Rupintrivir

Identification

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Name
Rupintrivir
Accession Number
DB05102
Type
Small Molecule
Groups
Investigational
Description

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.

Structure
Thumb
Synonyms
Not Available
External IDs
AG-7088 / AG7088
International/Other Brands
rupintrivir
Categories
UNII
RGE5K1Q5QW
CAS number
223537-30-2
Weight
Average: 598.6624
Monoisotopic: 598.280277827
Chemical Formula
C31H39FN4O7
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

Pharmacology

Indication

Investigated for use/treatment in viral infection.

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.

TargetActionsOrganism
UGenome polyproteinNot AvailableHRV-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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
Adenovirus type 7 vaccine liveThe therapeutic efficacy of Adenovirus type 7 vaccine live can be decreased when used in combination with Rupintrivir.
Anthrax vaccineThe therapeutic efficacy of Anthrax vaccine can be decreased when used in combination with Rupintrivir.
Bacillus calmette-guerin substrain connaught live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain connaught live antigen can be decreased when used in combination with Rupintrivir.
Bacillus calmette-guerin substrain danish 1331 live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain danish 1331 live antigen can be decreased when used in combination with Rupintrivir.
Bacillus calmette-guerin substrain tice live antigenThe therapeutic efficacy of Bacillus calmette-guerin substrain tice live antigen can be decreased when used in combination with Rupintrivir.
BCG vaccineThe therapeutic efficacy of BCG vaccine can be decreased when used in combination with Rupintrivir.
Human adenovirus e serotype 4 strain cl-68578 antigenThe therapeutic efficacy of Human adenovirus e serotype 4 strain cl-68578 antigen can be decreased when used in combination with Rupintrivir.
Rubella virus vaccineThe therapeutic efficacy of Rubella virus vaccine can be decreased when used in combination with Rupintrivir.
Typhoid Vaccine Live Ty21aThe therapeutic efficacy of Typhoid Vaccine Live Ty21a 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.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
Not Available

References

General References
  1. 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. [PubMed:17908951]
  2. 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. [PubMed:15673742]
External Links
PubChem Compound
6440352
PubChem Substance
175426944
ChemSpider
4944627
BindingDB
11243
ChEMBL
CHEMBL20210

Clinical Trials

Clinical Trials
Not Available

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 Solubility0.0306 mg/mLALOGPS
logP2.43ALOGPS
logP3.21ChemAxon
logS-4.3ALOGPS
pKa (Strongest Acidic)12.49ChemAxon
pKa (Strongest Basic)0.035ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count6ChemAxon
Hydrogen Donor Count3ChemAxon
Polar Surface Area156.7 Å2ChemAxon
Rotatable Bond Count16ChemAxon
Refractivity157.24 m3·mol-1ChemAxon
Polarizability62.48 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability0ChemAxon
Rule of FiveNoChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleYesChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9971
Blood Brain Barrier-0.6941
Caco-2 permeable-0.6567
P-glycoprotein substrateSubstrate0.7026
P-glycoprotein inhibitor IInhibitor0.6723
P-glycoprotein inhibitor IINon-inhibitor0.738
Renal organic cation transporterNon-inhibitor0.878
CYP450 2C9 substrateNon-substrate0.9279
CYP450 2D6 substrateNon-substrate0.8079
CYP450 3A4 substrateSubstrate0.5883
CYP450 1A2 substrateNon-inhibitor0.7447
CYP450 2C9 inhibitorNon-inhibitor0.6994
CYP450 2D6 inhibitorNon-inhibitor0.8321
CYP450 2C19 inhibitorNon-inhibitor0.6134
CYP450 3A4 inhibitorNon-inhibitor0.5347
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5074
Ames testNon AMES toxic0.6203
CarcinogenicityNon-carcinogens0.7646
BiodegradationNot ready biodegradable1.0
Rat acute toxicity2.6484 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9189
hERG inhibition (predictor II)Non-inhibitor0.553
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
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
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

Taxonomy

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 / Fatty acid ester / Fluorobenzene / Halobenzene / Aryl fluoride / Aryl halide / Monocyclic benzene moiety / Fatty amide / N-acyl-amine / Pyrrolidone
show 28 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

Targets

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 on October 21, 2007 16:23 / Updated on August 02, 2019 07:43