Delavirdine - CAS 136817-59-9
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Not Intended for Therapeutic Use. For research use only.
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Delavirdine is a non-nucleoside reverse transcriptase inhibitor (NNRTI). It is used as part of highly active antiretroviral therapy (HAART) for the treatment of human immunodeficiency virus (HIV) type 1.
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U 90152; BHAP-U 90152
1. A single amino acid change at Leu-188 in the reverse transcriptase of HIV-2 and SIV renders them sensitive to non-nucleoside reverse transcriptase inhibitors
Y. Isaka, S. Miki, S. Kawauchi, A. Suyama, H. Sugimoto. Arch Virol (2001) 146: 743–755
We next investigated the efficacy of NNRTIs (nevirapine, delavirdine, and efavirenz) to these mutants. HeLa-CD4 cells were used as target cells for HIV-1 NL432 and HIV-2 Rod (X4 viruses), while HeLa-CD4-R5 cells were used for HIV-2 GH-1, SIVmac and SIVagm (R5 viruses). The results are summarizedmin Table 1. NNRTIs had little if any antiviral effect on wild type SIVmac or HIV-2. Only SIVagm SA212 showed a high level of sensitivity to delavirdine and efavirenz. L188Y and L188C mutants of HIV-2, however, were sensitive to delavirdine and efavirenz, and HIV-2 GH-1-L188Y even showed a higher sensitivity to delavirdine than wild type HIV-1. L188Y and L188C mutants of SIVmac also showed significant sensitivity to delavirdine and efavirenz. Conversely, the substitution of the residue 188 from Y to L or C in HIV-1 dramatically decreased its sensitivity to NNRTIs. Thus, HIV-1-Y188L showed a 21-, 480- or >820-fold increase in EC50 of delavirdine, efavirenz or nevirapine, respectively, as compared with wild type HIV-1. Similarly, HIV-1-Y188C showed a 2.5-, 3.7-, or 72-fold increase inEC50 of delavirdine, efavirenz or nevirapine, respectively.As expected, AZT and 3TC, the nucleoside analogue RT inhibitors, had antiviral activity to all viruses with EC50 values within the range of 11–350 nM and 39–1,100 nM, respectively.
2. Delavirdine Clinical Pharmacokinetics and Drug Interactions
Jonathan Q. Tran, John G. Gerber and Bradley M. Kerr. Clin Pharmacokinet 2001; 40 (3): 207-226
Delavirdine is a highly specific HIV-1 reverse transcriptase inhibitor belonging to the bisheteroaryl-piperazine class of compounds. Delavirdine has shown promising results in combination with other antiretroviral agents in patients with HIV-1 infection and is approved for the treatment of HIV-1 infection in combination with nucleoside analogues and/or protease inhibitors. Unlike efavirenz and nevirapine, delavirdine is not an inducer of drug metabolising enzyme activity and, therefore, does not decrease systemic concentrations of coadministered drugs. Rather, in vitro and in vivo studies have demonstrated that delavirdine is an inhibitor of cytochrome P450 (CYP) 3A4 and thereby inhibits the metabolism of HIV protease inhibitors, which are all substrates of CYP3A4. By enhancing the pharmacokinetics of protease inhibitors, delavirdinemay have the clinically desirable effect of permitting either a reduction in the dose and/or administration frequency of coadministered protease inhibitors in the treatment of patients with HIV infection, or boosting the concentrations of protease inhibitors when used in salvage circumstances.
3. Clinical Pharmacokinetics of Non-Nucleoside Reverse Transcriptase Inhibitors
Patrick F. Smith, Robert DiCenzo and Gene D. Morse. Clin Pharmacokinet 2001; 40 (12): 893-905
Delavirdine exhibits pH-dependent dissolution in gastric acid and is least soluble at high gastric pH. Following absorption, delavirdine is highly protein bound (98%), primarily to albumin, and distributes across cell membranes with a steadystate volume of distribution (Vss) of approximately 0.8 L/kg. Penetration into the cerebrospinal fluid (CSF) is poor, with concentrations approximately 0.4%of that found in plasma, reflecting the extent of plasma protein binding. Delavirdine undergoes extensiveN-dealkylation via oxidative metabolism, with the primary circulating metabolite being N-deisopropyl-delavirdine, which does not appear to exhibit significant antiviral activity. The primary route of metabolism is via cytochrome P450 (CYP) 3A4, and delavirdine is a potent inhibitor of this enzyme, including auto-inhibition of its own metabolism. Delavirdine is also a significant inhibitor of other drugs that likewise undergo metabolism via this enzymatic pathway.
4. Effect of Food on the Steady-State Pharmacokinetics of Delavirdine in Patients with HIV Infection
Gene D. Morse, Margaret A. Fischl, Mark J. Shelton. Clin Drug Invest 2003; 23 (4): 255-261
Delavirdine mesylate is a non-nucleoside reverse transcriptase inhibitor with in vitro activity against HIV-1 and is currently approved as a component of combination antiviral therapy for HIV-1. Delavirdine demonstrates capacity-limited metabolism via the cytochrome P450 (CYP) system, with the N-dealkylated metabolite (N-DLV) being present in plasma during repeated dosing. Delavirdine has also been investigated with regard to its interaction potential with fluconazole, indinavir, saquinavir and amprenavir. Delavirdine is a weakly basic compound (pKa ≈ 4.45) with pH-dependent solubility (200-fold reduction from pH2 to pH7.5). In a prior single-dose study of delavirdine mesylate and concurrent food intake, the absorption of delavirdine was delayed and the area under the curve was reduced by 26%. Since the complex, nonlinear pharmacokinetics of delavirdine do not permit a simple extrapolation of the results of a single-dose study to steady-state, the present study was performed to evaluate the influence of food during multiple dosing.
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CAS 136817-59-9 Delavirdine

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