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
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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/22149257Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22149257
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL1930 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3207986 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | SINTROM Approved UseUnknown |
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Primary | SINTROM Approved UseUnknown |
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Primary | SINTROM Approved UseUnknown |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/2865109
Rats were treated with (R)-Acenocoumarol 1mg as a single dose
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23481478
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
Edited
Sat Dec 16 09:08:15 GMT 2023
by
admin
on
Sat Dec 16 09:08:15 GMT 2023
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Record UNII |
JRD7912W79
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Record Status |
Validated (UNII)
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Record Version |
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JRD7912W79
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66556-77-2
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Related Record | Type | Details | ||
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RACEMATE -> ENANTIOMER |