Danegaptide

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

Identification

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Name
Danegaptide
Accession Number
DB11821  (DB06340)
Type
Small Molecule
Groups
Investigational
Description

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

Structure
Thumb
Synonyms
Not Available
External IDs
GAP-134 / ZP1609
Categories
UNII
PA0Y7735AT
CAS number
943134-39-2
Weight
Average: 291.307
Monoisotopic: 291.121906039
Chemical Formula
C14H17N3O4
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

Pharmacology

Indication
Not Available
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
Toxicity
Not Available
Affected organisms
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

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. [PubMed:17845503]
  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. [PubMed:17568971]
External Links
PubChem Compound
16656685
PubChem Substance
347828168
ChemSpider
17589967
ChEMBL
CHEMBL560592

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedNot AvailableArrythmias1
1CompletedPreventionArrythmias1
1CompletedTreatmentHealthy Volunteers1
2CompletedTreatmentFocus of Study is STEMI1

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

Taxonomy

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-dipeptide / N-acyl-alpha-amino acid / Proline or derivatives / N-acyl-alpha amino acid or derivatives / N-acyl-l-alpha-amino acid / Alpha-amino acid amide / Alpha-amino acid or derivatives / Benzamide / Benzoic acid or derivatives / N-acylpyrrolidine
show 26 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on October 20, 2016 14:50 / Updated on September 02, 2019 19:32