83-12-5 Usage
Description
2-PHENYL-1,3-INDANDIONE, also known as Phenindione, is an indanedione class compound that functions as an anticoagulant and vitamin K antagonist. It inhibits the reduction of vitamin K1 epoxide to vitamin K1 by vitamin K1 epoxide reductase in a concentration-dependent manner, thereby affecting prothrombin synthesis and the conversion of vitamin K1 epoxide to vitamin K1 in vivo.
Used in Pharmaceutical Industry:
2-PHENYL-1,3-INDANDIONE is used as an oral anticoagulant for preventing and treating thrombosis, thrombophlebitis, and thromboembolism. It acts by altering the biosynthesis of coagulant proteins in the liver, similar to coumarin derivatives.
Used in Atherosclerosis and Thrombosis Research:
In rat models of diet-induced atherosclerosis or intravascular thrombosis, dietary administration of 2-PHENYL-1,3-INDANDIONE has been shown to inhibit aortic atherosclerosis or intracardial thrombosis, respectively.
However, due to several side effects such as polyurea, polydipsia, tachycardia, and others, 2-PHENYL-1,3-INDANDIONE is rarely used in practical medicine.
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.]
Check Digit Verification of cas no
The CAS Registry Mumber 83-12-5 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 8 and 3 respectively; the second part has 2 digits, 1 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 83-12:
(4*8)+(3*3)+(2*1)+(1*2)=45
45 % 10 = 5
So 83-12-5 is a valid CAS Registry Number.
InChI:InChI=1/C15H10O2/c16-14-11-8-4-5-9-12(11)15(17)13(14)10-6-2-1-3-7-10/h1-9,16H
83-12-5Relevant articles and documents
Synthesis and properties of macroheterocyclic compounds containing 1-imino-2-phenyl-1H-inden-3-amine fragments
Berezina,Fomina
, (2014)
Reaction of 1-imino-2-phenyl-1H-inden-3-amine with 3,3′-dichloro-, 2,2′-disulfo-, and 2,2′-dinitrobiphenyl-4,4′-diamines gave 2: 1 and 1: 2 linear condensation products and symmetrical macroheterocycles. The products were characterized by the IR, UV, and
Reinvestigation of Atipamezole Synthesis and Preparation of New Analogs
Karrabi, Behzad,Fakhraian, Hossein,Moghimi, Abolghasem
, p. 403 - 408 (2019/07/16)
-
Hydrindene-1,3-dione compound catalysis synthetic method
-
Paragraph 0045 - 0048, (2016/10/07)
The present invention relates to a formula (II) shown hydrindene-1,3-dione compound catalysis synthetic method which is as follows: in an organic solvent and under a nitrogen atmosphere, in the presence of a catalyst, an oxidant, and an organic ligand and an adjuvant, self cyclization of a formula (I) compound is performed, the formula (II) compound is obtained by after-treatment after the end of the reaction, the method uses the new catalyst, the oxidant, the organic ligand, the organic solvent and the adjuvant for comprehensive selection and optimization to achieve material high-speed conversion, the yield of the target product can be greatly improved, the needs of industrial production can be better met, and the method has a broad market prospect.
