Oglufanide

Identification

Name
Oglufanide
Accession Number
DB05779
Type
Small Molecule
Groups
Investigational
Description

Oglufanide is a synthetic dipeptide immunomodulator in development for the treatment of chronic hepatitis C viral infection. Oglufanide was originally developed to treat severe infectious disease in Russia (where it is a registered pharmaceutical), and was extensively studied in cancer clinical trials in the United States before being acquired by Implicit Bioscience in 2005. Oglufanide works as a regulator of the body's immune response, is being given by intranasal administration to patients with chronic hepatitis C viral infection.

Structure
Thumb
Synonyms
  • alpha-Glutamyltryptophan
  • Glutamyltryptophan
  • L-Glu-L-Trp
  • L-glutamyl-L-tryptophan
  • L-α-Glu-L-Trp
  • α-Glu-Trp
Product Ingredients
IngredientUNIICASInChI Key
Oglufanide disodiumQ60AU1LLNU237068-57-4GDLPAGOVHZLZEK-JBUFHSOLSA-L
Categories
UNII
4RHY598T5U
CAS number
38101-59-6
Weight
Average: 333.344
Monoisotopic: 333.132470724
Chemical Formula
C16H19N3O5
InChI Key
LLEUXCDZPQOJMY-AAEUAGOBSA-N
InChI
InChI=1S/C16H19N3O5/c17-11(5-6-14(20)21)15(22)19-13(16(23)24)7-9-8-18-12-4-2-1-3-10(9)12/h1-4,8,11,13,18H,5-7,17H2,(H,19,22)(H,20,21)(H,23,24)/t11-,13-/m0/s1
IUPAC Name
(4S)-4-amino-4-{[(1S)-1-carboxy-2-(1H-indol-3-yl)ethyl]-C-hydroxycarbonimidoyl}butanoic acid
SMILES
N[[email protected]@H](CCC(O)=O)C(O)=N[[email protected]@H](CC1=CNC2=CC=CC=C12)C(O)=O

Pharmacology

Indication

Investigated for use/treatment in hepatitis (viral, C).

Structured Indications
Not Available
Pharmacodynamics

Oglufanide regulates the body's innate immune response to defeat invading germs and cancer cells. It may control or reverse the suppression of the immune system which the hepatitis virus uses to defeat our normally healthy defenses.

Mechanism of action
Not Available
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
DrugInteractionDrug group
AcetyldigitoxinAcetyldigitoxin may decrease the cardiotoxic activities of Oglufanide.Approved
AcetyldigoxinAcetyldigoxin may decrease the cardiotoxic activities of Oglufanide.Experimental
BevacizumabBevacizumab may increase the cardiotoxic activities of Oglufanide.Approved, Investigational
CabazitaxelThe risk or severity of adverse effects can be increased when Cabazitaxel is combined with Oglufanide.Approved
CyclophosphamideCyclophosphamide may increase the cardiotoxic activities of Oglufanide.Approved, Investigational
CymarinCymarin may decrease the cardiotoxic activities of Oglufanide.Experimental
DeslanosideDeslanoside may decrease the cardiotoxic activities of Oglufanide.Approved
DigitoxinDigitoxin may decrease the cardiotoxic activities of Oglufanide.Approved, Investigational
DigoxinDigoxin may decrease the cardiotoxic activities of Oglufanide.Approved
DocetaxelThe risk or severity of adverse effects can be increased when Docetaxel is combined with Oglufanide.Approved, Investigational
GitoformateGitoformate may decrease the cardiotoxic activities of Oglufanide.Experimental
Lanatoside CLanatoside C may decrease the cardiotoxic activities of Oglufanide.Experimental
MetildigoxinMetildigoxin may decrease the cardiotoxic activities of Oglufanide.Experimental
OleandrinOleandrin may decrease the cardiotoxic activities of Oglufanide.Experimental, Investigational
OuabainOuabain may decrease the cardiotoxic activities of Oglufanide.Approved
PaclitaxelThe risk or severity of adverse effects can be increased when Paclitaxel is combined with Oglufanide.Approved, Vet Approved
PeruvosidePeruvoside may decrease the cardiotoxic activities of Oglufanide.Experimental
ProscillaridinProscillaridin may decrease the cardiotoxic activities of Oglufanide.Experimental
TrastuzumabTrastuzumab may increase the cardiotoxic activities of Oglufanide.Approved, Investigational
Food Interactions
Not Available

References

General References
Not Available
External Links
PubChem Compound
100094
PubChem Substance
347827743
ChemSpider
90450
ChEBI
73512
ChEMBL
CHEMBL2111029

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1CompletedTreatmentCancer, Ovarian1
2TerminatedTreatmentColorectal Cancers1
2Unknown StatusTreatmentCancer, Ovarian / Primary Peritoneal Cavity Cancer1
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kaposi s Sarcoma (KS)1

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 Solubility0.184 mg/mLALOGPS
logP-1.4ALOGPS
logP-1.5ChemAxon
logS-3.3ALOGPS
pKa (Strongest Acidic)3.3ChemAxon
pKa (Strongest Basic)9.62ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count7ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area149 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity84.81 m3·mol-1ChemAxon
Polarizability32.97 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, 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
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

Taxonomy

Description
This compound belongs to the class of organic compounds known as peptides. These are compounds containing an amide derived from two or more amino carboxylic acid molecules (the same or different) by formation of a covalent bond from the carbonyl carbon of one to the nitrogen atom of another.
Kingdom
Organic compounds
Super Class
Organic acids and derivatives
Class
Carboxylic acids and derivatives
Sub Class
Amino acids, peptides, and analogues
Direct Parent
Peptides
Alternative Parents
N-acyl-alpha amino acids / Gamma amino acids and derivatives / 3-alkylindoles / Amino fatty acids / Substituted pyrroles / Dicarboxylic acids and derivatives / Benzenoids / Heteroaromatic compounds / Amino acids / Carboxylic acids
show 8 more
Substituents
Alpha peptide / N-acyl-alpha-amino acid / N-acyl-alpha amino acid or derivatives / Gamma amino acid or derivatives / Alpha-amino acid or derivatives / 3-alkylindole / Indole / Indole or derivatives / Amino fatty acid / Dicarboxylic acid or derivatives
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dipeptide (CHEBI:73512)

Drug created on November 18, 2007 11:27 / Updated on November 09, 2017 03:52