NAV

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
3D
Similar Structures
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
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Pharmacology

Indication

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

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Contraindications & Blackbox Warnings
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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 Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
Not Available

Interactions

Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
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
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interactions in your software
AmbroxolThe risk or severity of methemoglobinemia can be increased when Oglufanide is combined with Ambroxol.
ArticaineThe risk or severity of methemoglobinemia can be increased when Oglufanide is combined with Articaine.
BenzocaineThe risk or severity of methemoglobinemia can be increased when Oglufanide is combined with Benzocaine.
Benzyl alcoholThe risk or severity of methemoglobinemia can be increased when Oglufanide is combined with Benzyl alcohol.
BupivacaineThe risk or severity of methemoglobinemia can be increased when Oglufanide is combined with Bupivacaine.
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 Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
PhaseStatusPurposeConditionsCount
3CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections / Kaposi's Sarcoma1
2TerminatedTreatmentColorectal Cancer1
2Unknown StatusTreatmentOvarian Cancer / Primary Peritoneal 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-MSsplash10-0k9x-9740000000-890ec1661e76a8511c69
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4i-0492000000-e887cc3dd6e19afecf3f
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ugi-1975000000-d438d8382c7f2fd7ba17
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-0pj0-8491000000-bd8d57b20ae71e895cb5
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-0umi-6890000000-acde36b0bba76a2e5340
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0a4r-9400000000-6e084d4ff7bcf3ea770b
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0536-4920000000-b2ee8ede33657a0c16fb
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-175.28976
predicted
DeepCCS 1.0 (2019)
[M+H]+177.64777
predicted
DeepCCS 1.0 (2019)
[M+Na]+184.50645
predicted
DeepCCS 1.0 (2019)

Drug created at November 18, 2007 18:27 / Updated at January 14, 2023 19:02