Danegaptide

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Danegaptide
DrugBank Accession Number
DB11821
Background

Danegaptide has been investigated for the treatment of Focus of Study is STEMI.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 291.307
Monoisotopic: 291.121906039
Chemical Formula
C14H17N3O4
Synonyms
  • Danegaptide
External IDs
  • GAP-134
  • ZP1609

Pharmacology

Indication

Not Available

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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Pharmacodynamics

Not Available

Mechanism of action

Danegaptide, a small modified dipeptide, is a selective second generation gap junction modifier with oral bioavailability. Danegaptide prevents postoperative atrial fibrillation (AF) and chronic AF in large animal models. In a canine model of acute sterile pericarditis, Danegaptide significantly reduced AF duration and overall AF burden. Danegaptide has a similar mechanism of action to its parent compound rotigaptide. Rotigaptide is a synthetic antiarrhythmic peptide (AAP) analogue which has been tested in vitro which shows prevention of prevents metabolic stress-induced atrial conduction velocity (CV) and rapidly reverts established atrial CV slowing. Rogitapeptide enhances gap junction conductance and coupling, increasing the amount of small molecules such as ions, metabolites and secondary messengers passing from one cell to another.

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
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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
Not Available

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as dipeptides. These are organic compounds containing a sequence of exactly two alpha-amino acids joined by a peptide bond.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Dipeptides
Alternative Parents
Proline and derivatives / N-acyl-L-alpha-amino acids / Alpha amino acid amides / Benzamides / Pyrrolidine carboxylic acids / N-acylpyrrolidines / Benzoyl derivatives / Tertiary carboxylic acid amides / Secondary carboxylic acid amides / Amino acids
show 7 more
Substituents
Alpha-amino acid amide / Alpha-amino acid or derivatives / Alpha-dipeptide / Amine / Amino acid / Amino acid or derivatives / Aromatic heteromonocyclic compound / Azacycle / Benzamide / Benzenoid
show 26 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available
Affected organisms
Not Available

Chemical Identifiers

UNII
PA0Y7735AT
CAS number
943134-39-2
InChI Key
BIZKIHUJGMSVFD-MNOVXSKESA-N
InChI
InChI=1S/C14H17N3O4/c15-7-12(18)17-8-10(6-11(17)14(20)21)16-13(19)9-4-2-1-3-5-9/h1-5,10-11H,6-8,15H2,(H,16,19)(H,20,21)/t10-,11+/m1/s1
IUPAC Name
(2S,4R)-1-(2-aminoacetyl)-4-benzamidopyrrolidine-2-carboxylic acid
SMILES
NCC(=O)N1C[C@@H](C[C@H]1C(O)=O)NC(=O)C1=CC=CC=C1

References

General References
  1. Kjolbye AL, Haugan K, Hennan JK, Petersen JS: Pharmacological modulation of gap junction function with the novel compound rotigaptide: a promising new principle for prevention of arrhythmias. Basic Clin Pharmacol Toxicol. 2007 Oct;101(4):215-30. [Article]
  2. Axelsen LN, Haugan K, Stahlhut M, Kjolbye AL, Hennan JK, Holstein-Rathlou NH, Petersen JS, Nielsen MS: Increasing gap junctional coupling: a tool for dissecting the role of gap junctions. J Membr Biol. 2007 Mar;216(1):23-35. Epub 2007 Jun 14. [Article]
PubChem Compound
16656685
PubChem Substance
347828168
ChemSpider
17589967
ChEMBL
CHEMBL560592
ZINC
ZINC000040836075

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentFocus of Study is STEMI1
1CompletedNot AvailableArrhythmia1
1CompletedPreventionArrhythmia1
1CompletedTreatmentHealthy Volunteers1

Pharmacoeconomics

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

Properties

State
Not Available
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility1.91 mg/mLALOGPS
logP-0.55ALOGPS
logP-3.3ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)3.32ChemAxon
pKa (Strongest Basic)8.13ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area112.73 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity74.08 m3·mol-1ChemAxon
Polarizability29.07 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Drug created on October 20, 2016 20:50 / Updated on February 21, 2021 18:53