Oglufanide

Identification

Generic Name
Oglufanide
DrugBank Accession Number
DB05779
Background

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.

Type
Small Molecule
Groups
Investigational
Structure
Thumb
Weight
Average: 333.344
Monoisotopic: 333.132470724
Chemical Formula
C16H19N3O5
Synonyms
  • alpha-Glutamyltryptophan
  • Glutamyltryptophan
  • L-Glu-L-Trp
  • L-glutamyl-L-tryptophan
  • L-α-Glu-L-Trp
  • Oglufanide
  • α-Glu-Trp
External IDs
  • IM 862

Pharmacology

Indication

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

Pharmacology
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Contraindications & Blackbox Warnings
Contraindications
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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

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.
DrugInteraction
Darbepoetin alfaThe risk or severity of Thrombosis can be increased when Darbepoetin alfa is combined with Oglufanide.
ErythropoietinThe risk or severity of Thrombosis can be increased when Erythropoietin is combined with Oglufanide.
Methoxy polyethylene glycol-epoetin betaThe risk or severity of Thrombosis can be increased when Methoxy polyethylene glycol-epoetin beta is combined with Oglufanide.
PeginesatideThe risk or severity of Thrombosis can be increased when Peginesatide is combined with Oglufanide.
Interactions
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Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Oglufanide disodiumQ60AU1LLNU237068-57-4GDLPAGOVHZLZEK-JBUFHSOLSA-L

Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
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
3-alkylindole / Alpha peptide / Alpha-amino acid or derivatives / Amine / Amino acid / Amino acid or derivatives / Amino fatty acid / Aromatic heteropolycyclic compound / Azacycle / Benzenoid
show 26 more
Molecular Framework
Aromatic heteropolycyclic compounds
External Descriptors
dipeptide (CHEBI:73512)
Affected organisms
Not Available

Chemical Identifiers

UNII
4RHY598T5U
CAS number
38101-59-6
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]carbamoyl}butanoic acid
SMILES
N[C@@H](CCC(O)=O)C(=O)N[C@@H](CC1=CNC2=C1C=CC=C2)C(O)=O

References

General References
Not Available
Human Metabolome Database
HMDB0028830
PubChem Compound
100094
PubChem Substance
347827743
ChemSpider
90450
ChEBI
73512
ChEMBL
CHEMBL2111029
ZINC
ZINC000001576166

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kaposi’s sarcoma1
2TerminatedTreatmentColorectal, Cancer1
2Unknown StatusTreatmentOvarian Cancer / Primary Peritoneal Cavity Cancer1
1CompletedTreatmentOvarian Cancer1

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 Solubility0.369 mg/mLALOGPS
logP-1.5ALOGPS
logP-2.2ChemAxon
logS-3ALOGPS
pKa (Strongest Acidic)3.44ChemAxon
pKa (Strongest Basic)8.45ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count5ChemAxon
Polar Surface Area145.51 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity84.29 m3·mol-1ChemAxon
Polarizability33.18 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

Drug created on November 18, 2007 18:27 / Updated on February 21, 2021 18:51