Rupintrivir
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Identification
- Generic Name
- Rupintrivir
- DrugBank Accession Number
- DB05102
- Background
Rupintrivir is a rhinovirus 3C protease inhibitor in development for use against human rhinoviral (HRV) infections. Rupintrivir was active against all 48 HRV serotypes tested in a cell protection assay in H1-HeLa cells. It is designed to combat colds caused by rhinovirus.
- Type
- Small Molecule
- Groups
- Investigational
- Structure
- Weight
- Average: 598.6624
Monoisotopic: 598.280277827 - Chemical Formula
- C31H39FN4O7
- Synonyms
- Rupintrivir
- External IDs
- AG-7088
- AG7088
Pharmacology
- Indication
Investigated for use/treatment in viral infection.
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- Pharmacodynamics
Not Available
- Mechanism of action
The 3C protease (3CP) enzyme is central to rhinovirus replication. By binding to and inhibiting this enzyme, AG7088 prevents rhinovirus replication in cells of the respiratory tract and stops cold symptoms developing.
Target Actions Organism UGenome polyprotein Not Available HRV-14 - 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.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 softwareAdenovirus type 7 vaccine live The therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Rupintrivir. Anthrax vaccine The therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Rupintrivir. Bacillus calmette-guerin substrain connaught live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Rupintrivir. Bacillus calmette-guerin substrain russian BCG-I live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain russian BCG-I live antigen can be decreased when used in combination with Rupintrivir. Bacillus calmette-guerin substrain tice live antigen The therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Rupintrivir. BCG vaccine The therapeutic efficacy of BCG vaccine can be decreased when used in combination with Rupintrivir. Human adenovirus e serotype 4 strain cl-68578 antigen The therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Rupintrivir. Rubella virus vaccine The therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Rupintrivir. Typhoid Vaccine Live The therapeutic efficacy of Typhoid Vaccine Live can be decreased when used in combination with Rupintrivir. Varicella zoster vaccine (live/attenuated) The therapeutic efficacy of Varicella zoster vaccine (live/attenuated) can be decreased when used in combination with Rupintrivir. Identify potential medication risksEasily compare up to 40 drugs with our drug interaction checker.Get severity rating, description, and management advice.Learn more - 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.
- International/Other Brands
- rupintrivir
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as 2-heteroaryl carboxamides. These are compounds containing a heteroaromatic ring that carries a carboxamide group.
- Kingdom
- Organic compounds
- Super Class
- Organic acids and derivatives
- Class
- Carboxylic acids and derivatives
- Sub Class
- Carboxylic acid derivatives
- Direct Parent
- 2-heteroaryl carboxamides
- Alternative Parents
- Fatty acid esters / Fluorobenzenes / Aryl fluorides / Pyrrolidine-2-ones / N-acyl amines / Enoate esters / Heteroaromatic compounds / Isoxazoles / Secondary carboxylic acid amides / Ketones show 9 more
- Substituents
- 2-heteroaryl carboxamide / 2-pyrrolidone / Alpha,beta-unsaturated carboxylic ester / Aromatic heteromonocyclic compound / Aryl fluoride / Aryl halide / Azacycle / Azole / Benzenoid / Carbonyl group show 28 more
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- RGE5K1Q5QW
- CAS number
- 223537-30-2
- InChI Key
- CAYJBRBGZBCZKO-BHGBQCOSSA-N
- InChI
- InChI=1S/C31H39FN4O7/c1-5-42-27(38)11-10-24(16-21-12-13-33-29(21)39)34-30(40)22(15-20-6-8-23(32)9-7-20)17-26(37)28(18(2)3)35-31(41)25-14-19(4)43-36-25/h6-11,14,18,21-22,24,28H,5,12-13,15-17H2,1-4H3,(H,33,39)(H,34,40)(H,35,41)/b11-10+/t21-,22+,24+,28-/m0/s1
- IUPAC Name
- ethyl (2E,4S)-4-[(2R,5S)-2-[(4-fluorophenyl)methyl]-6-methyl-5-[(5-methyl-1,2-oxazol-3-yl)formamido]-4-oxoheptanamido]-5-[(3S)-2-oxopyrrolidin-3-yl]pent-2-enoate
- SMILES
- CCOC(=O)\C=C\[C@H](C[C@@H]1CCNC1=O)NC(=O)[C@@H](CC(=O)[C@H](C(C)C)NC(=O)C1=NOC(C)=C1)CC1=CC=C(F)C=C1
References
- General References
- Binford SL, Weady PT, Maldonado F, Brothers MA, Matthews DA, Patick AK: In vitro resistance study of rupintrivir, a novel inhibitor of human rhinovirus 3C protease. Antimicrob Agents Chemother. 2007 Dec;51(12):4366-73. Epub 2007 Oct 1. [Article]
- Binford SL, Maldonado F, Brothers MA, Weady PT, Zalman LS, Meador JW 3rd, Matthews DA, Patick AK: Conservation of amino acids in human rhinovirus 3C protease correlates with broad-spectrum antiviral activity of rupintrivir, a novel human rhinovirus 3C protease inhibitor. Antimicrob Agents Chemother. 2005 Feb;49(2):619-26. [Article]
- External Links
- PubChem Compound
- 6440352
- PubChem Substance
- 175426944
- ChemSpider
- 4944627
- BindingDB
- 11243
- ChEMBL
- CHEMBL20210
- ZINC
- ZINC000003919807
Clinical Trials
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 0.0306 mg/mL ALOGPS logP 2.43 ALOGPS logP 3.21 Chemaxon logS -4.3 ALOGPS pKa (Strongest Acidic) 12.5 Chemaxon pKa (Strongest Basic) -0.59 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 6 Chemaxon Hydrogen Donor Count 3 Chemaxon Polar Surface Area 156.7 Å2 Chemaxon Rotatable Bond Count 16 Chemaxon Refractivity 157.24 m3·mol-1 Chemaxon Polarizability 62.56 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 0 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9971 Blood Brain Barrier - 0.6941 Caco-2 permeable - 0.6567 P-glycoprotein substrate Substrate 0.7026 P-glycoprotein inhibitor I Inhibitor 0.6723 P-glycoprotein inhibitor II Non-inhibitor 0.738 Renal organic cation transporter Non-inhibitor 0.878 CYP450 2C9 substrate Non-substrate 0.9279 CYP450 2D6 substrate Non-substrate 0.8079 CYP450 3A4 substrate Substrate 0.5883 CYP450 1A2 substrate Non-inhibitor 0.7447 CYP450 2C9 inhibitor Non-inhibitor 0.6994 CYP450 2D6 inhibitor Non-inhibitor 0.8321 CYP450 2C19 inhibitor Non-inhibitor 0.6134 CYP450 3A4 inhibitor Non-inhibitor 0.5347 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.5074 Ames test Non AMES toxic 0.6203 Carcinogenicity Non-carcinogens 0.7646 Biodegradation Not ready biodegradable 1.0 Rat acute toxicity 2.6484 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9189 hERG inhibition (predictor II) Non-inhibitor 0.553
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets

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1. DetailsGenome polyprotein
- Kind
- Protein
- Organism
- HRV-14
- Pharmacological action
- Unknown
- General Function
- Structural molecule activity
- Specific Function
- Capsid protein VP1: Forms an icosahedral capsid of pseudo T=3 symmetry with capsid proteins VP2 and VP3. The capsid is 300 Angstroms in diameter, composed of 60 copies of each capsid protein and en...
- Gene Name
- Not Available
- Uniprot ID
- P03303
- Uniprot Name
- Genome polyprotein
- Molecular Weight
- 242989.38 Da
Drug created at October 21, 2007 22:23 / Updated at February 21, 2021 18:51