DELAVIRDINE MESYLATE

US Previously Marketed

Details

Stereochemistry	ACHIRAL
Molecular Formula	C22H28N6O3S.CH4O3S
Molecular Weight	552.667
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=MEPNHSOMXMALDZ-UHFFFAOYSA-N

InChI=1S/C22H28N6O3S.CH4O3S/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;1-5(2,3)4/h4-8,13-15,24-26H,9-12H2,1-3H3;1H3,(H,2,3,4)

HIDE SMILES / InChI

Molecular Formula	C22H28N6O3S
Molecular Weight	456.561
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Molecular Formula	CH4O3S
Molecular Weight	96.106
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf | https://www.drugs.com/ppa/delavirdine.html

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

Targets

Primary Target	Pharmacology	Condition	Potency
Human immunodeficiency virus type 1 reverse transcriptase 70 Target ID: CHEMBL247 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf \| https://www.ncbi.nlm.nih.gov/pubmed/26162497 \| https://www.ncbi.nlm.nih.gov/pubmed/10514285	Inhibitor 8504		21.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
HIV-1 infection 156 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf	Primary		Approved 8583	RESCRIPTOR Approved Use RESCRIPTOR Tablets are indicated for the treatment of HIV-1 infection in combination with at least 2 other active antiretroviral agents when therapy is warranted. The following should be considered before initiating therapy with RESCRIPTOR in treatment-naive patients. There are insufficient data directly comparing antiretroviral regimens containing RESCRIPTOR with currently preferred 3-drug regimens for initial treatment of HIV. In studies comparing regimens consisting of 2 nucleoside reverse transcriptase inhibitors (NRTIs) (currently considered suboptimal) to RESCRIPTOR plus 2 NRTIs, the proportion of patients receiving the regimen containing RESCRIPTOR who achieved and sustained an HIV-1 RNA level <400 copies/mL over 1 year of therapy was relatively low (see DESCRIPTION OF CLINICAL STUDIES). Resistant virus emerges rapidly when RESCRIPTOR is administered as monotherapy. Therefore, RESCRIPTOR should always be administered in combination with other antiretroviral agents. Launch Date 1997

C_max

Value	Dose	Analyte	Population
12.6 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
18.8 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	300 mg 3 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
26.6 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	400 mg 3 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.18 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	N-DESISOPROPYL DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.88 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	300 mg 3 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	N-DESISOPROPYL DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.23 μM EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	400 mg 3 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	N-DESISOPROPYL DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
35 μM DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20705s03lbl.pdf	400 mg 3 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
180 μM × h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20705s03lbl.pdf	400 mg 3 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:		DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

T_1/2

Value	Dose	Analyte	Population
2.59 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
3.33 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	300 mg 3 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
4.12 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	400 mg 3 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
4.71 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	N-DESISOPROPYL DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
6.18 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	300 mg 3 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	N-DESISOPROPYL DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
7.5 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	400 mg 3 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	N-DESISOPROPYL DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
5.8 h DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20705s03lbl.pdf	400 mg 3 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

F_unbound

Value	Dose	Analyte	Population
2.3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	200 mg 3 times / day steady-state, oral dose: 200 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	300 mg 3 times / day steady-state, oral dose: 300 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
2.3% EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/9164415/	400 mg 3 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN
2% DRUG LABEL https://www.accessdata.fda.gov/drugsatfda_docs/label/1999/20705s03lbl.pdf	400 mg 3 times / day steady-state, oral dose: 400 mg route of administration: Oral experiment type: STEADY-STATE co-administered:	DELAVIRDINE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
400 mg 3 times / day steady, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10348755	unhealthy, >18 years Health Status: unhealthy Age Group: >18 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10348755	Disc. AE: Rash, Oral lesion... Other AEs: Fever, Thrombocytopenia... AEs leading to discontinuation/dose reduction: Rash (grade 3-4, 36%) Oral lesion (1 patient) Function liver abnormal (2 patients) Headache (grade 4, 1 patient) Other AEs: Fever (grade 3, 1 patient) Thrombocytopenia (1 patient) Nausea (1 patient) Fatigue (1 patient) Sources: https://pubmed.ncbi.nlm.nih.gov/10348755
400 mg 3 times / day multiple, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf	Disc. AE: Rash... AEs leading to discontinuation/dose reduction: Rash (3.2%) Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf

AEs

AE	Significance	Dose	Population
Fatigue	1 patient	400 mg 3 times / day steady, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10348755	unhealthy, >18 years Health Status: unhealthy Age Group: >18 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10348755
Nausea	1 patient	400 mg 3 times / day steady, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10348755	unhealthy, >18 years Health Status: unhealthy Age Group: >18 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10348755
Thrombocytopenia	1 patient	400 mg 3 times / day steady, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10348755	unhealthy, >18 years Health Status: unhealthy Age Group: >18 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10348755
Oral lesion	1 patient Disc. AE	400 mg 3 times / day steady, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10348755	unhealthy, >18 years Health Status: unhealthy Age Group: >18 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10348755
Function liver abnormal	2 patients Disc. AE	400 mg 3 times / day steady, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10348755	unhealthy, >18 years Health Status: unhealthy Age Group: >18 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10348755
Fever	grade 3, 1 patient	400 mg 3 times / day steady, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10348755	unhealthy, >18 years Health Status: unhealthy Age Group: >18 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10348755
Rash	grade 3-4, 36% Disc. AE	400 mg 3 times / day steady, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10348755	unhealthy, >18 years Health Status: unhealthy Age Group: >18 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10348755
Headache	grade 4, 1 patient Disc. AE	400 mg 3 times / day steady, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: steady Dose: 400 mg, 3 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/10348755	unhealthy, >18 years Health Status: unhealthy Age Group: >18 years Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/10348755
Rash	3.2% Disc. AE	400 mg 3 times / day multiple, oral Highest studied dose Dose: 400 mg, 3 times / day Route: oral Route: multiple Dose: 400 mg, 3 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	inhibitor 2438	substrate 1388 inhibitor 2507

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP3A 227 CYP2C19 2057 P-gp 1741 MRP1 116 MRP2 499 MRP3 246 CYP1A2 2153	CYP3A 220 P-gp 2052	P-gp 301

Drug as perpetrator

Target	Modality	Activity	Clinical evidence
CYP1A2 2333	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/11225565/	negligible
MRP1 232	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17172311/	yes [Inhibition 16.7 uM]
MRP2 625	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17172311/	yes [Inhibition 16.7 uM]
MRP3 326	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/17172311/	yes [Inhibition 16.7 uM]
CYP2D6 2546	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf#page=3;https://pubmed.ncbi.nlm.nih.gov/11124228/ Page: 3.0	yes [Ki 12.8 uM]
CYP2C9 2497	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf#page=3;https://pubmed.ncbi.nlm.nih.gov/11124228/ Page: 3.0	yes [Ki 2.6 uM]
CYP2C19 2141	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf#page=3; https://pubmed.ncbi.nlm.nih.gov/11124228/ Page: 3.0	yes [Ki 24 uM]
CYP3A 317	inhibitor 4027 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf#page=3;https://pubmed.ncbi.nlm.nih.gov/15544435/ Page: 3.0	yes [Ki 9.5 uM]	yes (co-administration study) Comment: coadministration of amprenavir with delavirdine resulted in an approximately 4-fold increase in amprenavir AUC to infinity (AUC∞) and a 6-fold increase in amprenavir Cmin Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf#page=3;https://pubmed.ncbi.nlm.nih.gov/15544435/ Page: 3.0
P-gp 1932	inducer 1966 Sources: https://pubmed.ncbi.nlm.nih.gov/12180537/	yes
P-gp 1932	inhibitor 4027 Sources: https://aac.asm.org/content/48/4/1073	yes

Drug as victim

Target	Modality	Activity	Clinical evidence
CYP2D6 1388	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf#page=3 Page: 3.0	likely
P-gp 2052	substrate 4014 Sources: https://aac.asm.org/content/48/4/1073	no
CYP3A 220	substrate 4014 Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf#page=3 Page: 3.0	yes	yes (co-administration study) Comment: Coadministration of RESCRIPTOR and drugs that induce CYP3A, such as rifampin, may decrease delavirdine plasma concentrations and reduce its therapeutic effect. With rifampin: 97% decrease in AUC Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/020705s018lbl.pdf#page=3 Page: 3.0

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:119573	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:119573
ChemicalBook	CB8292151	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB8292151
eMolecules	1989427	https://www.emolecules.com/cgi-bin/more?vid=1989427
MolPort	MolPort-003-846-188	https://www.molport.com/shop/molecule-link/MolPort-003-846-188
ZINC	ZINC000018516586	http://zinc15.docking.org/substances/ZINC000018516586

PubMed

Title	Date	PubMed
Prevalence and characteristics of multinucleoside-resistant human immunodeficiency virus type 1 among European patients receiving combinations of nucleoside analogues.	2000 Aug	10898683
Presence of 2',5'-Bis-O-(tert-butyldimethylsilyl)-3'-spiro-5"-(4"-amino-1",2"-oxath iole-2",2"-dioxide) (TSAO)-resistant virus strains in TSAO-inexperienced HIV patients.	2000 Jun 10	10875608
Delavirdine susceptibilities and associated reverse transcriptase mutations in human immunodeficiency virus type 1 isolates from patients in a phase I/II trial of delavirdine monotherapy (ACTG 260).	2000 Mar	10681363
Inhibition of clinically relevant mutant variants of HIV-1 by quinazolinone non-nucleoside reverse transcriptase inhibitors.	2000 May 18	10821714
Piperidinylethyl, phenoxyethyl and fluoroethyl bromopyridyl thiourea compounds with potent anti-HIV activity.	2000 Sep	11142631
Stereochemistry of halopyridyl and thiazolyl thiourea compounds is a major determinant of their potency as nonnucleoside inhibitors of HIV-1 reverse transcriptase.	2000 Sep 18	10999473
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.	2001	11402860
Saquinavir soft gelatin capsule: a comparative safety review.	2001	11347724
Delavirdine: clinical pharmacokinetics and drug interactions.	2001	11327199
The emerging roles of non-nucleoside reverse transcriptase inhibitors in antiretroviral therapy.	2001	11217868
Amino acid deletion at codon 67 and Thr-to-Gly change at codon 69 of human immunodeficiency virus type 1 reverse transcriptase confer novel drug resistance profiles.	2001 Apr	11264389
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	11477320
Antiviral drugs: current state of the art.	2001 Aug	11418355
Use of HIV protease inhibitors as pharmacoenhancers.	2001 Feb	11279888
Ritonavir, efavirenz, and nelfinavir inhibit CYP2B6 activity in vitro: potential drug interactions with bupropion.	2001 Feb	11159797
Site-directed mutagenesis of human immunodeficiency virus type 1 reverse transcriptase at amino acid position 138.	2001 Feb 1	11162823
Anti-HIV activity of aromatic and heterocyclic thiazolyl thiourea compounds.	2001 Feb 26	11229762
Inhibition of human cytochrome P450 isoforms by nonnucleoside reverse transcriptase inhibitors.	2001 Jan	11225565
Interaction of delavirdine with human liver microsomal cytochrome P450: inhibition of CYP2C9, CYP2C19, and CYP2D6.	2001 Jan	11124228
Impact of clinical reverse transcriptase sequences on the replication capacity of HIV-1 drug-resistant mutants.	2001 Jul 5	11437654
Phenotypic hypersusceptibility to non-nucleoside reverse transcriptase inhibitors in treatment-experienced HIV-infected patients: impact on virological response to efavirenz-based therapy.	2001 Jun 15	11416714
International perspectives on antiretroviral resistance. Nonnucleoside reverse transcriptase inhibitor resistance.	2001 Mar 1	11264999
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	11590517
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	11590527
New developments in anti-HIV chemotherapy.	2001 Nov	11562282
The stereoselective targeting of a specific enzyme-substrate complex is the molecular mechanism for the synergic inhibition of HIV-1 reverse transcriptase by (R)-(-)-PPO464: a novel generation of nonnucleoside inhibitors.	2001 Nov 30	11572864
HIV-protease inhibitors alter retinoic acid synthesis.	2001 Oct 19	11600826
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	11448730
Evolution of anti-HIV drug candidates. Part 3: Diarylpyrimidine (DAPY) analogues.	2001 Sep 3	11527705
Evolution of anti-HIV drug candidates. Part 1: From alpha-anilinophenylacetamide (alpha-APA) to imidoyl thiourea (ITU).	2001 Sep 3	11527703
Non-nucleoside HIV-1 reverse transcriptase (RT) inhibitors: past, present, and future perspectives.	2002	11945162
Synthesis, biological evaluation, and binding mode of novel 1-[2-(diarylmethoxy)ethyl]-2-methyl-5-nitroimidazoles targeted at the HIV-1 reverse transcriptase.	2002 Apr 11	11931611
Rhabdomyolysis with acute renal failure probably related to the interaction of atorvastatin and delavirdine.	2002 Apr 15	11959068
Determination of delavirdine in very small volumes of plasma by high-performance liquid chromatography with fluorescence detection.	2002 Apr 5	11996495
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	12477355
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	12367719
Hypersusceptibility to non-nucleoside reverse transcriptase inhibitors in HIV-1: clinical, phenotypic and genotypic correlates.	2002 Oct 18	12370521
Pharmacia pilots patent share for HIV drug.	2003 Apr	12680360
3-iodo-4-phenoxypyridinones (IOPY's), a new family of highly potent non-nucleoside inhibitors of HIV-1 reverse transcriptase.	2003 Dec 15	14643315
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	14685057
Delavirdine malabsorption in HIV-infected subjects with spontaneous gastric hypoacidity.	2003 Feb	12616670
Comparison of nine resistance interpretation systems for HIV-1 genotyping.	2003 Jun	12924541
Protease inhibitor-sparing regimens: new evidence strengthens position.	2003 Jun 1	12946062
Hypersusceptibility to non-nucleoside reverse transcriptase inhibitors in HIV-1.	2003 Jun 13	12799573
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	14612892
Modest decreases in NNRTI susceptibility do not influence virological outcome in patients receiving initial NNRTI-containing triple therapy.	2003 Oct	14640386
Identification and prediction of promiscuous aggregating inhibitors among known drugs.	2003 Oct 9	14521410
Susceptibility of HIV-2, SIV and SHIV to various anti-HIV-1 compounds: implications for treatment and postexposure prophylaxis.	2004 Feb	15040537
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	14742351
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	15115397

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 Mar 31 17:59:56 GMT 2025` Edited by `admin` on `Mon Mar 31 17:59:56 GMT 2025`
Record UNII	421105KRQE
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

DELAVIRDINE MESILATE

Preferred Name

English

DELAVIRDINE MESYLATE

Official Name

English

DELAVIRDINE MESILATE [JAN]

Common Name

English

DELAVIRDINE METHANESULFONATE [MI]

Common Name

English

DELAVIRDINE MESYLATE [ORANGE BOOK]

Common Name

English

DELAVIRDINE METHANESULFONATE

Common Name

English

U-90152S

Code

English

DELAVIRDINE MESYLATE [VANDF]

Common Name

English

RESCRIPTOR

Brand Name

English

Delavirdine mesylate [WHO-DD]

Common Name

English

PIPERAZINE, 1-(3-((1-METHYLETHYL)AMINO)-2-PYRIDINYL)-4-((5-((METHYLSULPHONYL)AMINO)-1H-INDOL-2-YL)CARBONYL)-, MONOMETHANESULPHONATE

Systematic Name

English

DELAVIRDINE MESYLATE [USAN]

Common Name

English

PIPERAZINE, 1-(3-((1-METHYLETHYL)AMINO)-2-PYRIDINYL)-4-((5-((METHYLSULFONYL)AMINO)-1H-INDOL-2-YL)CARBONYL)-, MONOMETHANESULFONATE

Systematic Name

English

DELAVIRDINE MESYLATE [HSDB]

Common Name

English

DELAVIRDINE MESILATE [MART.]

Common Name

English

1-(3-(ISOPROPYLAMINO)-2-PYRIDYL)-4-((5-METHANESULPHONAMIDOINDOL-2-YL)CARBONYL)PIPERAZINE MONOMETHANESULPHONATE

Systematic Name

English

1-[3-(Isopropylamino)-2-pyridyl]-4-[(5-methanesulfonamidoindol-2-yl)carbonyl]piperazine monomethanesulfonate

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C97453