emivirine emivirine 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 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)) bictegravir (bic) cabotegravir (cab) dolutegravir (dtg)# elvitegravir (evg) raltegravir (ral)# bi 224436† mk-2048† maturation inhibitors bevirimat† bms-955176§ fipravirimat§ protease inhibitors (pi)(discovery and development)1st generation amprenavir (apv)‡ fosamprenavir (fpv) indinavir (idv)◊ lopinavir (lpv) nelfinavir (nfv)◊ ritonavir (rtv)# saquinavir (sqv)◊ 2nd 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† nucleotide analogues/ntrtis: tenofovir disoproxil (tdf)# tenofovir alafenamide (taf) non-nucleoside (nnrti)(discovery and development)1st generation efavirenz (efv)# nevirapine (nvp)# delavirdine (dlv)‡ 2nd generation diarylpyrimidines etravirine (etr) rilpivirine (rpv) doravirine (dor) combined formulations abacavir/lamivudine# abacavir/dolutegravir/lamivudine° abacavir/lamivudine/zidovudine atazanavir/cobicistat bictegravir/emtricitabine/tenofovir alafenamide° cabotegravir/rilpivirine darunavir/cobicistat darunavir/cobicistat/emtricitabine/tenofovir alafenamide° dolutegravir/emtricitabine/tenofovir alafenamide dolutegravir/lamivudine° dolutegravir/lamivudine/tenofovir alafenamide° dolutegravir/lamivudine/tenofovir disoproxil°# dolutegravir/rilpivirine doravirine/lamivudine/tenofovir disoproxil efavirenz/emtricitabine/tenofovir disoproxil# efavirenz/lamivudine/tenofovir disoproxil# elvitegravir/cobicistat/emtricitabine/tenofovir alafenamide elvitegravir/cobicistat/emtricitabine/tenofovir disoproxil emtricitabine/tenofovir alafenamide emtricitabine/rilpivirine/tenofovir alafenamide emtricitabine/rilpivirine/tenofovir disoproxil emtricitabine/tenofovir disoproxil# lamivudine/nevirapine/stavudine lamivudine/nevirapine/zidovudine lamivudine/raltegravir lamivudine/tenofovir disoproxil# lamivudine/zidovudine# lopinavir/ritonavir# pharmacokinetic boosters cobicistat (c) ritonavir (r)# experimental agentsuncoating 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. 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 y 3d model (jsmol) interactive image chembl chembl35033 n chemspider 58529 n pubchem cid 65013 unii x87g8ix72o n comptox dashboard (epa) dtxsid80164437 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) nkey: mlilorufdvltsp-uhfffaoysa-n ninchi=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). n verify (what is yn ?) infobox references