Davunetide

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
Davunetide
Accession Number
DB12613  (DB05907, DB05588)
Type
Small Molecule
Groups
Investigational
Description

Davunetide has been used in trials studying the treatment of Progressive Nonfluent Aphasia, Progressive Supranuclear Palsy, Predicted Tauopathies, Including, Corticobasal Degeneration Syndrome, and Frontotemporal Dementia With Parkinsonism Linked to Chromosome 17.

Davunetide is the first drug to improve memory performance by impacting the mechanisms that lead to physical damage in the brain caused by neurofibrillary tangles, one of the two established pathological hallmarks that are common to amnestic mild cognitive impairment (aMCI) and Alzheimer's disease (AD). Davunetide is derived from a naturally occurring neuroprotective brain protein known as activity dependent neuroprotective protein.

Structure
Thumb
Synonyms
Not Available
External IDs
AL-108 / AL-208
Categories
UNII
GF00K3IIWE
CAS number
211439-12-2
Weight
Average: 824.934
Monoisotopic: 824.439217412
Chemical Formula
C36H60N10O12
InChI Key
DWLTUUXCVGVRAV-XWRHUKJGSA-N
InChI
InChI=1S/C36H60N10O12/c1-6-18(4)28(35(56)46-14-8-9-23(46)31(52)41-21(36(57)58)11-12-25(38)48)44-30(51)22(16-47)42-33(54)27(17(2)3)43-32(53)24-10-7-13-45(24)34(55)19(5)40-29(50)20(37)15-26(39)49/h17-24,27-28,47H,6-16,37H2,1-5H3,(H2,38,48)(H2,39,49)(H,40,50)(H,41,52)(H,42,54)(H,43,53)(H,44,51)(H,57,58)/t18-,19-,20-,21-,22-,23-,24-,27-,28-/m0/s1
IUPAC Name
(2S)-2-{[(2S)-1-[(2S,3S)-2-[(2S)-2-[(2S)-2-{[(2S)-1-[(2S)-2-[(2S)-2-amino-3-carbamoylpropanamido]propanoyl]pyrrolidin-2-yl]formamido}-3-methylbutanamido]-3-hydroxypropanamido]-3-methylpentanoyl]pyrrolidin-2-yl]formamido}-4-carbamoylbutanoic acid
SMILES
CC[C@H](C)[C@H](NC(=O)[C@H](CO)NC(=O)[C@@H](NC(=O)[C@@H]1CCCN1C(=O)[C@H](C)NC(=O)[C@@H](N)CC(N)=O)C(C)C)C(=O)N1CCC[C@H]1C(=O)N[C@@H](CCC(N)=O)C(O)=O

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action

Davunetide interacts with microtubules 1) preventing the formation of neurofibrillary tanges and protecting the network from a 'death signal' or 2) repairing the network if the brain cell death process has already begun. The restoration of the microtubule network explains the results shown in treated animals which have improved cognitive performance compared to untreated groups.

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
Not Available
External Links
PubChem Compound
9832404
PubChem Substance
347828827
ChemSpider
8008132
ChEMBL
CHEMBL2103826

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentCorticobasal Degeneration Syndrome / Frontotemporal Dementia With Parkinsonism Linked to Chromosome 17 / Predicted Tauopathies, Including / Progressive Nonfluent Aphasia / Progressive Supranuclear Palsy (PSP)1
2CompletedTreatmentMild Cognitive Impairment (MCI)1
2CompletedTreatmentMild Cognitive Impairment, So Stated1
2CompletedTreatmentSchizophrenic Disorders1
2, 3CompletedTreatmentProgressive Supranuclear Palsy (PSP)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
PropertyValueSource
Water Solubility0.343 mg/mLALOGPS
logP-2.6ALOGPS
logP-7.5ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)3.33ChemAxon
pKa (Strongest Basic)7.05ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count13ChemAxon
Hydrogen Donor Count10ChemAxon
Polar Surface Area355.85 Å2ChemAxon
Rotatable Bond Count22ChemAxon
Refractivity201.56 m3·mol-1ChemAxon
Polarizability82.56 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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 oligopeptides. These are organic compounds containing a sequence of between three and ten alpha-amino acids joined by peptide bonds.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Oligopeptides
Alternative Parents
Glutamine and derivatives / Isoleucine and derivatives / Asparagine and derivatives / Valine and derivatives / Proline and derivatives / Serine and derivatives / Alpha amino acid amides / N-acyl-L-glutamines / Pyrrolidinecarboxamides / N-acylpyrrolidines
show 16 more
Substituents
Alpha-oligopeptide / Glutamine or derivatives / Asparagine or derivatives / Isoleucine or derivatives / N-acyl-alpha-amino acid / N-acyl-alpha amino acid or derivatives / N-acyl-l-alpha-amino acid / Proline or derivatives / Valine or derivatives / Alpha-amino acid amide
show 38 more
Molecular Framework
Aliphatic heteromonocyclic compounds
External Descriptors
Not Available

Drug created on October 20, 2016 17:13 / Updated on September 02, 2019 19:44