ACENOCOUMAROL

ACENOCOUMAROL Basic information
Product Name:ACENOCOUMAROL
Synonyms:acenocoumarin;acenocumarol;acenokumarin;ascumar;g-23,350;g23350;g-23350;Nicoumalone(B.P.1980)
CAS:152-72-7
MF:C19H15NO6
MW:353.33
EINECS:205-807-3
Product Categories:Aromatics;Chiral Reagents;Heterocycles;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:152-72-7.mol
ACENOCOUMAROL Structure
ACENOCOUMAROL Chemical Properties
Melting point 196-1990C
Boiling point 486.76°C (rough estimate)
density 1.3979 (rough estimate)
refractive index 1.5000 (estimate)
storage temp. -20°C Freezer
solubility DMSO, heptane and xylene: ≥17mg/mL
pkapKa 4.7 (Uncertain)
form powder
color white to tan
Safety Information
Hazard Codes Xn
Risk Statements 63-22-36/37/38
Safety Statements 26-36/37
RIDADR 2811
WGK Germany 3
RTECS GN4900000
HS Code 2932.20.2000
HazardClass 6.1(b)
PackingGroup III
Hazardous Substances Data152-72-7(Hazardous Substances Data)
ToxicityLD50 orally in mice, rats: 1470, 1000 mg/kg (Leroux, Jamain)
MSDS Information
ACENOCOUMAROL Usage And Synthesis
Chemical PropertiesWhite Crystalline Solid
OriginatorSintrom ,Geigy ,US ,1957
UsesR-Enantiomer of Acenocoumarol. Vitamin K antagonist; structurally similar to Warfarin. Anticoagulant
UsesS-Enantiomer of Acenocoumarol. Vitamin K antagonist; structurally similar to Warfarin. Anticoagulant
Usesantimicrobial
UsesAnticoagulant agent: Vitamin K antagonist
DefinitionChEBI: A hydroxycoumarin that is warfarin in which the hydrogen at position 4 of the phenyl substituent is replaced by a nitro group.
Manufacturing Process16 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 FunctionAnticoagulant, Vitamin
Clinical UseAnticoagulant
Safety ProfilePoison by intraperitoneal route.Moderately toxic by ingestion. A human teratogen by anunspecified route. When heated to decomposition it emitstoxic fumes such as NOx.
SynthesisAcenocoumarin, 3-(α-acetonyl-p-nitrobenzyl)-4-hydroxycoumarin (24.1.11), is synthesized by a scheme completely analogous to making warfarin, but using p-nitrobenzalacetone.
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, 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.







MetabolismAcenocoumarol 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 Preparation Products And Raw materials
Raw materials4-Hydroxycoumarin-->4-Phenyl-1-butene
Argatroban rac 6-Hydroxy Acenocoumarol PHENPROCOUMON (R)-(+)-WARFARIN 3-(4-Nitrophenyl)propanoic acid 4-Hydroxy-3-benzylcoumarin 1-butyl-4-nitrobenzene 4-HYDROXY-3-METHYL-CHROMEN-2-ONE ACENOCOUMAROL EPA(CRM STANDARD) nitrofarin 6-PHENOXY-HEXAN-2-ONE ACENOCOUMAROL USP(CRM STANDARD) Acenocoumarol-D5 ACENOCOUMAROL rac 7-Hydroxy Acenocoumarol 2-PHENYLPROPANE-2-D1 1-SEC-BUTYL-4-NITROBENZENE

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