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
Structure for Oglufanide (DB05779)
- 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).
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!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.
Drug Interaction Integrate drug-drug
interactions in your softwareAmbroxol The risk or severity of methemoglobinemia can be increased when Oglufanide is combined with Ambroxol. Articaine The risk or severity of methemoglobinemia can be increased when Oglufanide is combined with Articaine. Benzocaine The risk or severity of methemoglobinemia can be increased when Oglufanide is combined with Benzocaine. Benzyl alcohol The risk or severity of methemoglobinemia can be increased when Oglufanide is combined with Benzyl alcohol. Bupivacaine The risk or severity of methemoglobinemia can be increased when Oglufanide is combined with Bupivacaine. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Oglufanide disodium Q60AU1LLNU 237068-57-4 GDLPAGOVHZLZEK-JBUFHSOLSA-L
Categories
- Drug Categories
- Adjuvants, Immunologic
- Amino Acids, Peptides, and Proteins
- Angiogenesis Modulating Agents
- Antidotes
- Antineoplastic Agents
- Cardiovascular Agents
- Compounds used in a research, industrial, or household setting
- Growth Inhibitors
- Growth Substances
- Immunologic Factors
- Oligopeptides
- Peptides
- Protective Agents
- 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
- External Links
- Human Metabolome Database
- HMDB0028830
- PubChem Compound
- 100094
- PubChem Substance
- 347827743
- ChemSpider
- 90450
- ChEBI
- 73512
- ChEMBL
- CHEMBL2111029
- ZINC
- ZINC000001576166
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 3 Completed Treatment Human Immunodeficiency Virus (HIV) Infections / Kaposi's Sarcoma 1 2 Terminated Treatment Colorectal Cancer 1 2 Unknown Status Treatment Ovarian Cancer / Primary Peritoneal Cancer 1 1 Completed Treatment Ovarian Cancer 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
Property Value Source Water Solubility 0.369 mg/mL ALOGPS logP -1.5 ALOGPS logP -2.2 Chemaxon logS -3 ALOGPS pKa (Strongest Acidic) 3.44 Chemaxon pKa (Strongest Basic) 8.45 Chemaxon Physiological Charge -1 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 145.51 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 84.29 m3·mol-1 Chemaxon Polarizability 33.18 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 splash10-0k9x-9740000000-890ec1661e76a8511c69 Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-0492000000-e887cc3dd6e19afecf3f Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-0ugi-1975000000-d438d8382c7f2fd7ba17 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0pj0-8491000000-bd8d57b20ae71e895cb5 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0umi-6890000000-acde36b0bba76a2e5340 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4r-9400000000-6e084d4ff7bcf3ea770b Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0536-4920000000-b2ee8ede33657a0c16fb Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 175.28976 predictedDeepCCS 1.0 (2019) [M+H]+ 177.64777 predictedDeepCCS 1.0 (2019) [M+Na]+ 184.50645 predictedDeepCCS 1.0 (2019)
Drug created at November 18, 2007 18:27 / Updated at January 14, 2023 19:02