Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C21H22NO4.Na |
Molecular Weight | 375.3934 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CC(C)C[C@H](NC(=O)OCC1C2=CC=CC=C2C3=CC=CC=C13)C([O-])=O
InChI
InChIKey=FOHZCXQEHXACQZ-FYZYNONXSA-M
InChI=1S/C21H23NO4.Na/c1-13(2)11-19(20(23)24)22-21(25)26-12-18-16-9-5-3-7-14(16)15-8-4-6-10-17(15)18;/h3-10,13,18-19H,11-12H2,1-2H3,(H,22,25)(H,23,24);/q;+1/p-1/t19-;/m0./s1
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 | C21H22NO4 |
Molecular Weight | 352.4037 |
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/8392562Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/1824872 | https://www.ncbi.nlm.nih.gov/pubmed/12477349 | https://www.ncbi.nlm.nih.gov/pubmed/23494891
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8392562
Curator's Comment: The description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/1824872 | https://www.ncbi.nlm.nih.gov/pubmed/12477349 | https://www.ncbi.nlm.nih.gov/pubmed/23494891
N-(Fluorenyl-9-methoxycarbonyl)leucine (NPC 15199) is an organic compound that demonstrates antiinflammatory effects. NPC 15199 and other N-(9-fluorenylmethoxycarbonyl)-protected amino acids are demonstrated to block recruitment of neutrophils into inflammatory lesions and to inhibit T-cell activation in vitro, and are classified as leumedins. N-(Fluorenyl-9-methoxycarbonyl)leucine is described to act as a chemically distinct ligand and modulator of PPARγ (peroxisome proliferator-activated receptor γ). N-(Fluorenyl-9-methoxycarbonyl)leucine is demonstrated to increase intracellular Ca2+ and to mobilize Ca2+ stores in human bladder female transitional cancer (BFTC) cells.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23494891 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/8392562
NPC 15199 (N-(Fluorenyl-9-methoxycarbonyl)leucine) was administered daily (10 or 100 mg/kg, s.c.) for 7 days
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/1824872
Fatty acid cyclooxygenase activity and 5-lipoxygenase activity were assessed using whole cell assays. Cyclooxygenase activity was measured by incubating arachidonic acid with 3T3 fibroblasts and measuring prostaglandin E2 synthesis. 5-Lipoxygenase
was measured in blood from CD-1 mice. To 1 ml of Hanks' balanced salt solution was added 10 p1 of blood. After 5 min, 0.3 mkCi (1 Ci = 37 GBq) of [3H]arachidonic acid was added, followed by 1 mkM ionomycin. Incubation was for 5 min at 37C, followed by centrifugation at 10,000 x g for 10 sec. Supernatant (250 mk1) was injected onto a reverse-phase HPLC column (HP Hypersil ODS 5 mkM, 200 x 4.6 mm) at room temperature and eluted with at linear gradient from water/ acetonitrile/trifluoroacetic acid (60:40:0.01) to water/ acetonitrile/trifluoroacetic acid (10:90:0.01) at 2 ml/min. [3H]labeled leukotriene C4 was quantitated using an in-line liquid scintillation detector (Radiomatic Instruments and Chemical, Tampa, FL). Test compounds (N-(FLUORENYL-9-METHOXYCARBONYL)LEUCINE) were added to the blood suspension at the beginning of the 5-min incubation before addition of radiolabeled substrate. Plasma corticosterqne was quantitated by radioimmunoassay
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:56:18 GMT 2023
by
admin
on
Fri Dec 15 15:56:18 GMT 2023
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Record UNII |
2RA0J362B8
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Record Status |
Validated (UNII)
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Record Version |
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