Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C11H11ClN4O2.ClH |
| Molecular Weight | 303.145 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.CN1CC(=O)N=C1NC(=O)NC2=CC(Cl)=CC=C2
InChI
InChIKey=BWCJZAGTBVMMTO-UHFFFAOYSA-N
InChI=1S/C11H11ClN4O2.ClH/c1-16-6-9(17)14-10(16)15-11(18)13-8-4-2-3-7(12)5-8;/h2-5H,6H2,1H3,(H2,13,14,15,17,18);1H
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C11H11ClN4O2 |
| Molecular Weight | 266.684 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16040814 | https://www.ncbi.nlm.nih.gov/pubmed/19126569
Curator's Comment: Description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/16040814 | https://www.ncbi.nlm.nih.gov/pubmed/19126569
Fenobam is a selective and potent metabotropic glutamate (mGlu)5 receptor antagonist with inverse agonist activity. Fenobam was previously investigated as an anxiolytic in a number of phase II studies in the early 1980s. These studies revealed a mixed picture of anxiolytic efficacy, with double blind, placebo controlled trials variously reporting the compound as active or inactive. This discrepancy was not easily reconciled based on patient numbers, dose level, duration of treatment, or outcome measures. The positive effects seen in animal models of fragile X syndrome (FXS) treated with fenobam or other mGluR5 antagonists, the apparent lack of clinically significant adverse effects, and the potential beneficial clinical effects seen in this pilot trial support further study of the compound in adults with FXS.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL3227 |
58.0 nM [IC50] |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | Unknown Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
|||
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7042771 Friedmann C, Davis L, Ciccone P, Rubin R. Phase II double-blind controlled study of a new anxiolytic, fenobam (McN-3377) vs placebo. Curr Ther Res 1980;27:144–51 Itil TM, Seaman BA, Huque M, Mukhopadhyay S, Blasucci D, Nq KT, Ciccone PE. The clinical and quantitative EEG effects and plasma levels of fenbam (McN-3377) in subjects with anxiety: an open rising dose tolerance and efficacy study. Curr Ther Res 1978;24:708–24 https://www.ncbi.nlm.nih.gov/pubmed/19126569 |
Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.9 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31568235/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
FENOBAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
3.6 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31568235/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
FENOBAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
1.4 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31568235/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
FENOBAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
167.4 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31568235/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
FENOBAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
183.6 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31568235/ |
150 mg single, oral dose: 150 mg route of administration: Oral experiment type: SINGLE co-administered: |
FENOBAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
|
67.8 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31568235/ |
50 mg single, oral dose: 50 mg route of administration: Oral experiment type: SINGLE co-administered: |
FENOBAM plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: UNKNOWN |
Doses
| Dose | Population | Adverse events |
|---|---|---|
300 mg 1 times / day multiple, oral (max) Highest studied dose Dose: 300 mg, 1 times / day Route: oral Route: multiple Dose: 300 mg, 1 times / day Sources: |
unhealthy n = 29 Health Status: unhealthy Condition: anxiety Sex: M+F Food Status: UNKNOWN Population Size: 29 Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Fenobam: a clinically validated nonbenzodiazepine anxiolytic is a potent, selective, and noncompetitive mGlu5 receptor antagonist with inverse agonist activity. | 2005 Nov |
|
| A mGluR5 antagonist under clinical development improves L-DOPA-induced dyskinesia in parkinsonian rats and monkeys. | 2010 Sep |
Patents
Sample Use Guides
Twelve subjects, recruited from two fragile X clinics, received a single oral dose of 50-150 mg of fenobam.
Route of Administration:
Oral
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:19:28 GMT 2023
by
admin
on
Fri Dec 15 15:19:28 GMT 2023
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| Record UNII |
18X2C0C12Z
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| Record Status |
Validated (UNII)
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| Record Version |
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-
Download
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Common Name | English | ||
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Systematic Name | English |
| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
232406
Created by
admin on Fri Dec 15 15:19:28 GMT 2023 , Edited by admin on Fri Dec 15 15:19:28 GMT 2023
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135564682
Created by
admin on Fri Dec 15 15:19:28 GMT 2023 , Edited by admin on Fri Dec 15 15:19:28 GMT 2023
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18X2C0C12Z
Created by
admin on Fri Dec 15 15:19:28 GMT 2023 , Edited by admin on Fri Dec 15 15:19:28 GMT 2023
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PRIMARY |
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ACTIVE MOIETY |