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Details

Stereochemistry ABSOLUTE
Molecular Formula C19H15NO6
Molecular Weight 353.3255
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

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

SMILES

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

InChI

InChIKey=VABCILAOYCMVPS-OAHLLOKOSA-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/t15-/m1/s1

HIDE SMILES / InChI

Molecular Formula C19H15NO6
Molecular Weight 353.3255
Charge 0
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
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 09:08:15 GMT 2023
Edited
by admin
on Sat Dec 16 09:08:15 GMT 2023
Record UNII
JRD7912W79
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ACENOCOUMAROL, (R)-
Common Name English
2H-1-BENZOPYRAN-2-ONE, 4-HYDROXY-3-((1R)-1-(4-NITROPHENYL)-3-OXOBUTYL)-
Systematic Name English
(R)-(+)-ACENOCOUMAROL
Common Name English
(+)-ACENOCOUMARIN
Common Name English
(+)-ACENOCOUMAROL
Common Name English
(+)-3-(.ALPHA.-ACETONYL-4-NITROBENZYL)-4-HYDROXYCOUMARIN
Systematic Name English
Code System Code Type Description
PUBCHEM
54699177
Created by admin on Sat Dec 16 09:08:15 GMT 2023 , Edited by admin on Sat Dec 16 09:08:15 GMT 2023
PRIMARY
FDA UNII
JRD7912W79
Created by admin on Sat Dec 16 09:08:15 GMT 2023 , Edited by admin on Sat Dec 16 09:08:15 GMT 2023
PRIMARY
EPA CompTox
DTXSID10873368
Created by admin on Sat Dec 16 09:08:15 GMT 2023 , Edited by admin on Sat Dec 16 09:08:15 GMT 2023
PRIMARY
CAS
66556-77-2
Created by admin on Sat Dec 16 09:08:15 GMT 2023 , Edited by admin on Sat Dec 16 09:08:15 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER