Details
Stereochemistry | ACHIRAL |
Molecular Formula | C26H32N2O5 |
Molecular Weight | 452.5427 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC=CC=C1N2CCN(CCCOC3=CC4=C(OC(=O)C(C)=C4C)C=C3OC)CC2
InChI
InChIKey=FQELZLMTAPJJOL-UHFFFAOYSA-N
InChI=1S/C26H32N2O5/c1-18-19(2)26(29)33-23-17-24(31-4)25(16-20(18)23)32-15-7-10-27-11-13-28(14-12-27)21-8-5-6-9-22(21)30-3/h5-6,8-9,16-17H,7,10-15H2,1-4H3
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/12177685Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/18465518 | https://www.ncbi.nlm.nih.gov/pubmed/9590466
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12177685
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/18465518 | https://www.ncbi.nlm.nih.gov/pubmed/9590466
Ensaculin is related to naturally occurring benzopyranones like scoparone. The compound is a potent functional antagonist of excitatory amino acid-induced convulsions and mortality. In receptor-binding studies, Ensaculin showed high affinity to dopaminergic (D2, D3), serotoninergic (5-HT1A, 5-HT7), and adrenergic (A1a, A1b) receptors in the nanomolar range. Ensaculin antagonizes NMDA responses in a voltage-dependent manner. Various studies support the notion that this compound could indeed have a broad range of nootropic properties. Although few patients presented postural hypotension and dizziness after receiving ensaculin in phase I clinical trials, this drug candidate was further discontinued in phase III due to potential side effects.
CNS Activity
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3737 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12177685 |
8.0 nM [IC50] | ||
Target ID: CHEMBL217 |
16.6 nM [IC50] | ||
Target ID: CHEMBL315 |
9.3 nM [IC50] | ||
Target ID: CHEMBL234 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12177685 |
27.7 nM [IC50] | ||
Target ID: CHEMBL219 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12177685 |
277.0 nM [IC50] | ||
Target ID: CHEMBL319 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12177685 |
4.7 nM [IC50] | ||
Target ID: CHEMBL3223 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12177685 |
2.4 nM [IC50] | ||
Target ID: CHEMBL1907608 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9926872 |
20.0 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
Cmax
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
9.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
16.8 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
35.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
25.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
7.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
AUC
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
43.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
99.5 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
202.9 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
255 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
61.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
T1/2
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
8.3 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
10 mg 1 times / day multiple, oral dose: 10 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
11.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
20 mg 1 times / day multiple, oral dose: 20 mg route of administration: Oral experiment type: MULTIPLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
13.7 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
20 mg single, oral dose: 20 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
16.1 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
60 mg single, oral dose: 60 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
|
17.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9590466 |
10 mg single, oral dose: 10 mg route of administration: Oral experiment type: SINGLE co-administered: |
ENSACULIN plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FED |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9590466
5 mg to 20 mg once daily.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12177685
Ensaculin inhibited rat brain acetylcholinesterase (AChE) activity in vitro with an IC50 of 0.36 uM without affecting the activity of butyrylcholinesterase or arylacylamidase.
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NCI_THESAURUS |
C45597
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208923
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C74243
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C112452
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155773-59-4
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ENSACULIN
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ACTIVE MOIETY