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Details

Stereochemistry RACEMIC
Molecular Formula C19H15NO6
Molecular Weight 353.3262
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACENOCOUMAROL

SMILES

CC(=O)CC(c1ccc(cc1)N(=O)=O)c2c(c3ccccc3oc2=O)O

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

Description
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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
Primary
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
Primary
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
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
60 ng/mL
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
205.9 ng × h/mL
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
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
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1 h
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
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
[Acute renal insufficiency caused by bilateral arterial thrombosis in a patient undergoing heparin treatment].
2002
Factors predictive of failure of Brescia-Cimino arteriovenous fistulas.
2002
[Half-stay and morbidity in a cohort of patients treated with urologic surgery iin the treatment with acenocumarol (Sintrom)].
2002 Apr
Thumbprinting due to ischemic colitis in a patient on oral anticoagulation.
2002 Aug-Sep
[Warfarin fetopathy].
2002 Jul
Low dose oral vitamin K to reverse acenocoumarol-induced coagulopathy: a randomized controlled trial.
2002 Jul
Role of oral anticoagulation and inoue balloon mitral valvulotomy in presence of left atrial thrombus: a prospective serial transesophageal echocardiographic study.
2002 Jul
Leu208Val and Ile181Leu variants of cytochrome P450 CYP2C9 are not related to the acenocoumarol dose requirement in a Spanish population.
2002 Jul 15
Effect of low-dose aspirin on the international normalized ratio variability in patients with mechanical heart valve prostheses.
2002 Jul-Aug
[Oral anticoagulant treatment: practical aspects and significance of anticoagulant clinics].
2002 Jun
Initiation of oral anticoagulant therapy in orthopedic and surgical patients: an algorithm compared with routine dosing.
2002 Jun
Overanticoagulation associated with combined use of antifungal agents and coumarin anticoagulants.
2002 Jun
Therapeutic quality control of oral anticoagulant therapy comparing the short-acting acenocoumarol and the long-acting phenprocoumon.
2002 Jun
Re: Webster K, Wilde J. Management of anticoagulation in patients with prosthetic heart valves undergoing oral and maxillofacial operations. Br J Oral Maxillofac Surg 2000; 38: 124-126.
2002 Jun
[HELLP syndrome associated to pulmonary thromboembolism and factor V Leiden].
2002 Jun 1
Platelet aggregation in different antithrombotic regimens. Possible proaggregant effect of low level oral anticoagulation.
2002 May
Treatment with vitamin K antagonists: frequency of indications and appropriateness of continuation.
2002 May-Jun
[Acenocoumarol (Sintrom) and fluinidione (Previscan) in pediatrics after cardiac surgical procedures].
2002 Nov
Overanticoagulation associated with combined use of antibacterial drugs and acenocoumarol or phenprocoumon anticoagulants.
2002 Nov
Pharmacogenetics of acenocoumarol: cytochrome P450 CYP2C9 polymorphisms influence dose requirements and stability of anticoagulation.
2002 Nov
The potential interaction between oral anticoagulants and acetaminophen in everyday practice.
2002 Oct
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 Oct
Extended venous thromboembolism prophylaxis after total hip replacement: a comparison of low-molecular-weight heparin with oral anticoagulant.
2002 Oct 28
No effect of acenocoumarol therapy on levels of endothelial activation markers in sickle cell disease.
2002 Sep
Intracranial bleeding: epidemiology and relationships with antithrombotic treatment in 241 cerebral hemorrhages in Reggio Emilia.
2002 Sep
The first experience with endovascular stenting of the iliac veins in patients suffering from post-thrombophlebitic disease.
2003
Acenocoumarol is not a safe alternative for anticoagulation in phenprocoumon-induced hepatic failure. Report of two cases.
2003
Ischaemic stroke in young people: a prospective and long-term follow-up study.
2003
[Prevention of postoperative bleeding in patients taking oral anticoagulants. Effects of tranexamic acid].
2003 Apr
Low rate of bleeding and thrombotic complications of oral anticoagulant therapy independent of age in the real-practice of an anticoagulation clinic.
2003 Apr
Acenocoumarol therapy in pediatric patients.
2003 Aug
Comparison of control and stability of oral anticoagulant therapy using acenocoumarol versus phenprocoumon.
2003 Aug
[Oral anticoagulation with vitamin K antagonists].
2003 Jan
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 Jul
Oral anticoagulant therapy: should doctors change the way they give patients explanations?
2003 Jul
Impact of pre-treatment INR level on the effect of intravenous low dose vitamin K in patients with excessive anticoagulation.
2003 Jul
Capillary whole blood testing by a new portable monitor. Comparison with standard determination of the international normalized ratio.
2003 Jul
Acenocoumarol pharmacokinetics in relation to cytochrome P450 2C9 genotype.
2003 Jul
Cluster-like headache due to warfarin therapy?
2003 Jul
Summaries for patients. How long should blood thinners be given to patients who have had a pulmonary embolism?
2003 Jul 1
Extended oral anticoagulant therapy after a first episode of pulmonary embolism.
2003 Jul 1
Low-molecular-weight heparin versus a coumarin for the prevention of recurrent venous thromboembolism in patients with cancer.
2003 Jul 10
Pharmacokinetic study of the digoxin-acenocoumarol interaction in rabbits.
2003 Jun
[Excess antivitamin K in elderly hospitalised patients aged over 70. A one-year prospective survey].
2003 Jun 14
A placebo-controlled pharmacodynamic and pharmacokinetic interaction study between tamsulosin and acenocoumarol.
2003 Mar
[Pharmacological interactions of statins].
2003 Mar 15
Clozapine and venous thromboembolism: further evidence.
2003 May
Pharmacogenetics of oral anticoagulants.
2003 May
Experience with enoxaparin in patients with mechanical heart valves who must withhold acenocumarol.
2003 May
Rofecoxib interaction with oral anticoagulant acenocoumarol.
2003 Sep
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
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.
Name Type Language
ACENOCOUMAROL
HSDB   INN   MART.   MI   USP-RS   WHO-DD  
INN  
Official Name English
MINI-SINTROM
Brand 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 [WHO-DD]
Common Name English
ACENOCOUMAROL [HSDB]
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
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
NCI_THESAURUS C263
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
WHO-VATC QB01AA07
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
Code System Code Type Description
WIKIPEDIA
ACENOCOUMAROL
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
CAS
152-72-7
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
NCI_THESAURUS
C75152
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
FDA UNII
I6WP63U32H
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
ChEMBL
CHEMBL397420
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
DRUG CENTRAL
48
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
MERCK INDEX
M1300
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY Merck Index
PUBCHEM
54676537
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
RXCUI
154
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY RxNorm
HSDB
3201
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
DRUG BANK
DB01418
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
EPA CompTox
152-72-7
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
ECHA (EC/EINECS)
205-807-3
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
LACTMED
Acenocoumarol
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
INN
503
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
MESH
D000074
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY
EVMPD
SUB05211MIG
Created by admin on Fri Jun 25 22:13:18 UTC 2021 , Edited by admin on Fri Jun 25 22:13:18 UTC 2021
PRIMARY