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
Structure for Danegaptide (DB11821)
- Weight
- Average: 291.307
Monoisotopic: 291.121906039 - Chemical Formula
- C14H17N3O4
- Synonyms
- Danegaptide
- External IDs
- GAP-134
- ZP1609
Pharmacology
- Indication
Not Available
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Contraindications & Blackbox Warnings
Avoid life-threatening adverse drug eventsImprove clinical decision support with information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events & improve clinical decision support.- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates.Improve decision support & research outcomes with our structured adverse effects data.- 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
- 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]
- 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]
- External Links
- PubChem Compound
- 16656685
- PubChem Substance
- 347828168
- ChemSpider
- 17589967
- ChEMBL
- CHEMBL560592
- ZINC
- ZINC000040836075
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 2 Completed Treatment Focus of Study is STEMI 1 1 Completed Not Available Arrhythmia 1 1 Completed Prevention Arrhythmia 1 1 Completed Treatment Healthy Subjects (HS) 1
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
Property Value Source Water Solubility 1.91 mg/mL ALOGPS logP -0.55 ALOGPS logP -3.3 Chemaxon logS -2.2 ALOGPS pKa (Strongest Acidic) 3.32 Chemaxon pKa (Strongest Basic) 8.13 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 112.73 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 74.08 m3·mol-1 Chemaxon Polarizability 29.07 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Drug created at October 20, 2016 20:50 / Updated at February 21, 2021 18:53