Page last updated: 2024-12-07

2-(2-methyl-4-chlorophenylamino)-2-imidazoline

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

2-(2-methyl-4-chlorophenylamino)-2-imidazoline, also known as **Mibefradil**, is a **calcium channel blocker** that was once used to treat **high blood pressure (hypertension)**.

**Why is Mibefradil important for research?**

Mibefradil is important for research due to its unique pharmacological profile and its **interaction with a wide range of drug metabolizing enzymes (CYP)**, making it a valuable tool in drug development and research.

**Here's a breakdown of its significance:**

* **Unique pharmacological profile:** Mibefradil is a **non-dihydropyridine calcium channel blocker** that exhibits high selectivity for **T-type calcium channels**. This unique profile makes it an intriguing molecule for exploring the role of T-type calcium channels in various physiological processes.
* **CYP interaction:** Mibefradil is a potent **inhibitor** of several cytochrome P450 enzymes (CYP), particularly **CYP3A4**. This property makes it crucial to understand its potential for drug-drug interactions. By studying Mibefradil's interactions with CYP enzymes, researchers can gain valuable insights into the metabolism of other drugs and develop strategies to minimize potential adverse effects.
* **Withdrawal from market:** Mibefradil was withdrawn from the market due to serious **drug-drug interactions** that led to adverse events like **heart rhythm problems and kidney damage**. Despite its withdrawal, its extensive research history provides a wealth of information about the complex interplay of drug metabolism, CYP interactions, and clinical outcomes.

**Research applications:**

* **Understanding T-type calcium channels:** Mibefradil is a valuable tool for studying the role of T-type calcium channels in various physiological processes like neuronal excitability, heart rhythm, and vascular smooth muscle contraction.
* **Drug-drug interaction studies:** Mibefradil's potent inhibition of CYP3A4 has contributed significantly to our understanding of drug-drug interactions and the development of strategies to predict and manage them.
* **Development of new drugs:** The research on Mibefradil has informed the design of newer calcium channel blockers with improved selectivity and reduced drug-drug interaction potential.

**In summary, Mibefradil is important for research because it provides a unique pharmacological profile, offers valuable insights into CYP interactions, and highlights the importance of understanding drug metabolism and drug-drug interactions in drug development.**

2-(2-methyl-4-chlorophenylamino)-2-imidazoline: RN given refers to parent cpd; structure in first source [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID77870
CHEMBL ID62674
SCHEMBL ID10689485
MeSH IDM0104797

Synonyms (9)

Synonym
cdmi
CHEMBL62674
4201-26-7
n-(4-chloro-2-methylphenyl)-4,5-dihydro-1h-imidazol-2-amine
1h-imidazol-2-amine, n-(4-chloro-2-methylphenyl)-4,5-dihydro-
2-(2-methyl-4-chlorophenylamino)-2-imidazoline
SCHEMBL10689485
DTXSID40194816
EN300-738510

Research Excerpts

Dosage Studied

ExcerptRelevanceReference
" The slopes of the individual dose-response curves were not significantly different which suggested a common mechanism of action."( Central and peripheral anti-inflammatory actions by clonidine and a structurally related imidazoline analog.
Holsapple, MP; Lowy, MT; Malave, A; Yim, GK, 1984
)
0.27
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (7)

Assay IDTitleYearJournalArticle
AID25092Ionization constant (pKa)1991Journal of medicinal chemistry, Jul, Volume: 34, Issue:7
Direct prediction of dissociation constants (pKa's) of clonidine-like imidazolines, 2-substituted imidazoles, and 1-methyl-2-substituted-imidazoles from 3D structures using a comparative molecular field analysis (CoMFA) approach.
AID1150956Octan-1-ol-aqueous buffer partition coefficient, log P of the compound at 10 to 20 mg at pH 7.4 by UV-spectroscopic analysis1976Journal of medicinal chemistry, Aug, Volume: 19, Issue:8
Clonidine and related analogues. Quantitative correlations.
AID26357Dissociation constant (pKa)1993Journal of medicinal chemistry, Oct-01, Volume: 36, Issue:20
QSAR's from similarity matrices. Technique validation and application in the comparison of different similarity evaluation methods.
AID1150958Hypotensive activity in rat assessed as change in mean blood pressure relative to control1976Journal of medicinal chemistry, Aug, Volume: 19, Issue:8
Clonidine and related analogues. Quantitative correlations.
AID1150955Retardation factor, deltaRm of the compound at pH 13 by TLC analysis1976Journal of medicinal chemistry, Aug, Volume: 19, Issue:8
Clonidine and related analogues. Quantitative correlations.
AID1150959Peripheral adrenergic activity in iv dosed pithed rat assessed as change in mean blood pressure1976Journal of medicinal chemistry, Aug, Volume: 19, Issue:8
Clonidine and related analogues. Quantitative correlations.
AID1150957Dissociation constant, pKa of the compound in water-ethyl alcohol1976Journal of medicinal chemistry, Aug, Volume: 19, Issue:8
Clonidine and related analogues. Quantitative correlations.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19904 (66.67)18.7374
1990's2 (33.33)18.2507
2000's0 (0.00)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 12.41

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index12.41 (24.57)
Research Supply Index1.95 (2.92)
Research Growth Index4.36 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (12.41)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]