Emivirine

Last updated
Emivirine
Emivirine.png
Names
Preferred IUPAC name
6-Benzyl-1-(ethoxymethyl)-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
Identifiers
3D model (JSmol)
ChEMBL
ChemSpider
PubChem CID
UNII
  • 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) X mark.svgN
    Key: MLILORUFDVLTSP-UHFFFAOYSA-N X mark.svgN
  • 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
  • CCOCN1C(=C(C(=O)NC1=O)C(C)C)CC2=CC=CC=C2
Properties
C17H22N2O3
Molar mass 302.36818 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Emivirine (MKC-442) is a failed experimental agent for the treatment of HIV. It is a non-nucleoside reverse transcriptase inhibitor. [1] 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. [2]

Related Research Articles

Antiviral drugs are a class of medication used for treating viral infections. Most antivirals target specific viruses, while a broad-spectrum antiviral is effective against a wide range of viruses. Unlike most antibiotics, antiviral drugs do not destroy their target pathogen; instead they inhibit its development.

Ribavirin Antiviral medication

Ribavirin, also known as tribavirin, is an antiviral medication used to treat RSV infection, hepatitis C and some viral hemorrhagic fevers. For hepatitis C, it is used in combination with other medications such as simeprevir, sofosbuvir, peginterferon alfa-2b or peginterferon alfa-2a. Among the viral hemorrhagic fevers it is used for Lassa fever, Crimean–Congo hemorrhagic fever, and Hantavirus infection but should not be used for Ebola or Marburg infections. Ribavirin is taken by mouth or inhaled.

Aciclovir

Aciclovir (ACV), also known as acyclovir, is an antiviral medication. It is primarily used for the treatment of herpes simplex virus infections, chickenpox, and shingles. Other uses include prevention of cytomegalovirus infections following transplant and severe complications of Epstein-Barr virus infection. It can be taken by mouth, applied as a cream, or injected.

Rimantadine

Rimantadine is an orally administered antiviral drug used to treat, and in rare cases prevent, influenzavirus A infection. When taken within one to two days of developing symptoms, rimantadine can shorten the duration and moderate the severity of influenza. RImantadine can mitigate symptoms including fever. Both rimantadine and the similar drug amantadine are derivates of adamantane. RImantadine is found to be more effective than amantadine because when used the patient displays fewer symptoms. Rimantadine was approved by the Food and Drug Administration (FDA) in 1994.

Umifenovir

Umifenovir, sold under the brand name Arbidol, is an antiviral medication for the treatment of influenza infection used in Russia and China. The drug is manufactured by Pharmstandard. Russian and China studies have shown it to be effective and it is approved in both countries while, it is not approved by the US FDA for the treatment or prevention of influenza because it was never applied for FDA approval since the drug company is in Russia not the US.

Moronic acid Chemical compound

Moronic acid is a natural triterpene. Moronic acid can be extracted from Rhus javanica, a sumac plant traditionally believed to hold medicinal applications. The molecule has also been extracted from mistletoe.

Idoxuridine

Idoxuridine is an anti-herpesvirus antiviral drug.

Interleukin 29

Interleukin-29 (IL-29) is a cytokine and it belongs to type III interferons group, also termed interferons λ (INF-λ). IL-29 plays an important role in the immune response against pathogenes and especially against viruses by mechanisms similar to type I interferons, but targeting primarily cells of epithelial origin and hepatocytes.

Pleconaril

Pleconaril (Picovir) is an antiviral drug that was being developed by Schering-Plough for prevention of asthma exacerbations and common cold symptoms in patients exposed to picornavirus respiratory infections. Pleconaril, administered either orally or intranasally, is active against viruses in the Picornaviridae family, including Enterovirus and Rhinovirus. It has shown useful activity against the dangerous enterovirus D68.

Herpes simplex Viral disease caused by herpes simplex viruses

Herpes simplex is a viral infection caused by the herpes simplex virus. Infections are categorized based on the part of the body infected. Oral herpes involves the face or mouth. It may result in small blisters in groups often called cold sores or fever blisters or may just cause a sore throat. Genital herpes, often simply known as herpes, may have minimal symptoms or form blisters that break open and result in small ulcers. These typically heal over two to four weeks. Tingling or shooting pains may occur before the blisters appear. Herpes cycles between periods of active disease followed by periods without symptoms. The first episode is often more severe and may be associated with fever, muscle pains, swollen lymph nodes and headaches. Over time, episodes of active disease decrease in frequency and severity. Other disorders caused by herpes simplex include: herpetic whitlow when it involves the fingers, herpes of the eye, herpes infection of the brain, and neonatal herpes when it affects a newborn, among others.

Maribavir

Maribavir is an experimental oral antiviral drug candidate licensed by ViroPharma from GlaxoSmithKline in 2003 for the prevention and treatment of human cytomegalovirus (HCMV) disease in hematopoietic stem cell/bone marrow transplant patients. The mechanism by which maribavir inhibits HCMV replication is by inhibition of an HCMV encoded protein kinase enzyme called UL97 or pUL97. Maribavir showed promise in Phase II clinical trials and was granted fast track status, but failed to meet study goals in a Phase III trial. However, the dosage used in the Phase III trial may have been too low to be efficacious.

Herpes labialis A herpes simplex virus infection of the lip

Herpes labialis, commonly known as cold sores, is a type of infection by the herpes simplex virus that affects primarily the lip. Symptoms typically include a burning pain followed by small blisters or sores. The first attack may also be accompanied by fever, sore throat, and enlarged lymph nodes. The rash usually heals within ten days, but the virus remains dormant in the trigeminal ganglion. The virus may periodically reactivate to create another outbreak of sores in the mouth or lip.

Laninamivir

Laninamivir (CS-8958) is a neuraminidase inhibitor that is a drug used for the treatment and prophylaxis of Influenzavirus A and Influenzavirus B. It is currently in Phase III clinical trials. It is a long-acting neuraminidase inhibitor administered by nasal inhalation.

Herpes simplex keratitis Medical condition

Herpetic simplex keratitis is a form of keratitis caused by recurrent herpes simplex virus (HSV) infection in the cornea.

3-Deazaneplanocin A Chemical compound

3-Deazaneplanocin A is a drug which acts as both a S-adenosylhomocysteine synthesis inhibitor and also a histone methyltransferase EZH2 inhibitor. Studies have shown that it has in vitro against a variety of different tumor cell lines.

Favipiravir Experimental antiviral drug with potential activity against RNA viruses

Favipiravir, sold under the brand name Avigan among others, is an antiviral medication used to treat influenza in Japan. It is also being studied to treat a number of other viral infections, including SARS-CoV-2. Like the experimental antiviral drugs T-1105 and T-1106, it is a pyrazinecarboxamide derivative.

Galidesivir

Galidesivir is an antiviral drug, an adenosine analog. It is developed by BioCryst Pharmaceuticals with funding from NIAID, originally intended as a treatment for hepatitis C, but subsequently developed as a potential treatment for deadly filovirus infections such as Ebola virus disease, Marburg virus disease, and Zika virus. Currently, galidesivir is under phase 1 human trial in Brazil for coronavirus.

MK-608

MK-608 is an antiviral drug, an adenosine analog. It was originally developed by Merck & Co. as a treatment for hepatitis C, but despite promising results in animal studies, it was ultimately unsuccessful in clinical trials. Subsequently it has been widely used in antiviral research and has shown activity against a range of viruses, including Dengue fever, tick-borne encephalitis virus, poliovirus, and most recently Zika virus, in both in vitro and animal models. Since it has already failed in human clinical trials previously, it is unlikely MK-608 itself will be developed as an antiviral medication, but the continuing lack of treatment options for these emerging viral diseases means that much research continues using MK-608 and related antiviral drugs.

NITD008

NITD008 is an antiviral drug classified as an adenosine analog. It was developed as a potential treatment for flavivirus infections and shows broad spectrum antiviral activity against many related viruses such as dengue virus, West Nile virus, yellow fever virus, Powassan virus, hepatitis C virus, Kyasanur Forest disease virus, Omsk hemorrhagic fever virus, and Zika virus. However, NITD008 proved too toxic in pre-clinical animal testing to be suitable for human trials, but it continues to be used in research to find improved treatments for emerging viral diseases.

CMX521

CMX521 is an antiviral drug discovered by Chimerix, which was developed for the treatment of norovirus, though it also shows efficacy against related viral diarrheas such as rotovirus and some sapoviruses, astroviruses and adenoviruses. It is a nucleoside analogue which acts as an inhibitor of viral RNA-dependant RNA polymerase.

References

  1. https://pubchem.ncbi.nlm.nih.gov/compound/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