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
SMILES
[Na+].CC(=O)C[C@H](C1=CC=C(C=C1)[N+]([O-])=O)C2=C([O-])C3=C(OC2=O)C=CC=C3
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
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| 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 |
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 |
|---|---|---|---|---|
| Primary | SINTROM Approved UseUnknown |
|||
| Primary | SINTROM Approved UseUnknown |
|||
| 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
Mon Mar 31 22:30:36 GMT 2025
by
admin
on
Mon Mar 31 22:30:36 GMT 2025
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| Record UNII |
47U523701N
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| Record Status |
Validated (UNII)
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| Record Version |
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RACEMATE -> ENANTIOMER |