ACENOCOUMAROL

First approved in 1957

Details

Stereochemistry	RACEMIC
Molecular Formula	C19H15NO6
Molecular Weight	353.3255
Optical Activity	( + / - )
Defined Stereocenters	0 / 1
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(=O)CC(C1=CC=C(C=C1)[N+]([O-])=O)C2=C(O)C3=C(OC2=O)C=CC=C3

InChI

InChIKey=VABCILAOYCMVPS-UHFFFAOYSA-N

InChI=1S/C19H15NO6/c1-11(21)10-15(12-6-8-13(9-7-12)20(24)25)17-18(22)14-4-2-3-5-16(14)26-19(17)23/h2-9,15,22H,10H2,1H3

HIDE SMILES / InChI

Molecular Formula	C19H15NO6
Molecular Weight	353.3255
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Description
Sources: https://www.esciencecentral.org/journals/acenocoumarol-in-thromoembolic-disorders-2329-6607-1000157.php?aid=61383
Curator's Comment: Description was created based on several sources, including https://www.old.health.gov.il/units/pharmacy/trufot/alonim/4140.pdf | https://www.ncbi.nlm.nih.gov/pubmed/27730796

Acenocoumarol is mono-coumarin derivative with racemic mixture of R (+) and S (-) enantiomers. Acenocoumarol is structurally similar to vitamin K and is competitively able to inhibit the enzyme vitamin K-epoxide reductase. It exerts anticoagulant action by preventing the regeneration of reduced vitamin K by interfering with action of vitamin K epoxide reductase. Acenocoumarol is prescribed as the anticoagulant in various thromboembolic disorders.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Vitamin k epoxide reductase complex subunit 1 isoform 1 22 Target ID: CHEMBL1930 Sources: https://www.esciencecentral.org/journals/acenocoumarol-in-thromoembolic-disorders-2329-6607-1000157.php?aid=61383	Inhibitor 8504

Conditions

Condition	Modality	Highest Phase	Product
Venous thromboembolism 12 Sources: https://www.esciencecentral.org/journals/acenocoumarol-in-thromoembolic-disorders-2329-6607-1000157.php?aid=61383 https://www.ncbi.nlm.nih.gov/pubmed/27730796	Primary	Approved 8583	SINTROM Approved Use Prophylaxis and treatment of venous thromboembolism, Atrial fibrillation, Post-myocardial infarction (with increased risk for thromboembolic complications), Bioprosthetic heart valves, Mechanical heart valves
Atrial fibrillation 131 Sources: https://www.esciencecentral.org/journals/acenocoumarol-in-thromoembolic-disorders-2329-6607-1000157.php?aid=61383 https://www.ncbi.nlm.nih.gov/pubmed/27730796	Primary	Approved 8583	SINTROM Approved Use Prophylaxis and treatment of venous thromboembolism, Atrial fibrillation, Post-myocardial infarction (with increased risk for thromboembolic complications), Bioprosthetic heart valves, Mechanical heart valves
Post-myocardial infarction (with increased risk for thromboembolic complications) 2 Sources: https://www.esciencecentral.org/journals/acenocoumarol-in-thromoembolic-disorders-2329-6607-1000157.php?aid=61383 https://www.ncbi.nlm.nih.gov/pubmed/27730796	Primary	Approved 8583	SINTROM Approved Use Prophylaxis and treatment of venous thromboembolism, Atrial fibrillation, Post-myocardial infarction (with increased risk for thromboembolic complications), Bioprosthetic heart valves, Mechanical heart valves

C_max

Value	Dose	Co-administered	Analyte	Population
60 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12844136/	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:		ACENOCOUMAROL, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
360 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12844136/	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:		ACENOCOUMAROL, (R)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

AUC

Value	Dose	Co-administered	Analyte	Population
205.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12844136/	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:		ACENOCOUMAROL, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
2602 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12844136/	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:		ACENOCOUMAROL, (R)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

T_1/2

Value	Dose	Co-administered	Analyte	Population
1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12844136/	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:		ACENOCOUMAROL, (S)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED
8.8 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/12844136/	8 mg single, oral dose: 8 mg route of administration: Oral experiment type: SINGLE co-administered:		ACENOCOUMAROL, (R)- plasma	Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
MRP2 499	P-gp 2052 MRP1 113 MRP2 252 BCRP 697 CYP1A2 1197 CYP2C19 1119

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/27925230/	yes

Drug as victim

Target	Modality	Activity
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11038154/	major
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11038154/	minor
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/11038154/	minor
P-gp 2052	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27925230/ \| https://pubmed.ncbi.nlm.nih.gov/23663291/	weak
BCRP 697	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27925230/	yes
MRP1 113	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27925230/	yes
MRP2 252	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/27925230/	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:53766	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:53766
ChemicalBook	CB9114003	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9114003
eMolecules	902195	https://www.emolecules.com/cgi-bin/more?vid=902195
MolPort	MolPort-002-798-798	https://www.molport.com/shop/molecule-link/MolPort-002-798-798

PubMed

Title	Date	PubMed
Rofecoxib interaction with oral anticoagulant acenocoumarol.	2003-09	12898082
Acenocoumarol therapy in pediatric patients.	2003-08	12911587
Comparison of control and stability of oral anticoagulant therapy using acenocoumarol versus phenprocoumon.	2003-08	12888873
Low-molecular-weight heparin versus a coumarin for the prevention of recurrent venous thromboembolism in patients with cancer.	2003-07-10	12853587
Summaries for patients. How long should blood thinners be given to patients who have had a pulmonary embolism?	2003-07-01	12834333
Extended oral anticoagulant therapy after a first episode of pulmonary embolism.	2003-07-01	12834314
Major bleeding during combined treatment with indomethacin and low doses of acenocoumarol in a homozygous patient for 2C9*3 variant of cytochrome p-450 CYP2C9.	2003-07	12876643
Oral anticoagulant therapy: should doctors change the way they give patients explanations?	2003-07	12876642
Impact of pre-treatment INR level on the effect of intravenous low dose vitamin K in patients with excessive anticoagulation.	2003-07	12876628
Capillary whole blood testing by a new portable monitor. Comparison with standard determination of the international normalized ratio.	2003-07	12866369
Acenocoumarol pharmacokinetics in relation to cytochrome P450 2C9 genotype.	2003-07	12844136
Cluster-like headache due to warfarin therapy?	2003-07	12807529
[Excess antivitamin K in elderly hospitalised patients aged over 70. A one-year prospective survey].	2003-06-14	12876525
Pharmacokinetic study of the digoxin-acenocoumarol interaction in rabbits.	2003-06	12808292
Clozapine and venous thromboembolism: further evidence.	2003-05	12755667
Pharmacogenetics of oral anticoagulants.	2003-05	12724615
Experience with enoxaparin in patients with mechanical heart valves who must withhold acenocumarol.	2003-05	12695457
[Prevention of postoperative bleeding in patients taking oral anticoagulants. Effects of tranexamic acid].	2003-04	12750624
Low rate of bleeding and thrombotic complications of oral anticoagulant therapy independent of age in the real-practice of an anticoagulation clinic.	2003-04	12695750
Prevention of thromboembolism in patients with mitral stenosis and associated atrial fibrillation: effectiveness of low intensity (INR target 2) oral anticoagulant treatment.	2003-04	12669133
[Pharmacological interactions of statins].	2003-03-15	12681161
[The implications of thromboembolism in chronic heart failure].	2003-03-15	12635370
Genetic and environmental risk factors for oral anticoagulant overdose.	2003-03	12634980
A placebo-controlled pharmacodynamic and pharmacokinetic interaction study between tamsulosin and acenocoumarol.	2003-03	12630984
Compliance and stability of INR of two oral anticoagulants with different half-lives: a randomised trial.	2003-03	12624628
Safety and effectiveness of low dose oral vitamin K1 administration in asymptomatic out-patients on warfarin or acenocoumarol with excessive anticoagulation.	2003-02	12604423
Low incidence of hemorrhagic complications of oral anticoagulant therapy in patients with atrial fibrillation in the daily practice of an anticoagulation clinic.	2003-01	12690920
[Oral anticoagulation with vitamin K antagonists].	2003-01	12638470
[Identification of factors responsible for oral over-anticoagulation in outpatients with heart disease].	2003-01	12550002
The first experience with endovascular stenting of the iliac veins in patients suffering from post-thrombophlebitic disease.	2003	12811390
Acenocoumarol is not a safe alternative for anticoagulation in phenprocoumon-induced hepatic failure. Report of two cases.	2003	12743448
Ischaemic stroke in young people: a prospective and long-term follow-up study.	2003	12499721
[Acenocoumarol (Sintrom) and fluinidione (Previscan) in pediatrics after cardiac surgical procedures].	2002-11	12503504
Overanticoagulation associated with combined use of antibacterial drugs and acenocoumarol or phenprocoumon anticoagulants.	2002-11	12428081
Pharmacogenetics of acenocoumarol: cytochrome P450 CYP2C9 polymorphisms influence dose requirements and stability of anticoagulation.	2002-11	12414349
Thumbprinting due to ischemic colitis in a patient on oral anticoagulation.	2002-10-31	12403394
Extended venous thromboembolism prophylaxis after total hip replacement: a comparison of low-molecular-weight heparin with oral anticoagulant.	2002-10-28	12390061
Treatment with vitamin K antagonists: frequency of indications and appropriateness of continuation.	2002-10-10	12372923
The potential interaction between oral anticoagulants and acetaminophen in everyday practice.	2002-10	12426965
Relationship between international normalized ratio values, vitamin K-dependent clotting factor levels and in vivo prothrombin activation during the early and steady phases of oral anticoagulant treatment.	2002-10	12368163
No effect of acenocoumarol therapy on levels of endothelial activation markers in sickle cell disease.	2002-09	12221677
Intracranial bleeding: epidemiology and relationships with antithrombotic treatment in 241 cerebral hemorrhages in Reggio Emilia.	2002-09	12217807
[Warfarin fetopathy].	2002-07	12162160
Low dose oral vitamin K to reverse acenocoumarol-induced coagulopathy: a randomized controlled trial.	2002-07	12152676
[Oral anticoagulant treatment: practical aspects and significance of anticoagulant clinics].	2002-06	12471648
Initiation of oral anticoagulant therapy in orthopedic and surgical patients: an algorithm compared with routine dosing.	2002-06	12162272
Platelet aggregation in different antithrombotic regimens. Possible proaggregant effect of low level oral anticoagulation.	2002-05	12174518
Effect of low-dose aspirin on the international normalized ratio variability in patients with mechanical heart valve prostheses.	2002-03-08	12759515
[Patient education for patients treated with anticoagulants. Nursing care, a relationship voyage].	2002	12510430
[Acute renal insufficiency caused by bilateral arterial thrombosis in a patient undergoing heparin treatment].	2002	12369135

Patents

Sample Use Guides

In Vivo Use Guide

The dosing of Sintrom (acenocoumarol) must be individualized. The usual starting dose of Sintrom in a normal weight person is between 2 mg/day to 4 mg/day without administration of a loading dose, if the prothrombine time (PT)/ International Normalized Ratio (INR) value before the start of treatment is within the normal range. Treatment may also be initiated with a loading dose regimen, usually 6 mg on the first day followed by 4 mg on the second day.

Route of Administration: Oral

In Vitro Use Guide

Acenocoumarol had no effect in unstimulated cells but in PHA-stimulated PBMC tryptophan breakdown and the formation of neopterin, as well as IFN-γ and TNF-α, were dose-dependently suppressed at concentrations as low as 10 μg/ml. Likewise, acenocoumarol dose-dependently inhibited tryptophan breakdown in IFN-γ stimulated Caco-2 cells. Interestingly, NF-κB expression was super-induced in the LPS treated cells.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:19:08 GMT 2025` Edited by `admin` on `Mon Mar 31 18:19:08 GMT 2025`
Record UNII	I6WP63U32H
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

MINI-SINTROM

Preferred Name

English

ACENOCOUMAROL

Official Name

English

NSC-760052

Code

English

2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-3-(1-(4-NITROPHENYL)-3-OXOBUTYL)-

Systematic Name

English

3-(.ALPHA.-ACETONYL-P-NITROBENZYL)-4-HYDROXYCOUMARIN

Common Name

English

ACENOCOUMAROL [HSDB]

Common Name

English

Acenocoumarol [WHO-DD]

Common Name

English

ACENOCOUMAROL [MART.]

Common Name

English

acenocoumarol [INN]

Common Name

English

ACENOCOUMARIN

Common Name

English

ACENOCOUMAROL [MI]

Common Name

English

NICOUMALONE

Common Name

English

Classification Tree Code System Code

WHO-ATC

B01AA07