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Details

Stereochemistry ACHIRAL
Molecular Formula C12H11N3.C4H2O4
Molecular Weight 311.2921
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 1
Charge -2

SHOW SMILES / InChI
Structure of MEFENIDIL FUMARATE

SMILES

[O-]C(=O)\C=C\C([O-])=O.CC1=C(CC#N)N=C(N1)C2=CC=CC=C2

InChI

InChIKey=BACLFYJGAMBEIX-WLHGVMLRSA-L
InChI=1S/C12H11N3.C4H4O4/c1-9-11(7-8-13)15-12(14-9)10-5-3-2-4-6-10;5-3(6)1-2-4(7)8/h2-6H,7H2,1H3,(H,14,15);1-2H,(H,5,6)(H,7,8)/p-2/b;2-1+

HIDE SMILES / InChI

Molecular Formula C4H4O4
Molecular Weight 116.0722
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 1
Optical Activity NONE

Molecular Formula C12H11N3
Molecular Weight 197.2358
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://www.ncbi.nlm.nih.gov/pubmed/3999024 | https://www.ncbi.nlm.nih.gov/pubmed/3749246

Mefenidil has been reported to be a selective cerebral vasodilator. It significantly increased cerebral blood flow (without stimulation of O2 uptake) and lowered cerebral vascular resistance without having significant effects in other circulatory regions. Increase in cerebral blood flow is not mediated via the beta-adrenergic receptor as the effect was not blocked by propranolol. However, the clinical usefulness of mefenidil as a cerebral vasodilator may be limited by the accompanying arterial hypotension due to systemic vasodilation, which was most prominent in heart and gut.

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Cardiovascular profile of 5-methyl-2-phenyl-4-imidazole-acetonitrile (MCN-2378), a cerebral vasodilator.
1975 Jan
Effect of mefenidil on cerebral and peripheral hemodynamics in dogs.
1985 May
Effects of mefenidil hydrochloride on cerebral blood flow in conscious and anesthetized rat.
1986
Patents

Sample Use Guides

In Vivo Use Guide
Curator's Comment: McN-2378 caused a more pronounced effect on cerebral blood flow than on femoral blood flow at the 2.5 and 5.0 mg/kg i.v. doses and this effect was significantly more prolonged at these doses.
Rhesus monkey: 2.5-5.0 mg/kg
Route of Administration: Intravenous
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 16:30:53 GMT 2023
Edited
by admin
on Fri Dec 15 16:30:53 GMT 2023
Record UNII
5QH19BF6YG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEFENIDIL FUMARATE
USAN  
USAN  
Official Name English
5-Methyl-2-phenylimidazole-4-acetonitrile fumarate (1:1)
Systematic Name English
MCN-2378-46
Code English
MEFENIDIL FUMARATE [USAN]
Common Name English
1H-IMIDAZOLE-4-ACETONITRILE, 5-METHYL-2-PHENYL-, (E)-2-BUTANEDIOATE (1:1)
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29707
Created by admin on Fri Dec 15 16:30:53 GMT 2023 , Edited by admin on Fri Dec 15 16:30:53 GMT 2023
Code System Code Type Description
FDA UNII
5QH19BF6YG
Created by admin on Fri Dec 15 16:30:53 GMT 2023 , Edited by admin on Fri Dec 15 16:30:53 GMT 2023
PRIMARY
CAS
83153-38-2
Created by admin on Fri Dec 15 16:30:53 GMT 2023 , Edited by admin on Fri Dec 15 16:30:53 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106836
Created by admin on Fri Dec 15 16:30:53 GMT 2023 , Edited by admin on Fri Dec 15 16:30:53 GMT 2023
PRIMARY
USAN
U-24
Created by admin on Fri Dec 15 16:30:53 GMT 2023 , Edited by admin on Fri Dec 15 16:30:53 GMT 2023
PRIMARY
PUBCHEM
6440686
Created by admin on Fri Dec 15 16:30:53 GMT 2023 , Edited by admin on Fri Dec 15 16:30:53 GMT 2023
PRIMARY
NCI_THESAURUS
C66073
Created by admin on Fri Dec 15 16:30:53 GMT 2023 , Edited by admin on Fri Dec 15 16:30:53 GMT 2023
PRIMARY
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ACTIVE MOIETY