Structure via PubChem · Public domain (PubChem)
emivirine
Sign in to saveAlso known as 6-benzyl-1-(ethoxymethyl)-5-(1-methylethyl)pyrimidine-2,4(1H,3H)-dione, MKC-442, 1-(ethoxymethyl)-5-(1-methylethyl)-6-(phenylmethyl)pyrimidine-2,4(1H,3H)-dione, 6-benzyl-1-(ethoxymethyl)-5-(1-methylethyl)uracil
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.
Chemical data
- Formula
- C17H22N2O3
- Molecular weight
- 302.37 g/mol
- IUPAC name
- 6-benzyl-1-(ethoxymethyl)-5-propan-2-ylpyrimidine-2,4-dione
- SMILES
- CCOCN1C(=C(C(=O)NC1=O)C(C)C)CC2=CC=CC=C2
- InChIKey
- MLILORUFDVLTSP-UHFFFAOYSA-N
- XLogP
- 2.6
- Polar surface area
- 58.6 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
- Indications
- HIV infection
via ChEMBL · EBI
Research
55 papers- Emivirine: an NRTI that functions as an NNRTI.BETA : bulletin of experimental treatments for AIDS : a publication of the San Francisco AIDS Foundation · 1999
- New developments in anti-HIV chemotherapy.Current medicinal chemistry · 2001
- Synthesis and Antiviral Evaluation of 1-[(2-Phenoxyethyl)oxymethyl] and 6-(3,5-Dimethoxybenzyl) Analogues of HIV Drugs Emivirine and TNK-651.Drug research · 2016
- New anti-HIV agents and targets.Medicinal research reviews · 2002
- New developments in anti-HIV chemotherapy.Biochimica et biophysica acta · 2002
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 302.163
Show 5 more facts
- chemical formula
- C₁₇H₂₂N₂O₃
- canonical SMILES
- CCOCN1C(=C(C(=O)NC1=O)C(C)C)CC2=CC=CC=C2
- World Health Organisation international non-proprietary name
- emivirine
- subject has role
- reverse-transcriptase inhibitor
- Commons category
- Emivirine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
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.
==References==
Excerpted from Wikipedia’s “emivirine” article, available under the CC BY-SA 4.0 licence.