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ACENOCOUMAROL

Product Name
ACENOCOUMAROL
CAS No.
152-72-7
Chemical Name
ACENOCOUMAROL
Synonyms
zotil;g23350;ascumar;g-23350;sintrom;syntrom;g-23,350;sinkumar;sinthrom;sintroma
CBNumber
CB9114003
Molecular Formula
C19H15NO6
Formula Weight
353.33
MOL File
152-72-7.mol
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ACENOCOUMAROL Property

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
pka
pKa 4.7 (Uncertain)
form 
powder
color 
white to tan
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Safety

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 Data
152-72-7(Hazardous Substances Data)
Toxicity
LD50 orally in mice, rats: 1470, 1000 mg/kg (Leroux, Jamain)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P302+P352IF ON SKIN: wash with plenty of soap and water.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML0074
Product name
Acenocoumarol
Purity
≥98% (HPLC)
Packaging
10mg
Price
$129
Updated
2024/03/01
Sigma-Aldrich
Product number
SML0074
Product name
Acenocoumarol
Purity
≥98% (HPLC)
Packaging
50mg
Price
$309.6
Updated
2024/03/01
TCI Chemical
Product number
A3186
Product name
Acenocoumarol
Packaging
50MG
Price
$139
Updated
2024/03/01
TCI Chemical
Product number
A3186
Product name
Acenocoumarol
Packaging
250MG
Price
$369
Updated
2024/03/01
Cayman Chemical
Product number
10010569
Product name
Acenocoumarol
Purity
≥98%
Packaging
10mg
Price
$57
Updated
2024/03/01
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ACENOCOUMAROL Chemical Properties,Usage,Production

Chemical Properties

White Crystalline Solid

Originator

Sintrom ,Geigy ,US ,1957

Uses

R-Enantiomer of Acenocoumarol. Vitamin K antagonist; structurally similar to Warfarin. Anticoagulant

Uses

S-Enantiomer of Acenocoumarol. Vitamin K antagonist; structurally similar to Warfarin. Anticoagulant

Uses

antimicrobial

Uses

Anticoagulant agent: Vitamin K antagonist

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

Safety Profile

Poison by intraperitoneal route.Moderately toxic by ingestion. A human teratogen by anunspecified route. When heated to decomposition it emitstoxic fumes such as NOx.

Synthesis

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.

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, 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.

Metabolism

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 Preparation Products And Raw materials

Raw materials

Preparation Products

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ACENOCOUMAROL Suppliers

Shanghai Boyle Chemical Co., Ltd.
Tel
021-50182298 021-50180596
Fax
+86-21-57758967
Email
sales@boylechem.com
Country
China
ProdList
2208
Advantage
55
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
Adamas Reagent, Ltd.
Tel
400-6009262 16621234537
Fax
021-64823266
Email
chenyj@titansci.com
Country
China
ProdList
14103
Advantage
59
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Daicel Chiral Technologies (China)CO.,LTD
Tel
021-50460086-9 15921403865
Fax
+86-21-50462321
Email
han_yajun@dctc.daicel.com
Country
China
ProdList
7189
Advantage
65
Sinopharm Chemical Reagent Co,Ltd.
Tel
86-21-63210123
Fax
86-21-63290778 86-21-63218885
Email
sj_scrc@sinopharm.com
Country
China
ProdList
9815
Advantage
79
Spectrum Chemical Manufacturing Corp.
Tel
021-021-021-67601398-809-809-809 15221380277
Fax
021-57711696
Email
marketing_china@spectrumchemical.com
Country
China
ProdList
9658
Advantage
60
TOKYO CHEMICAL INDUSTRY CO., LTD.
Tel
03-36680489
Fax
03-3668-0520
Email
Sales-JP@TCIchemicals.com
Country
Japan
ProdList
28387
Advantage
80
TCI Europe
Tel
320-37350700
Fax
+32 (0)37350701
Email
sales@tcieurope.eu
Country
Europe
ProdList
23671
Advantage
75
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View Lastest Price from ACENOCOUMAROL manufacturers

Dideu Industries Group Limited
Product
ACENOCOUMAROL 152-72-7
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons min
Release date
2021-08-04
Career Henan Chemical Co
Product
ACENOCOUMAROL 152-72-7
Price
US $1.00/ASSAYS
Min. Order
1ASSAYS
Purity
98%
Supply Ability
1kg,2kg,100kg
Release date
2019-07-09

152-72-7, ACENOCOUMAROLRelated Search:


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  • NICOUMALONE
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  • COUMARIN,3-(ALPHA-ACETONYL-PARA-NITROBENZYL)-4-HYDROXY-
  • (+)-3-(a-Acetonyl-4-nitrobenzyl)-4-hydroxycoumarin
  • (R)-(+)-Acenocoumarol
  • (R)-4-Hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-1-benzopyran-2-one
  • (R)-Acenocoumarol
  • (S)-(-)-Acenocoumarol
  • (S)-4-Hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-1-benzopyran-2-one
  • (S)-Acenocoumarol
  • ACENOCOUMAROL (NICOUMALONE)
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  • 4-Hydroxy-3-[(1R)-3-oxo-1-(4-nitrophenyl)butyl]-2H-1-benzopyran-2-one
  • NicoumaloneBp(Acenocoumarin)
  • 2-hydroxy-3-[1-(4-nitrophenyl)-3-oxo-butyl]chromen-4-one
  • 2-hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]chromen-4-one
  • 4-Hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]-2H-chromen-2-one
  • ACENOCOUMAROL USP/EP/BP
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  • F.?[[[[[1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indol-3-yl]acetyl]oxy]acetyl]oxy]aceticacid.