Emivirine

Emivirine
Names

Preferred IUPAC name 6-Benzyl-1-(ethoxymethyl)-5-(propan-2-yl)pyrimidine-2,4(1H,3H)-dione
Identifiers
CAS Number	149950-60-7 ^checkY
3D model (JSmol)	Interactive image
ChEMBL	ChEMBL35033 ^☒N
ChemSpider	58529 ^☒N
PubChem CID	65013
UNII	X87G8IX72O ^☒N
CompTox Dashboard (EPA)	DTXSID80164437 Edit this at Wikidata
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)^☒N Key: MLILORUFDVLTSP-UHFFFAOYSA-N^☒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 [77 °F], 100 kPa). ☒N verify (what is ^checkY☒N ?) 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.^[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]

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Antiviral drugs: antiretroviral drugs used against HIV (primarily J05)

Capsid inhibitors

Lenacapavir (LEN)

Entry/fusion inhibitors
(Discovery and development)

gp41 (Enfuvirtide (ENF, T-20))^◊
CCR5 (Maraviroc (MVC)
Vicriviroc ^†, Cenicriviroc ^†, Leronlimab ^†)
CD4 (Ibalizumab (IBA), Semzuvolimab ^§)
gp120 (Fostemsavir (FTR))

Integrase inhibitors
(Integrase strand transfer inhibitors (INSTI))

Maturation inhibitors

Protease Inhibitors (PI)
(Discovery and development)

1^st generation	Amprenavir (APV) ^‡ Fosamprenavir (FPV) Indinavir (IDV) ^◊ Lopinavir (LPV) Nelfinavir (NFV) ^◊ Ritonavir (RTV) ^# Saquinavir (SQV) ^◊
2^nd generation	Atazanavir (ATV)°^# Darunavir (DRV)°^# Tipranavir (TPV) ^◊ TMC-310911 ^§

Reverse-transcriptase
inhibitors (RTIs)

Nucleoside and
nucleotide (NRTI)

Nucleoside analogues/NRTIs: Abacavir (ABC) ^#
Didanosine (ddI) ^◊
Emtricitabine (FTC)
Lamivudine (3TC) ^#
Stavudine (d4T) ^◊
Zalcitabine (ddC) ^‡
Zidovudine (AZT, ZDV) ^#
Amdoxovir ^†
Apricitabine ^†
Censavudine ^†
Elvucitabine ^†
Islatravir (EFdA, ISL) ^§
Racivir ^†
Stampidine ^†

Non-nucleoside (NNRTI)
(Discovery and development)

1^st generation	Efavirenz (EFV) ^# Nevirapine (NVP) ^# Delavirdine (DLV) ^‡
2^nd generation	diarylpyrimidines Dapivirine (DPV) Etravirine (ETR) Rilpivirine (RPV) Doravirine (DOR) Elsulfavirine (ESV)

Combined formulations

Pharmacokinetic boosters

Cobicistat (c)
Ritonavir (r) ^#

Experimental agents

Uncoating inhibitors	TRIM5alpha (gene)
Transcription inhibitors	Tat antagonists
Translation inhibitors	Trichosanthin
BNAbs	Elipovimab
Other	Abzyme BIT225 ^† Calanolide A Ceragenin Cyanovirin-N Diarylpyrimidines Epigallocatechin gallate (EGCG) Foscarnet Fosdevirine ^† Griffithsin Hydroxycarbamide KP-1461 ^† Miltefosine Portmanteau inhibitors Scytovirin Seliciclib ^† Synergistic enhancers Tre recombinase Zinc finger protein transcription factor
Failed agents	Aplaviroc Atevirdine Brecanavir Capravirine Dexelvucitabine Droxinavir Lasinavir Emivirine Lersivirine Lodenosine Loviride Mozenavir Palinavir Telinavir

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

°DHHS recommended initial regimen options. ^◊Formerly or rarely used agent.

References

[edit ]

^ "Emivirine".
^ 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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