149950-60-7

Basic information

• Product Name: emivirine
• Synonyms: emivirine;6-benzyl-1-(ethoxymethyl)-5-isopropyluracil;MKC 442
• CAS NO: 149950-60-7
• Molecular Formula: C₁₇H₂₂N₂O₃
• Molecular Weight: 302.41
• Mol File: 149950-60-7.mol
• Article Data: 11

Chemical Properties

• Boiling Point: °Cat760mmHg
• Flash Point: °C
• Appearance: /
• Density: 1.133g/cm³
• Refractive Index: 1.542
• CAS DataBase Reference: emivirine(CAS DataBase Reference)
• NIST Chemistry Reference: emivirine(149950-60-7)
• EPA Substance Registry System: emivirine(149950-60-7)

Safety Data

• Hazardous Substances Data: 149950-60-7(Hazardous Substances Data)

Usage

Description

Emivirine, also known as Coactinon, is a pyrimidone derivative that functions as a non-nucleoside reverse transcriptase inhibitor. It is a uracil molecule substituted at positions 1, 5, and 6 by ethoxymethyl, isopropyl, and benzyl groups, respectively. Initially developed as an experimental agent for the treatment of HIV, it has shown potential in treating other diseases as well.

Uses

Used in Pharmaceutical Industry:
Emivirine is used as an antiviral agent for the treatment of HIV-1 infections. It acts as a non-nucleoside reverse transcriptase inhibitor, preventing the replication of the virus and thus helping to manage the infection in patients.
Used in COVID-19 Treatment:
Emivirine has also been identified as a potential treatment option for diseases caused by SARS-CoV-2, the virus responsible for COVID-19. Its antiviral properties make it a candidate for further research and development in this area.
Brand Name:
Emivirine is marketed under the brand name Coactinon by Mitsubishi Chemical Corporation in Japan.

Hazard

Moderately toxic by ingestion.

Safety Profile

Moderately toxic by ingestion. When heated to decomposition it emits toxic vapors of NOx.

InChI: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)

Upstream product

• 1020069-04-8 4-benzyl-5-isopropyl-2,6-bis-trimethylsilanyloxy-pyrimidine 
• 3188-13-4 ethyl chloromethyl ether 
• 718-08-1 ethyl 3-oxo-4-phenylbutyrate 
• 103-80-0 phenylacetyl chloride 
• 199851-91-7 6-benzyl-5-isopropyl-2-thiouracil 
• 1026065-34-8 1-Ethoxymethyl-6-(hydroxy-phenyl-methyl)-5-isopropyl-2-thioxo-2,3-dihydro-1H-pyrimidin-4-one 
• 6921-34-2 benzylmagnesium chloride 
• 225232-14-4 6-benzyl-2,4-dichloro-5-isopropylpyrimidine 
• 1780-42-3 2,4,6-trichloro-5-isopropylpyrimidine 
• 225232-58-6 6-benzyl-2,4-dimethoxy-5-isopropylpyrimidine 
• 909546-83-4 2-(4-bromo-2,6-dimethoxypyrimidin-5-yl)propan-2-ol 
• 909546-84-5 4-bromo-5-isopropyl-2,6-dimethoxypyrimidine 
• 462-95-3 formaldehyde diethyl acetal 
• 176519-55-4 6-benzyl-5-isopropylpyrimidine-2,4(1H,3H)-dione 

Downstream Products

• 165960-84-9 6-benzyl-5-isopropyl-3-(2-oxo-2-phenylethyl)pyrimidine-2,4(1H,3H)-dione 
• 1027144-85-9 6-Benzyl-1-butyl-5-isopropyl-3-(2-oxo-2-phenyl-ethyl)-1H-pyrimidine-2,4-dione 
• 1026720-95-5 6-Benzyl-5-isopropyl-1-(2-methoxy-ethyl)-3-(2-oxo-2-phenyl-ethyl)-1H-pyrimidine-2,4-dione 
• 1237521-96-8 3-(3-(4-acetylphenyl)propyl)-6-benzyl-1-(ethoxymethyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-92-4 6-benzyl-1-(4-(4-fluorophenyl)butyl)-3-hydroxy-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-91-3 6-benzyl-1-(3-(4-fluorophenyl)propyl)-3-hydroxy-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-90-2 6-benzyl-1-((4-fluorophenyl)ethyl)-3-hydroxy-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-89-9 6-benzyl-1-(4-(4-fluorophenyl)butyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-88-8 6-benzyl-1-(3-(4-fluorophenyl)propyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-87-7 6-benzyl-1-(2-(4-fluorophenyl)ethyl)-5-isopropylpyrimidine-2,4(1H,3H)-dione 
• 1281859-86-6 6-benzyl-1-(4-(4-fluorophenyl)butyl)-5-isopropyl-3-(2-oxo-2-phenylethyl)pyrimidine-2,4(1H,3H)-dione 
• 1281859-85-5 6-benzyl-1-(3-(4-fluorophenyl)propyl)-5-isopropyl-3-(2-oxo-2-phenylethyl)pyrimidine-2,4(1H,3H)-dione 
• 1281859-84-4 6-benzyl-1-(2-(4-fluorophenyl)ethyl)-5-isopropyl-3-(2-oxo-2-phenylethyl)pyrimidine-2,4(1H,3H)-dione 
• 847995-32-8 6-benzyl-3-[4-(benzyloxy)benzoyl]-1-(ethoxymethyl)-5-isopropyl-1,2,3,4-tetrahydropyrimidine-2,4-dione 

Relevant articles and documents

New efficient and flexible synthetic route to Emivirine and its analogs

A revised synthetic route to Emivirine (MKC-442) via properly substituted β-keto ester converted from Meldrum's Acid was developed. This method could be applied to the synthesis of a variety of MKC-442 analogues and open the way for their systematic biological evaluation.

3-Hydroxypyrimidine-2,4-diones as an Inhibitor Scaffold of HIV Integrase

Integrase (IN) represents a clinically validated target for the development of antivirals against human immunodeficiency virus (HIV). Inhibitors with a novel structure core are essential for combating resistance associated with known IN inhibitors (INIs). We have previously disclosed a novel dual inhibitor scaffold of HIV IN and reverse transcriptase (RT). Here we report the complete structure-activity relationship (SAR), molecular modeling, and resistance profile of this inhibitor type on IN inhibition. These studies support an antiviral mechanism of dual inhibition against both IN and RT and validate 3-hydroxypyrimidine-2,4-diones as an IN inhibitor scaffold.

Chemo- and regioselective functionalization of uracil derivatives. Applications to the synthesis of oxypurinol and emivirine

A novel route for the synthesis of 4,5-difunctionalized uracils using a chemo- and regioselective bromine/magnesium exchange reaction on 5-bromo-4-halogeno-2,6-dimethoxypyrimidines has been developed. Applications to the synthesis of pharmaceuticals such as oxypurinol and emivirine are reported.