delavirdine delavirdine delavirdine (dlv) (brand name rescriptor) is a non-nucleoside reverse transcriptase inhibitor (nnrti) marketed by viiv healthcare. it is used as part of highly active antiretroviral therapy (haart) for the treatment of human immunodeficiency virus (hiv) type 1. it is presented as the mesylate. the recommended dosage is 400 mg, three times a day. delavirdineclinical datatrade namesrescriptorahfs/drugs.commonographmedlineplusa600034pregnancycategory au: b3 routes ofadministrationby mouthatc codej05ag02 (who) legal statuslegal status us: ℞-only pharmacokinetic databioavailability85%protein binding98%metabolismliver (cyp3a4- and cyp2d6-mediated)elimination half-life5.8 hoursexcretionkidney (51%) and feces (44%)identifiers iupac name n-piperazin-1-yl}carbonyl)-1h-indol-5-yl]methanesulfonamide cas number136817-59-9 ypubchem cid5625drugbankdb00705 ychemspider5423 yuniidol5f9jd3ekeggd07782 ychebichebi:119573 ychemblchembl593 yniaid chemdb005059pdb ligandspp (pdbe, rcsb pdb)comptox dashboard (epa)dtxsid6022892 chemical and physical dataformulac22h28n6o3smolar mass456.57 g·mol−13d model (jsmol)interactive image smiles cc(c)nc1cccnc1n4ccn(c(=o)c3cc2cc(ns(c)(=o)=o)ccc23)cc4 inchi inchi=1s/c22h28n6o3s/c1-15(2)24-19-5-4-8-23-21(19)27-9-11-28(12-10-27)22(29)20-14-16-13-17(26-32(3,30)31)6-7-18(16)25-20/h4-8,13-15,24-26h,9-12h2,1-3h3 ykey:whbigikbnxzkfe-uhfffaoysa-n y (verify) although delavirdine was approved by the u.s. food and drug administration in 1997, its efficacy is lower than other nnrtis, especially efavirenz, and it also has an inconvenient schedule. these factors have led the u.s. dhhs not to recommend its use as part of initial therapy. the risk of cross-resistance across the nnrti class, as well as its complex set of drug interactions, makes the place of delavirdine in second-line and salvage therapy unclear, and it is currently rarely used. its manufacturing and distribution was discontinued in the united states and canada. interactions like ritonavir, delavirdine is an inhibitor of cytochrome p450 isozyme cyp3a4, and interacts with many medications. it should not be administered with a wide range of drugs, including amprenavir, fosamprenavir, simvastatin, lovastatin, rifampin, rifabutin, rifapentine, st john's wort, midazolam, triazolam, ergot medications, and several medications for acid reflux. adverse effects the most common adverse event is moderate to severe rash, which occurs in up to 20% of patients. other common adverse events include fatigue, headache and nausea. liver toxicity has also been reported. synthesis delavirdine synthesis: modification of the scheme that was done for ateviridine q.v. by performing the reductive alkylation with acetone gives 2 after removal of the protecting group. acylation of this amine with the imidazolide from 5-methylsulfonaminoindole-2-carboxylic acid (1) affords the amide, reverse transcriptase inhibitor, atevirdine.