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Details

Stereochemistry ACHIRAL
Molecular Formula C22H28N6O3S
Molecular Weight 456.561
Optical Activity UNSPECIFIED
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DELAVIRDINE

SMILES

CC(C)NC1=CC=CN=C1N2CCN(CC2)C(=O)C3=CC4=C(N3)C=CC(NS(C)(=O)=O)=C4

InChI

InChIKey=WHBIGIKBNXZKFE-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C22H28N6O3S
Molecular Weight 456.561
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Delavirdine is a nonnucleoside reverse transcriptase inhibitor (NNRTI). Delavirdine binds directly to reverse transcriptase (RT) and blocks RNA-dependent and DNA-dependent DNA polymerase activities. Delavirdine does not compete with template:primer or deoxynucleoside triphosphates. HIV-2 RT and human cellular DNA polymerases alfa, gamma, or delta are not inhibited by delavirdine. In addition, HIV-1 group O, a group of highly divergent strains that are uncommon in North America, may not be inhibited by delavirdine. Delavirdine is marketed under the trade name Rescriptor, indicated for the treatment of HIV-1 infection in combination with at least 2 other active antiretroviral agents when therapy is warranted. .

CNS Activity

Originator

Approval Year

PubMed

PubMed

TitleDatePubMed
Clinical pharmacokinetics of non-nucleoside reverse transcriptase inhibitors.
2001
Determination of serum levels of thirteen human immunodeficiency virus-suppressing drugs by high-performance liquid chromatography.
2001 Apr 13
High prevalence of genotypic and phenotypic HIV-1 drug-resistant strains among patients receiving antiretroviral therapy in Abidjan, Côte d'Ivoire.
2001 Apr 15
Antiretrovirals: simultaneous determination of five protease inhibitors and three nonnucleoside transcriptase inhibitors in human plasma by a rapid high-performance liquid chromatography--mass spectrometry assay.
2001 Aug
Antiviral drugs: current state of the art.
2001 Aug
New developments in anti-HIV chemotherapy.
2001 Jan-Feb
Impact of clinical reverse transcriptase sequences on the replication capacity of HIV-1 drug-resistant mutants.
2001 Jul 5
A randomized trial of nelfinavir, ritonavir, or delavirdine in combination with saquinavir-SGC and stavudine in treatment-experienced HIV-1-infected patients.
2001 Mar-Apr
Combination therapy with indinavir, ritonavir, and delavirdine and nucleoside reverse transcriptase inhibitors in patients with HIV/AIDS who have failed multiple antiretroviral combinations.
2001 May-Jun
Synthesis and anti-HIV-1 activity of new delavirdine analogues carrying arylpyrrole moieties.
2001 Nov
New developments in anti-HIV chemotherapy.
2001 Nov
Anti-human immunodeficiency virus drugs are ineffective against Pneumocystis carinii in vitro and in vivo.
2001 Nov 15
Drugs for HIV infection.
2001 Nov 26
Can delavirdine substitute for ritonavir?
2001 Nov-Dec
Baseline antiretroviral drug susceptibility influences treatment response in patients receiving saquinavir-enhancing therapy.
2001 Nov-Dec
HIV-protease inhibitors alter retinoic acid synthesis.
2001 Oct 19
Mismatched double-stranded RNA (polyI-polyC(12)U) is synergistic with multiple anti-HIV drugs and is active against drug-sensitive and drug-resistant HIV-1 in vitro.
2001 Sep
Evolution of anti-HIV drug candidates. Part 3: Diarylpyrimidine (DAPY) analogues.
2001 Sep 3
Interactions between antiretroviral drugs and drugs used for the therapy of the metabolic complications encountered during HIV infection.
2002
Non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors: past, present, and future perspectives.
2002
Determination of delavirdine in very small volumes of plasma by high-performance liquid chromatography with fluorescence detection.
2002 Apr 5
Structural requirements for potent anti-human immunodeficiency virus (HIV) and sperm-immobilizing activities of cyclohexenyl thiourea and urea non-nucleoside inhibitors of HIV-1 reverse transcriptase.
2002 Dec
Synthesis of novel N-1 (allyloxymethyl) analogues of 6-benzyl-1-(ethoxymethyl)-5-isopropyluracil (MKC-442, emivirine) with improved activity against HIV-1 and its mutants.
2002 Dec 19
New developments in anti-HIV chemotherapy.
2002 Jul 18
Simple and rapid quantification of the non-nucleoside reverse transcriptase inhibitors nevirapine, delavirdine, and efavirenz in human blood plasma using high-performance liquid chromatography with ultraviolet absorbance detection.
2002 Jul 5
Nelfinavir urinary stones.
2002 Mar
Delavirdine increases drug exposure of ritonavir-boosted protease inhibitors.
2002 Mar 29
Delavirdine in rescue regimens.
2002 May-Jun
New anti-HIV agents and targets.
2002 Nov
Polymorphisms of cytotoxic T-lymphocyte (CTL) and T-helper epitopes within reverse transcriptase (RT) of HIV-1 subtype C from Ethiopia and Botswana following selection of antiretroviral drug resistance.
2002 Nov
Hypersusceptibility to non-nucleoside reverse transcriptase inhibitors in HIV-1: clinical, phenotypic and genotypic correlates.
2002 Oct 18
3-iodo-4-phenoxypyridinones (IOPY's), a new family of highly potent non-nucleoside inhibitors of HIV-1 reverse transcriptase.
2003 Dec 15
Provider bias in the selection of non-nucleoside reverse transcriptase inhibitor and protease inhibitor-based highly active antiretroviral therapy and HIV treatment outcomes in observational studies.
2003 Dec 5
Delavirdine malabsorption in HIV-infected subjects with spontaneous gastric hypoacidity.
2003 Feb
Simultaneous determination of nine antiretroviral compounds in human plasma using liquid chromatography.
2003 Feb 5
Pharmacokinetic interaction between amprenavir and delavirdine after multiple-dose administration in healthy volunteers.
2003 Jan
Amino acid substitutions at position 190 of human immunodeficiency virus type 1 reverse transcriptase increase susceptibility to delavirdine and impair virus replication.
2003 Jan
Use of HIV-1 reverse transcriptase recovered from human plasma for phenotypic drug susceptibility testing.
2003 Jul 4
Comparison of nine resistance interpretation systems for HIV-1 genotyping.
2003 Jun
Protease inhibitor-sparing regimens: new evidence strengthens position.
2003 Jun 1
Toxicity of non-nucleoside analogue reverse transcriptase inhibitors.
2003 May
Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia.
2003 Nov 17
Modest decreases in NNRTI susceptibility do not influence virological outcome in patients receiving initial NNRTI-containing triple therapy.
2003 Oct
Pfizer announces free drug program.
2003 Sep
Drug resistance profiles of recombinant reverse transcriptases from human immunodeficiency virus type 1 subtypes A/E, B, and C.
2003 Sep
Sex-based differences in saquinavir pharmacology and virologic response in AIDS Clinical Trials Group Study 359.
2004 Apr 1
Susceptibility of HIV-2, SIV and SHIV to various anti-HIV-1 compounds: implications for treatment and postexposure prophylaxis.
2004 Feb
Novel benzophenones as non-nucleoside reverse transcriptase inhibitors of HIV-1.
2004 Feb 26
Clinical efficacy of antiretroviral combination therapy based on protease inhibitors or non-nucleoside analogue reverse transcriptase inhibitors: indirect comparison of controlled trials.
2004 Jan 31
Roles of conformational and positional adaptability in structure-based design of TMC125-R165335 (etravirine) and related non-nucleoside reverse transcriptase inhibitors that are highly potent and effective against wild-type and drug-resistant HIV-1 variants.
2004 May 6
Patents

Sample Use Guides

In Vivo Use Guide
HIV-1 infection (part of combination): Oral: 400 mg 3 times/day
Route of Administration: Oral
In Vitro Use Guide
In vitro anti-HIV-1 activity of delavirdine was assessed by infecting cell lines of lymphoblastic and monocytic origin and peripheral blood lymphocytes with laboratory and clinical isolates of HIV-1. IC50 and IC90 values (50% and 90% inhibitory concentrations) for laboratory isolates (n = 5) ranged from 0.005 to 0.030 uM and 0.04 to 0.10 uM, respectively. Mean IC50 of clinical isolates (n = 74) was 0.038 uM (range: 0.001 to 40 0.69 uM); 73 of 74 clinical isolates had an IC50
Substance Class Chemical
Created
by admin
on Mon Oct 21 19:49:41 UTC 2019
Edited
by admin
on Mon Oct 21 19:49:41 UTC 2019
Record UNII
DOL5F9JD3E
Record Status Validated (UNII)
Record Version
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Name Type Language
DELAVIRDINE
INN   MI   VANDF   WHO-DD  
INN  
Official Name English
DELAVIRDINE [VANDF]
Common Name English
PIPERAZINE, 1-(3-((1-METHYLETHYL)AMINO)-2-PYRIDINYL)-4-((5-((METHYLSULFONYL)AMINO)-1H-INDOL-2-YL)CARBONYL)-
Systematic Name English
DELAVIRDINE [INN]
Common Name English
DELAVIRDINE [WHO-DD]
Common Name English
DELAVIRDINE [MI]
Common Name English
Classification Tree Code System Code
NDF-RT N0000009948
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
WHO-VATC QJ05AG02
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
LIVERTOX 277
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
NDF-RT N0000175460
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
NCI_THESAURUS C97453
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
NDF-RT N0000175463
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
WHO-ATC J05AG02
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
Code System Code Type Description
DRUG BANK
DB00705
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
PRIMARY
NCI_THESAURUS
C65366
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
PRIMARY
INN
7234
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
PRIMARY
ChEMBL
CHEMBL593
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
PRIMARY
RXCUI
83816
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
PRIMARY RxNorm
MERCK INDEX
M4152
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
PRIMARY Merck Index
MESH
D020008
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
PRIMARY
EVMPD
SUB06949MIG
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
PRIMARY
WIKIPEDIA
DELAVIRDINE
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
PRIMARY
PUBCHEM
5625
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
PRIMARY
CAS
136817-59-9
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
PRIMARY
EPA CompTox
136817-59-9
Created by admin on Mon Oct 21 19:49:41 UTC 2019 , Edited by admin on Mon Oct 21 19:49:41 UTC 2019
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
TRANSPORTER -> INHIBITOR
Related Record Type Details
METABOLITE -> PARENT
Delavirdine is primarily metabolized by cytochrome P450 3A (CYP3A), but in vitro data suggest that delavirdine may also be metabolized by CYP2D6
MAJOR
Related Record Type Details
ACTIVE MOIETY