U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C12H11N3
Molecular Weight 197.2358
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEFENIDIL

SMILES

CC1=C(CC#N)NC(=N1)C2=CC=CC=C2

InChI

InChIKey=OTRQRKIYHATFKM-UHFFFAOYSA-N
InChI=1S/C12H11N3/c1-9-11(7-8-13)15-12(14-9)10-5-3-2-4-6-10/h2-6H,7H2,1H3,(H,14,15)

HIDE SMILES / InChI

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
Name Type Language
MEFENIDIL
INN   USAN  
USAN   INN  
Official Name English
1H-IMIDAZOLE-4-ACETONITRILE, 5-METHYL-2-PHENYL-
Systematic Name English
mefenidil [INN]
Common Name English
MEFENIDIL [USAN]
Common Name English
5-Methyl-2-phenylimidazole-4-acetonitrile
Systematic Name English
MCN-2378
Code English
Classification Tree Code System Code
NCI_THESAURUS C29707
Created by admin on Fri Dec 15 16:37:58 GMT 2023 , Edited by admin on Fri Dec 15 16:37:58 GMT 2023
Code System Code Type Description
SMS_ID
100000081458
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INN
5268
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FDA UNII
74WY8560J7
Created by admin on Fri Dec 15 16:37:58 GMT 2023 , Edited by admin on Fri Dec 15 16:37:58 GMT 2023
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EVMPD
SUB08704MIG
Created by admin on Fri Dec 15 16:37:58 GMT 2023 , Edited by admin on Fri Dec 15 16:37:58 GMT 2023
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EPA CompTox
DTXSID70206991
Created by admin on Fri Dec 15 16:37:58 GMT 2023 , Edited by admin on Fri Dec 15 16:37:58 GMT 2023
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PUBCHEM
65475
Created by admin on Fri Dec 15 16:37:58 GMT 2023 , Edited by admin on Fri Dec 15 16:37:58 GMT 2023
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ChEMBL
CHEMBL2106836
Created by admin on Fri Dec 15 16:37:58 GMT 2023 , Edited by admin on Fri Dec 15 16:37:58 GMT 2023
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USAN
T-14
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CAS
58261-91-9
Created by admin on Fri Dec 15 16:37:58 GMT 2023 , Edited by admin on Fri Dec 15 16:37:58 GMT 2023
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NCI_THESAURUS
C66072
Created by admin on Fri Dec 15 16:37:58 GMT 2023 , Edited by admin on Fri Dec 15 16:37:58 GMT 2023
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