Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C18H24Cl2N2O |
| Molecular Weight | 355.302 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CN([C@@H]1CCCC[C@H]1N2CCCC2)C(=O)C3=CC=C(Cl)C(Cl)=C3
InChI
InChIKey=JUBNVWGVNWIXMB-IAGOWNOFSA-N
InChI=1S/C18H24Cl2N2O/c1-21(18(23)13-8-9-14(19)15(20)12-13)16-6-2-3-7-17(16)22-10-4-5-11-22/h8-9,12,16-17H,2-7,10-11H2,1H3/t16-,17-/m1/s1
| Molecular Formula | C18H24Cl2N2O |
| Molecular Weight | 355.302 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 2 / 2 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
U-54494A is a unique and selective anticonvulsant agent acting by a Ca(2+)-related mechanism possibly through a subclass of kappa receptors. Voltage- and use-dependent block of the Na and K channels by U-54494A may be an important pharmacological basis for its anticonvulsant action. U-54494A, a racemic mixture of two enantiomers, is being developed and pre-clinically tested as an anticonvulsant drug candidate.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3614 |
|||
Target ID: Voltage-dependent sodium channels (mice) |
72.0 µM [IC50] | ||
Target ID: Voltage-gated potassium channels (mice) |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Pharmacokinetics of the individual enantiomers of cis-3,4-dichloro-N-methyl-N-[2-(1-pyrrolidinyl)-cyclohexyl]-benzamide monohydrochloride (U-54494A) in the dog. | 1996 |
|
| The effects of anticonvulsant agents on 4-aminopyridine induced epileptiform activity in rat hippocampus in vitro. | 1995-02 |
|
| First-pass effect of cis-3,4-dichloro-N-methyl-N-(2-(1-pyrrolidinyl)- cyclohexyl)-benzamide (U-54494) in rats--a model with multiple cannulas for investigation of gastrointestinal and hepatic metabolism. | 1994-11 |
|
| Anticonvulsant and related effects of U-54494A in various seizure tests. | 1993-10 |
|
| Two metabolites of anticonvulsant U-54494A: their anticonvulsant activity and interaction with sodium channel. | 1993-03-19 |
Sample Use Guides
Mice Intraperitoneal: ED50 = 28 mg/kg (15 min) and 38 mg/kg (30 min)
Mice Oral: ED50 = 61 mg/kg (30 min) and 65 mg/kg (60 min)
Mice Subcutaneous: ED50 = 24 mg/kg (15 min)
Route of Administration:
Other
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 19:54:16 GMT 2025
by
admin
on
Mon Mar 31 19:54:16 GMT 2025
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| Record UNII |
I3NE36R0XJ
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| Record Status |
Validated (UNII)
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| Record Version |
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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SALT/SOLVATE -> PARENT |
