Emivirine

Identification

Name
Emivirine
Accession Number
DB08188  (DB12488)
Type
Small Molecule
Groups
Investigational
Description

Emivirine has been used in trials studying the treatment of HIV Infections.

Structure
Thumb
Synonyms
  • 1-(ethoxymethyl)-5-(1-methylethyl)-6-(phenylmethyl)pyrimidine-2,4(1H,3H)-dione
  • 6-benzyl-1-(ethoxymethyl)-5-(1-methylethyl)uracil
  • Emivirine
External IDs
MKC-442
International/Other Brands
Coactinon
Categories
UNII
X87G8IX72O
CAS number
149950-60-7
Weight
Average: 302.3682
Monoisotopic: 302.16304258
Chemical Formula
C17H22N2O3
InChI Key
MLILORUFDVLTSP-UHFFFAOYSA-N
InChI
InChI=1S/C17H22N2O3/c1-4-22-11-19-14(10-13-8-6-5-7-9-13)15(12(2)3)16(20)18-17(19)21/h5-9,12H,4,10-11H2,1-3H3,(H,18,20,21)
IUPAC Name
6-benzyl-1-(ethoxymethyl)-5-(propan-2-yl)-1,2,3,4-tetrahydropyrimidine-2,4-dione
SMILES
CCOCN1C(=O)NC(=O)C(C(C)C)=C1CC1=CC=CC=C1

Pharmacology

Indication
Not Available
Pharmacodynamics
Not Available
Mechanism of action
TargetActionsOrganism
UGag-Pol polyproteinNot 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
Toxicity
Not Available
Affected organisms
Not Available
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
Influenza a virus a/california/7/2009 (h1n1) live (attenuated) antigenThe therapeutic efficacy of Influenza a virus a/california/7/2009 (h1n1) live (attenuated) antigen can be decreased when used in combination with Emivirine.
Influenza a virus a/perth/16/2009 (h3n2) live (attenuated) antigenThe therapeutic efficacy of Influenza a virus a/perth/16/2009 (h3n2) live (attenuated) antigen can be decreased when used in combination with Emivirine.
Influenza Vaccine (Live/Attenuated)The therapeutic efficacy of Emivirine can be decreased when used in combination with Influenza Vaccine (Live/Attenuated).
Varicella Zoster Vaccine (Live/Attenuated)The therapeutic efficacy of Varicella Zoster Vaccine (Live/Attenuated) can be decreased when used in combination with Emivirine.
Food Interactions
Not Available

References

General References
Not Available
External Links
KEGG Drug
D01055
PubChem Compound
65013
PubChem Substance
99444659
ChemSpider
58529
BindingDB
2337
ChEBI
44143
ChEMBL
CHEMBL35033
HET
MKC
Wikipedia
Emivirine
PDB Entries
1rt1

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
2CompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
2TerminatedTreatmentHuman Immunodeficiency Virus (HIV) Infections2
Not AvailableCompletedTreatmentHuman Immunodeficiency Virus (HIV) Infections1

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 Solubility0.116 mg/mLALOGPS
logP2.57ALOGPS
logP2.77ChemAxon
logS-3.4ALOGPS
pKa (Strongest Acidic)10.23ChemAxon
pKa (Strongest Basic)-3.9ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area58.64 Å2ChemAxon
Rotatable Bond Count6ChemAxon
Refractivity85.41 m3·mol-1ChemAxon
Polarizability32.87 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9969
Blood Brain Barrier+0.9483
Caco-2 permeable-0.5086
P-glycoprotein substrateSubstrate0.7355
P-glycoprotein inhibitor IInhibitor0.6713
P-glycoprotein inhibitor IINon-inhibitor0.9163
Renal organic cation transporterNon-inhibitor0.6774
CYP450 2C9 substrateNon-substrate0.7898
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6158
CYP450 1A2 substrateNon-inhibitor0.6647
CYP450 2C9 inhibitorNon-inhibitor0.8239
CYP450 2D6 inhibitorNon-inhibitor0.8929
CYP450 2C19 inhibitorNon-inhibitor0.7768
CYP450 3A4 inhibitorNon-inhibitor0.7367
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.7223
Ames testNon AMES toxic0.7342
CarcinogenicityNon-carcinogens0.7524
BiodegradationNot ready biodegradable0.7093
Rat acute toxicity2.5156 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.911
hERG inhibition (predictor II)Inhibitor0.5637
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 pyrimidones. These are compounds that contain a pyrimidine ring, which bears a ketone. Pyrimidine is a 6-membered ring consisting of four carbon atoms and two nitrogen centers at the 1- and 3- ring positions.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Diazines
Sub Class
Pyrimidines and pyrimidine derivatives
Direct Parent
Pyrimidones
Alternative Parents
Hydropyrimidines / Benzene and substituted derivatives / Vinylogous amides / Heteroaromatic compounds / Ureas / Lactams / Azacyclic compounds / Organopnictogen compounds / Organooxygen compounds / Organonitrogen compounds
show 2 more
Substituents
Pyrimidone / Monocyclic benzene moiety / Hydropyrimidine / Benzenoid / Heteroaromatic compound / Vinylogous amide / Lactam / Urea / Azacycle / Organic nitrogen compound
show 7 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyrimidone (CHEBI:44143)

Targets

Kind
Protein
Organism
Not Available
Pharmacological action
Unknown
General Function
Zinc ion binding
Specific Function
Gag-Pol polyprotein: Mediates, with Gag polyrotein, the essential events in virion assembly, including binding the plasma membrane, making the protein-protein interactions necessary to create spher...
Gene Name
gag-pol
Uniprot ID
P04585
Uniprot Name
Gag-Pol polyprotein
Molecular Weight
162041.05 Da
References
  1. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235]

Drug created on September 15, 2010 15:29 / Updated on December 16, 2018 06:54