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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H14NO6.Na
Molecular Weight 375.3073
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ACENOCOUMAROL SODIUM, (R)-

SMILES

[Na+].CC(=O)C[C@H](C1=CC=C(C=C1)[N+]([O-])=O)C2=C([O-])C3=CC=CC=C3OC2=O

InChI

InChIKey=MPRDFQJZNXOBJT-XFULWGLBSA-M
InChI=1S/C19H15NO6.Na/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;/q;+1/p-1/t15-;/m1./s1

HIDE SMILES / InChI

Molecular Formula Na
Molecular Weight 22.9898
Charge 1
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C19H14NO6
Molecular Weight 352.3176
Charge -1
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment: The description was created based on several sources, including http://file.scirp.org/Html/4-2201103_53725.htm | https://www.ncbi.nlm.nih.gov/pubmed/2865109

(R)-Acenocoumarol is a short-lived oral anti-coagulant, which, like warfarin, functions by inhibiting vitamin K epoxide reductase. (R)-Acenocoumarol has higher intrinsic anticoagulant potency than warfarin and phenprocoumon when evaluated in vitro. (R)-Acenocoumarol has a longer plasma elimination half-life (6.6 hours) and slower plasma clearance (1.9 L/hour), compared to the (S)-enantiomer (1.8 hours, 28.5 L/hour).1 The R-enantiomer is rapidly absorbed from the gastrointestinal tract with essentially complete oral bioavailability, whereas (S)-acenocoumarol undergoes extensive first-pass metabolism.1 Perhaps related to these pharmacokinetic characteristics, (R)-acenocoumarol is more potent in vivo as an anti-coagulant than the (S)-enantiomer. As the clearance of acenocoumarol is ~20-fold faster than that of warfarin, the plasma concentrations of acenocoumarol are substantially lower than those for warfarin in patients receiving long-term treatment. (R)-Acenocoumarol is a component of anticoagulant Sintrom.

Originator

Sources: British Journal of Clinical Pharmacology (1978), 5, (2), 187-8.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SINTROM

Approved Use

Unknown
Primary
SINTROM

Approved Use

Unknown
Primary
SINTROM

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
A pharmacokinetic-pharmacodynamic model for predicting the impact of CYP2C9 and VKORC1 polymorphisms on fluindione and acenocoumarol during induction therapy.
2012 Jan 1
Patents

Patents

Sample Use Guides

Rats were treated with (R)-Acenocoumarol 1mg as a single dose
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.
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:08:16 GMT 2023
Edited
by admin
on Sat Dec 16 09:08:16 GMT 2023
Record UNII
47U523701N
Record Status Validated (UNII)
Record Version
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Name Type Language
ACENOCOUMAROL SODIUM, (R)-
Common Name English
(R)-ACENOCOUMAROL SODIUM SALT
Common Name English
2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-3-((1R)-1-(4-NITROPHENYL)-3-OXOBUTYL)-, SODIUM SALT
Systematic Name English
Code System Code Type Description
PUBCHEM
91799740
Created by admin on Sat Dec 16 09:08:16 GMT 2023 , Edited by admin on Sat Dec 16 09:08:16 GMT 2023
PRIMARY
FDA UNII
47U523701N
Created by admin on Sat Dec 16 09:08:16 GMT 2023 , Edited by admin on Sat Dec 16 09:08:16 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER