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Emivirine

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Emivirine
Names
Preferred IUPAC name 6-Benzyl-1-(ethoxymethyl)-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
Identifiers
CAS Number
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
CompTox Dashboard (EPA)
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)Key: MLILORUFDVLTSP-UHFFFAOYSA-N
  • InChI=1/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)Key: MLILORUFDVLTSP-UHFFFAOYAG
SMILES
  • CCOCN1C(=C(C(=O)NC1=O)C(C)C)CC2=CC=CC=C2
Properties
Chemical formula C17H22N2O3
Molar mass 302.36818 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C , 100 kPa). ☒verify (what is  ?) Infobox references
Chemical compound

Emivirine (MKC-442) is a failed experimental agent for the treatment of HIV. It is a non-nucleoside reverse transcriptase inhibitor. While emivirine showed promising antiviral activity in vitro, it failed to show sufficient efficacy in human trials. However it is still notable as an early proof of concept, which led to the discovery of a number of related antiviral drugs.

Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)
Capsid inhibitors
Entry/fusion inhibitors
(Discovery and development)
Integrase inhibitors
(Integrase strand transfer inhibitors (INSTI))
Maturation inhibitors
Protease Inhibitors (PI)
(Discovery and development)
1 generation
2 generation
Reverse-transcriptase
inhibitors
(RTIs)
Nucleoside and
nucleotide (NRTI)
Non-nucleoside (NNRTI)
(Discovery and development)
1 generation
2 generation
Combined formulations
Pharmacokinetic boosters
Experimental agents
Uncoating inhibitors
Transcription inhibitors
Translation inhibitors
BNAbs
Other
Failed agents
°DHHS recommended initial regimen options. Formerly or rarely used agent.

References

  1. "Emivirine".
  2. Calenbergh SV, Herdewijn P. A heterogeneous collection of novel antiviral pyrimidines. Expert Opinion on Therapeutic Patents 2000; 10(3):289-295. DOI:10.1517/13543776.10.3.289
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