Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C18H26N2O3 |
| Molecular Weight | 318.4106 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 1 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
C[C@H](CO)NC(=O)C1=CC(\C=C/CCCC(=O)N(C)C)=CC=C1
InChI
InChIKey=SVYRYFAUQHVGAI-BMWLXYDHSA-N
InChI=1S/C18H26N2O3/c1-14(13-21)19-18(23)16-10-7-9-15(12-16)8-5-4-6-11-17(22)20(2)3/h5,7-10,12,14,21H,4,6,11,13H2,1-3H3,(H,19,23)/b8-5-/t14-/m1/s1
| Molecular Formula | C18H26N2O3 |
| Molecular Weight | 318.4106 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 1 |
| Optical Activity | UNSPECIFIED |
Approval Year
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 11:29:47 UTC 2023
by
admin
on
Sat Dec 16 11:29:47 UTC 2023
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| Record UNII |
D2QY1KLG2R
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| Record Status |
Validated (UNII)
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| Record Version |
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-
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1246960-09-7
Created by
admin on Sat Dec 16 11:29:47 UTC 2023 , Edited by admin on Sat Dec 16 11:29:47 UTC 2023
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D2QY1KLG2R
Created by
admin on Sat Dec 16 11:29:47 UTC 2023 , Edited by admin on Sat Dec 16 11:29:47 UTC 2023
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23730084
Created by
admin on Sat Dec 16 11:29:47 UTC 2023 , Edited by admin on Sat Dec 16 11:29:47 UTC 2023
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
Drugs: VSN-16R(Primary); Indication: Muscle spasticity; Focus: Adverse reactions, Proof of concept, Therapeutic Use; Sponsor: Canbex Therapeutics; Most Recent Events: 02 Nov 2015 Top-line results are expected to be available in 2016, according to a Canbex Therapeutics media release., 04 Sep 2015 Planned number of patients changed from 140 to 160, as per ClinicalTrials.gov record., 03 Mar 2015 New trial record
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ACTIVE MOIETY |
Key results: VSN16 relaxed mesenteric arteries in an endothelium-dependent manner. The vasorelaxation was antagonized by high concentrations of the classical cannabinoid antagonists, rimonabant and AM 251, as well as by O-1918, an antagonist at the abnormal-cannabidiol receptor but not at CB1 or CB2 receptors. It did not affect (3H)CP55,940 binding to CB1 receptors in rat cerebellum. The vasorelaxation was not pertussis toxin-sensitive but was reduced by inhibition of nitric oxide synthesis, Ca2+-sensitive K+ channels (KCa) and TRPV1 receptors. In conscious rats VSN16 transiently increased blood pressure and caused a longer-lasting increase in mesenteric vascular conductance. Structure-activity studies on vasorelaxation showed a stringent interaction with the target receptor.
Conclusions and implications: VSN16 is an agonist at a novel cannabinoid receptor of the vasculature. It acts on the endothelium to release nitric oxide and activate KCa and TRPV1. As it is water-soluble it might be useful in bringing about peripheral cannabinoid-like effects without accompanying central or severe cardiovascular responses.
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