4-Hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2H-1-benzopyran-2-on

Bezeichnung:4-Hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2H-1-benzopyran-2-on

CAS-Nr152-72-7

Englisch Name:ACENOCOUMAROL

CBNumberCB9114003

SummenformelC19H15NO6

Molgewicht353.33

MOL-Datei152-72-7.mol

Synonyma

Acenocoumarol

4-Hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2H-1-benzopyran-2-on

4-Hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2H-1-benzopyran-2-on physikalisch-chemischer Eigenschaften

Schmelzpunkt	196-1990C
Siedepunkt	486.76°C (rough estimate)
Dichte	1.3979 (rough estimate)
Brechungsindex	1.5000 (estimate)
storage temp.	-20°C Freezer
Löslichkeit	DMSO, heptane and xylene: ≥17mg/mL
pka	pKa 4.7 (Uncertain)
Aggregatzustand	powder
Farbe	white to tan

Sicherheit

Kennzeichnung gefährlicher	Xn
R-Sätze:	63-22-36/37/38
S-Sätze:	26-36/37
RIDADR	2811
WGK Germany	3
RTECS-Nr.	GN4900000
HS Code	2932.20.2000
HazardClass	6.1(b)
PackingGroup	III
Giftige Stoffe Daten	152-72-7(Hazardous Substances Data)
Toxizität	LD50 orally in mice, rats: 1470, 1000 mg/kg (Leroux, Jamain)

Gefahreninformationscode (GHS)

ACENOCOUMAROL Chemische Eigenschaften,Einsatz,Produktion Methoden

Chemische Eigenschaften
White Crystalline Solid
Originator
Sintrom ,Geigy ,US ,1957
Verwenden
Anticoagulant agent: Vitamin K antagonist
Verwenden
antimicrobial
Verwenden
S-Enantiomer of Acenocoumarol. Vitamin K antagonist; structurally similar to Warfarin. Anticoagulant
Verwenden
R-Enantiomer of Acenocoumarol. Vitamin K antagonist; structurally similar to Warfarin. Anticoagulant
Definition
ChEBI: A hydroxycoumarin that is warfarin in which the hydrogen at position 4 of the phenyl substituent is replaced by a nitro group.
Manufacturing Process
16 parts of 4-hydroxycoumarin and 19 parts of 4-nitrobenzalacetoneare thoroughly mixed and heated for 12-14 hours in an oil bath, the temperature of which is between 135°C and 140°C. After cooling, the melt is dissolved in a little acetone. The solution is slowly added to a lye made up from 6 parts of sodium hydroxide in 400 parts of water while stirring and then the mixture is stirred for 30 minutes. A little animal charcoal is then added, the mixture is stirred for a further 15 minutes, 400 parts of water are added and the charcoal and undissolved components are separated by filtration under suction. The clear solution is made acid to Congo red paper with hydrochloric acid and the product which is precipitated is filtered off under suction. 3-[α- (4'-Nitrophenyl)-β-acetylethyl]-4-hydroxycoumarin is obtained. MP 196-199°C.
It should be noted that the process is akin to that for Warfarin except that 4- nitrobenzalacetone replaces benzalacetone as a raw material.
Therapeutic Function
Anticoagulant, Vitamin
Clinical Use
Anticoagulant
Sicherheitsprofil
Poison by intraperitoneal route.Moderately toxic by ingestion. A human teratogen by anunspecified route. When heated to decomposition it emitstoxic fumes such as NOx.
Synthese
Acenocoumarin, 3-(α-acetonyl-p-nitrobenzyl)-4-hydroxycoumarin (24.1.11), is synthesized by a scheme completely analogous to making warfarin, but using p-nitrobenzalacetone.
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, fibrates, clopidogrel, cranberry juice, danazol, dipyridamole, disulfiram, dronedarone, esomeprazole, ezetimibe, fibrates, fluconazole, flutamide, fluvastatin, grapefruit juice, itraconazole, ketoconazole, levamisole, levofloxacin, macrolides, methylphenidate, metronidazole, miconazole, nalidixic acid, neomycin, norfloxacin, NSAIDs, ofloxacin, omeprazole, pantoprazole, paracetamol, penicillins, propafenone, ritonavir, rosuvastatin, SSRIs, simvastatin, sulfinpyrazone, sulphonamides, tamoxifen, testosterone, tetracyclines, thyroid hormones, tigecycline, toremifene, tramadol, trimethoprim, valproate, vitamin E, voriconazole.
Anticoagulant effect decreased by: acitretin, azathioprine, carbamazepine, enteral feeds, enzalutamide, fosphenytoin, griseofulvin, oral contraceptives, phenobarbital, phenytoin, primidone, rifamycins, St John’s wort (avoid), sucralfate, vitamin K.
Anticoagulant effects enhanced / reduced by: anion exchange resins, corticosteroids, dietary changes, efavirenz, fosamprenavir, tricyclics.
Analgesics: increased risk of bleeding with IV diclofenac and ketorolac - avoid concomitant use.
Anticoagulants: increased risk of haemorrhage with apixaban, dabigatran, edoxaban and rivaroxaban - avoid.
Antidiabetic agents: enhanced hypoglycaemic effect with sulphonylureas also possible changes to anticoagulant effect.
Ciclosporin: there have been a few reports of altered anticoagulant effect; decreased ciclosporin levels have been seen rarely.
Cytotoxics: increased risk of bleeding with erlotinib; enhanced anticoagulant effect with capecitabine, etoposide, fluorouracil, ifosfamide, sorafenib and tegafur; reduced effect with mercaptopurine and mitotane.
Stoffwechsel
Acenocoumarol is extensively metabolised, although the metabolites appear to be pharmacologically inactive in man. 29% is excreted in the faeces and 60% in the urine, with less than 0.2% of the dose being renally excreted unchanged.

ACENOCOUMAROL Upstream-Materialien And Downstream Produkte

4-Hydroxy-3-(1-(4-nitrophenyl)-3-oxobutyl)-2H-1-benzopyran-2-on Anbieter Lieferant Produzent Hersteller Vertrieb Händler.

152-72-7, ACENOCOUMAROL Verwandte Suche:

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