoffwechsel
Hepatically metabolised. Metabolites of phenindione often colour the urine pink or orange.
läuterung methode
Crystallise the dione from EtOH (m 156o) or CHCl3 (m 148-150o). [Beilstein 7 H 808, 7 III 4100, 7 IV 2570.]

2-Phenyl-1H-inden-1,3(2H)-dion Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

83-12-5, 2-PHENYL-1,3-INDANDIONE Verwandte Suche:

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