Acenocoumarol

Structural formula
	1: 1 mixture ( racemate )
General
Non-proprietary name	Acenocoumarol
other names	( RS ) -4-Hydroxy-3- [1- (4-nitrophenyl) -3-oxobutyl] coumarin; DL -4-hydroxy-3- [1- (4-nitrophenyl) -3-oxobutyl] coumarin; (±) -4-Hydroxy-3- [1- (4-nitrophenyl) -3-oxobutyl] coumarin;
Molecular formula	C 19 H 15 NO 6
External identifiers / databases
EC number	205-807-3
ECHA InfoCard	100.005.281
PubChem	54676537
DrugBank	DB01418
Wikidata	Q304088
Drug information
ATC code	B01 AA07
Drug class	Anticoagulants
Mechanism of action	Vitamin K antagonist
properties
Molar mass	353,33 g · mol -1
Physical state	firmly
Melting point	196-199 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances Caution
H and P phrases	H: 302-315-319-335-361
	P: 261-305 + 351 + 338
Toxicological data	513 mg kg −1 ( LD 50 , rat , oral )
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Acenocoumarol (also: acenocoumarol) is a drug from the drug class of anticoagulants . Chemically, acenocumarol is one of the 4-hydroxycoumarins .

Mechanism of action

Acenocoumarol sets the clotting tendency of blood down and prevents the formation of blood clots (thrombosis) in front. It works by blocking vitamin K , which is necessary for the formation of blood clotting factors II , VII , IX and X in the liver .

application areas

Acenocoumarol is indicated for the treatment and prevention of diseases which are associated with a pathologically increased tendency to clot and which can lead to the formation of blood clots. For example:

Atrial fibrillation
Heart valve replacement (mechanical)
deep vein thrombosis
Pulmonary embolism
Thrombophilia
Antiphopholipid syndrome

Contraindications

known hypersensitivity to the active ingredient and related anti-clotting drugs (coumarins)
pregnancy
Stomach - intestinal ulcers
Bleeding in the gastrointestinal tract, urinary tract and respiratory system
Cerebral hemorrhage
Pericardium effusion
Inflammation of the lining of the heart

severe hypertension

severe liver or kidney disease

increased bleeding tendency z. B. after operations

Dangerous at

Hyperthyroidism
Tumors
Kidney disease
impaired liver function
Inflammation, infection
Heart failure
epilepsy
elderly patients

Interactions

are possible with the following other drugs, among others:

Gout remedies

different hormones

Antibiotics and sulfonamides

Agents against arrhythmias

Dehydrating agent

Means against lipid metabolism disorders

Medicines for diabetes mellitus

other anti-coagulant preparations

Pain reliever and rheumatism medium

certain medicines (including ointments) for fungal infections

Drugs for epilepsy

birth control pills

Medicines for certain diseases of the stomach

Due to their high vitamin K content, fresh vegetables (spinach, cabbage) can reduce the anticoagulant effect of acenocoumarol, which must be taken into account with regard to the diet with foods with a high vitamin K content.

dosage

Acenocoumarol is taken once a day. Regular laboratory controls to determine the coagulability of the blood and constant adjustment of the dose to the results obtained are necessary.

Trade names

Sintrom (A, CH, NL, ES, I), Sinthrome (GB)

Individual evidence

^ The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 7, ISBN 978-0-911910-00-1 .

↑ There is not yet a harmonized classification for this substance . A labeling of acenocoumarol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was accessed on December 16, 2019, is reproduced from a self-classification by the distributor .

↑ Acenocoumarol data sheet from Sigma-Aldrich , accessed on February 16, 2020 ( PDF ).

↑ Entry on acenocumarol in the ChemIDplus database of the United States National Library of Medicine (NLM), accessed on December 16, 2019.

[MERCK_Index-1] The Merck Index: An Encyclopedia of Chemicals, Drugs, and Biologicals , 14th Edition (Merck & Co., Inc.), Whitehouse Station, NJ, USA, 2006; P. 7, ISBN 978-0-911910-00-1 .

[2] Template: CL Inventory / not harmonized There is not yet a harmonized classification for this substance . A labeling of acenocoumarol in the Classification and Labeling Inventory of the European Chemicals Agency (ECHA), which was accessed on December 16, 2019, is reproduced from a self-classification by the distributor .