N-(2-Aminoethyl)-1-aziridineethanamine

Identification

Summary

N-(2-Aminoethyl)-1-aziridineethanamine is an experimental ACE2 inhibitor for the treatment of cardiovascular disease and Severe Acute Respiratory Syndrome.

Generic Name
N-(2-Aminoethyl)-1-aziridineethanamine
DrugBank Accession Number
DB15643
Background

First described in the literature in 2004, N-(2-Aminoethyl)-1-aziridineethanamine is an experimental angiotensin converting enzyme 2 inhibitor investigated for its use in treating cardiovascular disease and its activity against Severe Acute Respiratory Syndrome (SARS).1

Type
Small Molecule
Groups
Experimental
Structure
Thumb
Weight
Average: 129.207
Monoisotopic: 129.126597495
Chemical Formula
C6H15N3
Synonyms
  • N-(2-((2-Aminoethyl)amino)ethyl)aziridine
  • N-(2-aminoethyl)-1 aziridine-ethanamine

Pharmacology

Indication

This experimental drug was being researched for its use in the treatment of cardiovascular disease and SARS-CoV infections.1

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

Angiotensin II constricts coronary blood vessels and is positively inotropic, which under normal circumstances, would increase vascular resistance and oxygen consumption.2 This action can eventually lead to myocyte hypertrophy and vascular smooth muscle cell proliferation.2 N-(2-Aminoethyl)-1-aziridineethanamine may inhibit ACE2, preventing these actions from occurring.1

N-(2-Aminoethyl)-1-aziridineethanamine binding to ACE2 may lead to a conformational change in ACE2, shifting the residues that would bind SARS-CoV S-glycoprotein, preventing viral attachment and entry.1

TargetActionsOrganism
UAngiotensin-converting enzyme 2
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
Medicalerrors
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Not Available
Food Interactions
No interactions found.

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
K93WMR7E2S
CAS number
23435-23-6
InChI Key
XJNAQZHMIAKQOK-UHFFFAOYSA-N
InChI
InChI=1S/C6H15N3/c7-1-2-8-3-4-9-5-6-9/h8H,1-7H2
IUPAC Name
(2-aminoethyl)[2-(aziridin-1-yl)ethyl]amine
SMILES
NCCNCCN1CC1

References

General References
  1. Huentelman MJ, Zubcevic J, Hernandez Prada JA, Xiao X, Dimitrov DS, Raizada MK, Ostrov DA: Structure-based discovery of a novel angiotensin-converting enzyme 2 inhibitor. Hypertension. 2004 Dec;44(6):903-6. doi: 10.1161/01.HYP.0000146120.29648.36. Epub 2004 Oct 18. [Article]
  2. Goa KL, Balfour JA, Zuanetti G: Lisinopril. A review of its pharmacology and clinical efficacy in the early management of acute myocardial infarction. Drugs. 1996 Oct;52(4):564-88. doi: 10.2165/00003495-199652040-00011. [Article]
  3. Laurent S: Antihypertensive drugs. Pharmacol Res. 2017 Oct;124:116-125. doi: 10.1016/j.phrs.2017.07.026. Epub 2017 Aug 2. [Article]
ChemSpider
89317
BindingDB
50233798
ChEMBL
CHEMBL398940
ZINC
ZINC000019366387

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility400.0 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.1ChemAxon
logS0.49ALOGPS
pKa (Strongest Basic)9.78ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area41.06 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity38.69 m3·mol-1ChemAxon
Polarizability15.71 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
Not Available

Targets

Drugtargets
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Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Zinc ion binding
Specific Function
Carboxypeptidase which converts angiotensin I to angiotensin 1-9, a peptide of unknown function, and angiotensin II to angiotensin 1-7, a vasodilator. Also able to hydrolyze apelin-13 and dynorphin...
Gene Name
ACE2
Uniprot ID
Q9BYF1
Uniprot Name
Angiotensin-converting enzyme 2
Molecular Weight
92462.4 Da
References
  1. Huentelman MJ, Zubcevic J, Hernandez Prada JA, Xiao X, Dimitrov DS, Raizada MK, Ostrov DA: Structure-based discovery of a novel angiotensin-converting enzyme 2 inhibitor. Hypertension. 2004 Dec;44(6):903-6. doi: 10.1161/01.HYP.0000146120.29648.36. Epub 2004 Oct 18. [Article]

Drug created on March 23, 2020 18:20 / Updated on June 12, 2020 16:53