Acenocoumarol

(BAN, rINN)
Acenocoumarol Chemical formula
Synonyms: Acénocoumarol; Acenocoumarolum; Acenocumarin; Acenocumarol; Acenokumarol; Asenokumarol; G-23350; Nicoumalone; Nikumalon. (RS)-4-Hydroxy-3-[1-(4-nitrophenyl)-3-oxobutyl]coumarin.
Cyrillic synonym: Аценокумарол.

💊 Chemical information

Chemical formula: C19H15NO6 = 353.3.
CAS — 152-72-7.
ATC — B01AA07.
ATC Vet — QB01AA07.

Pharmacopoeias.

In Br. and Pol.

BP 2008

(Acenocoumarol). An almost white to buff-coloured odourless or almost odourless powder. It exhibits polymorphism. Practically insoluble in water and in ether; slightly soluble in alcohol and in chloroform; dissolves in aqueous solutions of alkali hydroxides.

💊 Adverse Effects, Treatment, and Precautions

Effects on the fetus.

In a group of women who received acenocoumarol for anticoagulant prophylaxis of mechanical heart valves during pregnancy,1 fetal loss occurred in 13 of 61 pregnancies where oral anticoagulation was continued during the first trimester. Apart from 1 case of hydrocephalus no malformations were reported in the remaining neonates.
1. Meschengieser SS, et al. Anticoagulation in pregnant women with mechanical heart valve prostheses. Heart 1999; 82: 23–6.

💊 Interactions

The interactions associated with oral anticoagulants are discussed in detail under warfarin. Specific references to interactions involving acenocoumarol can be found there under the headings for the following drug groups: analgesics; antiarrhythmics; antibacterials; antidepressants; antifungals; antigout drugs; antihistamines; antineoplastics; antiplatelets; antivirals; diuretics; gastrointestinal drugs; immunosuppressants; lipid regulating drugs; sex hormones; and vaccines.

💊 Pharmacokinetics

Acenocoumarol is readily absorbed from the gastrointestinal tract and is excreted chiefly in the urine mainly as metabolites. It is extensively bound to plasma proteins. Figures reported for elimination half-life vary; UK licensed product information gives a range of 8 to 11 hours. Acenocoumarol crosses the placenta; only small quantities have been detected in breast milk. It is given as a racemic mixture; the R-isomer is more potent. The stereo-isomers have different pharmacokinetics. Metabolism of the S-isomer is mediated mainly by the cytochrome P450 isoenzyme CYP2C9, which shows genetic polymorphism; other isoenzymes as
well are involved in the metabolism of the R-isomer.
1. Ufer M. Comparative pharmacokinetics of vitamin K antagonists: warfarin, phenprocoumon and acenocoumarol. Clin Pharmacokinet 2005; 44: 1227–46.

💊 Uses and Administration

Acenocoumarol is an oral coumarin anticoagulant with actions similar to those of warfarin. It is used in the management of thromboembolic disorders. The usual dose is 4 to 12 mg on the first day and 4 to 8 mg on the second day; subsequent maintenance doses range from 1 to 8 mg depending on the response. Acenocoumarol is given in a single dose at the same time every day.

💊 Preparations

BP 2008: Acenocoumarol Tablets.

Proprietary Preparations

Arg.: Acenotromb; Antitrom; Azecar; Cumarol; Fortonol; Saxion; Sintrom; Austria: Sintrom; Belg.: Sintrom; Canad.: Sintrom; Chile: Acenox; Coarol; Isquelium; Neo-Sintrom; Fr.: Mini-sintrom; Sintrom; Gr.: Sintrom; Hung.: Syncumar; India: Acitrom; Israel: Sintrom; Ital.: Sintrom; Mex.: Sintrom; Neth.: Sintrom Mitis; Pol.: Sintrom; Syncumar; Port.: Sintrom; Spain: Sintrom; Switz.: Sintrom; UK: Sinthrome.
Published October 17, 2018.