FENOBAM

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 Search

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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7042771
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Metabotropic glutamate receptor 5 39 Target ID: CHEMBL3227 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16040814	Antagonist 2778		58.0 nM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Fragile X syndrome 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19126569	Primary	Not Provided 504	Unknown Approved Use Unknown
Allodynia 3 Sources: https://clinicaltrials.gov/ct2/show/NCT01981395	Primary	Phase I 428	Unknown Approved Use Unknown
Anxiety 267 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	Phase II 1132	Unknown Approved Use Unknown

C_max

Value	Dose	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	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: https://pubmed.ncbi.nlm.nih.gov/7042771	unhealthy n = 29 Health Status: unhealthy Condition: anxiety Sex: M+F Food Status: UNKNOWN Population Size: 29 Sources: https://pubmed.ncbi.nlm.nih.gov/7042771	Sources: https://pubmed.ncbi.nlm.nih.gov/7042771

Sourcing

Vendor/Aggregator	ID	URL
1PlusChem LLC	1P01E586	https://www.1pchem.com/search?query=1P01E586
ApexBio Technology	B7035	https://www.apexbt.com/catalogsearch/result/?q=B7035
Axon MedChem	1345	https://www.axonmedchem.com/product/1345
BOC Sciences	57653-26-6	http://www.bocsci.com/description.asp?cas=57653-26-6
Chem Scene	CS-0021515	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0021515
ChemDiv	H025-2029C	http://chemistryondemand.com:8080/eShop/search_results.jsp?idnumber=H025-2029C
ChemShuttle	139022	https://www.chemshuttle.com/catalogsearch/result/?q=139022
Fluorochem	M03843	http://www.fluorochem.co.uk/Products/Product?code=M03843
MedChem Express	HY-101478	https://www.medchemexpress.com/search.html?q=HY-101478&ft=&fa=&fp=
MolPort	MolPort-002-494-450	https://www.molport.com/shop/molecule-link/MolPort-002-494-450
MuseChem	I006260	https://www.musechem.com/product/I006260.html
Princeton BioMolecular Research	OSSK_727527	http://www.princetonbio.com/order_online?common_id=OSSK_727527
Tetrahedron	TS73565	http://www.thsci.com/search.do?q=TS73565
TimTec	ST45270299	http://www.echemstore.com/catalogsearch/result/?q=ST45270299
Tocris	2386	https://www.tocris.com/search.php?Type=QuickSearch&Value=2386
eMolecules	4344705	https://orderbb.emolecules.com/search/#?query=4344705
eMolecules	49240321	https://orderbb.emolecules.com/search/#?query=49240321
mcule	MCULE-9260864714	https://mcule.com/MCULE-9260864714/

PubMed

Title	Date	PubMed
		252160068
Fenobam: a clinically validated nonbenzodiazepine anxiolytic is a potent, selective, and noncompetitive mGlu5 receptor antagonist with inverse agonist activity.	2005 Nov	16040814
A mGluR5 antagonist under clinical development improves L-DOPA-induced dyskinesia in parkinsonian rats and monkeys.	2010 Sep	20452425

Patents

Sample Use Guides

In Vivo Use Guide

Twelve subjects, recruited from two fragile X clinics, received a single oral dose of 50-150 mg of fenobam.

Route of Administration: Oral

In Vitro Use Guide

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

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