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Details

Stereochemistry ACHIRAL
Molecular Formula C11H11ClN4O2.H2O
Molecular Weight 284.699
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of FENOBAM

SMILES

O.CN1CC(=O)N=C1NC(=O)NC2=CC(Cl)=CC=C2

InChI

InChIKey=UNFQKKSADLVQJE-UHFFFAOYSA-N
InChI=1S/C11H11ClN4O2.H2O/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);1H2

HIDE SMILES / InChI

Description
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.

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
58.0 nM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
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 Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.9 ng/mL
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
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
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

AUC

ValueDoseCo-administeredAnalytePopulation
167.4 ng × h/mL
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
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
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

Doses

DosePopulationAdverse 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

PubMed

TitleDatePubMed
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

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
Fenobam rarely exhibits cytotoxic effects in C6 cells at concentrations of 50-150 ng/ml. Fenobam (150 ng/ml) strongly enhanced the protective effect of PEP-1-FK506BP against H2O2-induced toxicity and DNA fragmentation in C6 cells.
Name Type Language
FENOBAM
USAN  
USAN  
Official Name English
1-(M-CHLOROPHENYL)-3-(1-METHYL-4-OXO-2-IMIDAZOLIN-2-YL)UREA MONOHYDRATE
Systematic Name English
UREA MONOHYDRATE, N-(3-CHLOROPHENYL)-N'-(4,5-DIHYDRO-1-METHYL-4-OXO-1H-IMIDAZOL-2-YL)-
Systematic Name English
MCN-3377-98
Code English
FENOBAM [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29756
Created by admin on Fri Dec 15 15:16:53 GMT 2023 , Edited by admin on Fri Dec 15 15:16:53 GMT 2023
Code System Code Type Description
DRUG BANK
DB12931
Created by admin on Fri Dec 15 15:16:53 GMT 2023 , Edited by admin on Fri Dec 15 15:16:53 GMT 2023
PRIMARY
NCI_THESAURUS
C80666
Created by admin on Fri Dec 15 15:16:53 GMT 2023 , Edited by admin on Fri Dec 15 15:16:53 GMT 2023
PRIMARY
MESH
C032794
Created by admin on Fri Dec 15 15:16:53 GMT 2023 , Edited by admin on Fri Dec 15 15:16:53 GMT 2023
PRIMARY
SMS_ID
100000081299
Created by admin on Fri Dec 15 15:16:53 GMT 2023 , Edited by admin on Fri Dec 15 15:16:53 GMT 2023
PRIMARY
ChEMBL
CHEMBL239800
Created by admin on Fri Dec 15 15:16:53 GMT 2023 , Edited by admin on Fri Dec 15 15:16:53 GMT 2023
PRIMARY
CAS
63540-28-3
Created by admin on Fri Dec 15 15:16:53 GMT 2023 , Edited by admin on Fri Dec 15 15:16:53 GMT 2023
PRIMARY
FDA UNII
07O6708M02
Created by admin on Fri Dec 15 15:16:53 GMT 2023 , Edited by admin on Fri Dec 15 15:16:53 GMT 2023
PRIMARY
WIKIPEDIA
FENOBAM
Created by admin on Fri Dec 15 15:16:53 GMT 2023 , Edited by admin on Fri Dec 15 15:16:53 GMT 2023
PRIMARY
EPA CompTox
DTXSID60979763
Created by admin on Fri Dec 15 15:16:53 GMT 2023 , Edited by admin on Fri Dec 15 15:16:53 GMT 2023
PRIMARY
PUBCHEM
135416855
Created by admin on Fri Dec 15 15:16:53 GMT 2023 , Edited by admin on Fri Dec 15 15:16:53 GMT 2023
PRIMARY